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| Ep. 145 – Solving the Go-to-Market Riddle with Rick Nee - Part 1 | 23 sept. 2026 | 00:24:37 | |
In this episode of Selling Intelligence, Rick Nee, Chief Revenue Officer at Alcatraz, joins Mark Petruzzi and KK Anderson to unpack what happens after a company reaches product market fit and the challenge shifts from finding customers to building a go-to-market organization that can scale. Rick explains why revenue leaders should resist bringing a fixed playbook into a new company and instead use customer behavior, sales data, and the buyer journey to determine what the organization actually needs. He shares how Alcatraz has built its revenue structure around vertical pods, creating tighter feedback loops between sales, SDRs, customer success, and other customer-facing roles. The conversation also dives into the importance of cleaning CRM data before making strategic decisions, identifying the metrics that actually matter, and reverse engineering performance by vertical to determine where to invest people, capital, and resources. What You’ll Learn:
Key Topics:
Guest Spotlight: Rick Nee Rick Nee is Chief Revenue Officer at Alcatraz, a Cupertino-based company focused on facial authentication for physical security. As a revenue leader, Rick focuses on solving the go-to-market challenges that emerge after product market fit, using data to determine how teams should be structured, which verticals deserve investment, and where companies can scale most effectively. In this conversation, Rick shares a practical approach to building revenue organizations around real customer behavior rather than assumptions, industry benchmarks, or rigid playbooks. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more conversations with revenue leaders on building smarter, more scalable go-to-market organizations. Mark (00:30) Welcome back to Selling Intelligence. I'm Mark Petruzzi here with my co-founder and co-host KK Anderson. KK Anderson (00:37) Here's a number we're sitting with. A sales organization that goes from three people to 25 in 24 months has effectively rebuilt itself every quarter. Most leaders in that position reach for the standard playbook because it's the fastest thing available. But our guest today treated the playbook as a starting point instead of an answer and went to his own data to decide what to keep. Mark (01:00) Rick Nee is Chief Revenue Officer at Alcatraz, the Cupertino company replacing badges with facial authentication, backed by more than $100 million in capital and trusted by Fortune 100 Enterprises AI data centers, airports, universities, and professional sports teams. Rick, welcome to Selling Intelligence. Rick Nee (01:23) Thanks for having me. I am very excited to be here. this is exciting and these are topics that I'm pretty passionate about. Mark (01:28) Excellent. All right, first topic, solving the go-to-market riddle. You have said that stage the stage that energizes you the most is the one right after product market fit. When finding customers who want to buy is no longer the problem. Describe what actually changes for a revenue leader at that moment. Rick Nee (01:46) It's a great question. So I didn't figure this out so a little bit later in my career. People ask, hey, do you want to work at a startup? And that can mean a lot of different things, a series D with a thousand customers versus a pre-series or series A, where you're trying to find that product market fit. And so I think you have to like think about where you want to be on that journey. and then if we really define what product market fit means. I was listening to someone the other day from HubSpot and they said, product market fit doesn't mean two two customers that have bought your product and hey, we have figured this out. when I define product market fit, I'm looking at, okay, a subset of customers have not only bought your product, they're using it and you've retained them. And so then there's that there's that point, that drop, that inflection point where, okay, we now have a growing set of customers that not only are buying, but are also staying with us. And so when you get to that part of the journey, it often requires a remodel. And the folks and the in the way that you were going to market to get those first customers is not necessarily what's going to get you to the next level. I call folks that are in that series A, I call them pirates. They're just out there, they're with the founder. They might be that founder led AE. They're literally trying to figure out what is going to stick, right? And it often is not what they initially think. when I came to Alcatraz, they had already figured out was interested and who was buying our And so then I that what the GTM riddle, what excites me about that is then you have to take a look at it and you have to say, okay, what type of salesperson do I need? Are we an enterprise motion? Are we a mid-market motion? Are we a director? Are we channel? do we need hunters and farmers or both? what use cases and personas and verticals should we focus on? What custom what sets of customers should we say no to? So when you look at all of that based on some of those first customers, you'll find that you're gonna have to make some changes. And it doesn't mean you just rip and replace, it means there's iterations and you're still testing. But I think That is where I love to thrive, where you start to build what I would call truly for scale. I know that everybody likes to say, hey, scale. You know, everybody wants the But really thinking about how you're gonna build, because if you do it the wrong way, you're gonna build and attenuate out in a in a in a bad way, right? And so you wanna obviously get it right. But that's where I like to come in. I don't wanna go figure out if this product is gonna gain traction in the market. And some people live for that, right? And if you do, then that's where you should go. But for me, it's sort of figuring out this riddle and how do you get to the next five hundred customers or whatever set of AR, whatever your goal may be. KK Anderson (04:14) So you touched on it a little bit, but if you don't mind, go a little bit deeper and walk us through the the pieces of this riddle or puzzle, like as you call it, as you see them today, and maybe even give us give us some glimpse into what you're thinking about as you're moving into to 2027 with your how you're gonna put the pieces of that riddle together for Alcatraz. Rick Nee (04:34) Well, I mean, first you have to start with what you think about your playbook and you think about what you know, what riddle you're trying to solve. There are there are real stakeholders with real goals that may not necessarily be the ones that you you're marching towards, but they are what they are, right? You have the board, you have investors, you have the CEO, you different different folks and stakeholders that are like, This is what we need to do. So I think the lens that you immediately have to take as you're figuring out this riddle is what is the most efficient and effective way to get an ROI and to grow sales fast? And often that means reverse engineering the data, right? everyone talks about AI, but if you look at Claude and you pipe that into your HubSpot and you start to cue the different leading and lagging indicators. You should be able form a pretty strong hypothesis of what you should and shouldn't do as you march down a path, which is an annual number. and and that let's face it, the average CRO lasts 14 or 16 months, depending on which data you're looking at in this as world. So I I would say if you're you're figuring out that riddle, it let's keep it simple, stupid. Let's look at Eight to ten metrics and be clear-eyed on what we should make our immediate, what I'll call low-hanging fruit. And let's go get some quick wins as we're thinking about that remodel. Earn some trust. You can actually miss your first or second quarterly target if it's trending in the right direction with the plan, right? So I'm looking at okay, which verticals? Who do I have here that can actually Stay with the company as we as we scale. Again, a series A pirate, a hunter, might not necessarily be the right fit for a series B. You're going to look at which use cases, the sales cycling, your win rate, your your deal size land versus expand. And then through all of that, you can start to put in place what I would call your vertical structure, which I know we're gonna talk a little bit about today, but I think Most CROs that come into these roles at this point, I think what happens when they're trying to solve this riddle is is they see eight, ten, twelve, fourteen things that they could do and they try to do all of them when they should probably only be doing one or two of them and go get those wins and then go build out from there. Mark (06:41) Excellent. So Rick, most earlier stage CROs and are in a standard shape. They come in, there's a sales director of some sort, an SDR, customer success person. What do you what do you keep from that initial structure and shape? And where do you immediately give yourself permissions to kind of blow it up and start again? Rick Nee (07:01) So a few things. I love this question. And I would say 10 years ago I was probably at fault for what I'm gonna tell you say not to do. but I guess as you get older and you've been through this a few times, you you learn you learn from those mistakes and you and you try to do the right thing moving forward. And and for me, you see this a lot with job this you see this a lot with job roles, open CRO roles or VP of sales roles. It's like we're looking for someone with a playbook. And it's like, okay, great. Well, the playbook for cyber company A or physical company B doesn't necessarily mean you're gonna take that playbook and it's gonna be a perfect overlay. And if anyone says that, I have a playbook and it will I can just turn this thing on, then you should run the other way. I think there's a lot that we've learned in the industry. I think there's more data. There's more networking opportunities. There's podcasts like this where there's lots of nuggets and things that you can extract from, right? I was listening to one six months ago and a CRO had said, hey, you should really look at your webinars and doing them this way. And I thought, that's a great idea. I haven't haven't looked at that. So great. So that, you know, you you're gonna take some of those new things and add it. But I would say any playbook that you're gonna bring in and assume it's gonna work somewhere else. Let's say it's 50. To 70% applicable, which means there's a pretty big could be 50%, it could be 30%, that you're gonna have to call audibles and and lean into what the business needs, right? so for us, vertical pod, everyone's gonna tell you, hey, you're gonna need a sales director, you're gonna need an SDR, you're gonna need success person, you're gonna need, you're gonna need this. I think, yes, I think the I think the clarity of role is very important. But you know, for us, it's been SDR sales directors. we have our inside sales rep that look that is doing some of that success stuff and some of the renewal stuff. We have channel account managers that are doing a little bit of a a different role than you would see in other orgs where they're helping us drive lead generation, but not necessarily deals. and we've had to like lean in heavily. We have found through our data. That service and support is super critical to retaining and expanding customers. Sounds obvious, but when you have an early Series B company and you have cash and you're making investments, the easy button is to say, I'm just gonna go hire more sales directors. I'm gonna go hire more SDRs. I'm go. And I think before you do that, you should understand your buyer journey and look at the complexity of what you're selling. And my last company, out of the box cloud cyber tool. The post and pre-sale support on the technical side was not as great. And so the the answer was you should accelerate sales directors and SDRs. Here, we are selling a physical security solution that's very simple to deploy, but based on what our customer wants with that, and if they're doing an on-prem deployment or they're gonna they want us to be baked into their environment, those are a little bit more complex. And so we have found we need. Just as many folks post-sale as we do pre-sale. again, that was not something from my playbook. So I think you have to look at the buyer journey. You have to look at what's working, where customers are happy, where things are sticky, and and go there. And and don't be afraid to question those that are overly dogmatic on hey, you need to be using these AI, these nine AI tools, and you need to have a person, a success team that's this big based on the series or revenue or. Then you should I should always start with the well, why? What are they doing? What are they not doing? What what is this role doing? And so I'm a big believer in giving folks enrolls multiple things to do, to stretch them where they might be doing renewals and mid market sales, or they might be doing success and post sale this or deployment and and pre-sales engineering, whatever. I just I think you have to look at what's right. And the gift that keeps on giving there, Mark, is a lot of thought leaders in the in the go-to-market space will say, Well, you need this size team and you need to do this. And then I think the answer is, well, I have limited capital. So I have to I have to make the most efficient, effective investments here. And often that means a series B where You're asking people to do multiple things. And then it's into a role that's not the traditional customer success role. It's not a traditional renewal specialist. They're doing multiple things. I think the more you grow up and you go to Series C, Series D, or IPO, then specialization probably becomes more and more relevant, right? but I think at B, you still want folks that are a bit of generalists in some of the roles that they're doing so that you can get more from the team if that makes sense. KK Anderson (11:21) And you said pod. And I imagine as well in in your world, where I think it's probably becoming more normal and more accepted to have a facial recognition, security instead of just a badge. You know, everyone's just been carrying badges for a hundred years and we're used to swiping our badges, to get into every building and to do everything. but I imagine in that pod structure, then there's a super close relationship between you know, your inside sales team and your C S that's in that pod and your AE and like what are we what feedback are we hearing from the market? Like what Rick Nee (11:50) Yeah. KK Anderson (11:51) objections are we getting? What obstacles are we facing? Like I bet that's Rick Nee (11:54) That's yeah, I that that's exactly right. That's why I love the power of the vertical pod. It's it's really a feedback loop at at its core. That's KK Anderson (12:04) Right. Rick Nee (12:04) really what it is, because there is so much good information on a hundred person startup team. And I could guarantee you that fifty, sixty percent of that knowledge transfer doesn't happen because of the unintended silos that are built. That was sort of my genesis into the vertical pod. Verticals, I believe, buy and have different cycles and and things of that nature. But really, KK it was to speed up the feedback loop. And an SDR. So I actually I have the SDR, the inside sales rep, and if we have a success person actually reporting to that sales director, and other In other companies, they might have those reporting to the function leads. But what I'm actually trying to do is I'm trying to look at that customer journey from a new logo intro meeting to a large expansion opportunity. I'm trying to make sure that that knowledge transfer is happening all the time. And then they can adjust their discovery, they can adjust their new logo targeting, they can make introductions or present new use cases to similar customers. That all KK Anderson (13:06) Right. Rick Nee (13:07) happens when you're doing the vertical I don't really get when when folks tell me, well I'm the I'm the enterprise rep and I'm the mid KK Anderson (13:13) Yeah. Rick Nee (13:13) market and I sell to everybody. Perhaps that does make sense to be fair. it probably does. I'm sure it does. KK Anderson (13:19) Not in your world. You know, a university looking for security is gonna be very different than in an airport, right? Wouldn't don't you Rick Nee (13:26) Right. Yeah. yeah. And I have learned I have learned so much from our sales directors on that. But you're right, like a a higher ed higher ed population where, you know, everyone's carrying a mobile phone and the concept of a badge is sort of foreign to a lot of them. versus a data center where it might be two or three factor where every single room or row or wherever you're going in a data center. you're doing multiple multiple authentications to get somewhere, those are very, very different. problems or things you're trying to serve. as your sales director, imagine jumping from a higher ed one where he's worried about students losing badges all the time to a triple, triple three factor use case where it's government sensitive data, data and and the the team is just used to and has to do a certain set of workflow things just to get to their job. They're just very, very different. KK Anderson (14:18) Yeah, really interesting. And last thing I'll say before we move into the next topic around kind of reverse engineering that data is that I would say, Mark, and correct me if I'm wrong, but we're you know, we're so lucky we get to talk to CROs every day on this on this show. And almost all of them have been pivoting to a vertical Rick Nee (14:37) Yeah. KK Anderson (14:37) pod structure. And I think it's because of the feedback loop, but it's also because of this trust recession that we're in and being able to be more human and be more differentiated and really get into subject matter expertise. Like it seems like it is the hottest topic over the last couple of months. Mark, do you agree? Mark (14:53) Yeah, I do agree. I I think it's been building longer than just the last few months. I think it's been really building over ten, twelve years. And I especially saw that in the software industry, especially enterprise software. KK Anderson (15:06) Mm-hmm. Mark (15:07) So yeah, but definitely there's a newfound momentum in that as well. KK Anderson (15:11) Yeah. And I think maybe even just for a mid-sized series, A through is what I really what I'm referencing and and the verticalization, but I think it's the right call. Okay, Rick Nee (15:20) Yeah. KK Anderson (15:21) so let's go into reverse engineering data before you, change the model. And when we say model, we mean your go to market, you know, puzzle pieces or riddle, if you will. and we chatted in the prep session and you've vindicated that, there's enough tools now. There's AR, there's AI, there's CRM, there's all kinds of data out there that you can reverse engineer and and form a strong hypothesis quickly. Like what is what does that actually look like for you? Like what data are you looking at? What are you reverse engineering? Like how are you using that to solve your riddle? Rick Nee (15:52) I first, like just a blanket statement. I'm always surprised, and I would bet this is for at least half of series A, maybe transition into series B, that no not many have taken a a a true look at the data in and really tried to form a hypothesis on it. Of course, everybody looks at the data to some degree, but there's there's a few caveats and one. By time you inherit a CRM system, if you're coming into a series B, you have to question the integrity of it, first of all. Right. p field have been added, fields have been taken out, and now we have AI which could spit out all that data, and you know, a lot will tell you that data's dirty. and and it it just is. And so KK Anderson (16:28) Yeah. Rick Nee (16:28) you got that, and you have perhaps a few folks that are investors or board members that say, This is why we invested, and we believe. Early that this was the type of customer in the DL size. And then the data says something different. So I I would encourage and I recommend to anyone that's coming into a a product market fit, how I defined it, where you know you get customers who are starting to buy starting to buy and starting to actually retain, before you really plug in all of the data to start looking at these different KPIs or leading or lagging indicators. You have to clean it up. And so that sounds like a very, very painful task. And if and we're fortunate now, we have a RevOps leader that is helping with that. But the way I did it for the first six months here in the last two roles that I've had is export, look at export all the win-loss data on a spreadsheet, and then go get those outliers and get them out of the data. There's just weird things that you don't know or that have inflated or and go get to the median. Go get to go figure out what your sales cycle length really is. Go build your taxonomy of basic vertical structure. go do all of that. And the hypothesis is that I was able to form by doing a cursory or just a basic cleanup of the data. And then instruct your RevOps or your sales ops team to say, okay, now that I've cleaned X, Y, and Z. Can we go make these fixes in our CRM so that moving forward, this is a little bit quicker? So I would always encourage people, you gotta you, you have to do some cleaning up. And if you're not willing to roll your sleeves up as a CRO at series A, series B to do that, then I don't I don't actually don't think you should be in the job because you know you come from a big company or series D or you know, yes, doing a few hundred million in the R, all that sort of. Done for you. But I think at the A and B level, you've got to roll your sleeves up. And then you have to look at the data. And there's a few data points where you look at them initially and you're like, you know what? It's the integrity is just not there. So that's still a hypothesis. But I can see the DL size. I can see which verticals are buying. I can see the sales cycle length now that I've removed outliers. You know, yeah, what you know, if you have some sales cycle, yeah, if you have sales cycle length, you have a hundred deals over five years that were all closed in a day, you're like, wait a minute, nobody, what's going on here? it was just somebody was rebuilding a quote, and so now it looks like it was the sales cycle. They finally put the right KK Anderson (18:40) They finally put it in C R because their manager said they Rick Nee (18:44) they finally put it in CRM. Exactly, right? So remove all of that stuff, right? So but sales cycle length, deal size, which verticals you're buying. Pipeline coverage by pipeline coverage by vertical, by rep. you could start to look at all of that, number of new logos, the percentage of LAN versus expand, how quickly from LAN to expand. And through that, you start to see what I would say the the most important KPIs that you need, win rate, right? So we have a certain pipeline coverage number. That is not as aggressive as what the industry says because of our win rate. And so again, after you clean the data. So once you have all that, the next level is then to say, okay, I see what the data is telling me, but now let's actually go a step further and let's look at what the vertical data is telling me. KK Anderson (19:33) Mm. Rick Nee (19:34) The vertical data will have different. Performance. Some verticals are going to have very long sales cycles, but the deals are bigger. Some are much quicker, but the deal is smaller. some require a more technical resource that it in in these things that whatever. And so you start to look at that and you say, geez, I think I I think I needed to hire this type of person and they need to focus on these verticals. But maybe these these verticals, I can tell you right now, the persona of my sellers are different based on the verticals they're in, what those verticals need. And so again, that's the power of the verticals, is that what I initially knew was a communication loop. And to Mark's point earlier, like this has been an eight, 10, 12 year vertical, people have been sort of banging on this door. It started to catch my attention when publicly traded companies like Cloudflare and some others said, Hey, we're outperforming because we have the structure. So of course there is a there's a revenue piece, but the the piece that that I would say in the last year that's stuck with me with the verticals is not only the feedback loop and the outperforming in revenue, but actually What is needed in those verticals based on what that vertical data is telling you? And I can I it some of them look the same, right? Or pretty close, but some of them are wildly different. And when you're thinking about near and far-term revenue targets, you need both. You need those bigger swings that are going to take longer, and you need to make certain investments and certain comp plans and certain types of people for those. And then you need someone else that can do what I call the run rate quicker business. And that's a different set of folks and investments. And so that's that's what reverse engineering data means to me. I look at it every 30 days and every 90, and I encourage any revenue leader to do this. I take a Friday afternoon, probably six Starbucks iced coffees, and I just KK Anderson (21:12) Yeah. Rick Nee (21:14) I I I block my calendar for the day. and I basically say to myself, okay, I'm a venture capital private equity investor. I'm gonna go deep into this. I'm gonna look at cohorts. I'm gonna look at verticals. I'm gonna look at time series trends. And okay, this is still looking what we thought, or this one's starting to get more interesting. So I think 30 look, 60 look, and then not every 90 year, and maybe at the six month mark. You're really digging because that's when you're starting to think about 2027, right? You're starting to think of okay, I need to start thinking about my budget and my plan for next year. And I should have enough of a signal from six months to know where the puck is going to some degree. Of course, things change, but that's what I mean when I'm talking about reverse engineering the data. and I think you have to do it. I think you can work with your sales or rev ops leader, but I think you have to be in as the as the chief revenue officer. KK Anderson (22:02) Roll up your sleeves. Rick Nee (22:03) Yeah, you gotta roll Mark (22:03) Yeah. Rick Nee (22:04) it up and And with Claude, which is my favorite AI tool, and again, they're all great. the prompts you can get very creative contextually with the prompts as you're sort of pressure testing your own bias or your own, you got the data, but you then you can kind of try to convince yourself based on the data that this is always right. But like, no, tell me where tell me where I'm not looking. What are the blind spots? What about this? And and you'll start to see other things willing. start to uncover. And so it to me it's a fun exercise. If you like data, it doesn't happen often. Yeah. The aha KK Anderson (22:31) Mm. We love data. We love data here at AGS, that's for sure. Mm-hmm. Rick Nee (22:35) moments, Mark (22:35) Yeah. Rick Nee (22:36) they don't come often, but when they do, good or bad, you're like, KK Anderson (22:39) Yeah. Rick Nee (22:39) okay, that this is a very compelling thing that I need to have a discussion with the senior leadership team about. KK Anderson (22:44) And I'm sure your board appreciates Mark (22:44) Perfect. KK Anderson (22:45) that. Mm-hmm. Rick Nee (22:46) Yeah, definitely. Mark (22:47) So Rick, I think this is a good place for us to pause for episode one and move into episode two. The idea that a vertical can carry its own economics and that these economics are what earn you the next four people is worth sitting with a little bit longer. KK Anderson (23:04) So reading the data before you change the structure is just as I mentioned, the same discipline that we employ here at AGS, and specifically inside our two millimeter club, which is a small group coaching residency of sales managers, leaders from non-competitive companies that come together in a data-driven coaching program where they learn to identify using data. And coach the small shifts in seller behavior that add up to exponential movement and pipeline. We have eight-week cohorts that launch monthly. If you're interested, you can apply at www.get-ags.com forward slash two millimeter club, two mm club. In part two, Rick takes us into the talent side of his go-to-market riddle, how he turns sales directors into industry voices, why he promotes from SDR seat instead of hiring senior talent in, and what a 90% retention rate actually takes to hold. Mark (24:04) That is part two. We will see you there. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 144 – Building Predictable Pipeline and Breaking Revenue Silos with Thurman Sneed - Part 2 | 16 sept. 2026 | 00:23:22 | |
General Episode Description: In Part 2 of Selling Intelligence, Thurman Sneed, Chief Revenue Officer at Marigold, returns to show how the same “do the math” mindset can transform everything from account coverage and customer conversations to seller development and AI adoption. Thurman explains why Marigold moved from a round robin model to vertical specialization, how CSMs and SDRs can grow into revenue generating roles, and why a tighter ICP helps teams focus their resources where they can create the most impact. The conversation also explores how sellers can use customer data and benchmark insights to build stronger business cases and quantify value for executives. Thurman shares how his team is applying AI to sales coaching, account preparation, pipeline generation, and churn prediction, while keeping human judgment at the center. The goal is not AI for the sake of AI. It is using technology where it can genuinely improve speed, capacity, decision making, and revenue outcomes. What You’ll Learn:
Key Topics:
Guest Spotlight: Thurman Sneed Thurman Sneed is the Chief Revenue Officer at Marigold, where he leads sales, customer success, revenue operations, and marketing. With a career that began in accounting and auditing before expanding into operations and revenue leadership, Thurman brings a distinctive financial and operational perspective to the CRO role. His leadership philosophy centers on disciplined execution, data driven decision making, cross-functional alignment, and helping teams turn ambitious revenue goals into practical, achievable actions. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more GTM insights from leading voices in sales, revenue, and business growth. Subscribe wherever you get your podcasts. Mark (00:38) Welcome back to Selling Intelligence. If you're just joining in, you're in the right place. And if you come straight from part one, we picked up where we left off. KK Anderson (00:48) In part one, Thurman Sneed made three things clear. He came into the revenue seat through accounting and operations rather than through a quota. And that lens is why he thinks in arithmetic. He discovered that the individual level math he assumed his managers were doing with sellers was not actually happening. And he treats every function inside the company as a customer, which is what makes the outside selling work. Mark (01:14) So in part two we get practical. Thurman rebuilt the coverage model, taught people who have never carried a quota to carry one, pointed the same math at his customers, and now deciding where AI belongs in all of this. Thurman, welcome back. Let us pick up right here. Thurman (01:33) Thank you, Mark. Mark (01:34) So Thurman, Rebuilding the coverage model. So Thurman, you inherited a model where accounts were assigned round robin and reps were specialized by platform. What was the first change you made and why that one first? Thurman (01:48) Yeah, the first thing that we did is we decided that we were going to have a vertical coverage model as opposed to round robin. And I made that first because I wanted fo I wanted our sales team to learn the customer, to, to learn the terminology, to be very specific, and to enjoy, what they were doing every day, as opposed to today I wake up and I'm gonna be serving. this industry, the next day, I get a hospital, the next day I get an amusement park. It didn't seem fair, just from a basic level, so why not assign to a vertical and become specialist in that space? KK Anderson (02:23) So and in doing that allows them to almost brand their expertise and be thought of as trusted advisors and being able to solve the business problems that your customers are out there facing. Thurman (02:35) Yes, truly to be able to solve it in a in a very meaningful way because they understand how they drive their outcome. So back to doing the math, how do they actually need to produce their pipeline, their conversions, their sales, whatever that might be, even if it's a not for profit, how do they need to drive more donations? if it's a government entity, what are they trying to produce as an outcome as opposed to it being so different in every conversation? KK Anderson (03:03) Right. And your your product at Marigold is you know, they're they're looking for they're using Marigold because they want to drive business and communications and conversions and so that's that's really important. Mm-hmm. Thurman (03:18) With specific audiences. And it's not always the same way that you drive that content KK Anderson (03:23) Right. And Thurman (03:24) to those audiences. KK Anderson (03:25) it's definitely a way to create differentiation, When you can help with their problems. So you gave people who had been processing renewals for years a quota. So they're not used to a quota. It's kind of like handing the finance guy a quota, like you got, Thurman (03:39) This is that. KK Anderson (03:39) and you told them, you know, you're gonna train them and tell them to take advantage of of what they did not realize they already knew. And so Like what what did that teaching look like week to week? We have so many, we have so many customers. I've seen it a hundred times, where all of a sudden a CSM turns into a, quota carrying member of the sales team. So tell us how you did it. Thurman (04:00) Well, one of the first things is to inject confidence in what they already knew. They have been involved in so many customer conversations. So many times a customer has has actually explained to them the pain that they are actually that they endure. And I love it when it's a case of when we bring on a new customer and that CSM is onboarding them and they're connecting with the challenge that they were having elsewhere. Right. So they have learned that or they were learning that over the years, but not necessarily turning that lens and looking at it from a different angle. What if I took these customers that I have made happy and asked them to introduce me to another department at a university? Or is literally leveraging the relationships that they had built with their customer set? Right. And so the training became more of let's inject the confidence because you know the platform better than some of our brand new sellers right now. You actually live in the platform. You've lived the customer experience. You've gone through the benchmark conversations and the performance conversations with a customer. Change that lens to someone that is reaching out that has not experienced that yet. Mark (05:12) Yeah, and I love how, Thurman, you're taking this more into the prescripted side. So let's go even a little further. you moved your SDRs from setting meetings to owning and closing the smaller deals themselves. What does that do for a seller's development, particularly an early stage seller, that handing off the meeting could never do? Thurman (05:34) Yeah, and we didn't move them holistically, but what I wanted to do was to ensure that our SDR team had a career path and that they understood that career path very early versus late. Right. And so ultimately that close closing of the deal is what we all think of, that's the account executive, But if we could help them get a little feel for why am I passing off this customer that I can go ahead and assist now? I understand why why do I need to set up a meeting and make them wait a few days or a period of time when I can go ahead and service service them? And that's what an AE needs to do, If I can solve that pain, I can hear that pain, I'm hearing the challenges. Let's just go ahead and close the deal. and when they get ready and they're further into their career, a year, 18 months into their career, and they're ready to go to That transition is so much faster. But at the same time, what it allows is it allows me to know who really does not want to do sales. Right. And do you want to be an SDR for from a career perspective? That's also okay. Do you want to transition and become a CSM one day? That's also okay. Right. But it allows those that are in this position that we traditionally think of as our bench for sales. to be able to make that career decision very early. KK Anderson (06:54) So y you put it you in one of your th your therminisms, In the in our prep video was we started talking. you put it as eighty twenty, stop fishing in oceans, fish in lakes and ponds, do the math. No, how do you pick which lakes? Thurman (07:08) With to to be maniacal about the true ICP. we KK Anderson (07:12) Love that. Thurman (07:12) and again, there's it's easier coming out of my mouth than it sometimes is, but it's actually possible. Especially, you know, you go into a situation, it's like, wow, we're marketing to such a large audience. How can we make sure that a smaller audience actually hears us, though? And is that When you do the math, is that gonna have more ROI and efficiency than trying to be so wide? And every single time it does. And so I used this literally the other day and I had to explain it, but I said, I'm fishing for wells and ponds. I know that that doesn't sound right, but I think everybody understands what I'm trying to say. I'm gonna focus on this vertical and I am going to go after fewer, right? wells in that pond because I'm so focused and I know that we can serve them, When you fish in too big of an ocean, you're trying to sell sell to everyone, you're not helping your marketing team, you're not helping your sales team and helping them get educated, on a space that we can work. You're not you're not helping those SDRs. Everybody's kind of everywhere and not knowing how to really hit the outcome. KK Anderson (08:18) I love it. We had a guest recently on our podcast and his his saying was you can't teach a fish to climb a tree. Thurman (08:26) I like that. I might have to have it to reuse that one. KK Anderson (08:28) We're gonna have to have some outtakes. Outtakes of all the the fun analogies that we get on the show. Mark (08:29) Yeah. Thurman (08:34) Yeah. Mark (08:34) All right, so let's to our next topic here. so you've taught your team how to do the math from a sales perspective. Let's go into a little bit of doing the math for and with the customer. So your company has years of benchmark data sitting inside a platform that nobody was using in a sales conversation. What changed the first time? a seller put it in front of a customer and how has it evolved from there? Thurman (09:03) Yeah, this this is probably one of the most fun things because this this ties into the teaching. It's and it also ties into the cross-functional are CSMs using this with customers. This is where you are. But guys, wait a minute. Salespeople, about this on the front end? That's exactly what your prospects are trying to achieve. So the first time this happened, a rep put together their own ROI calculator. And they said it to the customer that was apprehensive about going ahead and signing a deal. And they needed to be able to show this to their board member to get approval. That was the that was the very first time. And then the next thing you know, is like we have a signed deal in two days. It was just it's awesome to see because I wasn't involved in it. It was the teaching starting to take place. I have this information that you actually don't have. This is how you compare to others and how. Our software, our recommended change in process is gonna help you achieve these numbers. KK Anderson (09:58) You told us about one one of your sellers walked a CEO through what a cheaper alternative would have cost him in emails. You know, Marigold is an email communication platform. Thurman (10:07) Yes. KK Anderson (10:09) and like what it would cost him in emails that never reach an inbox. And you know, he Thurman (10:14) so KK Anderson (10:14) came back and signed the next day. Tell tell us a little bit about that story. Thurman (10:17) Yeah, this one had to do with deliverability. And we know that you know some platforms don't have as high deliverability rates as others. and the rep explained, hey, you can go with that option, but let me just give you one metric, deliverability, right? And if you do the math on that deliverability, you may have forty thousand fewer emails hitting the inbox. How would that if you go through your math and your conversion, how KK Anderson (10:40) Yep. Thurman (10:41) would that translate into the lower tiers? And it became the light bulb moment for the CEO when he signed the next day. So KK Anderson (10:49) Right. Thurman (10:50) just awesome. Mark (10:50) Love it. KK Anderson (10:51) And it's ironic Mark (10:51) So KK Anderson (10:52) too, 'cause it's all part of the conversion math for a seller, right? How many Thurman (10:56) Yes. KK Anderson (10:57) emails do you have to send to get these conversions to get the get the conversation? So yeah, cool. Mark (11:02) So Thurm Thurman, Thurman (11:03) Exact same. Mark (11:04) yep, what what about what has to be true about a seller before you really can trust them to make a numbers argument in front of an an executive? Thurman (11:13) But they get the numbers for themselves. KK Anderson (11:17) That's so good. Thurman (11:19) Yes. and that's why I wanna make sure that they get the numbers for themselves. If they can do the math for themselves, they can do the math for any customer. KK Anderson (11:26) Right. So, for our CRO audience out there, you know, most most of most companies, most BDB companies are probably sitting on all kinds of data that they have not ever thought about being able to quantify and turn into an ROI, or selling argument. would you agree with that? Like I just like kind of what comes to mind as I as I say that, do you think that's Thurman (11:47) When I go back through the history of the many companies that I've worked for, I KK Anderson (11:50) Mm-hmm. Thurman (11:51) absolutely agree with that. And it it goes back to and I this happens unnaturally or naturally, I guess you would say, that folks end up in silos and you just don't know. And it's just if you don't end up in environments where you're sharing and speaking and finding out, I didn't know that you had that. It could really be as simple as that. I did not know that we had that. KK Anderson (12:13) Right. And so like what would you where would you go looking? Like finance Thurman (12:17) The first KK Anderson (12:17) products, like where would you if you are listening to this and you're like, huh, I wonder what we have. Thurman (12:22) I would first go to product KK Anderson (12:24) Yeah. Thurman (12:25) and I would and I would start to understand what does what are the metrics that the product team has that we may not be aware that's in XYZ platform. Right. And can I use some of that information that's being collected in order to tell a story at the end of the day? That's what we're doing, right? To tell a story. Because They don't the engineers don't always know the story that you're trying to express to a customer. But that's where I would start first. Mark (12:54) All right, so our next topic here and final topic for this time with Thurman is the concept of AI where it earns its place. So not AI for the sake of AI or not AI. I mean it's gotta earn the right to be used. And KK and I know this space well. We've worked really hard to build metric models. where you really can can build upon a focus of AI to ROI. And with those models, with the the work we do with our clients, we make sure we analyze where we're going to get the most bang for our buck for our clients. And we analyze and we know exactly how it's impacted it when it's when it's done. So with your team, you know, they watched you, I'm sure. Teaching and coaching and they I'm sure loved it. but then you went a step further and you built a sales coach out of your own material. What did people start doing with that tool that you never really expect? Thurman (14:00) Yeah. Well, first and foremost, they were wild and it didn't take a long time for them to start using it. But what the first thing that they started doing with it is preparing. and the second thing that they actually started doing with it was evaluating what they had previously done on an opportunity or evaluating an opportunity and what they could do next. Now being able to see what what they said or heard in a gone call. what notes that were documented in Salesforce. All all these different connections that they were able to pull together in a matter of seconds, just not realizing, right? KK Anderson (14:35) So you know, what's interesting about AI is that a lot of this a lot of these things could have been done before AI, but they weren't. And a lot of times it's because it just it would take so long. you talked you talked about that in our in our prep call, and I thought it was was really interesting. So what like in your opinion? What does AI actually change for a salesperson? Mark (14:57) Yeah. Thurman (14:58) But it allows them to be quicker, to do things and and save time and to have an imagination in some particular cases, Because if I now I can go and put in an ask a question and when you're surprised, my God, now what else can I ask? And get some guidance. And it's I don't want it, I don't ever want to take the human out then from our perspective, both from our product perspective as well as our sales perspective, is not to take what the AI output is and say, I don't need to filter it. It is now I can use my critical thinking skills all the time, And to focus on what is what is that result, what is it guiding me to do, but does that make sense is where I want them spending the time. Right. Let me build a model, something that I can reuse. Let me help prepare and understand what is happening at this particular company because all that data is out there. But before, who really wanted to spend the time researching every single prospect realistically that they were engaging with if they had to hit numbers that we were talking about, the math. KK Anderson (16:04) Right. Thurman (16:04) So the math became easier, faster. Because I can take this, I can read it, my God, I know how to apply it. Let's go. Right. So KK Anderson (16:13) Spot on. Yeah. And it's I mean, gone are the days where we would, you know, be searching for something on the internet, have to copy and paste it and put it in a document and compile all of your research and then read through it all and try and draft and come up with some differentiating statements and then decide which ones to use. And I mean it would be a two hour process. Right? Yeah, exactly. And now Thurman (16:33) Yes. Per. Yeah. KK Anderson (16:37) now You can do it in a split second and then you can ask it to you can it can help you be critical in your analysis of it to identify what's most important Thurman (16:46) Yeah. KK Anderson (16:47) what what's the most important problem that customer is trying to solve. Really good. so go yeah, go ahead, Mark. Mark (16:51) So Thurman, yeah. So okay. So one of the things we wanted to make sure we learned from you as well that you have four SDRs presently, and my understanding you have no plan to add a fifth because of some of the things you're building with AI. how do you think about headcount once capacity stops being a function of people? Thurman (17:15) That is a very good question, Mark. and the reason why I kind of gave you guys that input is for two reasons. One, you asked a question in episode one about I think it was episode one that came in, about us going through the SDR and teaching them to close deals. So that if that capacity relates first and foremost to that particular piece, right? This pit particular position. Is the one that is at the cusp of being able to help an AE be more effective, build more pipeline, build more meetings. We all know that that is the math. We need more meetings, But at the same time, this same position is the one that is allowing me to have more sales reps in reality, Because the more that they can take on the low end, the more my AEs can deal with the higher end. And you guys do the math. The more time. the more deals on the higher end, right? With the same win rates, I'm gonna make more money at the end of the day, So that that's that's what's happening for me with the AI. Everybody's gonna become more efficient. This SDR role is is the cusp of the beginning of the math. KK Anderson (18:21) It really is. It's such an exciting time. you know, we've had guests on who have who have said that the S Dr role is coming to an end, and I totally It's it is just changing shape, right? The Thurman (18:30) it's not. It's changing shape. Mark (18:33) Yeah. KK Anderson (18:34) the ability for them to be a differentiator and you know It's just it's changing shape and I think it's gonna be it's gonna be really exciting to see where AI can take that. So now you're looking at AI to predict churn better than than some of the tools you bought to do exactly that. what what has to be true about your data, before that works? Thurman (18:55) Well, as in any project, almost regardless of what it is, we got to make sure that the data is actually clean. but but the second most important part about the data is that we're it's accessible. and when I say accessible, if we wanna see the actions that someone takes in the platform or the actions that someone is taking in the market outside of us. Right, being able to see that someone is looking at a competitor in advance as an example, right? Is that accessible information to us? If it's accessible, can we use it? Can we apply that almost to what they're doing on the on the other people's websites to what they're doing in the platform and put a formula together to say, these two things are related and it's gonna result in turn. Now we can insert the human back into. the situation and say, let me make a phone call. Let me find out what may be going on before they ever know. Before we ever get a sense that they are considering alternatives. Mark (19:55) Beautiful. Well, Thurman, let's go on to our rapid fire part of our segment, and it's five questions, same five every episode. And let let me set you up with your first one. What was the first product or service you ever sold? Thurman (20:11) See when talk about this before, but it was Quizno Sandwiches. KK Anderson (20:14) Aha Mark (20:15) Nice, okay. KK Anderson (20:17) Okay, Thurman, who is your favorite CRO or CEO that you follow? Thurman (20:22) My f ooh, that's well, that's really tough. I'm gonna say my current, Lisa Mayer is my favorite CEO. KK Anderson (20:29) There you go, getting brownie points. Thurman (20:31) Yeah. Mark (20:32) So a leadership or go to market practice you believe every sales and marketing leader should adopt. Thurman (20:38) Leading by example, servant leadership. KK Anderson (20:40) I love it. Now for my favorite question, Thurman. Advice you would give your twenty one year old self. Thurman (20:46) Determine what you're going to own. In my particular case, I would tell people, invest in real estate as soon as you possibly can. KK Anderson (20:53) Ha ha ha ha ha. Mark (20:54) Excellent. Okay. So Thurman, this has been absolutely terrific. Where should people go to follow you and follow what you're working on? Thurman (21:04) I would say first go to LinkedIn. I have found myself loving to post. So I try to post at least once a week about a therminism, but I'm actually it's kind of fun because I'm bringing people along in my journey. I've been CRO for about eight or nine months now and I'm sharing some of those and it's been pretty fun. KK Anderson (21:22) Well, if you take one thing out of this conversation, take this. Nobody on your sales team is going to believe a number you have not sat down and show them. So do the math. It's a magical, very simple, way to think about it. and actually everything Thurman walked us through today comes back to, you know, managers sitting down with their sellers and managers coaching their sellers and walking them through the journey and the pathway on how to get. things done. And that's exactly what we do inside the two millimeter club, which is an AGS program. It's a small group data-driven coaching program for frontline sit sales managers. You're in a room with up to eight sales managers from non-competitive companies. They will learn to identify and coach the small shifts in seller behavior that add up to exponential movement and pipeline. They're Six months the cohort the whole program is six months, but you can break it down into two month sections and they launch monthly. If you're interested, come look at get ags dot excuse me, get dashags.com forward slash two mm club. That's wwget ags dot com. Thurman, thank you so much for joining us today. and we look forward to having you again sometime on Selling Intelligence. Thurman (22:44) Thank you, KK. Thank you, Mark. I enjoyed it. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 143 – Building Predictable Pipeline and Breaking Revenue Silos with Thurman Sneed - Part 1 | 09 sept. 2026 | 00:20:22 | |
General Episode Description: In this episode of Selling Intelligence, Thurman Sneed, Chief Revenue Officer at Marigold, joins Mark Petruzzi and KK Anderson to unpack a simple but often overlooked discipline in revenue leadership: do the math. Drawing from his background in finance, operations, and revenue leadership, Thurman explains how sellers can turn an intimidating quota into a practical action plan by understanding their pipeline, win rates, gaps, and the time they have left to close them. The conversation also explores how Thurman’s finance background shapes the way he approaches forecasting, pipeline quality, and cross-functional leadership. He shares why revenue teams need a single source of truth, how leaders can eliminate bloated pipeline, and why sales, marketing, customer success, and RevOps perform better when they understand each other’s goals and operate as one connected revenue organization. What You’ll Learn:
Key Topics:
Guest Spotlight: Thurman Sneed Thurman Sneed is the Chief Revenue Officer at Marigold, where he leads sales, customer success, revenue operations, and marketing. With a career that began in accounting and auditing before expanding into operations and revenue leadership, Thurman brings a distinctive financial and operational perspective to the CRO role. His leadership philosophy centers on disciplined execution, data driven decision making, cross-functional alignment, and helping teams turn ambitious revenue goals into practical, achievable actions. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more GTM insights from leading voices in sales, revenue, and business growth. Subscribe wherever you get your podcasts. Mark (00:30) Welcome to Selling Intelligence. I am Mark Petruzzi here as always with KK Anderson. Today we are talking about a phrase that most revenue leaders say and almost nobody actually does. KK Anderson (00:43) Do the math. Our guest uses it with his team constantly, and the first time you hear it, you might think it sounds a little cold, but it's quite the opposite. He uses it to take a seller who is convinced they are going to miss and show them on paper why they are not and how they can close the gap. Mark (01:02) So Thurman Sneed is the chief revenue officer at Marigold. He started his career as an auditor at Arthur Anderson, spent years running go-to-market operations. He has sat in the chief operating officer seat, and now leads revenue. Thurman, welcome to the show. Thurman (01:20) Thank you, Mark. Glad to be here. Mark (01:22) Welcome to Selling Intelligence. I am Mark Petruzzi with KK Anderson and this is the show for revenue leaders who would rather diagnose than guess. KK Anderson (01:32) Here's the thing that got our attention. Our guest spent years in operations assuming that sales managers underneath him were sitting down with individual sellers and walking them through their numbers. Then he took the revenue seat and found out that they were not. Not the team level math, the individual level math. Mark (01:49) Thurman Sneed, aka the Thurminator, I've heard that recently, is the chief revenue officer at Marigo, where he owns sales, customer success, revenue operations, and marketing. He came up through accounting and operations rather than through a quota, which makes him a rare profile in this seat and a very powerful one. Thurman, thanks for being here. Thurman (02:14) Thank you, Mark, for having me. I'm excited. Mark (02:16) So you have a phrase your team hears from you constantly. Do the math. Take us inside the first time you sat down with a rep and actually did it. What went on that that page? Thurman (02:28) Well, the first thing that went on that page was a little bit of a challenge in asking what is your current pipeline? And you might think that the person would reel that off just really quickly, but it wasn't that quick. So the but that was the first part of the math. What is your current pipeline? Okay. So once we get to that number, I ask a second question. What is your win rate? Your personal win rate. On top of what is the win rate for that vertical, that industry? What what have others experienced potentially? Especially in the c in this particular case, it was a new rep. And I wanted to make sure that this individual knew the history of this particular vertical. And so we went on a journey for every step. That win rate, I let The individual rep picked what they wanted to use versus the historical because they were more conservative than the historical. The second piece of that was all right, there's a gap there once you exhaust your existing pipeline. Let's take that gap, apply that same win rate the opposite way, right? And that's that's how much pipeline you need to be able to see that has the potential to close in the in the rest of the year. So you can think about that and say, I like to think of things in a very similar way that I do in real estate because I love investing in real estate. But how many different ways can you close that gap now with 11 months left? Way one, marketing didn't turn off. So you're going to continue to get some business from marketing inbound leads. Number two, you have an SDR that's assigned to work with you. What are you two going to work together to go get from two perspectives? One from a new division or cross-selling type of perspective, and one from a new logo in your territory perspective. But how are you going to map that out and drive the amount of pipeline that you want to see and close, still applying that same win rate to it? And then the last piece I wanted them to understand. Is don't forget that there's a CSM in the organization or CSMs, it could be plural, that are also working in your same vertical. Have you had a conversation with them? Have you become friends? Are you all working as a team to realize that part of you closing your number is actually them introducing you to people that they know, giving you referrals? And so by the time we finished that conversation, someone that was thinking, my God, how in the world am I going to hit my quota? It had been put into more digestible chunks and an action plan that they could go and take and say, most importantly, if I start this today versus starting this six months from now, I'm going to blow my quota out. Right. And that's what I KK Anderson (05:12) I love it. Thurman (05:13) want this individual to leave the table with. KK Anderson (05:15) I love it. And you if you've got someone's average deal size, you've got their win rate, you've got, their quota, you can so easily back into the number of activities that they need to generate to be able to, you know, and then have your conversion rates every step of way. You need to make this many phone calls and this many people, this percent will answer, this percent won't. The ones that answer, this percent will be a qualified, this percent won't. For the ones that are qualified, and it just goes trickles trickles down. But to the point where that every single day, well, I mean, like for me, for example, if I don't have at least 10 calls that are related to a an op a business opportunity on my calendar, there's a big problem. Right. Thurman (05:58) Yes. KK Anderson (05:59) And so, and I know that I need to reach out to, you know, a hundred people a week. And if I do that, then then I'm gonna be able to feed, feed that, feed that pipeline. And so, and you mentioned a new rep, and the new rep has a lot of resources behind them, like you said, through SDR and CSM and getting referrals. Tell me about how you apply this for like your your long-standing reps who aren't who maybe they know what they need to be doing, but they're not doing it. Thurman (06:25) It's exactly the same math, believe it or not. And the and the thing is the beauty of it being a new rep is that the new rep gets to start it from the beginning of their journey. For a rep that has been doing it, they might have picked up the habits of not doing the math and sitting down, not just at the beginning of a fiscal year, but all the time. Because once that becomes a consistent thing, they will never find themselves without pipeline. But we all know. We find we find reps that end up in a situation where they don't have pipeline and it's because they stopped doing the math. KK Anderson (06:57) That's right. Mark (06:58) So Thurman, you put time into the equation as well, not just the overall pipeline. So what does a seller understand differently once they see what eleven months buys them compared to ten months compared to less than that? Thurman (07:15) Yeah, so what a what a rep is gonna see is that they're gonna run out of time if they don't start today. if you Mark (07:20) Mm-hmm. Thurman (07:20) if you if you and it goes it could actually apply to anything in our lives, and that's that's really the way that I try to bring it home. Most of us have something personal that we want to try to take care of in a certain period of time, and it's it makes the conversation easier. When you can apply it back to the business perspective too. Right? So you can only get so far if you run out of time. You some at some point in time, the end of that quota year happens. And I can do, I can do nothing about it. Whether that is going to my marketing team and saying, hey, can we make a correction? Whether that is going to my CSM and saying, Hey, can you introduce me to this person today versus three months from now? Every every bit of that time makes a difference. KK Anderson (08:08) So every CRO listening right now, Thurman, I could almost guarantee it has a seller on their team who is qu probably quietly certain they are they're gonna miss their number. They're not gonna they're not gonna hit it. What are what are if you are that CRO and you have a seller in that position, like what's the first thing you're gonna do with them? The first three numbers you're gonna put in front. Thurman (08:31) Well the first the first numbers that I'm gonna put in front of them is Did you what did you do last year? Or what did you do last period? And try to get to the point of understanding how did that occur? Did that occur through volume? Did that occur through some anomaly? Because again, back to if you're if you didn't do the preparation before, you only can drive so much in a certain period of time. So do you need to go produce an anomaly? for whatever that anomaly might be in your size of business, or do you need to go after volume? and those those can be those can result in different actions. So the first thing is what is the gap? How can I actually close that gap? Can I close that gap with three or do I need 20 types of things to KK Anderson (09:15) And then you put them on some kind of a tighter accountability cadence with you? Thurman (09:19) Tighter, tighter account yes, tighter accountability with the management team, tighter accountability with marketing, KK Anderson (09:25) Mm-hmm. Thurman (09:26) to go and close that gap in a meaningful way. Everything needs to come down to the point that it's achievable. Not not something that is a pipe dream, so to speak. It needs to be written down in a way that the rep believes that their counterparts believe when I say counterparts, their teammates believe that it can be achieved. KK Anderson (09:45) Mm-hmm. Mark (09:45) All right. Well, let's, Thurman, let's take you back to your your journey from the finance seat to the revenue seat. you started your career as an auditor and an accountant, and somewhere along the way, I would imagine that somebody, CIO or someone else, tapped you on the shoulder and told you to go lead a CRM project. And I do know that you've you got into the first C. CRM project and you said you had some really big takeaways, especially from your finance perspective to begin with. What did what did you see by working with the sales team for the first time in your career? Thurman (10:25) Well, working with I realized I worked with fine, I mean with the sales team from the jump, really. so when I left Arthur Anderson and I got into my first role, I didn't think of it that way. I was still in fine finance and including the opportunity that you're alluding to, I was still squarely in finance. but I was in a cross functional type of finance role. I was to help them do their pipeline management. I was to help them do their forecasting, even revenue recognition off the deals that they booked. And so because of that, I just I developed a a different type of relationship than a lot of people developed, mainly because of the setup of that type of organization and how we were in the middle and the glue between the sales team and the rest of the organization. KK Anderson (11:12) So for years you were the right hand to a series of CEROs doing doing the work they were uncomfortable right? Going to finance, going to marketing, building the report. So what what does a revenue leader gain when they stop hand handing those conversations to somebody else? Thurman (11:30) To me, you gain respect and the ability to have conversations when in a non-threatening type of way. I think a lot of times when a CRO would go to a finance person, it becomes a you better do this, or I need you to do this, or that type of thing. And having that finance background, I could understand why finance might say no. And then I could return that back around into. why finance would say yes. And I could only do that because of that, that finance background that I had. And I because I knew what they were trying to protect the company from or what have you. Same thing from an operational perspective is when we when we would develop reports and things along those lines, I wanted to avoid people coming into a room and saying your report is wrong. Or those are not the numbers that I see. And so because I was in that again, finance operational type of lens all the time, we I want to remove those types of barriers. Here's our single source of truth. We're all going to come to the meeting and we're going to use the same report. And at first, that is extremely uncomfortable for people to do. One, because they want to speak from their report and their lens. And another is that's not gonna necessarily show me in the greatest light, right? But when once KK Anderson (12:46) Yeah. Thurman (12:47) you start to operate as a team and you pull the thread all the way through, and everybody understands, what, we have the same goal. At the end of the day, we're all trying to drive the same success. We might as well use this same report and be able to see how marketing is doing, how sales is doing, et cetera. because that's the best way for us to change them. Mark (13:06) So Thurman, what does someone trained in finance see in a pipeline that a leader who came up carrying a number just looks at differently and reads differently as well? Thurman (13:17) Yeah, so for me, and I was I was probably being able to cut through the anomalies a lot faster. being able to decipher what is real versus in bloated or inflated. We all have been there, We've seen pipelines like that. We go to new companies and we say, what is the first thing that a CR does? let me let me get out the bloated pipeline. Let me kill kill all of those deals that are never gonna happen. From a finance perspective, I can do that quicker. sometimes you might end up in situations where you don't actually have the ability to have the sales teams take it out, Meaning that you have to live with the bloated pipeline and you have to act like you don't see that is there. But now in this role, I can just say, you know what, just let's kill those deals. I always wanna just see what is the real quality pipeline that we are working so that we can be honest and truthful. And again, identify what you were alluding to earlier, what is our real gap that we are tr solving for? KK Anderson (14:13) Do you feel like your numbers and your your forecast is more accurate because of that background? Thurman (14:17) my y absolutely it is. KK Anderson (14:19) Yeah. You you should like you should do like a master class, Thurman, for Thurman (14:24) So KK Anderson (14:25) you can you can promote it to our audience and how to how to nail your forecast with a by you know, with your finance background. Thurman (14:31) It it takes a lot of uncomfortable situations though. Yeah. KK Anderson (14:36) Well, and you said in our our prep call that this is the most fun you've had in a long time in the seat that you're in now. so what is it about this seat that finally puts all of it to work at once and it's kind of the the great coming together of all of your years of experience and what you're doing in your future. Tell us tell us tell us why. Thurman (14:54) it's I think it's appreciating the blessing that I had in the way that I came up, honestly, and being able to share that through teaching. I can't decipher when I'm speaking from a finance perspective, an ops perspective, an overarching business. It's hard for me to distinguish that. And it's because of, you know, the different experiences that I was blessed to to be a part of. but my thermonisms kind of represent that, So as I started to speak about those and just Appreciate the fact that people that have worked with me for so long have heard me say these things all the time. And I live by them, whether that is directionally correct or 80-20. They all mean they're all tied together and trying to get us to focus on the right things, focus on the real pain. Let's not focus on the exceptional type stuff that actually drains our time, drains our energy. and gets in the way of us actually producing the outcome we're seeking. Mark (15:48) All right, so let's move down to the whole concept of breaking down the silos. Your stated passion is getting people to understand what sits a little to their left and a little to their right. What does that look like as a standing practice inside a revenue team, not only as a value on a wall? Thurman (16:07) So, so for me, what that looks like is someone genuinely and every person, literally, I want every person in my team at some point to do this, is to ask someone that is not in their function, what are their goals? What have they actually been asked to achieve in their function? Especially those that are to the left or right. So think about this from if you're in sales, think about marketing to your left, upstream of you. Think about that CSM that's downstream of you. So many times a sales can sell something and hand it over, and then it's painful to the life of that CSM that's inheriting it. What if that looked differently? What if you truly understood what made retaining a customer easier? And you could do something in your selling process to help that. So That's what it looks like though, just just leaning a little bit, not trying to go deep and become marketing, not trying to go deep and become the CSM, but just at being being comfortable getting closer to someone and not sitting back to back to them and not really ever asking that type of question. Another way that I like to do this is to build cadences that include everyone, as opposed to marketing having their cadence, sales having their cadence, CSMs having their cadence. Let's actually bring everybody together so that they can actually hear and see one another and ask questions that can be that every function has to address. How am I going to make sure that we optimize this? KK Anderson (17:32) So in a almost in a round table setting where you're bringing in the internal functions and you're you know, it's an internal customer motion. Thurman (17:40) Yes, that's kind of what my staff meetings look like, actually. KK Anderson (17:43) Mm-hmm. Yep. I love that. And it's so true. If we treat the cross-functional areas in our company as internal customers, and we're always wanting to, be fanatical about the customer experience, whether it's internal or external. and that's a guiding a guiding value in a North Star. I mean, that's the way to do it. and especially today with AI. Which you know, an AI workflow breaks down breaks down the silos. You can't even you can't even really think about a company in in terms of departments anymore because, what you can do with AI cross functionally is incredible with being able to to connect the different departments and connect the units. And if you don't know what the other's doing, then you're gonna have a hard time. Thurman (18:26) Yes, that's very true. I like that analogy today. I KK Anderson (18:29) Yes. Mark (18:30) All right, well Thurman, I think this is a good place for us to pause our session one. You've given people some something already that's very concrete to take back. And I I want to let it sit for a minute here before the the next step. KK Anderson (18:47) Yes. I especially enjoyed hearing the story about a seller who walked in nervous about how they were gonna hit the number and did the math and walked out energized and and let's just hope they did hit their number. you didn't tell us if they did, but I bet they did, knowing you. so what Thurman just described is also the work we do here at AGS inside the two millimeter club. And the two millimeter club is our small group. data driven coaching program for frontline sales managers where they learn to identify and coach the small shifts in seller behavior that add up to exponential movement movement and pipeline. We have four eight-week cohorts that launch monthly. And if you'd like to learn more, you can apply at get-ags.com forward slash two mm club. That's get-ags.com. Ford slash two MM Club. Now come back next week in part two. Thurman takes us takes the same math and points it straight at the customer and tells us where AI actually earns its place in a revenue team. Stay with us. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 142 – Measuring AI ROI and Turning Adoption into Business Outcomes with Denis Scott - Part 2 | 02 sept. 2026 | 00:21:31 | |
General Episode Description: In Part 2 of this conversation, Denis Scott continues the discussion by exploring what AI accountability looks like inside boardrooms, executive teams, and private equity backed organizations. He explains why leaders must move beyond tracking AI adoption and begin measuring how AI investments contribute to business performance, operational efficiency, and long term enterprise value. The conversation also examines what separates AI mature organizations from those still experimenting with adoption. Denis shares why AI fluency is becoming a competitive advantage, how organizations can build stronger measurement frameworks, and why the future belongs to companies that combine human judgment with AI driven execution. What You’ll Learn:
Key Topics:
Guest Spotlight: Denis Scott Denis Scott is the Chief Marketing Officer at Laradin, an AI execution intelligence company focused on helping organizations measure AI adoption, productivity, and business impact. Prior to Laradin, Denis held senior marketing leadership roles at OpenTable, Lyft, SurveyMonkey, Fanatics Betting and Gaming, CharterUp, and other leading technology companies, where he built data driven marketing organizations and enterprise growth strategies. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more conversations with today’s leading revenue executives, AI innovators, and GTM leaders. Subscribe wherever you get your podcasts. Mark Petruzzi (00:00) Welcome back to Selling Intelligence. I'm Mark Petruzzi. Alan Rudolph (00:03) And I'm Alan Rudolph. This is part two with Dennis Scott, CMO of Laradin. Be sure to go back and listen to part one fascinating discussion. this broad, you know, where are we today in this in this AI world? But if you want to start here, let's bring you up to speed. Dennis Scott spent over 20 years in marketing at firms like Open Table and Lyft, SurveyMonkey, Fanatics, Betting, and Gaming before becoming CMO of Charter Up. In part One, he told us what brought him into Laradin, an AI execution intelligence company built to answer the question most enterprises cannot answer today. Is the AI spend actually working? He walked us through why 72% of enterprises call AI adoption their biggest challenge. I mean, just fascinating data. And how does Laradin Scott platform reveal when companies finally see their own AI usage data. Mark Petruzzi (00:59) So in part two, we get into the boardroom where we love to be. What this means for private equity bac pr private equity backed companies staring down an exit, and what it actually looks like on the other side once an organization gets measurement done right, whether they are a private equity portfolio company, other s medium sized organizations, or even the enterprise ones. We're all stressing and being challenged by the same things. Dennis, welcome back. Denis Scott (01:28) Thank you for having me back. This is great. Yeah, I really enjoyed the conversation in the first one. Alan Rudolph (01:32) You know, Dennis, as I sit in board meetings where AI spend is being, addressed at a line item level, and sponsors are asking about measurement, about business value, and management teams are trying to defend what they did, why they did it, where where is my expense? Where's my capital allocation, etc.? What should a portfolio company CEO be able to show a board today that most simply cannot? Denis Scott (01:58) Yeah, this is exactly where our product lands often is in board conversations, right? And so we are finding that teams are leveraging our Larid and data to have those conversations. And so what they're really trying to show the board is is really the two thing, well, three things I should say. One, how has our organization adopted AI, So is it is it only engineering? Is it across functions? What what does it look like AI within within the the company? The second thing is, what does our spend look like on AI? And Alan Rudolph (02:30) Mm. Denis Scott (02:31) that number, whatever that number may be, naturally that leads to, well, I don't know, is that good or bad? Are we spending enough or are we doing too little? so then that naturally leads to, well, what are the business outcomes from that investment? And so as a marketer, I think about you ask those same questions around a marketing budget, Like, wow, this is an investment. What are we getting for that? How is it looking? Alan Rudolph (02:52) Mm. Denis Scott (02:52) How is it impacting the business? And so really leaders should be able to go into those boardrooms and have that conversation. And that's exactly why we find a lot of organizations coming to us and saying, I have this problem. I don't know how to answer these questions. Right. Alan Rudolph (03:07) Got it. Mark Petruzzi (03:07) So Dennis, with the world class companies that you have been the marketing leader of and the rooms you have been in with executive teams on board having to defend your budgets and proving impact, what's the difference between a CMO who can walk into that conversation with data and the one that who's still working off of andotes? Denis Scott (03:29) I think it's the a piece, and I'm glad you asked that, Mark. It's a piece that's really helped me define my own career. I actually learned early on that senior marketing leaders that were really successful actually are are able to speak to data and look at things like ROI and investments and budgets and forecasts. I think now marketing leaders are actually facing this new question, which everybody's facing, which is not only what is your marketing investment, but how are you leveraging AI with that? And being able to speak to those, I think is really starting to separate the the CMO world in many ways. I've always realized going into a conversation with CEOs and CFOs, The creative is great and they love to see that and that represents the brand, but they're naturally going to ask you, what are the outcomes? Right. And so I think AI is the same way for marketing leaders. What are the outcomes? What are you seeing from that? so I just think I've seen it all over LinkedIn that the the role of a CMO has changed to sort of almost like a part data analyst slash engineer in some ways, right? Alan Rudolph (04:35) awesome. So put your put yourself in the seat of a portfolio company six months before sale. What would you tell them to start measuring right now so that when AI adoption gets discussed during the due diligence process, you can drive the conversation versus, sort of s you know, the blank stare what as the questions get asked. Denis Scott (04:57) Yeah, I think the the idea here, Alan, is you want to be concrete, You want when posed that question, you want to be able to say, this is how we're using AI. This is how much it's costing us, and this is what we're using it for. And that's how this drives the business, right? And if you think about a conversation where you walk in and say, Hey, we have great AI adoption. we think the costs are this. I don't know exactly Alan Rudolph (05:20) Mm-hmm. Denis Scott (05:21) what it's doing. It's going to be tricky because as on those exits, a lot of that is the a lot of the due diligence is around the numbers, And so the more concrete you can be across all of those numbers, the more confidence you're gonna build in and be able to close that deal. I just think we we can't avoid that these questions are coming around AI for everybody, Mark Petruzzi (05:42) Yeah, and just to remind everyone that we use these examples around private equity for two reasons. One is we have a very successful private equity group that Alan leads for us at AGS. but even Alan is not a private equity own only guy. He's been in in in many publicly traded companies and other types of companies throughout his career. So Dennis, when you when you look at that, again when you're dealing with a public company, you have a very, very distinct process where everything is being analyzed of every quarter of every year. is is this a good analogy that we're doing with private equity? Because now private private equity has has built those kind of processes. They look at it very similar to what what needs to happen for a public company from a reporting perspective. Is there any Are there any differences or is it just a nice setup that just allows you to work with companies, whether they are, private equity owned or whether they are public organizations as well? Denis Scott (06:43) It's good question, Mark. I think about it in terms of of of one of the words I love to use for marketers as well is accountability. And I Alan Rudolph (06:50) Mm-hmm. Denis Scott (06:51) I think that's really the idea behind the process. every three months, when I worked in public companies and I worked in prepping for their earnings calls and even joining their earnings calls, marketing was always a big topic, And it was because, outside of salaries and if you were in a retail company leases. Marketing was one of the larger line items. So naturally analysts would push on that, right? And say, Well, how's this working? And I used to think to myself after we got off the call, okay, I've got three months until I have to be able to say something again of what we've done. Right. And it sort of it creates that sense of urgency. Like I can't go back Alan Rudolph (07:23) Right. Denis Scott (07:27) and say, Well, I didn't do anything the last three months, And I think in a world where AI is changing. not weekly. I mean, it's changing daily, if not hourly, To to wait three months feels fair because three months from now, who knows what AI is going to look like, what models are out there, how teams are using Alan Rudolph (07:44) Mm. Denis Scott (07:45) it. And so I think private equity adopting that notion of that kind of quarterly check-in and what's changing what is completely fair in a world that's moving this fast. so yeah. I liked the model that held me accountable as a CMO for sure. and so I think adopting that, I just think the complexity of it might be doing that across a whole portfolio of companies is is obviously more complex, You have to be the Mark Petruzzi (08:06) Yes. Yeah. Alan Rudolph (08:07) Yep, yep. Denis Scott (08:08) analyst for a lot of earnings calls, if you will. Mark Petruzzi (08:11) Yeah. Yeah. Alan Rudolph (08:11) Yeah. Mark Petruzzi (08:12) And the good news with private equity firms, almost all of them are managing very tightly to each quarter. So it's really no different than a public approach. Matter of fact, some of them are are really looking at every one of those numbers monthly as well to make sure they don't find themselves behind the eight ball. Okay. So the next topic, the path forward, what AI mature organizations actually look like. These are the the ones that you described that have really built up their acumen versus, a lot of companies that are still just trying to get a feel for AI. So when Alan Rudolph (08:48) Mm. Mark Petruzzi (08:49) you look across organizations already using Laradin's data well, what do AI mature ones actually do differently day to day? Not just what shows up on a dashboard. Denis Scott (09:00) Yeah, it it's interesting. I think the the even the idea that organizations are are coming to Lariden shows that they are very aware of of this AI challenge, the the ones that may not be thinking about this yet. And we have conversations with companies that are very frank and say, Hey, I haven't we haven't really even started our AI journey yet. Can you can you help us here, That that does still exist. But If you think about it, we have clients across so many different verticals, We have healthcare, Alan Rudolph (09:29) Mm-hmm. Denis Scott (09:31) tech, travel, construction, right? AI is one of the most interesting things in our lifetimes of how it's really across every industry. I mean, doctors are using like it's just so interesting, the adoption of it. And I think those that are embracing it and what we see in our data is. Some of our early customers are actually some of the most proficient, users of AI and really driving value out of it. And it in some ways it was almost like a gut check, Like I'm doing this right. and so I think those organizations that have been embracing it, open-minded to it, and also finding pockets where it could be better or I'm not using the right tool, those sort of things, those companies are actually seeing a tremendous amount of value. not only in understanding their data, but also just in knowing where they're at. And the horizontal nature of our product, there's also usually an opportunity, you'll find a function or a team where it's like, as much as w these teams are using it, this team is maybe lagging a little bit. Right. And so it also gives you a little a sense of focus. And I think that's what really separates them is that all teams are are leveraging AI across the organization to drive more of those business outcomes in their areas. Alan Rudolph (10:42) Got it. Great Dennis. so as you're talking Mark Petruzzi (10:43) Before we Alan Rudolph (10:44) about these with these different, pros customers today across all these industries, you track something called AI fluency, different than just adoption. What's the difference, Why does the leadership team need to care about fluency versus adoption? Denis Scott (10:59) So the easiest way to describe this is adoption. And I'll go back to a world that I lived in. And when we had to report to our private equity owners on on that quarterly basis, I would generally just ask my teams, are you using AI? And it was a yes, no, right. And then, Alan Rudolph (11:16) Hmm. Yep. Denis Scott (11:17) generally it was a survey, and then I would say, Is it working? And a hundred times out of a hundred, everybody would say, Yes, right, because were set, were told, hey, you gotta adopt AI, and you don't want to say, no, it's not really working for me. Right. and so adoption tends to be yes-no type question throughout teams and functions. And you you always find there are teams not adopting it, and there's reasons why, or maybe it doesn't make sense. Alan Rudolph (11:40) Mm-hmm, mm-hmm. Denis Scott (11:42) or maybe they don't even have access to tools, I mean, and so it's not necessarily a bad thing, but it's a yes-no question. Fluency for us is really How are you using these tools? Right. Are you just using the tool to do research that you could potentially do through search that, is now costing the company money that, you know, doesn't have to? Alan Rudolph (12:04) Used to be free, Denis Scott (12:05) free. That's right. Yeah. Or, the advertiser paid for it. Now it's your company's paying for it, right? And so do I need to be using AI for this? Is that the right tool? versus all the way up to like, hey, we're actually creating great code at a faster rate and we're using it for code review in this way. Like that's how we start to score what are the types of prompts, what are people doing with it, And we score those prompts and we put those those folks into categories or groups. I should say we don't do it individually, we do it at the the sort of manager level as long as the team is big enough. Alan Rudolph (12:37) And that's all driving back to business outcomes, I mean what Denis Scott (12:38) That's right. about the business. Alan Rudolph (12:40) a fascinating example of, it was free yesterday and now I go to my favorite AI tool today and it cost me money. That I mean, every CFO that's listening to that comment is is ready to pull their hair out and or call you, Dennis. I mean, one or the other, right? Denis Scott (12:54) I'm smiling because I've done, search marketing. I won't say for how long, but it's it it's over it's got a two in front of it. but I always thought about search. I kind of started early in the digital side on the SEO side and got into paid and was like, I'm then the advertiser. And so like I really want to optimize those free clicks, but then I'm paying for it. And now folks are using AI and it's like, well, now the company's incurring the cost of that search. And pe I don't think people think of it that way, It's like when should you be using search and when should you be using AI is really interesting. Alan Rudolph (13:25) He was a sure. Absolutely. Mark, bring us home. Mark Petruzzi (13:27) And ca and com yeah, and can companies wanna spend money, especially CFOs, only on what they want and they've analyzed and they've decided to spend money on. Not money that they they they don't either have to or know they're going to. So Dennis, that's very insightful the whole session, but even some of those final points there. So last question before we move on to the our lightning round. If a revenue or market marketing leader listening today wanted to go from flying blind to AI mature in the next two quarters or so, what's the recipe you'd recommend? Denis Scott (14:08) Yeah, I'm gonna shamelessly say that the Laridan data would really help you understand even your starting point where you're at. I think that's one of the hardest things. You know, if I was to say to a marketing leader, you know, how is your team using AI? And you were to say, we're, we're doing it for I don't know, image editing or that sort of thing. It's like, well, if I was to say how much does that cost? Not many people are able to answer that, And so to be a really effective marketing leader, it's like, I really want to kind of understand my cost structure, how people are using it, where there are opportunities to use it more, and are we are we seeing business outcomes? And I think the the way I think about AI is how can I use these tools to speed the process up so that I spend my human time doing these quality elements, like, reviewing the content. editing into the voice, the right voice, that that sort of thing where you're really putting that that that human stamp on what's going out to the world about your brand about your business. And so I think marketing leaders that kind of balance that AI usage with the human aspect and the quality of people on Alan Rudolph (15:13) Yeah, yeah. Denis Scott (15:14) their team is where you're going to see those. That's to me world class now. and so people probably don't know where they're at on that curve sometimes. I know as a marketing leader in prior roles, I sure didn't know exactly that equation. And now obviously I sit in a in a biased seat where I see that more. But that's really what we're seeing the best marketing leaders do. Alan Rudolph (15:35) Got it. Mark Petruzzi (15:35) Excellent. Let's move to rapid fire. So Dennis, what was the first product or service you ever sold throughout your life? Denis Scott (15:43) Yeah, when when I was fifteen years old, I walked down to the mall in San Francisco. I grew up in San Francisco by my house called Stonestown. I walked into a Nordstrom's and I applied for a job and they asked me if I could start that day. And I was I was stocking shoes in the back for the half yearly sale. And then Alan Rudolph (16:02) Mm. Denis Scott (16:03) the sale started on my day three, and our two salespeople were late and didn't show for the sale to start. So my My manager asked if I wanted to be a shoe salesperson, and I said yes. and I sold shoes on and off at Nordstrom's for six years. Alan Rudolph (16:19) We're not gonna go down Mark Petruzzi (16:19) Very cool. Alan Rudolph (16:20) that path, but we could ask you a lot of discussions there. So we'll Denis Scott (16:22) Okay. Alan Rudolph (16:23) leave we'll leave that one lying. Who is your favorite CMO or marketing leader that you follow? One name. Denis Scott (16:30) One name. I would go with Veneet at Chime. I love following what he says. I love what that team has done. I think they push AI in really interesting ways. yeah, I Alan Rudolph (16:39) Awesome. Denis Scott (16:39) great follow on on on LinkedIn. Mark Petruzzi (16:42) Great. So what is a leadership or go to market practice you think every sales and marketing leader should adopt? Denis Scott (16:48) I think it's really trying to understand the solutions for your customers, right? Whether that's a B2C product or a B2B product, the the the human element of why do they need my product is really Alan Rudolph (17:01) Mm. Denis Scott (17:01) powerful. Or what does my product do that makes them more successful and where they're at, Or more confident in who they are. so I think Alan Rudolph (17:08) Yep, yeah. Denis Scott (17:10) that notion of not marketing to people, but really trying to understand the solution you're providing, right? is really powerful for both sales and marketing to be aligned against and do that in your go to market motion together. Alan Rudolph (17:22) Yeah. Great Dennis. Okay, here's here's a little teaser. You're now twenty one years old, or you were twenty-one years old at what point? What advice today would you give that twenty-one year old self? Denis Scott (17:34) So it's a really interesting one. I think the data piece I feel confident that I kind of embraced early on. The Alan Rudolph (17:40) Yeah. Denis Scott (17:41) piece I think I'd advise myself and I tell this to all marketers is really being adaptable, The business is always gonna change, the tools are gonna change, everything's gonna change. I know we talked about every three months reporting to the board. Well, That's because everything changed in those three months. Right. I mean, we used to joke in tech that six months was a long time. Now three months in AI feels like a really long time. right. And so just being adaptable. And I think my my 21 year old self would have walked in and said, I know how this works. I'm going to do it this way. Right. And it's like, no, just know it's going to change. Mark Petruzzi (18:15) Amazing stuff. great. Well, Dennis, th thanks for bringing real data to a topic that is mostly running on very qualitative processes right now, not quantitative ones. Where should people go to find your work and Laradin's? and also I'll I'll put it out there, anyone, of course, going directly to Laradin, great. But anyone who wants to reach out to me, Alan or KK, please do that as well because we have we have really grown very fond of the product and the product set and can help you figure out the way to really turn it on as well. Denis Scott (18:52) Yeah, that's great. I mean, I'm thank you all. This is this has been fun and it's it's really exciting topics and work that's going on. happy for anybody to to visit us at Laridan, visit our website. I think our leadership team are are some really interesting follows on LinkedIn as well. we are sitting on data that that in many ways nobody is sitting on, and so We're doing research and we're sharing that as well. We're producing white papers. so there's a lot more coming that I think is gonna be really helpful for people to read and kind of understand on a lot of these trends and what we're seeing, even there's a new model out every day. Well, we're testing it and using them all. so yeah, that's great. Alan Rudolph (19:32) Great. Thanks, Dennis. We'll make sure all that data's in the show notes. And if what Dennis said about measuring the AI impact sits with you, that's exactly the conversation we're having inside our PE advisory practice. Tying AI adoption directly to an EBITDA multiple at exit. Learn what it learn more about this. Come visit us at getags.com and learn about the PE advisory practice. Mark Petruzzi (20:00) And if this conversation conversation was useful for you, send it to your leader or another member of your network who you think may need it most. I'm Mark Petruzzi. Alan Rudolph (20:11) And I'm Alan Rudolph and this is Selling Intelligence. We'll see you next time. Thank you. Mark Petruzzi (20:16) All the best. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 141 – Measuring AI ROI and Turning Adoption into Business Outcomes with Denis Scott - Part 1 | 26 août 2026 | 00:27:20 | |
General Episode Description: In this episode of Selling Intelligence, Denis Scott, Chief Marketing Officer at Laradin, joins Mark Petruzzi and Alan Rudolph to explore one of the biggest questions facing business leaders today: how do you measure whether AI is actually delivering business value? Drawing from his experience leading marketing at companies like OpenTable, Lyft, SurveyMonkey, and Fanatics, Denis explains why AI adoption is no longer enough. Organizations now need visibility into how AI is being used, where it creates measurable outcomes, and where it introduces unnecessary complexity. The conversation explores the challenges of measuring AI investments, hidden AI costs across organizations, and how executives can connect AI usage directly to business performance. What You’ll Learn:
Key Topics:
Guest Spotlight: Denis Scott Denis Scott is the Chief Marketing Officer at Laradin, an AI execution intelligence company focused on helping organizations measure AI adoption, productivity, and business impact. Prior to Laradin, Denis held senior marketing leadership roles at OpenTable, Lyft, SurveyMonkey, Fanatics Betting and Gaming, CharterUp, and other leading technology companies, where he built data driven marketing organizations and enterprise growth strategies. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more conversations with today’s leading revenue executives, AI innovators, and GTM leaders. Subscribe wherever you get your podcasts. Mark Petruzzi (00:00) Welcome to Selling Intelligence. I'm Mark Petruzzi. Alan Rudolph (00:03) And I'm Alan Rudolph. Mark Petruzzi (00:04) Every company we work with has the same exact story right now. Budget is improved, tools rolled out, adoptions declared a win in some sort of a board deck, and almost nobody can tell you with real data whether any of it has moved the business at all. Alan Rudolph (00:22) Our guest built his career on the marketing side of some of the biggest consumer brands in tech, and now he's on the other side of that exact problem. Dennis Scott spent over 20 years leading marketing at Open Table, Lyft, SurveyMonkey, and Fanatics Betting and Gaming, and most recently served as CMO of Charter Up. He's now CMO of Laradin, an AI execution intelligence company built by the team that created the original. Digital Measurement Infrastructure at ComScore. Dennis, welcome to Selling Intelligence. Denis Scott (00:56) Hi everybody and Alan and Mark, thank you so much for having me. Excited to be here. Mark Petruzzi (01:00) Excellent. So we'll jump right into topic one. it and it's entitled From Consumer Marketplaces to AI Measurement, Dennis's Plant Path to Laradin. So, Dennis, you spent your career building brands people trust. they trust the the those companies with their money and their time. Companies like Open Table, Lyft, SurveyMonkey. What did you see that pulled you towards an enterprise AI measurement company at this point in your career? Denis Scott (01:27) Yeah, I think I've had the fortune of working for some great brands throughout my career, which has been an incredible experience. But one of the things that, as a marketing leader, you're always accountable for is really the the measurement, given that you're you're usually one of the largest line items on a PL. And as we all know, this AI explosion three years ago, none of us were really living in this world. And now It's sort of the topic of the day every day, every and so as a marketing leader, one of the problems I saw was this is really hard to quantify and understand. And how do we how do we figure this out? And so when I learned and heard about Laridan and the team that was running it, I almost ran to it living here in the Bay Area, being surrounded by this AI challenge and opportunity. To know that somebody is actually solving how do I think about this? How do I understand this? And how do I communicate this to leadership, to boards, to investors? Alan Rudolph (02:26) Awesome. great intro, Dennis. So Laridan's entire pitch is built on radical honesty. Love that comment about what's Denis Scott (02:34) Right. Alan Rudolph (02:35) actually happening within a company, within a company from an AI spend standpoint. And that's not always flattering, as we know in today's marketplace. So, how is marketing that kind of product different from marketing some of the journeys that you've been on more of a consumer brand? Denis Scott (02:52) Yeah, I steal from that old adage in marketing, half of my marketing is working, I just don't know which half. And so I think we should we should always be open to the idea that not everything is working. And you know, as a measurement platform and identifying opportunities for organizations through workflows, and we can get in deeper into that, I think it's actually important to share the good and the bad. Right, or I would say the good and the opportunity, right? And it is different than marketing a consumer brand because often a consumer brand, there's this this almost one-to-one relationship. Whereas in an enterprise type motion, you're you're solving across these large organizations, right? And those those opportunities that you're identifying. we are a very horizontal product working across all functions. You may not even know where those opportunities lie or where things are are going really well. And so I think you just are are talking about a one-to-many relationship and how we can help solve a f a, sort of organizational wide opportunity slash challenge, and so I think that's where. In a consumer brand, you could be talking to to people that fit your constituents, right? whatever it is. Alan Rudolph (04:05) Mm-hmm. Denis Scott (04:05) when I worked at Clorox, I worked on STP. It's like our our our target set was 18 to 34 year old males, And so Mark Petruzzi (04:11) Mm-hmm. Denis Scott (04:12) that was that one-to-one relationship. Whereas now it's like, hey, you're talking to senior executives about, yeah, how do we understand this AI investment and what are the business outcomes we're seeing from it? So it's there's still a personal element to it, but it's a much larger solved in some ways. Alan Rudolph (04:28) Got it. Mark Petruzzi (04:28) Yeah, and Dennis, what's interesting is when w as I've learned about Laradin over the last couple months, it strikes me as a company that is building that kind of consumer relationship just with executives rather than all consumers. So, and the way I look at it, especially having the the fact that I'm on two boards, any board director should be building their relationship with with Laradin because in that standpoint, these are all the things that at the board level and the senior executive level, these this is all the data you need to know, especially about something AI. And by the way, I think I'd like to take that quote you just made about marketing and make it about AI. because same thing, I know my Denis Scott (05:14) Right. Same thing. Mark Petruzzi (05:16) AI is working. I just, I just don't know which half. So and and every company, every single company, big and small, is going through that same challenge right now. Denis Scott (05:26) it's interesting, Mark. You sit in the right spot here for who our our target audience is, which is boards are asking these questions, investors are asking these questions. if you look at earnings calls a year ago, tokens didn't come up that often. Now that's skyrocketed as far as questions go, Alan Rudolph (05:43) Right. Denis Scott (05:44) But if you think about it, right, th I'm gonna make a silly statement, but if I used to say, hey, on an earnings call and I was fortunate enough to prep a lot of these and work side by side and be on these calls because marketing was such a large investment, right? So let's say marketing you're spending fifty million dollars, naturally they would say, Hey, what are you getting for that investment? How is that working? Right. Those are the right questions to ask. We often now find that in AI, it's like, hey, you're spending $50 million, what are you getting for that? And it's very hard to answer. I don't blame people. This is what we're solving, but but boards are asking those questions, investors are asking those questions, CFOs are asking those questions, And that's really what we're building and where our customers see the value is, shoot, I'm getting that question from my board and I don't know how to answer it. Right now I'm using surveys and asking people, and I think I know what people are using, and it's really kind of it's very, very challenging, to answer that. Mark Petruzzi (06:39) Yeah. And it has to Alan Rudolph (06:39) Yeah. Mark Petruzzi (06:40) be and it has to be so much more precise than that for it to really work. Meaning the the surveys, the feeling the feelings, the a lot of companies, even some big ones that I work with, are looking at wow, they just wanna get AI in the hands of their their employee base. It's not about that. It's it's it takes a lot more precision. So Dennis, you're a CMO of a company who you measure marketing and really every other function from an AI productivity standpoint. Does that change how you think about proving your own team's impact internally? Denis Scott (07:16) Yeah, it's a really interesting question. I mean, you kind of it's one of those the expression like you should be drinking your own water, your own champagne, whatever expression you want to use. So, we are an AI first company and we it's AI native built. really AI adoption across our company is a hundred percent, but we all use it. It's how you use it and how proficient you are. And that's part of what we get into at. Alan Rudolph (07:40) Okay. Denis Scott (07:41) can we help you understand how people are using AI, not just are they adopting it? Right. And so at a company where I'm at, I myself even as a CMO, I'm very hands-on in AI, I'm able to do a lot without having to ask other teams or other people. And I think that's how we approach a lot of what we do. Now it doesn't It doesn't replace the human element of measuring quality or understanding is that as a marketer on brand or not on brand and how do we word this? I kind of have a general rule of thumb. If it's under 500 words, write it myself. just because I want to get that voice and tone right. Sure, I use AI sometimes on longer pieces to to help get me started. And then I always go in with that human touch. But yeah, I think in in the type of company we work in, which I think Is honestly how a lot of companies are going to operate and look Alan Rudolph (08:32) Hmm. Denis Scott (08:32) as they progress. Maybe we're a little bit ahead because we live and breathe this every day. but I think that's how companies will operate. And I actually think it's pretty exciting because what people end up doing is I spend my time doing the things I want to do rather than some of the things that used Alan Rudolph (08:47) The same. Denis Scott (08:48) to be the the pain to try to get to. Right. Alan Rudolph (08:51) Right. Denis Scott (08:52) so you're actually taking humans and you're saying, You're doing the most important task in spending your time there rather than some of these other tasks that AI can just speed up and help you with. Alan Rudolph (09:01) Yeah. Great great feedback, Dennis. So let let's move on to a another topic, so relevant today, which is again, where where does Larin play? How do we measure? What kind of data is available to us? It's a fascinating statistic in terms of AI spend last year, six hundred plus billion dollars, Just a phenomenal number. and again, it all comes back to, when I think about how do we drive business value. Right. How do how does how do our customers, how do our clients, whether it's AGS, Larada, et cetera, how do they drive business value? So Larada's own research in terms of the research I've been doing found that 72% of enterprises say AI adoption has become their biggest challenge, Every C level executive, They want to do AI. How do I measure it? And obviously, 600 plus billion, if I'm not getting value, then it's ultimately hurting the bottom line. So walk us through what it actually looks like inside a company. What are leaders getting wrong? Denis Scott (09:57) Yeah, great question, Alan. I think what's really interesting is if we rolled back the clocks to a year ago, AI adoption was the topic of the day. And it was almost the sort of this binary question, yes or no? Are you using it? Are you adopting it? Yes. Okay, well, Alan Rudolph (10:11) Right, right. Denis Scott (10:11) great. That that adds to the value of your organization, Or no, it's like, you guys better learn how to do this, right? And so I think there was this almost mad rush to tell. as a leader, to tell your teams or to tell your organization we have to adopt AI, we have to do it. And I even lived in that world where it was was a mandate. Everybody has to be using AI, But that that tells you how at that time sort of almost uneducated were in what you could actually do with that kind of notion of like you have to use Alan Rudolph (10:39) Hmm. Yep. Denis Scott (10:40) it because there's a cost behind it, right? And that's exactly what you're speaking to with that investment. And In anything you do in business, when you have a large number like that, naturally the question is going to follow. And this is why Laridin exists. I mean, and Jim and Russ have really built their career around this. When you're throwing a lot of money at things, it doesn't mean it's right or wrong, but you're going to have to measure it and tell that story and understand it. And that's really what we've built. And so I think the challenge for leaders was we rush so fast to say, our team's using it yes or no. Alan Rudolph (11:14) Mm-hmm. Denis Scott (11:14) And now that we're a bit more sophisticated and understand these tools and quite honestly have seen examples, particularly this May, where companies had spent their whole budget by April that we all know, and or somebody was spending five million dollars a day because they were gamifying, AI adoption and token spend. Well, all of a sudden it hit us of like, well, what what is the value? What is the business outcome? And I think That's the number one question now, which is is a great question and probably the most Mark Petruzzi (11:37) Yeah. Denis Scott (11:41) important question that we get from organizations and senior execs and quite honestly boards as well is not only what is my spend and how do I make sure I'm getting that Because that is actually pretty complex to even get to that number, Alan Rudolph (11:53) Mm. Denis Scott (11:54) but then what are the business outcomes I'm seeing from that spend? Right. And that's the piece I think. we kind of hear those questions in that order, like, I don't really fully understand this. And then, but by the way, what am I getting for that? And so that's where w Laridan is really built to connect those dots. But that question didn't exist a year ago, We almost we almost bought ourselves a year by checking the box. Yes, we're using AI, right? And now the question naturally has come is like, okay, but what are you getting for that? Right. And I think budget Alan Rudolph (12:21) Yeah. Yeah. Yeah. Denis Scott (12:22) season is probably a very interesting time to be having this conversation because Mark Petruzzi (12:27) Okay. Denis Scott (12:27) When you go in to the board and say, I need thirty percent more token usage next year, every board member is gonna say why? And if you can't answer that, that's gonna be a tricky conversation to have, So Alan Rudolph (12:38) Hmm. Got Mark Petruzzi (12:39) Yeah, Alan Rudolph (12:40) it. Mark Petruzzi (12:40) you know. And that's one of the reasons why at AGS we have built set of offerings that really is built around AI to ROI. we use that term and I'll give a little credit to a close friend of mine for for naming his podcast after that. you know, and I should be clear, he he he came up with the podcast first, so I guess I've we've run with it from there. His name is Ray Reich. He has been an incredible CEO and leader in the benchmarking space, starting more on the finance side, more on the like private equity metrics that private equity firms are looking at before they acquire a company. and he's now moved moved very deeply into the AI space as well. So at the end of the day, what we say at AGS is AGS amplifies like I'm sorry, AI amplifies whatever motion, whatever process you have, whether it's in go to market or other functional teams, whatever you've built already, it's going to amplify it. And that's going to give you either a good or bad, meaning these there's lots of poor processes out there that are being amplified amplified every single day. So how does that match the pattern that you're seeing in Laridan's data? is AI adoption exposing execution problems that were already there? And is that happen often? not as often. What are you seeing out there? Denis Scott (14:07) Yeah, we measure millions of of kind of moments, when you think about our customer base, we have tens of thousands of of users on our platform, And so the Alan Rudolph (14:17) Mm-hmm. Denis Scott (14:18) when you think about workflows and how AI is being used, and think about your own personal experience, how often you're you're touching an AI tool, it's it's for a lot of people, it's almost daily. but really there's some interesting patterns that we see. One is this is one of the things we like to measure is again, not just adoption, but proficiency. And it's it's proprietary how we've done that and scored that, but essentially it's looking at the types of things you're using AI for, So what are the prompts? And one of the the challenges we see is folks you are using AI, but they're using it in a way that isn't necessarily, more productive. So I'll give you an example. We have seen where, back in the day you used to write an email and maybe you would reread it before you send it and you make a few edits and you would send it. Now we see at times people are taking every email they're writing, dropping it into AI. It's not getting the voice right, it's not getting the the tone right, it's adding dashes, it's doing things you don't want. And that email now has has gone into this AI world where maybe there's 15 takes, 20 takes to get this email right. Whereas like Alan Rudolph (15:23) Holy cow. Denis Scott (15:24) You didn't need AI in that instance, You just kind of added a bottleneck to the process, whereas there are other things where I think about a go to market motion with an enterprise sales team. It's like the ability to take something like a gong call, digest that, move that into a sales force. Like now what teams are doing is actually preparing better for the next call because AI is doing some of that, call it task. type work and moving data around and summarizing, and there are even AI tools where it's like, okay, now I'm gonna, I'm gonna mirror the client and you can have a practice run. Right. So in that sense, it's actually amplifying it because it's back to what were talking about. It's like actually the salespeople are spending their time doing the most important task, which is prepping for this call and understanding their customer and what the needs of that customer are. Right. So There's positives and negatives, especially in a Alan Rudolph (16:15) Yeah. Denis Scott (16:16) go-to-market motion, that we see. What our tool actually does that's interesting as well is we will identify within your workflows, one of the most interesting is when AI is there and when AI is not within the exact same workflow. And often what you see is AI is is a helpful tool or you're able to do more complex things. It doesn't always mean it's faster, but but the outcomes are better. but there's also opportunities where we identify. You've added AI into this workflow and it's really not helping. It's causing a lot more friction. and so Alan Rudolph (16:45) Mm-hmm. Right. Right. Denis Scott (16:47) that's the honesty element of our our platform and tool and the feedback we want to give to customers. We tried to make everything look great. you we're not being honest with customers, And so that's really an interesting thing about AI: is where is it, where is it really having an impact for the positive and where is it actually creating? More friction or being a bottleneck and not actually producing great value. Alan Rudolph (17:07) Right. I love that comment, Dennis, about the dashes in an email. Like we've all been there, right? No way. Did who Denis Scott (17:12) Reha. Alan Rudolph (17:14) who wrote this email and why are those dashes there? So anyway Exactly. Denis Scott (17:17) Exactly. Who am I talking to? Alan Rudolph (17:20) Is it is it Claude ChatGBT or is it actually the person I want to talk to? So every CFO I've worked with inside a portfolio company good news, they can tell you exactly how much money they've spent on AI tools by month, by quarter, by year, whatever time period they want to look at. But we're not there yet in terms of the return, Coming back to that comment about the business outcome. Why is that gap so much wider for AI than other technology investments, whether it was ERP, CRM, marketing automation, though those initiatives all had very well defined Charters, project plan, scope, and ROI. AI AI we're struggling with. And so why is that data succinctly? Denis Scott (18:00) I think there's two factors. One is the speed of which we all adopted AI, So got ahead of ourselves and we all started using it. And then the CFO would get a bill, And go, wow. Okay. Alan Rudolph (18:07) Yep. sh darn. Denis Scott (18:12) there are also, I will just say there are some hidden costs to AI that they're we find this almost every time with customers. We have had customers where, they say, Hey, we're using these tools and it's kind of in the tens to twenties, right? Alan Rudolph (18:25) Only. Denis Scott (18:25) And then we actually implement our solution and we can see all the tools being used and it's often in the hundreds, And part of that that is happening is is naturally, if I'm on a marketing team and I decide to use a product, let's say like Canva, and I Alan Rudolph (18:39) Mm-hmm. Denis Scott (18:40) just grab a license for myself so I can edit some photography or videos, I may just swipe my credit card and expense it like a travel expense, like a meal, And so that's really hard for a CFO to completely understand what are all the tools and where is all my hidden cost on AI that I don't even technically get a bill for. It looks like 20 bucks and marketing has somebody doing this, So that that that's part of the complexity of it. But this the second thing is exactly what you were saying, Alan, which is well, what are these teams doing and did that What were those outcomes? And that's why we built our workflows product connected to that token usage, right? Which is What did the team use it for? Where was AI within this workflow? And we can see within those workflows, going back to our example of a sales team, you can watch that process of prepping for a call. It's like, where was was a tool introduced? And then, was that call effective, successful? Right. That's where it starts Alan Rudolph (19:33) Mm-hmm. Denis Scott (19:34) to come into, I'm starting to really understand the outputs of how how teams are doing this. Right. And I'll give you an example from from the marketing side of things, a kind of hidden cost in marketing. And we've we've had a couple of customers come to us and say, I can't fully understand why my marketing team is spending so much in in token usage. Well, one of the heaviest things you can do in token usage is video creation and editing. Why? Because it's so heavy on the data side of things. And you know, you used to outsource this sometimes to to third party companies that would do a lot of the editing for you. And now Some of the teams are trying to do it in-house, themselves. But what they don't realize is is that AI cost of what they're doing. Now, you could argue the business outcome is good because I didn't have to outsource it, or geez, this token. And that's kind of the decision making process we're hearing a lot of organizations make on these different workflows and what teams are using what AI and even what version they're using, That that really plays into it. I mean, the That is where the complexity starts to add up, Which is, well, what version of Claude are they using when they did that? Alan Rudolph (20:37) Right. Denis Scott (20:38) most CFOs don't have all of that data because it changes Alan Rudolph (20:41) Granular. Denis Scott (20:41) all the time. I mean, these models change honestly every week. And, if you were to go across Claude versus OpenAI versus Gemini versus codex, that they're all kind of priced differently and it evolves, right? And Alan Rudolph (20:53) Mm. Yeah. Denis Scott (20:54) There's discounts, there's not dis it's really hard. and so that's why we we create that view for customers to really understand that. Alan Rudolph (21:00) Thank you, Mark. Mark Petruzzi (21:01) Good good stuff. yeah, let's finish up episode one here with topic three. and that is Inside Scout, what enterprise AI usage data actually reveals. So when a leadership team sees the organizational AI usage data for the first time, what's the thing that surprises them most, other than they have token spend? That always surprises them, and that's Denis Scott (21:26) Right. Mark Petruzzi (21:27) usually not good news. And then really what are the gems that they're finding in in the the having that data for the first time as well? Denis Scott (21:34) Yeah, I think there's two things that really jump out at me. One is, and again, this speaks to the horizontal nature of what we've built, is I think a lot of leadership teams think about AI and often naturally think about engineers and developers, And they're the ones using AI, coding has changed. and that is a very true story. And those teams are often your heavy users. But when you look horizontally across teams, it's people teams, it's marketing teams, it's finance teams, and then Alan Rudolph (22:01) Mm-hmm. Denis Scott (22:03) starting to to really understand, geez, AI is really being used across my organizations, And so I think that's one of the eye-openers is is really what their true adoption is. The second thing that we often see with the adoption piece is we score that proficiency. And we do that based on how it's being used and also within. within these workflows, how that how effective it is. And you will actually find there are teams that you didn't think about outside of engineering that are are quite advanced at times. And then you'll have the opposite, which is is more the challenge is like, geez, that team really doesn't know how to use this tool, which is is fair quite honestly. They they've never really been enabled or learned or how do I do this? And they're using it because they were told they had to, right. And so That often becomes some of our first conversations. And then the second piece that really jumps out as well is just and we spoke to this a little bit earlier of like I had no idea this many tools were being used. And that's probably the eye-opener. I think most organizations and most customers we talk to think they have a, and they do have a relatively good grasp of the heavy usage tools. It's the kind of long tail, like if you think about search queries back in the day. It's like, yeah, I understand really kind of those big terms, but it's like all these other long tail terms that are ending up driving things to my site. We see that with AI. What is what is the long tail of AI tools across your business? and often those are unauthorized and that that's okay. Like we're not saying that's a good or bad thing. We just want to identify it. And those might be some of your most Proficient users are the ones actually adding tools because they're keeping up with the the newest platforms or or what they could be doing differently in their roles. And so we don't want to discourage that. We just want to identify it because organizations don't see that. Alan Rudolph (23:51) Got it. So as we talk about the gap between the teams that are super AI efficient, And fluent in terms of how to which tools to pick, how to use tools, et cetera, versus the teams that, they log in because they check a box, they need to say they're AI efficient. How big is that gap in practice? What separates the two? Like can can the tool actually, help us digest and sort of that A where are we in that trend line in terms of AI fluency? Denis Scott (24:21) Yeah, we just actually, it's a great question, Alan. We just actually were looking at data around engineering, because we've had engineers on our platform the longest. So that's kind of the longest Alan Rudolph (24:31) Mm-hmm. Denis Scott (24:32) we can look at. And overall we've seen engineering output basically increase one and a half times over what it used to be, right? And Alan Rudolph (24:39) Okay. Denis Scott (24:40) this is this is based around adopted good code. And what we see is kind of our P90 users, who we score as the highest, most proficient users, are actually driving that. We've seen them actually get more effective and efficient at a two and a half times clip, And so what happens with that is well, if you're doing that math, actually our lowest quartile, the folks that are are sort of the least proficient in in how we score it, actually haven't moved at all. Now you would have thought the whole curve moved up. But it we've kind of talked about. I don't know if it's the right phrase, but the idea is like the rich are getting richer, like the top Mark Petruzzi (25:14) So Denis Scott (25:15) P90 group is actually getting more and more effective and really understanding these tools. And, as the new models come out, they're knowing when to use it, when not, All of those aspects. Whereas that sort of bottom quartile hasn't moved at all over time. And so Alan Rudolph (25:30) Yeah. Got it. Denis Scott (25:31) that That gets back to this kind of enablement idea, Like how are we training teams and how do we take our best, most effective AI champions and have them sort of train and teach the others in the org? Alan Rudolph (25:42) Got it. Mark Petruzzi (25:42) what Dennis just described about measuring AI impact is exactly the conversation we're having inside our P advisory practice every day and our our AI to ROI group as well. So and that's tying AI adoption directly to EBITDA multiple. Multiples at exit. This allows companies to take in board ready results. There's no long-term commitment required to start from an AGS perspective. And learn more at get-ags.com slash P advisory. And look for us next week for part two with Dennis. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 140 - How Great CROs Build Revenue Engines That Actually Scale with Lance Haffner - Part 2 | 19 août 2026 | 00:23:54 | |
General Episode Description: In this episode of Selling Intelligence, Lance Haffner, Chief Revenue Officer at Papaya Global, returns to discuss one of the biggest challenges facing modern revenue leaders: creating demand for problems buyers do not yet recognize. He shares practical strategies for validating market fit, identifying the right buyer personas, building effective sales processes, and knowing when it’s time to pivot. The conversation also explores the growing trust deficit created by AI in sales. Lance explains why AI should enhance, not replace, human interactions, how revenue teams can use AI to improve forecasting and sales execution, and why speed, simplicity, and transparency are becoming essential competitive advantages. Finally, he shares leadership lessons from building a CRO organization from the ground up and the timeless sales disciplines every revenue leader should never overlook. What You’ll Learn:
Key Topics:
Guest Spotlight: Lance Haffner Lance Haffner is the Chief Revenue Officer at Papaya Global, where he leads the company’s global revenue organization through its next phase of growth. With leadership experience spanning staffing, HR technology, and enterprise SaaS, Lance is known for building scalable revenue functions, applying data driven decision making, and combining AI with disciplined sales execution to accelerate growth. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more conversations with today’s leading revenue executives, sales innovators, and GTM operators. Subscribe wherever you get your podcasts. Mark Petruzzi (00:36) Welcome back to Selling Intelligence. I'm Mark Petruzzi. KK Anderson (00:40) And I'm KK Anderson. This is part two with Lance Hafner, Chief Revenue Officer at Papaya Global. Be sure to go back and listen to part But if you want to start here, let us bring you quickly up to speed. Lance told us how he has moved from staffing sales into HR and then into revenue leadership by applying a business enablement mindset where he wherever he sat and what it's taken to build papaya's first ever CRO function. While the company shifts from years of product investment into a scale up phase. Mark Petruzzi (01:12) In part two, we get into how Lance is building demand for a problem most buyers don't know they have yet, the trust deficit. Lance is watching this show up directly into his AI enabled sales motion. And we'll go into and we'll analyze how he uses AI day in and day out to diagnose what's actually happening inside his sales team. Lance, welcome back. Lance Haffner (01:36) Thanks, Laura. Thanks, KK. Happy to be here again. Mark Petruzzi (01:39) Great. So yeah, let's jump into creating demand for a problem buyers do not know they have. you've compared the awareness problem you're facing to introducing a genuinely new category. How do you build go-to-market motion around the pain point most buyers don't even know they have yet? Lance Haffner (01:56) This is such a great question. And and it's it's it's been salient a few times in my my career. if you look back over the years and you look back at the new we as consumers, things that have been launched in the consumer market. I remember this this thing in in two thousand and six, seven, Apple releases the iPhone and we didn't even know we needed a handheld computer device that didn't have keys. In fact, it was absurd to think about it. I was a Blackberry fan to be honest, and I wanted my keys and I resisted for two years. Mark Petruzzi (02:26) Ha ha KK Anderson (02:28) Was it clipped on your belt, Lance? Did you have it clipped on your belt? Lance Haffner (02:32) I look, I may have had a clip. Yes, I may have had a clip. yeah. I mean look, we can go Mark Petruzzi (02:36) I'm not gonna admit to that, Lance. KK Anderson (02:38) yes you are. Lance Haffner (02:39) back to you, we can go back to the days you had the pager clipped, right? Not less, yeah, or Mark Petruzzi (02:42) Yeah, yeah. Lance Haffner (02:43) the mo onto KK Anderson (02:43) Yeah. Lance Haffner (02:44) the Motorola Razor, onto the Blackberry telephone. But I know it's a consumer, that's really a consumer application review, but this the Point still stands. We didn't know that we needed that. It's like we actually, in fact, some people took the antithesis side, the antithetical side of I hate keys, I don't want them. Not only do I not need it, is it not a pain? I don't want it. And so I think lots of CROs and businesses deal with this. You're it you're entering market with a new product. I want to be clear, sometimes it's not a new product. I, you know, in a prior job, it wasn't a new product, but it was a new application of that solution in market. but it's the same. Right? Whether it's new or not, it's the same. you're dealing with with the problem of of market awareness and creating that demand. So first and foremost, I think coming back up to my, in our prior conversation, when I talked about moving from moving into scale, make sure market fit exists. Even if people aren't aware they have pain, make sure you got a market fit fit. You're dealing with the insights KK Anderson (03:40) Right. Lance Haffner (03:40) RevOps leader's creating, your Markovs leader who should who's likely. According to RevOps, the insights your product team has, particularly your product marketing team who's done the research, competitive analysis. They're reading, the analysts and seeing what the analysts are saying about you in market, about other solutions. Do you got the market fit? Let's agree that you do. You've done the analysis. There's not just a TAM, but ultimately you have some serviceable, addressable market that you can actually sell that product into. All right. That's point number one. Don't go off the gut thesis. I try to do it all the time. I gotta be honest. I'm preaching to myself here. We we get a thesis, we have bias on that thesis, and then we go look for everything to confirm the bias. No. Go look at the data and confirm that you actually have market fit and you actually have a market that you can sell, that you can service, and that you can obtain, and you can be successful successful. Number one. Number two, I you know. If anyone can figure out how to make it really successful, a product or a pain that people don't know they need or have a pain they don't know they have, they're gonna be wealthy. by the way, people have done that. And they are, they were very wealthy. So but I don't think KK Anderson (04:42) Ha ha ha. Lance Haffner (04:44) it's it's not easy. we one of my leaders, another colleague, I have the fish, the fish can't climb the tree colleague who's who's brilliant sells mine. And another one says, Lance, I call this normalized power. Having a conversation with the buyer, I'm going through my methodology process, I'm listening for the signals, and they just don't know they have pain. and I go back to the Apple versus BlackBerry method. None of us knew we had pain. In fact, it we had maybe an antithetical view of it. Not only do I not have pain, it sounds painful to go to a screen without prescribed buttons that are, can be precise. So so there's there's this normalized pain that exists. I think the key to getting through that is two things. One, you've got the right buyer persona. sometimes go back to my example of where you have a product and market. It's not a new product and market, but maybe it's a new application, new go-to-market motion. We're thinking of it differently and how the buyer can apply that. who is the buyer though? Because the buyer might have shifted. Formerly, you might have been working with the HR department. Now you're in finance and you're particularly a layer down in KK Anderson (05:45) Right. Lance Haffner (05:45) finance, maybe with treasury. Do you have the right buyer persona? Because if you don't, you have zero chance of helping them see the pain that they're that they they have. Okay, number one. So be dogged about landing on the right buyer persona and let that feedback loop happen. Listen to the sales calls, receive the sales feedback. Why am I not converting? Why am I disqualifying? Listen, watch, and be hyper quick. On pivoting. Go back to the bow tie we talked about, right? You're all on top of funnel here going through your sales stages. Your RevOps leader is acutely watching this and giving you real-time feedback and you're shifting. Could be your campaign in market right now and the pitch in the campaign. Could be a lot of things, right? But you're watching. And then lastly, I would say the process itself, and I already mentioned it, but the sales process you're going through has to be spot on because the process is there to help them identify the pain. Now, for 80 foot percent of what we sell, they know the pain. So it's easy. We know the pain before we go in generally, but we get that out of them through our sales process, whatever methodology you're using. I've used Spice by Winnie our friends at Winnie My Design, so roll out that in my last KK Anderson (06:50) Mm-hmm. Lance Haffner (06:51) job, but but Matic Challenger, whatever you're using, right? Go through that pain process, and there, right, right, is in my opinion, kind of the inflection point of them understanding that they actually do have the pain. And and that's the hardest piece to get through. So let me let me headline that just quickly because I said a lot of words. Do you have right market fit? Using the insights from your analysis through RevOps, marketing ops, through product marketing. don't have bias confirmation. Many of us want to believe, this is great. Let's go sell this. Let's apply this this way. Prove that out. Don't have bias confirmation. Come down here, think about your sales process. think through buyer persona. Are you are you now with the right buyer within the organization? And do you have the right pitch through pain or through your methodology? Excuse me, are you getting them through the pain process and helping them identify? And you and you have feedback loops that are telling you very quickly, real time, is it working or is it not? And you're pivoting. And by the way, I'm gonna say KK Anderson (07:43) Mm. Love that. Lance Haffner (07:44) this last thing. This is gonna be hard for me to say. Give up when when you're done. When the data tells you. This isn't working. Stop investing resources because you're burning, you're burning money, you're burning funds, you're burning resources and opportunity of other things you can be selling. And I think that's a really KK Anderson (07:59) Right. Lance Haffner (08:00) important note here is then it's time to probably say, we tried this, it didn't work, let's close the book on it. And that's really hard for a guy like me to say. KK Anderson (08:08) Right. we have this, you know, I've been teaching this philosophy for, over a decade now. and I call it the two sale mentality. And that is that every sale, I don't care if you're selling Girl Scut cookies or you're selling multi-million dollar software, it's two sales. The first sale is getting your customer to articulate why they need to change. And the second sale is why you and why now. And so It occurs to me as I listen to you speak, Lance, that that's exactly what you're doing when you're selling to someone who doesn't know they have a problem yet, their eyes haven't been open, you have to really nail that first sale and pull the pane. And once you get that, then you can go into, why papaya and why now? Lance Haffner (08:48) Why Papaya and why not? I love it, yeah. I love it. Okay. KK Anderson (08:52) okay, so yeah, and do you feel like your sales team is good at doing that? So as far as like selling value to something that they don't know that they need, like I think you're you nailed it when you talked about the sales process, but it really is everything, doing it in the right order. Lance Haffner (09:06) everything. Yeah. It is everything. And yes, I think so. I think look, I'm biased. I think I've got some extraordinary sellers and I think they really do KK Anderson (09:13) Right. Lance Haffner (09:14) care. Like let's let's maybe go to the we've been talking in kind of a technical manner, but let's go to our people. Yeah, I think they care and I think they do understand. Certainly they're motivated, they're sellers, but I think the best sellers do care about the value they can bring their customer. And I think that shows up in the processes they employ and the methods. They use to work through the sales process. So it's not just about identifying the pain. It's about I have conviction that I can help you. And this solution can save you time, it can save you money, whatever, whatever the value prop is. And and so yeah, I think my sellers are doing. I think they're fantastic, and I think they see they see the vision. And frankly, some of them are leading us, right? I've got some great sellers leading us, giving us market insights that we then back through process, very quickly take that in, the feedback loop. and iterate KK Anderson (09:59) Mm-hmm. Lance Haffner (10:00) w what we need to iterate to to help them be successful. KK Anderson (10:03) It's all about the loop. Mark Petruzzi (10:04) Beautiful. Lance Haffner (10:06) It's all about the lube. Mark Petruzzi (10:08) Lance, what tells you that the messaging is actually starting to land in the market? What what tools Lance Haffner (10:13) Yeah. Mark Petruzzi (10:14) and what approaches do you look at to really understand that? Lance Haffner (10:17) Yeah, don't overthink this. I think I'm an Occam's Razor fan, another colleague who brought that to me. Usually, the simplest answer is the right answer. if you Mark, going back to what we started the call with, or as we talked about the CRO function, those insights will show up pretty quickly. now they may not be they're they're going to tell you a variety of things that may not be overly structural in nature, but if you have your system set up. From top of funnel through closed loss through to activation through retention. Go there. Remember the bow tie and to KK's point. We may have a really good sales process and pitch. We don't have market fit just yet, but man, the pitch sells it and we get it in, we install, but yet we turn six months later. That's no good. Those insights are telling you, they're giving you real-time feedback. So your question is, how do I know the map the message is working? Start at top of funnel. I can see the outbound scripts are working and that we are qualifying. leads. They are becoming opportunities. I can see the same in in lead gen and in marketing. But I can see in the SDR outbound motions. I'm producing Topafuna pipeline. Number one. Number two, I'm converting that pipeline. It's happening. And this is all again, Mark, real time set up through your systems and processes and your sell stack and your insights coming from your revenue. Obviously, here. I do want to say this, it has to be bifurcated a bit. Bifurcated's maybe the wrong It has to be highlighted. You kind of have to have a bit of a tiger element about this, that you're watching it discreetly, explicitly. If you're not, then it can kind of get it, it can get in the overall noise of the funnel and your insights and your data and the pipeline management. So make sure you've got it set out separately. But if you got the right structure in place, you are going the key, the simple key. You're going to get those insights immediately, and then you can pivot. And ultimately, back to I love KK taking us through the other side of the funnel. If I'm beginning to turn, turn, churn, okay, man, it's working up here, great, but I'm an ARR business and my churn is is not good. And so we may have to go back to the drawing board and rethink market fit, product design, whatever. I C P KK Anderson (12:11) I C P, yeah. Yeah. Lance Haffner (12:13) all of it. Yeah. KK Anderson (12:15) Okay, let's move into talking about the trust trust deficit, you know, that Lance Haffner (12:20) Yeah. KK Anderson (12:20) we are all in right now with our AI enabled sales motion. And, you we talked about this when we when we met in our in our prep call and how, we're in a world where buyers aren't always sure that like they're even dealing with a real person anymore, right? that someone actually wrote a human actually wrote their email. that It's even a real person on the phone that's calling them. And so how does that show up in your world and what do you do about it? Lance Haffner (12:46) Yeah, you all had a podcast on this a month or two ago that was really good that I listened to and kind of informed and influenced some of my thinking. Yeah, I made a call the other day. I won't give you the company I call, but I'm a customer and and it was a small company by the way, local to me. So service provider for my home. We'll just say, mechanical stuff in your home. And I needed to get the tech back out and I call and I hear this voice, it's like, Hey, Lance, thanks for calling. And I said, yes, thanks. Yep, lights after calling from da da da da da and about da da da. And then there's like the four second pause. Great, thanks for calling in about that today. I'm like, Mark Petruzzi (13:22) Ha ha ha ha. Lance Haffner (13:23) I was so excited. I got a call almost immediately. It sounded real. And then I'm like, you're not real. You're not real. So it's showing up everywhere in our lives. And and then bring it apply it in our business. you had said on this last podcast, we've had automations out for a while, marketing automations that see the signals and they respond. And so this isn't new, but it is it is exponentially. My opinion is this. I think I think we we need to be we should be using the technology. It makes us more efficient, and if we can get it right, it will improve the customer's life. It will, it absolutely will. I believe that. Had that system, in my example, me calling the tech back out, been as responsive and and conversational as a human being and ultimately got me through the process efficiently, I just I wouldn't have cared. I wouldn't have, as long as the outcome was what it needed to be. So that's my opinion. The outcomes need to get to where they are. I think we've got to be smart about how we apply AI and the automations within our business. Again, automations have been around a long time, all through the funnel, even in the sales process. We set up sequences that are automated, that are managed by our CRMs and our outreach systems for our sellers that are not a seller necessarily, right? And so so they've existed for a long time. They've just become very dynamic and agentic. Because the agents can can work. So I think we've got to perfect the processes. I don't think we resist. I think we bring them in, we perfect the processes. I also, this is an interesting thing. I don't think you necessarily deny the fact that it is that you're using AI. I think it's okay. I think people can be okay with it. Mark Petruzzi (14:56) Well, Lance, I even go a step further with some of this when when I make those calls like you do and I hear an AI person on the phone, I'm actually happy sometimes because I know that I'm just gonna get through this faster. If it's a good AI, right? It's gotta be done right. But I'm looking at this and saying, Wow, I'm not gonna get put on hold for I'll be back to you in three minutes. I'll be back to you in three minutes. That's what humans tend to do with us. and I don't know if they're just taking a break in between or if they their computer systems are so slow, but AI is so fast that they come back and they say, Okay, give me ten seconds and I'll have an answer for you and I like that. So you've you've said that th nowadays the sales motion shouldn't be a AI, just AI, and certainly shouldn't just be human led as well. It's gotta be both. Lance Haffner (15:50) Gotta be both. Yeah. Mark Petruzzi (15:50) So yep, and it's gotta be what so where do you draw the line on what Lance Haffner (15:55) Yeah. Mark Petruzzi (15:55) has to stay human within your sales motion? Lance Haffner (15:58) Yeah. Well, like I want to relate this to Papaya and Papaya Global and our really how our our North Star and our vision. our vision is you'll never work alone. And we embrace artificial intelligence and our ability to build it into our product and solution and enable our people and our customers to be successful. So whether it enables our people to serve our customer or it enables our customer to serve themselves, the nexus of human and And artificial intelligence technology is where Papaya sits, particularly in workforce. Just take that philosophy and apply it to your revenue organization. And and that internal facing, this isn't really a customer or a deficit of trust as it relates to AI, but maybe I'm moving internal to say, look, I become we can become so efficient in pipeline analysis and forecasting with the intelligence going out and looking at our population. one in a former job I dropped all my calls into CRM out there that everyone loves. I won't name but and I got insights within about five minutes. Thousands of calls across twelve months. And I had immediate insights about my sales process, my pitches, what's happening, why am I close losing, where where are we going right in close one? Predictive forecasting, there's so many tools, AI tools we have today at our fingertips. We have never been more efficient or productive. This As CROs. Pivot back to the customer. Mark, yes, let's embrace it. Let's not deny the fact that we're using it. We're using it, buyer, to make your journey frictionless, better, more expeditious. Speed and simplicity are what are the two most fundamental, basic, foundational things needed for sales success, in my opinion. We forget about them all the time. We can use AI to remove friction from the process, to expedite the process, and to make it simple. And our customers, our buyers, will embrace that. Since we're in that clunky phase right now. We're trying to normalize what it looks like and how it feels. And there's the whole scary element of AIT right out there that I think people get. Mark Petruzzi (17:54) Cool stuff. All right. Well, this has been really great, Lance. we'd like to close up with a really quick rapid fire section. it's Lance Haffner (18:02) Let's do it. Mark Petruzzi (18:03) KK's favorite part of this this whole podcast. So first question for you, what was the first product or service you ever sold? Lance Haffner (18:12) Yeah, I did tell you all in in when we talked the first time and you mentioned it on our last podcast. I did sell staffing solutions, Headhunter. that was really my first first job. But before that, for about six months, I did get my real estate license and I attempted to sell real estate. I sold one house in six months, and I had a I remember I'll never forget my first and last buyer said, Hey, how old are you? I'm like, Yeah, I'm 19. have you ever bought a have you ever bought a house? I'm like, Nope. And that was the last whole house I ever sold, so. Mark Petruzzi (18:41) Lance, that is such a story and I have the same mirror of a story for you. I Lance Haffner (18:46) De Mark Petruzzi (18:47) did it I bet you I was eighteen, probably a freshman in college, Lance Haffner (18:50) Uh-huh. Mark Petruzzi (18:52) eighteen or nineteen. I did it for about six months. I actually sold one as well, so it was nice to get that that commission. But then I looked at and said, Yeah, I think I need to get a little older before I come back to this and never did. Lance Haffner (19:07) I'm out. Exactly. We're kindred spirits smart. Yeah. KK Anderson (19:09) That's Mark Petruzzi (19:09) That's KK Anderson (19:10) funny. Okay, Mark Petruzzi (19:10) beautiful. KK Anderson (19:11) Lance, who is your favorite CRO or CEO that you like to follow? Lance Haffner (19:15) Yeah, my favorite right now is Scott Kirby, CEO of United Airlines. great turnaround story at United. I happen to be a United customer. I fly a lot, so I've got the premier 1K status. But set my status status aside, of course, my experience with United is always going be great. should be. and by the way, every customer's experience should be good, irrespective of the premium statuses. But I'll say this. He came in, he acknowledged that United's service network products suffered and hadn't hadn't been going the way that the board nor he nor the customers want. And he has changed United's trajectory. I have great, he's just kind of a real guy too. Own it, be open KK Anderson (19:52) Yeah. Lance Haffner (19:52) about it, and that's what I like about Scott. KK Anderson (19:54) All right, shout out to Scott Mark Petruzzi (19:55) Very cool. KK Anderson (19:56) Scott Kirby. Mark Petruzzi (19:57) so okay, leadership or go to market practice, every sales and marketing leader should adopt. Lance Haffner (20:03) Don't forget the basics. in the end, this is about some of the fundamental things, pipeline management, rigor, and discipline in your process. We CROs especially get caught up in in, I don't want to say the clouds, but the strategy and ensuring and keeping our vision grand and large and overlooking the entire org as we should. I also still have a weekly pipeline review every week. So the basics to any leader, not just revenue leaders. KK Anderson (20:29) My favorite question, Lance, and I was gonna say advice you would give your twenty one year old self, but maybe I should say nineteen year old self selling real estate. Lance Haffner (20:36) my gosh, so many things. relax, everything will be okay. I was high strung and I looked it up even when I had my own business. like if I had if I lost a deal, I was so devastated. And I just look back and say, relax, it's okay. I mean, you're gonna be okay. That's what that's what this gray gives you is that that that comfort to know it's gonna be okay because you have been through those things. That'd be my advice. Mark Petruzzi (21:00) Beautiful. Lance, so thank you so much for the clarity you bring to all of this. particularly the vantage point of being of the unconventional path into the CROC. You know, what it takes to build a revenue function from nothing and what AI actually looks like in the hands of an operator using it well every day. Where should people go to find your work? Lance Haffner (21:21) Yeah, so look, find us at papayaglobal.com. You can find me on LinkedIn. I think my handles are Lance Hafner, or just search Lance Hafner and Papaya Global. You'll find me on the Papaya Global website. You'll find me on LinkedIn. Reach out. I love I'd love to to to to connect with other thought leaders. I'd love to debate someone who who believes differently. I love that. for sure. I'm an Aries, so I'm a bit of a fiery debater. But I have loved my time and enjoy my time with you all. I'll put a plug-in for the podcast. I think I think it's it's the thought leaders you bring on, the ideas you think about. I think what I love most, it's very diverse. You have you have leaders and thoughts from all across the spectrum on how they think about this. And there's nothing richer than to hear different views and perspectives that I can build into my own practice. So thank you for having me on and for producing this podcast. KK Anderson (22:10) Well, thank you, Lance. That that is encouraging to hear. And that's our goal. So hearing it straight from you, our, you know, ideal audience is is who you are. And that means a lot. And we'll put all of that in the show notes as far as your LinkedIn profile and how they can reach you. And to our audience, if what Lance said about building a revenue function from the ground up is sitting with you, that is the work we do at AGS. And particularly inside the two millimeter club, which is a small group coaching residency for frontline sales leaders where they learn to identify and coach the small shifts in seller behavior that add up to exponential movement in pipeline. We have eight-week cohorts designed to help sales leaders find more business and win more business. Cohorts launch monthly, and you can apply on our website at get-ags.com. Mark Petruzzi (23:02) Great. And if this conversation was useful, please send it to a leader on your team who needs it most or a friend, former colleague as well. I am Mark Petruzzi. KK Anderson (23:12) And I'm KK Anderson and this is Selling Intelligence and we will see you next time. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 139 - How Great CROs Build Revenue Engines That Actually Scale with Lance Haffner - Part 1 | 12 août 2026 | 00:23:52 | |
General Description: The path to becoming a Chief Revenue Officer doesn’t always begin in sales. In this episode of Selling Intelligence, Lance Haffner, Chief Revenue Officer at Papaya Global, shares how an unconventional career through staffing, recruiting, and HR prepared him to lead one of the most important functions inside a modern SaaS company. Lance explains why great revenue leaders must think like business operators first and sales leaders second. Drawing on his experience as Papaya Global’s first CRO, he discusses how understanding talent, operations, and organizational strategy creates a stronger foundation for scaling revenue than focusing on sales alone. The conversation also explores the evolution of the CRO role, why today’s revenue leaders must oversee the entire revenue bow tie instead of just the sales funnel, and how Revenue Operations has become one of the most strategic functions in modern go-to-market organizations. Lance shares practical insights on aligning marketing, sales, customer success, and product while avoiding common scaling mistakes as companies expand into new markets. What You’ll Learn:
Key Topics:
Guest: Lance Haffner is Chief Revenue Officer at Papaya Global, where he leads the company’s global revenue organization. Before becoming CRO, Lance built his career across staffing, recruiting, HR leadership, general management, and revenue operations. His unique perspective allows him to connect talent strategy, business operations, and revenue growth into a unified go-to-market approach that helps organizations scale more effectively. Resources Mentioned:
#SellingIntelligence #RevenueLeadership #ChiefRevenueOfficer #RevenueOperations #B2BSales Mark Petruzzi (00:29) Welcome to Selling Intelligence. This is the full conversation with Lance Hafner, Chief Revenue Officer at Papaya Global. We have broken it into chapters in the description. Take it from the top or jump into the segment most relevant to where you are today. Enjoy the show. Welcome to Selling Intelligence. I'm Mark Petruzzi. KK Anderson (00:51) And I'm KK Anderson. Mark Petruzzi (00:53) Most people who end up running revenue for a company came up through sales. Our guest today didn't. He started in staffing and headhunting, crossed into HR, and built his way into the C suite from a function most operators treat as compliance, not growth. KK Anderson (01:10) Lance Hafner is Chief Revenue Officer at Papaya Global, a global payroll and workforce payments platform, where he's the first person ever to hold that title. Before Papaya, he ran general management and then revenue for a large payments and payroll business. After building his early career full cycle and staffing sales, he's also one of the most hands-on AI users we've talked to on this show, using it daily. To diagnose his own sales team's performance, Lance, welcome to Selling Intelligence. Lance Haffner (01:41) Thanks, KK Mark. Happy to be here. KK Anderson (01:43) We are thrilled to have you. Let's let's dive right into our first topic and would love to learn about your journey from HR to CRO, which is certainly an unconventional path for the C suite. And you started in staffing and headhunting sales, moved into HR, you ended up running revenue for large business units. What's kind of the through line between those roles that You didn't see at the time you were on the journey, but when you look back now you can see it clearly. Lance Haffner (02:12) Yes, yes. So great question. And thanks again for having me today. I like to say when people see my HR background in my profile or we're having, a conversation, the us I would say eighty percent are a bit shocked, but to your point, unconventional. You're an enigma, Lance, and I agree with that. you don't you don't see it. But there are a few of us out there, we exist. so I as you said, I cut my teeth in in staffing. And so my my colleagues who are staffing, head hunting, recruiting, outsourcing my hats off. And back then we didn't call it SDR, but I was an SDR and made my way into account executive. Where to your point, full cycle AE, although I did have the SDR, I qualified a lot of my own and took that from top of funnel through through close one. And even working through to make sure my my recruits started, my recruits stayed, and I got my fee. So even through maybe activation back then as well. But and that led to an entrepreneurship role, which was great. I loved it. That was also very sales focused and continuing the staffing theme. but like a lot of young entrepreneurs and small businesses, it scaled up very quickly, it scaled down very quickly. and I found myself wanting to go back to work. So I did. And I went back in recruiting client side, and recruiting sits in HR. So that's really the nexus of my kind of staffing sales beginning roots to HR. And then I turned into an HR career that I decided I loved the discipline, I loved it for a variety of reasons. But one of the things that compelled me most is I saw a lot of compliance HR, which by the way, I don't want to discount that. it's required, we need it, it's important. But I also saw the need for strategic HR, particularly how does it enable the business to grow? Which is a bit of a, if we're all if we're being honest here, folks, that hey, I'm a strategic HR professional, I want to sit at the table and I want to enable the business to grow. You hear that all the time from HR pros. How do you actually make it happen? And I think I found my way into making it happen. And and that was that was kind of the path to HR. Any questions, comments? I'll pivot over to the how how that move into revenue and sales. Mark Petruzzi (04:13) Yeah, well, it's I mean, you and I have had this discussion already in the past, Lance, and the idea of coming from these unconventional or less conventional paths, I immediately reacted to that by saying, Wow, some of the best CROs that I know out there today have come from that kind of unconventional path. Lance Haffner (04:34) Yeah. Mark Petruzzi (04:34) So I don't think that means you don't, you shouldn't go into sales if that's what you want to do. But I think that means you really have to understand, everything in an organization. You have to look at it as a business person, not just a salesperson. And when you do that and you grow throughout your career, you typically turn into a a great CRO. Lance Haffner (04:58) yeah. Mark, hey, Kim, let me tag on that. I love it because I think we're gonna talk about this a bit later, about the CRO function itself and building it from scratch. Look, go back to that HR role and I wanna visualize something you just said that I think is important. I actually my mantra for my team and I was we are business professionals who do HR. And that that very simple statement was to kind of demonstrate, visualize this. We are not HR pros, although we are, let's be honest. We are business professionals, members of this business who are here to achieve the business's objective. And we will do that through our HR practice. Whether we're ensuring governance and compliance, whether we're ensuring total rewards, compensation, benefits are competitive, whether we're ensuring we're bringing talent in, acquiring it, developing it, whether we're ensuring that the C-suite as an HR pro you are workforce management strategies and everything you're doing propels the business through its people. You're taking your your lens of that discipline and applying it to business growth. No different than the CRO. you are a business professional pro executive who has to grow the business through the functions of sales, marketing, revenue operations, et cetera. Mark Petruzzi (06:01) Excellent. All right. So you've talked about bringing a business enablement mindset to HR instead of that old compliance mindset. So tell us a little more, take us a little deeper into what did that what did that actually look like in practice? And how did it change how your business partners saw the function? And again, we could touch on this, we don't have to go deep, and then really transition it into how do you take those mindsets. and bring it into the CRO role as well. Lance Haffner (06:31) Yeah, good good question. first and foremost, I already talked through the functions of HR generally. And it it can it can expand or or contract a bit, but the functions we talked through. and it's a vast discipline, right? You have you have professionals who come up and tell the rewards and do nothing else. you have professionals who come up in recruiting and stay there, et cetera, payroll, etc. and so I think the my perspective was this. My business has an objective. It wants to grow revenue. It wants to expand in regions, whatever that's that North Star is and the objectives that they have to achieve to hit that North Star. And then I back into my HR function. And what most, what is most critical to hitting that? Well, in HR, generally it's going to be talent acquisition and development. Bring the right talent in, retain, develop them, retain them, because without the people, you can't do that. Secondly, it's going to be workforce management. What does that mean? Well, so it's not just about bringing people in. That's sales, right? But let's talk about NHR, maybe the sales translation to segmentation coverage. Where do they go? How do they get there? What are their motions as professionals to achieve the objectives? How many engineers do I need? So that workforce management to ensure you've got, even though you have people coming in the door, those inputs are right, the right people, where you're placing them to achieve the objectives. and by the way, in this one's fundamental but and simple but often missed by HR pros, understanding what the business does. There I hate to say it, but I think there's some some of my colleagues out there KK Anderson (07:56) Yeah. Lance Haffner (07:57) who don't fully understand their business. And they'll say to you, look, I'm an I'm an expert in ABC and total rewards and in recruiting or payroll. Great, and you should be. But I don't know. I can't I can't rationalize being the most effective HR pro executive without understanding truly the basis of your business and what it does. Mark Petruzzi (08:17) Yeah, and Lance, that also applies to the sales rep level, even the CRO level. There are there are people Lance Haffner (08:23) Exactly. Mark Petruzzi (08:24) there are people that are so into and focused on the craft of selling that they really don't truly understand what their in some ways Lance Haffner (08:34) Yeah. Mark Petruzzi (08:34) what their product offering is and in other ways really why their company is successful. Lance Haffner (08:39) Mark, it's so right. How many times have you had a sales leader say, look, I can sell widgets, I can sell this, I can sell that? And there's almost this kind of implied, implicit, like it does I don't care what the business does. Now, depending on the context of that statement, it absolutely can be right. They're saying I know my craft and discipline and I can apply it anywhere. But some of them truly are like, yeah, I don't know, I don't care. I care about bringing the right, sales function. So I hear you, I totally. KK Anderson (09:01) So Lance, you are Papaya's first chief revenue officer. And it appears that you're shifting to a go-to market and a scale focus. So, so tell us about how you started. Like what did you have to build in Lance Haffner (09:16) Yeah. KK Anderson (09:16) your first few months that, a CRO walking into an established seat wouldn't necessarily have to think about? Like tell us about how that journey began for you. Lance Haffner (09:25) Yeah, thank you, KK. So let's can I maybe a little context and I'll I'll get to your KK Anderson (09:29) Sure. Lance Haffner (09:30) question. So I took my first CR role about four years ago, I think. and new to me as a CRO, I've been a GM president before that. So of course my remit of GM included revenue. but anyway, my point of being a a CRO as a first and even my last job was let's Let's go understand exactly what the function and discipline of CRO is. What what does the revenue function represent And you really had this evolution over the past 20 to 25 years, particularly the Genesis being kind of SaaS and tech, right? And understanding that the B2B buyer is much different than it's ever been. And you need some function to bring the disparate revenue buckets or functions together, i.e. the revenue leader. So I had to go do some research. And if I'm being honest, you're kind of like, why would you ever become the CRO if you're even having to research what the CRO does? And I think for a variety of reasons I got the opportunity, one being such that that the GM role I was pretty successful in and had demonstrated that as a GM, I was very revenue focused. So back to your I think that's important, right? What is a CRO? And by the way, let's define it. The CRO is responsible from really cradle to grave revenue. What is cradle to grave? top of funnel and everything that's coming in funnel and the lead sources coming in top of funnel, bringing that through the funnel and pipeline to close one. By the way, that's that's that's marketing and growth up top of funnel, but also your sellers, your your SDRs, which could be growth down through your sales team, through conversion, and through activation and through retention. Let's and let's let's can we stop there for just a moment? A lot of folks when they when they discuss revenue, A lot of sales leaders really, but even some revenue leaders they talk about the funnel, right? You visualize the funnel, and the funnel has an end in some revenues leaders' mind. That end is close one. Great. But really, I think conventional or contemporary CROs in the past five years have started to evolve that to the revenue bow tie. Pivot the funnel on its side, everything coming in from the left. your lead sources, SDR. Growth inbound through marketing, lead gen, partners, self-source, whatever. I have a lead source that's coming through. I'm qualifying that lead into opportunity and I'm closing. and by the way, there's feedback loop there in the in the in the left side of the bow tie. Close one is center and great, but we're not done. We've got to activate revenue, particularly in an ARR business with SaaS, with with recurring revenue. We've got to expand it, we've got to retain it. And so I think the contemporary revenue function today. may not own all of that, but they absolutely should have oversight and remit and coordinate the owners. And in some organizations, they do own all of those functions. I don't own all of them. I own a lot of them, but I don't. I am very much dependent on colleagues in the business. All right. Stop there. Anything there you all would add or debate me on? Mark Petruzzi (12:21) No, no debates. I think that's it's taking us further into the just your mindset and what you do every day. So you went from a role where marketing was only a dotted line into you to one Lance Haffner (12:35) Yeah. Mark Petruzzi (12:36) where you now own the full function directly. KK Anderson (12:39) Uh-huh. Mark Petruzzi (12:40) and by the way, a little perspective on that. I worked with a lot of companies when the concept was moving, particularly software companies where the concept was moving from, okay, like if I'm gonna take this revenue number, I need to own all this. And we didn't even Lance Haffner (12:57) Yeah. Mark Petruzzi (12:57) call it the CRO yet, but Lance Haffner (12:59) Yeah. Mark Petruzzi (13:00) it it then turned into that. And now we've gone full circle where there are a lot of CROs who don't own all the things that you own. They just they want Lance Haffner (13:07) They don't. Yeah. Mark Petruzzi (13:09) the title, but they're really just a SVP of sales or a sales leader. So What is having that full remit change the way you operate Lance Haffner (13:17) Yeah. Mark Petruzzi (13:18) day to day? Lance Haffner (13:19) Yeah, yeah. So good question. And coming back, I love to I get a little verbose and digress. So thanks for corralling me back here and last selling back part. Yeah. So Mark Petruzzi (13:26) no, no worries. KK Anderson (13:26) Ha ha ha. Lance Haffner (13:28) building the CRO functions from scratch andor my remit every day. so here's the beauty of it, and you all know this. and my my colleagues out there know this. When those functions build themselves disparately, marketing, if sales can't sell, it's marketing's fault. or sales can sell or excuse me, marketing can't qualify. the leads, sales saying, I can't I can't close your leads marketing, or if it's all SDR outbound motion, SDR, these are crap leads, you're not qualifying. Meanwhile, marketing is saying, Hey sales, you saw you can't close. I need closers and eat a lot of this. And by the way, you never get away from that. It's just kind of intrinsic and innate. and I kind of smile because we all deal with this every day. But the CRO thinks about that in kind of this linear fashion. And they think about those gates from top of funnel all the way through to activation, continue through the gates of activation starting, expanding and retaining and preventing churn. Or if you have churn, fine, and then loop back. And that feedback loop coming under each of those, okay, loop back to why and return them. this is a product matter. Let's go over here. Why did we close go back up to top of funnel or left of bow tie? So I'm thinking about that entire value chain, if you will. And where are the gaps? By the way, one thing I haven't said that is a huge miss on me at this point, and I can't believe I've not said it to all my RevOps pros out there. The current CR also is very much building the systems and processes that allow those functions that sit in that bow tie KK Anderson (14:56) Mm-hmm. Lance Haffner (14:56) to operate in the most efficient, effective way. I would say to you: no offense to my marketing colleagues, no offense to my sales colleagues. I think the revenue ops leader has become the right hand of the CRO. And without that strong person, the CRO and his colleagues or those functions he owns, we are we're kind of steering a ship without without the ability to see or a plane or whatever metaphor you want to use there, but we're kind of driving blind. so every day I'm looking at the throughput of top of funnel through to activation, and I'm finding those gaps and I'm filling. And sometimes those gaps come outside of revenue. I already mentioned one. If we're not closing, because let's say we have let's say it's a feature set, table stakes. I don't have it, we've lost it, the market's gone a different direction. I'm now immediately over with product. and we're having the discussion. Let's say actually product's perfect, but I've got some market fit issues because how we think about The product in market and how our buyers think about it is off. All right, I'm back up here with product marketing having that conversation. Let's say, let's move to the other side. Now let's move over here to retention and churn. I have a service issue. Call, and we're not hitting SLAs to pick up the call, our automations aren't working well. Great. Now I'm dealing with ops. But my job is thinking about that entire bow tie and finding the KK Anderson (16:11) Mm-hmm. Lance Haffner (16:11) gaps and problems and then coordinating either within my own shop or externally to fill. So that's that's kind of how I think about it in big picture. So back to KK Anderson (16:19) Right. Lance Haffner (16:19) your question, one last thing. I come in, what are we doing here? The first thing is survey the landscape, where are the functions built? By the way, the functions may be extraordinary. You may not have a lot of work to do within the discipline or the function. Mark Petruzzi (16:32) Yeah. Lance Haffner (16:33) Your job now is to connect it all, tie it together, align them, and ensure that things are working in concept in concert. So yeah. KK Anderson (16:41) And it's making sure we're big believers of Jocko's winning by design bow tie here at AGS. We talk about it all the time, right? Find we call Lance Haffner (16:48) Yes. Yes. KK Anderson (16:50) it find more, win more, keep more. Yes. I've got the same book right here. Lance Haffner (16:52) That's right. That's right. Mark Petruzzi (16:53) Yep, there you go. Huh. KK Anderson (16:55) yeah, and we talk about it in a lot of our episodes actually as well. but Lance Haffner (16:59) Yeah, I know. KK Anderson (17:00) that like the more overlap you can create and the tighter handshake you can create between the three segments, the better. Right. And Lance Haffner (17:07) A hundred percent. KK Anderson (17:08) and you may be, you may, and this it also kind of goes into this diagnostic model. If you picture your bow tie and then the various metrics that your KPIs that your RevOps leader is Lance Haffner (17:18) Yep, yep. KK Anderson (17:19) pulling at each stage, you might be able, you might see something that's happening in FineMore up here on the left hand side of the top of the funnel that is Lance Haffner (17:26) Mm-hmm. KK Anderson (17:27) gonna signal, hey, in six months, you're gonna have an issue over here with retention because guess what? You're not getting the right leads, they're not the right people, Lance Haffner (17:33) That's right. KK Anderson (17:34) they're not gonna stay, they're not gonna have the right, they're not gonna Lance Haffner (17:36) Yeah. KK Anderson (17:37) be the right fit for us, right? And so all of a sudden as CRO, Lance Haffner (17:38) Yep. That's right. KK Anderson (17:40) you see that and you can go back and mitigate and make tweaks there. So it's just it's fascinating. Lance Haffner (17:43) That's right. You did you did such a great job, KK, of of maybe demonstrating that better than I. in a very simple manner. You're exactly right. that visibility and the systems and processes in place to move quickly and fix it when you see it. So KK Anderson (17:58) Right. Yep. So really good. Mark Petruzzi (17:59) All right. Well, well, before we close up episode one, Lance, let me ask you to to go quickly into, shifting a company from the invest mode to a scale mode. no, you've done that a couple of times, few times in your career now. So the first question with that is how do you diversify your go to market motions across the typical markets that we deal with, enterprise, mid market? Lance Haffner (18:23) Yeah. Mark Petruzzi (18:24) incubation groups and high fast growth organizations without losing focus on what's already working. Lance Haffner (18:31) my gosh, it's so salient for me, Mark. And every organization, particularly when they're looking to build the revenue function out or expand it or just overhaul it. This is one of the major discussion points. I would say we're really good at this. We're up market. We're selling this solution. It's enterprise. We've structured an organization around, particularly a revenue organization, around the enterprise motion. Great. What else can we do? Because I look at it and I'm doing my analysis and I see the I see so much more opportunity. Where does that analysis start? I would say first first of all, you're you're meeting with product marketing and you're having a conversation about market fit, how they see the product. I like to think of the product marketers. this is probably the major wrong analogy, but I think of them as kind of the oracles of their product. they are they're close, they're the clo one of the closest to product, but they're also sitting in marketing, they're thinking about the market and And so you're having that conversation with them and you're determining where are other opportunities, where do we have fit? And back to KK's point, you're not making a mistake in in introducing a new motion into a new segment, into a new region, that ultimately, while your sales pitch is great, you can convert those deals, you're gonna lose them later. So you do your you do your segmentation, you do your market analysis, where do I tan tan salmon sum? Where can I go after it? And then what's my coverage? How am I segmenting? So back to your point. I've got a mid-market solution that's fantastic, but I don't have I have an enterprise motion, I have a SMB motion, and I miss the I miss the the the mid-market. By the way, we talk about motions all the time. I think it's a bit overused. but really when I say motion, obviously I visualize how that deal, lead, makes its way through top of funnel through the organization. And how we've structured everything to accommodate that. It looks it can look different. SDR can be different. The ratio of SDRs to sellers can be different. Obviously, your Legion activities, your campaigns, where you're attaching those buyers, where you're excuse me, where you're touching those buyers, the signals that you're looking at, and then bring that on down through through sales. an enterprise, absolutely, you're gonna have lots of sales engineering and solutions consulting and you're gonna engage. It's gonna be a long cycle process. In market, it starts to compress. And in SMB, frankly, you can have one day closes. Are you structured to allow for that? and the processes are diverse enough and robust enough to do it. And then lastly, here's another big mistake I think about, because I've made it. one of my one of my colleagues says, a fish can't climb a tree. What he means by that is when I show up with a brilliant idea because I'm looking for revenue opportunities, I'm like, hey, you know these sellers in this line of business who are enterprise sellers and they're selling, five million dollars a year and they're probably closing three deals, and these are long cycle, high-intense sales processes. And I'm like, why can't they just refer one of these a day? They're running into it. And He'll push back on me and he'll be, I know we're running into Atlance, but that's a fish, and you're asking him or her to climb the tree. And honestly, we'll be better served by focusing that prospect lead elsewhere in the org. So look, you can debate that. I actually still think that they should refer over to their SMB colleagues that leave. I think it's great. But that's not my point. My point is make sure that your organization, that you're not attempting to teach fish to climb trees. The motions are proper. structurally everything's proper. and by the way, again, that all stops starts up here with your product marketing friends, with your product friends, with your revenue ops leader who has done a lot of analysis him or herself and making those decisions. So I think long story short, it's really the CRO doing what they best do. Mark Petruzzi (22:03) Yeah. And a fisk you can't teach a fish to climb up a tree. I love it. Yeah, KK Anderson (22:08) I love that. Mark Petruzzi (22:10) I would love to ha I'd love to meet your friend that came up with that one because that's a that's a that's a great one. So Lance, what a KK Anderson (22:14) Ha ha ha ha. Lance Haffner (22:15) He's good. He get he's good. Mark Petruzzi (22:17) great discussion thus far. We're gonna pick right back up here next week in part two. Lance Haffner (22:23) Okay. KK Anderson (22:23) And what Lance just described about shifting a company's organization and revenue into a bowtie structure is the exact work that we do and teach inside the two millimeter club, which is our small group coaching residency for first-line sales leaders. They learn to identify and coach the small shifts in seller behavior that add up. To exponential movement in pipeline development and in closing pipeline. They're eight-week cohorts and they launch monthly. If you're interested, apply at www.get dashags.com forward slash two mm club. That's get-ags.com forward slash two millimeter club. Join us next week for part two with Lance Hafner. Mark Petruzzi (23:11) Beautiful. Great. Okay, let's let's go to the to part Lance Haffner (23:14) So Mark Petruzzi (23:14) two opening. Lance, great job. This has been great thus far. Lance Haffner (23:20) All right. Thank you. 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| Ep. 138 - High Tech Requires High Touch: Bridging the Human AI Gap with Dr. Noah St. John - Part 2 | 05 août 2026 | 00:15:47 | |
General Description AI is transforming every aspect of sales, but technology alone isn’t enough to drive better performance. In Part 2 of this conversation, Dr. Noah St. John returns to Selling Intelligence to explore why organizations investing heavily in AI, automation, and coaching still struggle to achieve meaningful results. Building on the Human AI Gap introduced in Part 1, Noah explains why trust has become the most valuable currency in business. He discusses the growing trust recession created by AI-generated content, the importance of authentic expertise over polished marketing, and why buyers must look beyond promises to evaluate real outcomes and proven results. The conversation also shifts to revenue leadership, where Mark Petruzzi and KK Anderson explore how CROs and CEOs can help teams embrace AI without losing the human judgment, experience, and tribal knowledge that drive long-term success. Through practical examples, including Ford Motor Company’s AI missteps, Noah demonstrates why AI should amplify human capability instead of replacing it. What You’ll Learn
Key Topics
Guest Dr. Noah St. John is a bestselling author, keynote speaker, performance coach, and founder of SuccessClinic.com. Over nearly 30 years, he has helped entrepreneurs, executives, and revenue leaders overcome the hidden mental barriers that limit performance. As the creator of the Human AI Gap framework, Noah combines neuroscience, psychology, and business strategy to help organizations successfully bridge the gap between human behavior and rapidly evolving AI technology. Resources Mentioned
#SellingIntelligence #AIforSales #SalesLeadership #HumanAIGap #RevenueLeadership Mark Petruzzi (00:38) Welcome back to Selling Intelligence. I'm Mark Petruzzi. KK Anderson (00:42) And I'm KK Anderson. This is part two with Dr. Noah St. John. Be sure to go back and listen to part one. But if you want to start here, let us bring you up to speed. Noah has spent close to 30 years studying why capable people underperform. He has written 27 books and coined the term human AI gap, the distance between 200,000 year old brains, the caveman, as he calls it. And the fastest technology ever built, which of course is AI. In part one, he drew the line between mindset, which the industry has worn out, and what he calls the inner game, the unconscious programming that decides whether skill and technology ever get used. Mark Petruzzi (01:24) In part two, we get to the operator level. What Noah's highest growth clients do differently and what the inner game looks like under real quota and board pressure. Noah, welcome back. Dr. Noah St. John (01:35) Thank you, great to be here. Mark Petruzzi (01:36) So let's go to to our first topic of our second episode with Noah, and that is high tech requires high touch. The trust recession. You guys all know out there we talk about that trust recession often, and we really want to get some perspective from Noah on this as well. So, Noah, you also have talked about a trust recession in this space. Where there's too many people with strong marketing skills and weak t teaching ability, or c or strong sales skills and weak coaching ability, how does that dynamic show up for a B2B buyer who is evaluating a coaching or advisory investment right now? Dr. Noah St. John (02:17) Well, I mean, this is a huge topic, and I do talk about it a lot, as you mentioned. so very simply, it's exactly what you were saying is that there are a lot of great marketers, great self promoters, great salesmen, who suck at teaching. They suck at coaching, they just there's no there Mark Petruzzi (02:32) Yeah. Dr. Noah St. John (02:32) there, as I like to say. There's no there there. and so the problem is that is the very problem because they're so good at self promotion and marketing. Just lots and lots of people bought their stuff. They gave them money and they found out there's nothing here. Hello? What the heck is going on here? They promised the sun, moon, and the stars, and they gave me a pile of dirt, So it's it's really, really bad. I have my own spreadsheet. I call it the spreadsheet of death, you know, because I paid all these clowns tons of money. I mean, much more money than I'd like to admit, only to find out they can't teach every way out of a paper bag. So it's it's really bad. Now, obviously, I'm not alone in that. I spent a lot more than most people, probably, But the point is that, unfortunately, hundreds of thousands, if not millions of people have experienced the same thing that I have, which is hello, you didn't tell me anything. So it's incredibly annoying and it's and it's and it's frustrating and it's painful and it's costly. And so I think one of the things that we have to do as leaders, if you are evaluating a B2B or a B2C. program, you know, and when I say life changing, I know that sounds like a cliche again, but that is what it really is because that has always been my focus is Taking care of the three pounds of gray matter that really is just ignored for the most part. And so one of the things that I think people need to do is look at the case studies. Look at the case studies, the real people who have gone through program including Gary Vaynerchuk. Jenny McCarthy, Stephen Covey, Jack Canfield, John Assarath, Neil Donald Walsh. I mean, you know, the luminaries go on and on. And then, of course, just the regular, everyday CEO, CMO, CRO, entrepreneur I have always said, I've always said this, that it's much more important that people have gotten results rather than. I say how much money I've made. Because when you look at those gurus out there, that's what they're always talking about. I made all this money. Look at my yacht. Look at my boat. Look at my helicopter. Now, nothing wrong with that. We all want nice things, right? We all want yachts and boats and helicopters. Nothing wrong with that. But my question always is: well, have you helped anyone else? And usually the answer to that question is, what? so That's the problem. And so I and maybe I went overboard the other way. Maybe I've gone too far the other way. I don't know. But I'd rather brag about my clients than me. You'll notice I talk way more about my clients than myself for that precise reason. Because we live in a trust recession, I'm always like, Well, don't believe what I say. And I'll just have to say this because everybody knows it's there right now. You also have to make sure that those are actual human beings, on a video. Like because of course we all know that AI can create AI user generated content now. And it's pretty easy to spot still today at the time of this recording. I mean, I can tell in one second, and I think most people can too. I mean, but you just gotta be careful, because hell, it's the greatest thing in the world. Wait a minute, is that a human or not a human? Hmm. We just might want to check that. KK Anderson (05:21) Yeah. And you know, you could even ask, like, hey, are you human or are you not? Even when you're chatting with a website, is this an AI agent or is this a human that's named Linda? Right. Dr. Noah St. John (05:30) Right. Exactly. Well, I was talking about just the videos, you know, the actual videos that I mean we s KK Anderson (05:35) Mm-hmm. Dr. Noah St. John (05:35) we see AI UGC all over the place now. And again, as I said, it's it's relatively easy to spot now, but is it always gonna be easy to spot? Probably not. I mean, it's just gonna keep getting better and better. So you you you know, you better get in now before it gets worse. KK Anderson (05:48) So w when you think about what high touch actually looks like in practice for you at this point in your business, like what talk to me a little bit about how, thanks to AI, and creating the trust recession and then you're having to we have to go back now and accommodate for that. Like what does that look like for you and your business and for your clients? What's caused what's what's been successful, I suppose. Dr. Noah St. John (06:08) Well, I mean, it we it doesn't have to be complicated. At least in my case, you know, what we do is a is a very simple intake form and we see where you are. We get a baseline of where you are over the last twelve months. By the way, when you go to KK Anderson (06:20) Right. But to get but to even get to that point where they're interested. Like that marketing Dr. Noah St. John (06:24) So I talked about the caveman but there's also a caveman calculator So that's one of the things that I love is the caveman calculator. And you can actually see how much the caveman is costing you right now. So that's a really important point of if you are not if you haven't learned how to tame the caveman in your brain, you're gonna be paying the caveman. You're gonna be paying, as I call it, the caveman tax. Because it's absolutely one million percent is going to be holding you back. like Adam, that story I mentioned earlier. it takes longer to close a client typically now than it ever did for that precise reason. So, you know, as a business owner, you you want to make sure that you're putting out correct content, both in terms of video and And articles, blog posts, books, et cetera. Right. So that's the point, is that is why we do operate with high tech high touch. And that's one of the ways that we do it is making sure that everybody is accounted for at the level they're at at the time. KK Anderson (07:17) Okay. That's super interesting. and Noah, we're gonna jump to the next topic and we're gonna touch back on the inner game a little bit, but specifically as it re relates to a revenue operator. And I know you've worked with, CEOs and and leaders of all different, you know, types of businesses. And so and kind of thinking about that experience, like when you s when you strip away the tactics and the tools, what is the inner game pattern that separates those, client that has the exponential six hundred percent growth from one that's kind of stalls at thirty percent? Dr. Noah St. John (07:52) Well, as I mentioned earlier, you know, when when people listen to me, they get enormous growth. If they don't, then they won't. KK Anderson (07:58) Well they listen to you, which means they do the work. Dr. Noah St. John (08:01) exactly, And see, well, nobody's when you pay me money, you listen. That's the beautiful KK Anderson (08:03) Why would they not listen? Like what are the reasons that you come across why they don't? Right. Dr. Noah St. John (08:08) The people who invest, right? When they invest, they're invested, and that means boom, I want my ROI. I want my return on investment. Boom, I'm to take action. One of the things that I've known for is helping people to take action where they had been stalled previously. Right. I'll give you another example. I mean, I was talking with another client of mine, and he is has a very big biodiesel fuel. You know, a nine-figure business. And he is not a very loquacious person, very soft spoken, very hard close to the vest and so forth. and one of the times that we were talking in one of our earlier sessions, he said to me, Noah, I have A Bachelor of Science from a major university. I'm not going to say the name of the university. Now, I almost fell off my chair when he said that, because this is not a man known for being, loquacious and being, big with his words. And I was like, wow, no kidding. Okay. And, now he has gone on to actually sell that company and make a very nice exit. My point of that is that when you are when you invest, you're invested. So for those of you listening and thinking that whether it's yourself or your team, so if you are a CRO who is pulling your hair out because you're saying, But Noah, I've given my team everything. I've given them all the tools, all the training, all of the things that they should be, they should just be exploding. I will always ask you, but have you helped them with their inner game? Or is that all outer game stuff? That's why I started this conversation with that Venn diagram I talked about. I mean, inner game, outer game. Ninety nine percent of people are spending all their time, money, and effort on outer game. It's not wrong, you to do it. But have you spent any time on the inner game? KK Anderson (09:36) And so are you te are you teaching the leaders so you're teaching the leaders then how to coach their teams on the inter game or are you coaching the teams directly? Dr. Noah St. John (09:45) Well, both. It depends on what they want. Like I talked about, it was it's all bespoke and customized and personalized. So that goes back to the licensing that I was talking about. There's no more guesswork. Mark Petruzzi (09:54) So Noah revenue leaders are under enormous pressure right now, a special Dr. Noah St. John (09:58) Yes, yes. Mark Petruzzi (09:59) amount of pressure that we really haven't seen throughout at least my career. They're dealing with this AI transition process, their their overall team capacity, quota, quota, quota, and then the boards have gotten a lot more direct and vocal, going after sales leaders as well. So What does the inner game look like when the stakes are as high as they are and the timelines are as short as they are? Dr. Noah St. John (10:24) Well, it's an incredibly stressful situation. You're absolutely right. And this is something that I help people with every single day. But the point is that AI has really changed the perspective of a lot of people in this way. They believe, mostly incorrectly, that if I just toss AI at this, then I'll just it'll solve all my problems. I'll make all this money. I'll give you an example of how this didn't work. and by the way, this was not a company that I was involved with. But Ford Motor Company, we all well know Ford Motor Company, they recently made big headlines because they fired all their what's called the gray beards, right? All the guys that had been on the front lines, you know, the engineers had been there for 30, 40 years, right? So Ford got all excited about AI and said, we don't need these gray beards, right? It's those annoying humans I was talking about earlier. we're paying them all this money. We don't need them. Hey, all right, we'll let them go and we'll let the AI run the whole schlumiel. Didn't not work out so well. So what did they have? They had billions of dollars. They save they saved millions, yes, and maybe tens of millions, but they had billions of dollars in recalls because the AI didn't understand all the things the gray beards knew. They and the graybeards just know this without even thinking, right? So it's not like a gray beard, and you understand the term that I'm using there, right? That someone who's just been on the front lines doing this. They they do it without thinking. They're literally KK Anderson (11:36) Tribal knowledge. Yeah. Dr. Noah St. John (11:38) unconscious. So they don't even know. They just do things because they know how to do things. But if they even were to sit down and say, try start start to or try to train an AI in what they know, they couldn't even do it anyway. Because they might be able to tell them, say, 80%, but there's 20% that they don't even know they know. Does that make sense? They're unconsciously competent. And so the point is Ford had to, it was very embarrassing, egg on the face. We got to hire all the graybeards back. And oops, sorry about all those recalls. Do you see what I mean? So that's an example of how it. It's it's AI is not a magic solution. It's not a magic pill. But it does, as you mentioned earlier, it accelerates what's already there. Okay. So what we wanna do is we wanna bridge that human AI gap. We want humans and AI working together. And I think that is the future. Mark Petruzzi (12:22) Excellent. KK Anderson (12:22) Love it. Mark Petruzzi (12:23) really good stuff, Noah. Dr. Noah St. John (12:25) I was very excited to get money you know on the internet. Remember internet, yay, internet from literally countries I never even heard of. And it was it was KK Anderson (12:32) Yeah. Dr. Noah St. John (12:33) very exciting. KK Anderson (12:33) Okay. Favorite CRO or CEO that you follow? Dr. Noah St. John (12:37) gosh. my favorite CEO, I guess, you know, today is a name that is a somewhat controversial, but Alex Hormozy. Some people know him, some people don't. But he's I think he's he's pretty good. He he does a nice job. And of course Gary Vee, my good friend Gary Vee is always good for a great story and great motivation. KK Anderson (12:55) Yes. I enjoy Alex's content as well and Gary's content. Dr. Noah St. John (12:59) that is surveys. Surveys are useless. Sorry. but and the reason is very simple because human beings will tell you what you they think you want to hear, and we'll do something totally different. So pre-market or go-to-market surveys are essentially useless. The best thing to do is just put up an ad, put up a quick sales page, run some traffic to it, see if anybody buys it. Boom, we're done. KK Anderson (13:20) Okay, Noah, my favorite question advice you would give your twenty one year old self. Dr. Noah St. John (13:25) Don't buy from those friggin' idiots. Get away from that spreadsheet of death. Do your homework, son. Go past the headlines, go past the marketing speak. Don't don't believe them until you do your homework. That's what I wish I would have known. Mark Petruzzi (13:37) Nice. Okay. KK Anderson (13:37) You've been burned. You've been burned. Mark Petruzzi (13:39) Our Dr. Noah St. John (13:39) yeah. Mark Petruzzi (13:40) our last one is your favorite sales or marketing book? Dr. Noah St. John (13:43) you know what? It always goes back to the classics for me. Dale Carnegie, How to Win Friends and Influence People. I just don't see how you can go wrong with that one. Mark Petruzzi (13:50) I love it. Noah, this has been a great conversation and exactly the kind of cave con conversation we have built this show for. So thank you for the clarity you bring to this. Thank you for the inner game and your your knowledge transfer there, the human AI gap, and the pac practical path through it. Where should people go to to find your work? Dr. Noah St. John (14:14) Go to noahn.com. That's my name, noasaintjohn.com. Easy to remember. Mark Petruzzi (14:18) Ha ha ha. KK Anderson (14:19) I love it. You've said that a time or two, huh? Okay. Dr. Noah St. John (14:21) Indeed. KK Anderson (14:22) We will put all of that in the show notes. And if what Noah said about the inner game is sitting with you, again, that's the work we do inside the two millimeter club, which is our small group data-driven coaching program for frontline sales managers. They learn to identify and coach the small shifts in seller behavior that add up to exponential movement and pipeline. cohorts launch monthly and we'd love to have your sales managers join us. You can apply at www.get-ags.com forward slash two mm clubs. Mark Petruzzi (14:58) And if this conversation was useful, please send it to the leader or team member that you know who you think needs it most. I'm Mark Petruzzi. KK Anderson (15:07) And I'm KK Anderson and this is Selling Intelligence. We will see you next time. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 137 - The Human AI Gap: Why Your Team Isn’t Using AI to Its Full Potential with Dr. Noah St. John - Part 1 | 29 juil. 2026 | 00:26:18 | |
General Episode Description: In this episode of Selling Intelligence, Dr. Noah St. John, bestselling author, performance expert, and founder of SuccessClinic.com, joins Mark Petruzzi and KK Anderson to explore why so many organizations continue to struggle with execution despite investing heavily in technology, training, and AI. Drawing on nearly three decades of research and more than 250 documented client success stories, Noah argues that the biggest barrier to growth isn’t a lack of skills or better tools. It’s what he calls the inner game. While most organizations obsess over CRM systems, AI platforms, sales methodologies, and go-to-market strategies, they often ignore the beliefs, mental patterns, and internal wiring that determine whether those investments actually translate into performance. The conversation introduces Noah’s concept of the Human AI Gap, the growing disconnect between our 200,000-year-old human brain and the fastest-moving technology ever created. He explains why fear often outweighs logic when organizations introduce AI, why employees naturally resist change, and why leaders must address human psychology before expecting meaningful AI adoption. Mark, KK, and Noah also discuss the distinction between the inner game and outer game, the role beliefs play in sales performance, why coaching mindset creates exponential business growth, and how understanding different personality patterns can help leaders guide their teams through the AI revolution. What You’ll Learn:
Key Topics:
Guest Spotlight: Dr. Noah St. John is a bestselling author, keynote speaker, business growth strategist, and founder of SuccessClinic.com. Over nearly 30 years, he has authored 27 books and helped hundreds of entrepreneurs and organizations improve performance through his research on mindset, productivity, leadership, and human behavior. His work combines neuroscience, psychology, and business strategy to help organizations overcome internal barriers to execution. Through his coaching and frameworks, clients have documented growth ranging from 600% to more than 1,500% across multiple industries. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more conversations with today’s leading experts in sales leadership, AI, revenue growth, and go-to-market strategy. Subscribe wherever you get your podcasts. Mark Petruzzi (00:28) Welcome to Selling Intelligence. This is the full conversation with Dr. Noah Saint John. We have broken it into chapters in the description. Take it from the top or jump to the segment that's most relevant to where you are right now. Enjoy the show. Mark Petruzzi (00:28) Welcome to Selling Intelligence. This is the full conversation with Dr. Noah Saint John. We have broken it into chapters in the description. Take it from the top or jump to the segment that's most relevant to where you are right now. Enjoy the show. I'm Mark Petruzzi. KK Anderson (00:43) And I'm KK Anderson. Mark Petruzzi (00:45) Every revenue leader has watched the same thing play out. You hire strong people, you buy the technology, you fund the training, and performance still does not move. It does not improve. Our guest today argues that the constraint is not the skill set or the stack. It's what he calls the inner game, the internal wiring that determines whether any of it actually gets used. And Noah St. John has Close I spent close to thirty years studying it. We're really excited to have you here as well. KK Anderson (01:16) Dr. Noah St. John has authored 27 books. 27. Built more than 200 client funnels and documented more than 250 case studies of clients adding between 600 and 1,500% growth. He's also coined the term we are going to spend most of this conversation on called the human AI gap. We are running a 200,000 year old brain. against the fastest technology ever built. And the distance between the two is where execution breaks down. Noah, welcome to selling intelligence. Dr. Noah St. John (01:50) Thank you. It's great to be here. Mark Petruzzi (01:51) No as you have been doing this work since nineteen ninety seven. A lot has certainly changed in how industry talks about mindset and performance today than back then. What is your framework address that the standard mindset conversation misses? Dr. Noah St. John (02:06) Well, it's interesting you bring that up, Mark, because from my perspective, the conversation hasn't changed that much out there. They're basically saying the same thing they always have. I started in a three hundred square foot basement apartment with eight hundred dollars and a book on HTML. So I had nothing. I had no money, no marketing experience, no sales, no training of any kind like that. But what I did have Was something that I bet every single person listening to this program also has. And that is a deep burning desire to make a difference, to make an impact, to help people all around the world. And so I had been studying personal growth and reading literally hundreds and hundreds of success and self-help books for decades. And they all basically said the same thing: set your goals, work hard, use affirmations, all the same thing we've heard a million times. And I really tried to apply those things. I worked as hard as I could, but as hard as I tried, I couldn't seem to get ahead. I just couldn't get it to work. And so I was so frustrated by that that I realized that I've got to find a better way. And so after reading all those hundreds of books and spending so many years, that's when I realized, and I had literally had a flash of insight back in 1997. That's when I that's why I started the company back then. And I realized that we had been taught. How to succeed. We've been reading all these books called How to Succeed Books. Well, of course, that makes perfect sense, right? If you want to do something, you want to know how to do it, right? How to succeed. But what I realized is there was something that they were all missing. All of these books and all these trainers, all these gurus were missing right from page one. And that was they forgot to tell us that for millions of people, they never gave themselves permission to succeed in the first place. So, really, from my perspective, the conversation out there has really not changed that much. But the conversations that I'm having with my clients, that's what's really causing those increases that you mentioned a moment ago 600%, 800%, 1500% increases because of my frameworks. KK Anderson (03:57) and these are all in in sales, right? In go to market. That's the primary target audience for your programs. Dr. Noah St. John (04:04) Yeah, well, I mean, it's really all across industries. it's across literally dozens and dozens, scores of industries. real estate, chiropractic, health, healthcare, wealth managers, SaaS companies, just it literally runs the gamut because what I'm teaching is about the human the human KK Anderson (04:20) Mm-hmm. Dr. Noah St. John (04:21) mechanism. And as I have often said to my clients and in my keynote speeches when I give keynote presentations. You know, people who are running companies as an example, people who are in charge of companies or in charge of teams, divisions, organizations, they have all of the outer game stuff. They have all of the KK Anderson (04:35) Right. Dr. Noah St. John (04:36) outer things that they're supposed to be doing. But what are they doing to protect the three pounds of gray matter that runs the whole thing, that runs the whole team, that runs the whole organization? Usually the answer is nothing or not much. So that's what KK Anderson (04:48) Right. Dr. Noah St. John (04:49) I protect. And that's one of the reasons we see these enormous increases. KK Anderson (04:52) and so that's the term you use, inner game, right? Outer game Dr. Noah St. John (04:55) Yes. KK Anderson (04:56) and inner game. I love that by the way. Dr. Noah St. John (04:58) Yes. KK Anderson (04:59) and so walk us through what that distinction means in practice. So like our audience is largely chief revenue officers and heads of sales. So if you're s if you're talking to you know, one of a CRO sitting in a chair right now, like what should they be doing with the inner game and Dr. Noah St. John (05:16) Well, it really comes down to the fact that I am the nerdiest nerd in this industry. I'm such KK Anderson (05:22) Yeah. Dr. Noah St. John (05:22) a nerd. I'm like the Sheldon Cooper of self-help, the sel Sheldon Cooper of business growth. And what I mean by that is I'm such a nerd that when you read any of my books like Power Habits or any of my other books, I have tons of graphs and charts, but charts. But one of the things I love the most are Venn diagrams, right? We nerds love Venn diagrams. And so Mark Petruzzi (05:38) Ha ha. Dr. Noah St. John (05:39) my favorite Venn diagram of all time is a very simple one. It's just two circles that meet in the middle. On the one hand, you've got the inner game, and on the other hand, you've got the outer game. Two circles that meet in the middle. So inner game is everything that happens between your ears that you can't see directly, but it affects everything that you do. So for example, in my keynote presentations or workshops or leadership summits, one of the things that I often ask my audience members is, I'll say to them, What is one area of your life where your beliefs don't affect you? And here's what people do they go, And I go, exactly. There's no place your beliefs don't affect you, right? There's no place in your entire life where your beliefs don't affect you. Your beliefs affect your health, your wealth, your finances, your team, your career, your organization, everything. But here's the funny thing about it: you can't see a belief. You can only see the effects of a belief. And that's why people can be doing really well in one area of their life, but maybe they're stuck or struggling in another. For example, maybe. Your career is going really well. Maybe your business is going great, but maybe your health is suffering because you're working 80, 90, 100 hours a week. You see what mean? So yes, you're doing great in terms of career and money, but your health is suffering. And maybe your relationships are suffering too. You see? Or vice versa. Maybe your health is great, but you're not making the money you want. See? So it's, it's, it's not cookie cutter, one size fits all. It's a very bespoke, customized, personalized approach that we take with every individual client. So that's the inner game. But then we also have the outer game. Now that's the other circle. So the outer game is everything you can see directly. That's all of your CRM, all of the customer service, all the, you know, customer facing, market facing activities that you're probably spending tons of time, money, and effort on, which you should. You have to do that. But here's what's funny. So many people have spent so much time, money, and effort on the outer game. But nobody has shown them how to actually master their inner game. Now, let me give you a a real life example for one of my clients. I was speaking at a seminar in Los Angeles for a thousand entrepreneurs, CROs, CEOs, business owners, you know, seven, eight, nine-figure earners. Very successful crowd, right? So I was speaking, I only spoke for about 30 minutes. And I was walking off the stage, a man came up to me and he said, Noah, you are the coach I've been looking for. I want to hire you as my coach. Now, I didn't know this man from Adam. Ironically, his name was Adam. True story. KK Anderson (07:50) Yeah. Dr. Noah St. John (07:51) I said, okay, what's going on? He said, Well, Noah, I own this SaaS company and we grew to seven figures, four million in revenues really fast. But he told me, we have been plateaued for the past four years. Four years. We've been stuck at this level. And he said, I've I've thrown hundreds of thousands of dollars at this. I've hired every marketing guru on the planet, named all the big gurus. He said, we can't break through that income ceiling. And he said, as soon as I heard you speak about inner game and outer game and head trash and foot on the brake, everything you just said, he said, I knew you were the coach I've been looking for. So he literally decided to hire me on the spot. That's why I love working with high achievers, right? Because they make decisions quickly and friendly. Don't dilly dally. I gotta think about it or whatever. He just let's go. So anyway, KK Anderson (08:30) Nice. Dr. Noah St. John (08:30) I coached him and his leadership team for 18 months, just 18 months. And in that, in that time, in 18 months, we were able to get his company that had been stuck for the previous four years to over 20 million. In revenues in less than 18 months. That's a 600% increase, right? You talk about 600%. KK Anderson (08:45) Mm-hmm. Dr. Noah St. John (08:46) That's an example. We like to call that hockey stick, right? Hockey stick, you along like this, and then we install my frameworks and then you go hockey stick right through the roof. So what was amazing about that, and the lesson for everyone listening is he had, just like most people, had spent all that time, money, and effort on the outer game. And hey, it got him to seven figures. Nothing wrong with that. But he knew he could do more. He knew he was capable of more, but no one had been able to show him how to actually break through that ceiling. So it wasn't until I showed him how to actually master his inner game that he was able to do that hockey stick growth. So that's an example of how powerful this really is. Mark Petruzzi (09:19) Noah, that's that's really interesting and I'm sure really really helpful to our audience as well. So you have two hundred and fifty plus documented case studies and with almost every one of them or probably every one of them showing significant growth. When you look across these clients, what is the single biggest pattern that separates the ones who got those kind of results with Ones that maybe didn't get the same level of return. Dr. Noah St. John (09:45) Well, I love that question, Mark. And you're gonna you're gonna hate my answer. And it's gonna sound terrible. But the answer is that when people listen to me, they get hockey stick growth. If you don't listen to me, you're not gonna get that growth. That sounds terrible, right? But it's really true. And that's what we've seen. It's funny because I literally had a client years ago who said to me, and by the way, we were able to add seven figures to his business while he was taking more time off. And He said to me, Noah, do you realize that your coaching is the only coaching that fixes every other coaching? And I thought about that. And I go, You're right. Yeah, that's that's a that's a good way to say it. Yeah. I love that he said it. I didn't say that. I was like, yeah. and he also said, you know, Noah, when you actually do your power habits framework, it can never not work. And I said, Yeah, that's true too. Yeah, you're right. So the point is. If you follow it and see, I want people to realize that this didn't just come out of thin air. It came from, as I talked about earlier, literally years and years and decades of study, of reading hundreds of self-help books because I'm such a nerd. And by the way, I just want to mention something real quick because it I think it helps for the context. That, you know, where why I did this, because I grew up poor in a rich neighborhood. And I know that sounds like a total cliche. It's a total cliche, but it's true. I grew up in this little town called Kennybunkport, Maine. Which is one of the wealthiest communities in New England. KK Anderson (10:58) Ooh, wow. Mm-hmm. Dr. Noah St. John (11:01) But my family was dirt poor. I mean that literally, because we lived at the bottom of a dirt road in a drafty unfinished house. My parents ended up losing to foreclosure when I was just 15 years old. So I was very painfully exposed to the gap, the chasm between the haves and the have nots. The haves was everyone else, and the have nots was my family. So I hated being poor. I just hated it. We've all heard motivational speakers get on stage and say, Well, we were poor, but we were happy. We didn't know we were poor. Well, my family, we freaking knew we were poor. So it wasn't happy, Mark Petruzzi (11:26) huh. Dr. Noah St. John (11:26) it sucked. And so my point is that that was really the reason, the impetus be behind all the work that I'm doing today was I really hated growing up poor in a rich neighborhood. Because you know, driving around, going to school, and I go to my friend's house, and they'd have things like, food and clothes and stuff. And I'm like, wow, food, what's that like? I know I'm exaggerating a little bit, but still, you get the idea. But anyway, KK Anderson (11:46) Yeah. Mark Petruzzi (11:47) Yeah. Dr. Noah St. John (11:49) that's really where this came from. So it was my hunger. To not be poor, to that hatred of being poor, of growing up poor, which I was. And, you know, KK Anderson (11:56) Mm-hmm. Dr. Noah St. John (11:56) saying, but why isn't this working? You know, I'm re I'm reading all these books and they all say the same thing. Say it goes, think positive, work hard. Okay, I'm doing that. what's missing? And that's why, again, going back to my point, they made earlier, my first book, Permission to Succeed, and as you mentioned, 27 books later, you know, it really came from what aren't they telling us? What is missing? Because they're all talking about surface stuff. there's nothing wrong with the advice. You know, work hard. Okay. Yeah, thanks. I mean, no kidding, right? It's like saying, breathe. Remember to breathe. thank you. I forgot. what I'm saying? Again, KK Anderson (12:28) No. Dr. Noah St. John (12:28) I'm I'm exaggerating a little bit, but not much. So that's that's really the point of where this work comes from. So it's a point to answer your question. That's where this work came from. A very painful, frustrating place. KK Anderson (12:38) Well Dr. Noah St. John (12:38) And you know, really the purpose of my work is to help other people avoid that pain and frustration. KK Anderson (12:42) That sounds like a definitely a formative story. And especially in Kenny Bunkportman, I could only imagine. Noah, let's let's move on to our second topic, which is the human AI gap. And when we met and chatted, you talked about taming the caveman in your brain, which I thought was hysterical. Dr. Noah St. John (13:01) Thank you. KK Anderson (13:03) so before we get into, you know, what to do about it, right? Describe the gap for me. itself. Like what's actually happening when a capable sales leader struggles to adopt and leverage AI? Dr. Noah St. John (13:14) Okay, so as everyone listening to this program knows, this is like the biggest conversation right now, probably in all of business, you know, let alone in terms of sales and selling and all of those things. But absolutely the biggest conversation is we have this enormous influx of AI, artificial intelligence, and it's everywhere. But why is it not really landing? Why is nothing really working? Why is it not changing? Why is it not helping our bottom line? This is the biggest conversation that I'm hearing, across the board. And so this is where my work now evolved basically, if you think about what we're really talking about, we're talking about human psychology, right? And I mean, you both know how what a great topic that is. And I know this show is all about that. And that's what all sales is is we're talking about human psychology. Humans do what they believe is in their best interest in the moment. That's Dale Carnegie 101, right? So but if we go back much further than that, when we're talking about humans, We're talking about the fact that we have, as I like to call it, a caveman brain. The human being, as we know it today, Homo sapiens, most experts agree that it was evolved about 200,000 years ago. About 200,000 years ago, about 10,000 generations. Right? So we humans have evolved, and here we are, right? 200,000 years later. So what's interesting is not much has changed with the three pounds of gray matter upstairs here in those 200,000 years. Not really, not much. All right. We humans, the brain is very much like a computer, right? We've heard that many times. A computer, of course, has hardware and software, right? So the hardware hasn't changed that much in 200,000 years. But the software is what is where the human AI gap is coming in now. And what do I mean by that? So you've got this 200,000-year-old brain, hasn't changed that much. It's up against the fastest technology that's ever been invented by humankind, AI. So here is the battle, friends. It is happening in your brain right now. 200,000 year old caveman, fastest technology ever built. Boom, there's the battle. Who do you think's winning? Exactly. You got it. The caveman's winning. Caveman's gonna win every time. That's precisely what no one's talking about. This right here that I've been sharing now is exactly the point that everyone is missing. They're missing it because they keep going on the outer game. See how this is all coming together? They're focused on the outer game, right? Well, we got to throw more tools at them. You know, buy but spend more on AI. Spend more on no, no, no. I'm not saying those things are wrong or bad. I'm saying you're missing the entire point. The entire point is this caveman in there. And the caveman does one thing. Its main job is to keep you not dead. That's its main job, is to keep you not dead. Now, what's the best way to keep you not dead? The best way to keep you not dead is don't go for something you're scared of. If it's scary, it might bite your head off. It could be a saber-toothed tiger. It could be a woolly mammoth that will trample you to death. Right? Now, of course, we KK Anderson (15:57) Uh-huh. Dr. Noah St. John (15:58) don't have a lot of saber-toothed tigers and woolly mammoths anymore. But guess what? AI is that to the brain. The K-Man's going, it looks scary. I mean, let me give you some concrete examples. Now, when I started my company, SuccessClinic.com, in 1997 in my 300 square foot basement apartment, that was the very beginning of the internet revolution, right? And I'm sure. Many people listening can remember being online in the 90s. Remember that? Remember KK Anderson (16:22) Yeah. Dr. Noah St. John (16:22) that? I mean, it was pretty bad, right? But I mean, that's what we had to deal with. So, you know, that was the internet revolution. I was there at the very beginning of it. And it was just me and Al Gore back then. Now that joke doesn't land as well as it used to, so I'm gonna stop telling that joke. Sorry. But anyway, I Mark Petruzzi (16:34) Ha ha ha. KK Anderson (16:35) You're dating your you're definitely dating yourself, Noah. Dr. Noah St. John (16:38) know, right? Terrible. All right, we're gonna scratch that joke. But anyway. The internet revolution, if you remember, took about seven years to reach its zenith. About seven years. Well, guess what? Here we are in the second revolution, the AI revolution. It only took about seven months. So it's literally ten times faster. The K-Man hasn't changed. The hardware's still there. The software is is freaking out right now. So there's that human AI gap that I talk about. So I unpacked a a lot of it. There's still way more to unpack, but I hope that answered your question. KK Anderson (17:04) So what's the answer? How do we ta how do we tame the brain? Dr. Noah St. John (17:08) Well, one of the first things that we do is we have to understand what type of caveman you are. Because I have realized that there are four distinct caveman types that we have, right? Because everybody's different. So there are KK Anderson (17:19) It's a great idea. Dr. Noah St. John (17:20) four distinct types. So, like you talked about disc earlier, this is Similar but different. All right. You know, in this they talk about the D I S C, whatever. But the four types are the chief, the spark, the keeper, and the watcher. All right. So the chief is exactly what it sounds like, right? The chief. So I'll give you an example from 200,000 years ago. Okay. So there's a woolly mammoth over there, and you're hungry. All right. So what are you gonna do? Well, if you're a chief, What you're gonna do is you're gonna just rush over at the woolly mammoth and grab your spear and try to kill him. Right? Just let's go. All right, charge, full speed ahead. Don't think about it, but don't hesitate. Okay, so that's you know, it's fine. I mean, that's nothing wrong with that. Remember, everybody has pros and cons. Nobody's perfect. Everybody has, good news and bad news, strengths and weaknesses, right? So for a chief, their strength is action, right? Determination. Boom, let's go. What's the drawback? not so good at delegating, maybe not so good at listening. You know, Steve Jobs, classic chief, right? Steve Jobs, famous for not having so much patience, shall we say, right? So a great example of a chief there. All right. So that's the chief. Then we have the spark. The spark, okay, sees the holy mouth. Hey, everybody, let's go. All right, let's all get together. Well, we'll all charge them. All right, let's go, let's go. And so the spark is like that natural salesperson, right? There, they could sell ice to an Eskimo. They got great personality, the life of the party, right? That's the spark. They were probably the one who invented fire. Boom, boom, boom. Hey, what does this do? wow, look at that. Isn't that cool? Right. So that's the spark. Right. Then you have the keeper. Now the keeper looks at the looks at the volume man and they go, you know what? We gotta make sure that the women and children are safe before we charge. Okay, because this KK Anderson (18:45) Mm-hmm. Dr. Noah St. John (18:45) is really important. I mean, we don't want them to get hurt. All right. This is this is dangerous. So, all right, let's just make sure that they're safe. Everybody's safe. See, so they're the keeper of the flame, right? So they're that that just that warm type. We all know someone like this. My wife is KK Anderson (18:58) Yeah. Dr. Noah St. John (18:58) like this, right? She's the warm, the always giving a hug, right? We all know someone KK Anderson (19:01) The Guardians. Mm-hmm. Dr. Noah St. John (19:02) like that. That's the keeper, the keeper of the flame, the keeper. of the community, right? Very important. Right. So remember I talked earlier, strengths and weaknesses, right? So the Spark, going back to the Spark for a moment, right? Their strength is, they're great personality, sell ice to it as well. They're one of their weaknesses is follow through. they might forget to send that email, might forget to send the invoice, right? And they're they're like, they're great at starting, but they not so great at finishing, right? The keeper, in the same regard, great, great, loving, you know, warm, Relationships are great, KK Anderson (19:31) Mm-hmm. Dr. Noah St. John (19:31) but maybe they find it hard to speak up for themselves. Maybe they have trouble asking for a raise, right? So that's the keeper type. And then finally you have the watcher. Now, what's the watcher gonna do? The watcher is gonna do exactly what it sounds like, right? They're gonna watch, they're gonna observe, they're gonna, they're gonna track the migration patterns over three months and say, okay, now if we go over here and see, then they we can trap them right in this. ravine here and then KK Anderson (19:52) Yeah. Dr. Noah St. John (19:52) because they go through and see they're the ones that were drawing on the caveman on the caveman wall, right? On the cave walls. Right? Because KK Anderson (19:56) They're looking at details. Mm-hmm. Dr. Noah St. John (19:58) that okay, we gotta track it. You see what I mean? As you can tell, obviously I'm a watcher, right? I'm I'm the nerd. That's the nerd, right? Back caveman nerds. That was us. That was spreadsheets back then. So KK Anderson (20:08) So then how so your style then determines how you handle AI and how you react to AI. Dr. Noah St. John (20:14) to a great degree, yes. To a great whether you're a chief, spark, keeper, or watcher, and KK Anderson (20:19) Mm-hmm. Dr. Noah St. John (20:19) you know, literally what to watch out for based on your caveman type. KK Anderson (20:22) Okay. Mark Petruzzi (20:23) So Noah, at AGS we say all the time that AI amplifies whatever motion you already have, good or bad. And not even emotion, whatever general energy you have going into a particular process, it can it amplifies that. Well that cause a lot causes a lot of of unintended consequences along the way as well. So that also means that execution quality is the prerequisite for AI deployment. Does that match what you are seeing with clients right now? Dr. Noah St. John (20:55) Well, yeah, I mean, the point is that I I wanted to talk a moment again about the internet revolution versus the AI revolution. Right? These KK Anderson (21:03) Mm-hmm. Dr. Noah St. John (21:04) are the two revolutions that we've literally had over the last 30 years. Okay, so going back to the internet revolution, now what the internet revolution did, at least from my perspective, one of the things that it did was it leveled the playing field. So here I am, you know, this guy in Hadley, Massachusetts, no money, no connections whatsoever. But what did I do? I created a website. I built one of the very first personal development, business development websites on planet Earth, called it successclinic.com, boom. And instantly I can compete all around the world. That was never possible before. So the internet gave us all, it empowered us. It gave us all that opportunity that never existed before in human history. Never. Because think about it. Before, you know, you would have to buy a printing press if you wanted to have a newspaper. That's pretty darn expensive. You have to buy a radio. Station, you'd have to buy a TV station. These are all very, very expensive propositions. But hey, you just put up a website, boom, you can start selling, and that's exactly what I did and what millions of people did back then, right? And have been for these last 30 years. Well, now with AI, what are we hearing? All we're hearing is AI is coming to take your job. That's all we're hearing. In fact, what's sad and funny is that in the graduation period that we just had recently, and I'm sure we all heard stories about the fact that. graduate speakers were getting booed off the stage at these graduation ceremonies at major colleges and universities all across the country. They were getting booed off the stage because they were saying about AI. And AI is coming to take your job or whatever they were saying, boo, you know, so what I like to say is internet, yay, AI, boo. And that is what so many people are experiencing right now. So what we're also talking about Is human emotion, right? We're always talking about that, at least I am. And the two main emotions that we're dealing with here are human fear and human greed. Human fear and human greed. Now, let's look at capitalism, right? We're running a business. You're you're a CRO, you're a CEO, you're a CMO, you're running a company, you're running a team, you're running an organization. What's your job? Your job is to increase bottom line, your job is to increase profits. No kidding. That's a capitalist society. So you look at this thing called AI and you go, ooh. Hmm, now wait a minute. We have to pay these annoying things called human beings. Now, human beings are incredibly annoying. Number one, you gotta pay them. Number two, they're always complaining. Number three, they take time off. Number four, they have families. Number five, they take vacation. I mean, what is these? What all my what we could do? Why don't we get rid of these annoying things called human beings? And we'll just have the robots do everything. Huh, that sounds great, says everybody on this side of the ledger, right? Human greed. But then what about this side of the ledger? Human fear. Everybody who's an employee on the other side of that ledger goes, my gosh, AI is coming for my job. And that's everything they're hearing. So why do you think they're getting booed off the stage? Internet, yay, AI boo. So that is where we have to. If you're a leader, what do you do? How do you attend to that? Well, you have to just first of all just take talk about it. You have to tell the truth to the troops. You have to tell them the truth. Are they being replaced? Or you don't know? Tell them you don't know. I was just reading about the fact that a pilot, this is just made national news, an airline pilot was recently applauded at Atlanta, the Atlanta airport, because he announced the fact that the flight was gonna be late. Now, when was the last time you heard about a pilot being applauded for a flight being late? And the reason is because the pilot did something very smart and very simple, which was he just told the truth. He said, I'd like to announce to everybody that we are gonna have to delay the flight. Because I made an inspection and I'm not satisfied that this plane is safe for takeoff and landing. So I'm having make sure that it's everybody safe. And so yes, we will be delayed. And I apologize for that. This is not the gate agent's fault. Don't take it out on them. It's all it's all me. It's my decision. Hung up and everybody applauded. Now, isn't that beautiful? We can all learn from that. That's the type of thing you have to do as a CRO, as a CEO, as a CMO, as a leader, as a team leader. These are the types of things we have to do now as a KK Anderson (24:47) Really, really great stuff. Okay. this is where we are going to pause part one, audience. And what Noah just has just described related to the inner game and the mindset is actually the work we do inside the two millimeter club here at AGS. It's our small group data-driven coaching program for frontline sales managers. And they learn to identify and coach. The small shifts in seller behavior that are largely related to that inner inner game that that Noah talks about that add up to exponential movement in pipeline. there's six months cohorts, six month programs, cohorts launch monthly. And you're welcome to go apply at get-ags.com forward slash two mm club. Again, it's get dashags.com. Forward slash two millimeter club. Join us next week for part two with Dr. Noah St. John. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 136 - The Trust Recession, the Death of the BDR, and the Return of the Full Cycle AE with John Tecce - Part 2 | 22 juil. 2026 | 00:22:06 | |
General Episode Description: In Part 2 of this Selling Intelligence conversation, John Tecce, Vice President of Growth at 2X, explores what the next generation of go-to-market organizations will actually look like as AI, automation, and human expertise continue to converge. John explains why the future isn’t about replacing people with AI, but combining human judgment with agentic workflows to create faster, more adaptive revenue teams. He shares how organizations can break down departmental silos, rethink traditional operating models, and shift from fixed headcount to more flexible, scalable growth strategies. The discussion also dives into practical examples using platforms like Gong and Clay, why most AI initiatives stall before delivering business value, and how today’s revenue leaders can prepare their organizations for a fundamentally different way of working. What You’ll Learn:
Key Topics:
Guest Spotlight: John Tecce John Tecce is the Vice President of Growth at 2X, where he helps B2B organizations modernize their go-to-market strategies through the combination of AI, automation, and human expertise. He works with enterprise leaders to build scalable revenue operating models that improve efficiency, accelerate growth, and prepare organizations for the next generation of GTM execution. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more conversations with the leaders shaping the future of AI, sales, and go-to-market strategy. Subscribe wherever you get your podcasts. Mark Petruzzi (00:38) Welcome back to Selling Intelligence. If you're joining for the first time, this is part two of our conversation with John Tesey, Vice President of Growth at 2X. KK Anderson (00:49) In part one, we got into why digital outbound has hit a wall and why the BDR to AE model is collapsing and what they've done at 2X to remedy that and how they're working with their customers to overcome it. We talked a lot about how we're back to old school with sending things like in-person Vino letters and how we can build our new go-to-market engine so that we're harnessing on what is human and how we combat the trust recession. It's an excellent session. Please go back and listen to it. Mark Petruzzi (01:20) In this half we get into what human agentic go to market actually means in practice, how 2x is helping clients turn fixed headcount into flexible spend, and what every CRO can do before they buy another tool. John, let's pick it back up. KK Anderson (01:36) All right, welcome back John. John Tecce (01:37) Thanks for having me back. KK Anderson (01:38) 2X just called itself the first human-agentic go-to-market services firm. Really cool. Unpack that for us. What does human-agentic actually mean in terms of how work gets done on a client engagement? And tell us, tell us more. John Tecce (01:54) Let's start with the humanagentic and then we'll go into go to market. So humanagentic, what you're seeing across the board right now is software and services are converging. and there's been this sort of hard line between like what are we doing with tech and we're bringing in tech and it was a very linear process. We're gonna buy the tool and then we're gonna later either buy the services or figure out the operating model for how to operationalize the tool. And it was very sort that waterfall style of things and and as you were buying more tech and tools, you were sort of trying to layer on the the skill set and operating model. And really at this point, and and arguably before this point, but certainly now, what we're finding is the customer doesn't care whether it's technology or product or people that's getting the work done. They care, are you getting the work done? And is there a human accountable to that work getting done? And so as a as an organization, we have now you know we've pioneered the marketing as a service space. Starting about about a decade ago with the formation of 2X and the creation of that category. And then as we've seen this shift, and we'll get into go-to-market shortly here, but into how work gets done, and and most of our clients are trying to accomplish growth at the fastest possible and lowest possible cost way, this humanogenic way of getting the work done really is the the path forward and is the the killer app of this generation, if you will. And then from a go-to-market standpoint, what we've seen is the convergence of The last probably two decades, we've seen the bifurcation of marketing, sales, and the customer office, right? with the establishment of, as we talked about before, the BDR function is the go-to-market and the handoff, and now the client office with CSMs and account managers. And what we've found is sort of a back to the future moment where everybody realized the customer is at the center of this, whether it's a prospective or current customer, we're all using the same tech, we're all using the same data, and we're all responsible for driving growth for the company. So why are we operating in these silos when really at the end of the day, we're all trying to drive towards a revenue target? So we've found that the convergence of software and services, along with this conversion of go-to-market, you've seen a lot of GTM titles lately that have popped up as a result, have led to this moment where human and AI are able to effectively deliver upon that, while at the same time there's less of a concern at a siloed level of on the client side who owns it. They all own growth. Mark Petruzzi (04:01) So John, two of two X's top partnerships are gong and clay. Walk us through a specific use case where the combination of these tools with human judgment produces an outcome that neither can produce alone. John Tecce (04:15) Yeah, so it's interesting. with most enterprise data is unstructured. It's in emails, it's in Slack messages, it's in video transcripts, it's in these Gong transcripts, right? and so we we acquired a a top implementation partner of Gong last year, outbound funnel, with in mind this convergence that we talked about. We were in marketing as a service, as a category, we created it, we've led it for a while. we saw this convergence happening, said, hey. There's so much richness from a go-to-market standpoint that is in Gong transcripts. While at the same time, Gong themselves have also gone through a convergence in RevTech and moved into with like Gong Engage, right? And being able to become a full full platform revenue provider. And so we we kind of saw this happening. And then at the same time, we saw the emergence of go-to-market engineering with clay as the as the primary platform there in terms of data enrichment. as you both know, and I'm sure all the listeners know, the number one hindrance to scale personalized outbound is data, hygiene and cleanliness, as well as the ability to then activate it with with agentic workflows. And so we acquired Clay's largest partner earlier this year as well. And so when you think about that combination of things, you're looking at a place where, hey, we have the ability to now synthesize prospector client transcripts, right? And we have the ability to then and drive better segmentation hygiene and agentic activation of contact data. And so you're in a place now where the future vision you can look forward and say, well, wait a minute. There's a very simple way for us to take, for example, a a conversation had at 9 a.m. you know with a with a prospect and that transcript can be synthesized by a commercial intelligence platform maybe like known while for example two extras acquired but the the concept remains hey we can synthesize that even just an AE could look at it and say cool wait a minute I could go flag to a go-to market engineer in my organization who could use clay to then immediately enrich and say, okay, client mentioned these three things. Well, do we have contact data for the people at the company that would own those things? Maybe yes, maybe no, maybe it's unclean. All right, well if we could update that and then we could use clay to run an out an automated outbound play to them about a product or service that they mentioned on this call, right? Now you're looking at the same type of effect that In B2C, we always joke that our devices are listening to us, right? All of a sudden you see you get served an ad for something that was mentioned. To be clear, I'm not promising any of that any means. all of what we just talked about is sort of art of the possible and systems architecture work with with agents and and humans involved. But that's the type of thinking when we think about go to market, we think about where does a gentic play in, where do where do off-the-shelf tools like Gong and Clay kind of come in. And that's the exciting a lot of the conversations we're having with our clients right now around, okay, I've made investments in these tools. KK Anderson (06:29) Mm-hmm. John Tecce (06:44) But also I know I need to build out with Agentik and I know I need a human in the mix. how do we do that? And and as a firm, we are in that human agentic world to be able to help. KK Anderson (06:52) So to be able to do that, you can't have a world where you're operating in silos. It's all cross-functional workflows that, it just feels very different than what we all learned in business school. John Tecce (07:05) And how the organizations are structured. That's the other th part that I think we've noticed is a lot when you talked about operating model earlier, a lot of organizations were okay, well, RevOps owns Gong and marketing has the marketing automation platform and Clay was brought in by somebody and and hey, we're all messing around with Claude or Chat GPT and having to to organizationally bring everybody together to start to make those decisions together, it's a forcing function for that to start to happen. It's been a very interesting exercise over the last couple of months as as everybody's starting to think through what this agentic future looks like. KK Anderson (07:34) So, and like in just another example that a client of ours is working through with agencies, Gong picks up a CSM talking about a potential upsell or cross-sell, and then it immediately fires off an email to the AE saying, hey, this just happened, like it's live. Call them now, right? There's so many different things they could do. So with your clients who are building the art of the possible and I know it's all happening in real time and it's new and not a lot have, right? Not a lot, there's not a lot of frontier organizations out there truly that have gone past just using Claude and GPT. Like what are some best practices around orchestrating these kinds of things? Is it just another, is it another platform or another tool that you're using that's gonna hold all of these agents in these workflows or like what does that look like? Like when you're, and I guess my last question is, when you're talking to clients about these things, like what, what kind of objections do they have? Like where does it break? Like where does this human agentic like model, I don't know. Tell me what you think. John Tecce (08:36) Yeah. I'll start with the latter. Where does it where do the conversations break? The first one is in very similar to a decade or a decade and a half ago when the IT part of the organization was navigating the shift from on-premises storage and compute to cloud-based storage and compute with AWS and Azure and later Snowflake and Databricks. it's the same conversation about fixed cost to variable cost. KK Anderson (08:54) Mm-hmm. John Tecce (09:02) We are seeing that as a organizations are not currently prepared to, especially in go-to-market, break the predictability of their CAC or of similar metrics of understanding, okay, well, what is this gonna cost me? Everybody is aware of the ceiling of AgenTic and of these operating models and the flexibility and tools like clay that are consumption-based and token tokens are the big topic right now, cost of tokens and governance. KK Anderson (09:25) Right. John Tecce (09:27) And the first thing that happens is everybody realize, whoa, okay, wait a minute. We might be limited in our our ability and our output right now, but we also have cost predictability. And so what I think the number one thing that's holding back most organizations in this way is is that conversation. And then the unknown, exactly. The unknown and just the the the very way that they account for customer acquisition cost, for sales productivity cost, a lot of a lot of those measures. Mark Petruzzi (09:34) Yeah. KK Anderson (09:43) The unknown. John Tecce (09:52) So that's I think the first thing. I think the second thing does become a very boring but necessary conversation about accountability, races, SLAs. Okay, well, as we're building this out, the big difference between the peers in the IT organization and the go to market organization is when IT was making this decision, they had visibility to their workloads. That's how it works in IT, right? You can see, okay, these jobs are passing through the server to the compute. We have the it's all metric, right? It's all there. You had IT tickets and SLAs and things like that. Go to market organizations do not have workflow visibility. They do not typically have strong SLAs. and that's one of the key core components to anything that is going to be agentic by nature is understanding what is who is accountable for what. what is the baseline? And are we just smashing the AI button because I saw somebody on LinkedIn say they automated an entire thing with Claude over the weekend. Or are we actually trying to solve a problem against a meaningful baseline? And I found that most organizations do not have a baseline within which to measure. And their AI mandate is just, I don't know. I see everybody else on LinkedIn doing all this cool stuff, and you know, we should be doing it too. I feel like we're behind. and so that's often where I think I see it break the last of the three would be kind of a related point but the o the political ownership of it. well, hey, The the revenue office, they signed the clay contract and we're marketing and we can't really, you know, that's that's their licenses, that's not my licenses, right? Or hey, sales ops owns the gong instance, and we can't really, you know, it's a pain and whatever. And so there's a lot of those political realities and organizational dynamics that we are finding, especially as you'd imagine, the further up market you move in the enterprises. But there is a lot of that technical operational and organizational debt that's getting in the way of those conversations. the ones that we're seeing move the fastest right now, of course, are more blank slate in nature, but not, you know, are yeah, we're seeing like, you you're seeing the startups and the and the solopreneurs move fast because they got no other that that's what they're they can do. But that like, you know, 300 to thousand person, you know, B2B SaaS organization, right? Where there's they're well funded enough to be able to make the investments, but they're not hampered by a lot of that organizational. at that are really able to make those decisions of hey, I don't need to go hire three more people. I don't need to bring in more tools in a monolithic way. I just need to go like build out in this agile way. Those are the ones that I'm seeing the most that are able to move the fastest. Mark Petruzzi (12:08) Great. All right. Well, let's move to our final topic with John. The operating model rethink, what to own, what to outsource, and how to decide. So John, you described the conversation you are having with clients right now about converting fixed headcount into flexible spend. Walk us through how that conversation starts and what's the core question that opens it up. John Tecce (12:30) Typically the core question is some type of organizational mandate. Everybody needs to grow. Everybody wants that the growth is always a target, right? But the question is, are we is our operating model aligned with growing to that rate in any realistic way? Right. And if the answer is yes, then great. You can probably make incremental improvements and iterations to get there. If the answer is no, our operating model is not physically or operationally aligned with getting to that growth target. Okay, we need to rethink this. our our position on this is there's really kind of three layers to thinking through it. And this comes from our our CMO, Lisa Cole, who put out a book recently on this exact topic around what what you need to own, what and and from our perspective, that's what you need to be the best in the world at. Those are your differentiated for your organization capabilities that only you can deliver in a best in class way. And a lot of times that requires deep corporate knowledge, deep market knowledge, segment knowledge, those type of things. So think brand strategy, think product marketing strategy from a CRO standpoint, targeting, the pricing and packaging, like things that don't you can outsource getting help on, and you should probably get get advisory on that, but you need to own those decisions in-house. What we found, and most organizations have found, is the vast majority of the jobs to be done that don't fit that category can very easily be outsourced and or automated. And I think the and or is really the key here. A lot of organizations are also thinking through: okay, I have a cost reduction mandate, I have a growth mandate, and then I have an AI mandate. How the hell do I thread that needle? our perspective is ultimately if you are locked up in fixed headcount. which most organizations are at a pretty high level, you are not in a position to have that sort of slider on this on the jobs to be done to the AI component. You can DIY it, but it's going to take you longer, which is going to then distract you from your current growth target. It's also probably not going to get you to the point you need to get to from a cost reduction standpoint. So our position is to look at that as a jobs to be done exercise and then be able to set your operating model up in a way that allows you with that slider flexibility to to automate or not automate. Maybe we go too far with automation and then hey, all right, we gotta we gotta back that out, right? versus if you make if you're absent that flexibility, you're in a pretty tough position in this currently a very dynamic market. so those are kind of the the way we we help clients think through it. and of course self servingly probably recommend to to find a partner from a humanogenic services perspective to KK Anderson (14:50) Sure. Absolutely. And last question before we move into the rapid fire questions, which we know is everyone's favorite. So you are inside a firm that's actively building the model that, as we've chatted about, most CROs are still trying to understand. So what would you say is the single most common mistake that you see leaders making? when they're trying to rethink their operating model and what does the version that actually works look like? Where would you point someone to get started on? John Tecce (15:21) I think the most common mistake is is unfortunately at the human level of not accepting sooner how different the operating models will be going forward and needing to make tough decisions to get there. And that's a that's a that's a difficult conversation to have across the board in terms of of looking at your operating model, looking at your work structure, looking at how you built the organization, understanding that decisions that were made even prior to February of this year when Claude Cowork went generally available. We're in a fundamentally different world in June of 2026 than we were even in February or March. And not, you know, there are emotions tied to that obviously, but also being having the pragmatism of understanding that KK Anderson (15:54) Wow. John Tecce (16:03) reality and then being able to act accordingly. you know, that's it's hard. That's that's probably the hardest thing. And it's hard to even call it a mistake at a human. I have a team. I love my team. and and and the organization around us as well. But at the same time, you know, as companies continue to transform, like having that vigilance and not viewing January 2026 as recent, I think is probably the biggest one. Mark Petruzzi (16:18) Yeah. KK Anderson (16:24) Right. One of the things I would say is that I feel like the product owner may say, yeah, but that's mine. That's product. That's in my lane. But that's a marketing thing. You need to go talk to the marketing person about that. That's a sales thing. The second they start thinking in these departmental silos, that's, I think, where the first mistake is. It is so hard to. And that's really the job of today's CEO is how do you break the mindset to where people aren't thinking that? They're not thinking like departments. They're thinking like, cross-functional handshakes. John Tecce (17:00) And and I think thinking about the the the okay, well last time I did this, I hired this role and I hired that role and I hired the third role. it's a different world now, right? So even just I see this with go-to-market engineering right now. A lot of people say, we'll just go hire a go-to market engineer. Okay, well that that title hasn't existed for longer than about twelve months. Number one, do you even know what a go-to-market engineer is? And and we're hiring them to do what? To do the AI thing. They're gonna help us build. Okay, well, to do and like starting to get so also defaulting off of I'm just gonna run the same playbook I've run and maybe I'll just plug in a new fancy title to do it versus fundamentally rethinking how the work gets done, the jobs to be done part of it, and then backing into it that way. I think that's what the you asked about what the version that actually works, the organizations we see that are leading there are the ones that are breaking it down, not by what is the title that's gonna do the work, but the jobs to be done and how do I optimize those jobs to be done. KK Anderson (17:50) And are they just taking their C-suite and putting everyone in a room and... battling it out until they figure it out. John Tecce (17:56) Seeing more of that than I I've seen certainly in the years that I've been here. number one. Number two, it seems they're they are starting to appoint a VP level person to own them. I was just on with with someone in a private equity back SaaS company this week whose title is VP of Go to Market Transformation. She was in the ops, I think RevOps function prior to that. but they tasked her with, no, you we need to do this and you need to be the cohesive person to go drive this across these organizations. At both an executive alignment standpoint and also a director and functional level alignment standpoint. And so I do see that as well. KK Anderson (18:26) Okay, this has been a fabulous interview. Let's do some quick rapid fire. And it does need to be rapid, because I know we've all got hard stops coming. Mark, why don't you kick us off? Mark Petruzzi (18:36) All right. So John, what was the first product or service you ever sold? John Tecce (18:40) I sold copiers and multifunction printers for Rico in Montgomery County, Pennsylvania, not too far from where I'm standing right now. KK Anderson (18:47) That's awesome. Who is your favorite CRO or CEO that you follow? John Tecce (18:52) Who that I follow. well, I've quite literally followed RCO or Ryan Heineg now to three different jobs. So I have to from a career standpoint, I I guess I have to say him. but I really like a lot of what what Jeremy Donovan puts out for for insight partners. candidly we're insight-backed pork co, so I guess I have to say that, but I do like a lot of his insight. Mark Petruzzi (18:59) Huh. KK Anderson (18:59) There you go, that's good answer. Ryan Haying. Mark Petruzzi (19:11) All right, so a leadership or go to market practice every sales and marketing leader should adopt. John Tecce (19:16) mindfulness and at least encouraging some various forms whether it is meditation, whether it is breathing exercises, whether it is therapy, whether it is something like that, perfectionism is something that plagues the B2B sales profession in particular. and viewing a lot of these mental and emotional ways to develop, you know, through that, I think is is paramount. KK Anderson (19:34) Wow, I love that. Okay, and my favorite last question, advice you would give your 21 year old self. John Tecce (19:40) it's all temporary. Everything is temporary. Every rejection you get, every win you get. to stay neutral, I think, to borrow a a term that I've seen quite a bit of late, from from Trevor Moad, the late Trevor Moad who wrote two books on this topic, but stay neutral, you know, I had a gentleman who I worked directly with who was about twice my age when I started and I'll never forget I was melting down by a customer issue. He's like, You're not even gonna remember the name of that customer in twelve months. You know, at twenty, twenty one, twenty two years old and he was right. So I gotta give him credit for that. KK Anderson (20:04) Yeah, yeah. I love it. Mark Petruzzi (20:07) John, this has been the kind of conversation our audience needs right now. so thank you for that. An operator who already made the decisions most leaders are still avoiding and who can speak from inside the results. before we let you go, please tell the audience where they can find you in 2x, the firm, the podcast, whatever you want to point them to. John Tecce (20:26) all of the above. So you can find us at 2x.marketing, although I believe the dot marketing will change with the convergence of GTM. So we'll stick with 2x.marketing for now. 2x on LinkedIn. you can also find me personally on LinkedIn. My last name is TangoEcho, Charlie Charlie Echo, T-E-C-C-E. There's not many of us. you'll either find me or Michael T C, my father, who does a lot of good stuff on LinkedIn too. So add him while you're there. and and follow all of the above. KK Anderson (20:50) Awesome, okay, we will make sure to include all of that in the show notes. John, thank you so, much. This was a genuinely productive two sessions. Thank you. John Tecce (21:00) Thank you. Mark Petruzzi (21:00) From selling intelligence, I'm Mark Petruzzi. KK Anderson (21:03) I'm KK Anderson. And one more thing before you go. If you'd like to go deeper on how to set up agentic workflows for your go-to-market motion, contact 2X for sure. And if you want to learn how to do it, head to get-ags.com forward slash academy. We have expert accelerators and career operators who have built workshops specifically for revenue leaders navigating this shift. Some of them are complimentary, so go and get yours today. It's worth your time. Thanks so much for listening. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 135 - The Trust Recession, the Death of the BDR, and the Return of the Full Cycle AE with John Tecce - Part 1 General Episode Description: | 15 juil. 2026 | 00:24:34 | |
In this episode of Selling Intelligence, John Tecce, Vice President of Growth at 2X, joins Mark Petruzzi and KK Anderson to explore why traditional digital outbound is losing effectiveness and what today’s sales organizations must do instead. John shares why B2B selling is facing a “trust recession” fueled by AI-generated communication, rising outreach volume, and declining buyer confidence. As inboxes become saturated and automation reaches its limits, he argues that sales leaders can no longer rely on activity metrics or volume-based prospecting to generate predictable pipeline. The conversation also examines why 2X intentionally built its revenue organization without BDRs, why the full cycle AE is becoming increasingly important, and how timeless sales fundamentals like relationship building, trust, community engagement, and human connection are becoming competitive advantages once again. Mark, KK, and John discuss why quantity is no longer the best predictor of sales success, how experienced sellers can combine AI with classic sales principles, and the mindset required for modern account executives to thrive in an increasingly uncertain market. What You’ll Learn:
Key Topics:
Guest Spotlight: John Tecce John Tecce is Vice President of Growth at 2X, where he leads half of the company’s revenue organization with a team of full cycle account executives operating without a traditional BDR model. A third-generation sales professional, John combines classic relationship-driven selling with modern AI-enabled execution. He has become a leading voice on the future of go-to-market strategy, helping organizations rethink outbound sales, trust building, pipeline generation, and revenue operations in an increasingly AI-driven marketplace. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more conversations with today’s leading revenue operators, sales executives, and GTM innovators. Subscribe wherever you get your podcasts. Mark Petruzzi (00:28) Welcome to Selling Intelligence. Our guest today is John TC, Vice President of Growth at 2X, the firm that just its declared itself the first human agentic go-to-market services firm. John runs half of 2x's revenue organization, a team of 12 full-cycle AEs with no BDRs. And he is third generation sales who has spent the last year watching the tools that built his career stop working at scale. Two X recently announced its acquisition of known well, and John has a front row seat to where the market is heading. KK Anderson (01:05) Personal note before we start, when John, Mark and I spoke in preparation, we landed on the same diagnosis from two very different directions and he is living it inside his own team and we are diagnosing it with clients every week. The instinct everyone has is to add more activity. John's answer is the opposite and that's what makes this conversation well worth your time. Mark Petruzzi (01:30) Here are the topics we will cover today. In part one, three things: why Digital Outbound has hit a wall and what that means for every CRO. The death of the BDR and the return of the full cycle AE. And old school fundamentals through new mechanisms, how the best reps apply forever concepts through AI-enabled execution. Then in part two, which drops next week. We will get into two additional topics. What human agentic go-to-market actually means when you combine human agents and tech and the operating model of rethink: what to own, what to outsource, and how to decide. John, welcome to Selling Intelligence. John Tecce (02:13) Great to be here. KK Anderson (02:13) We are thrilled to have you. Okay, let's jump right into it. So much great stuff to cover today. And let's start with this idea of the trust recession and why digital outbound has hit a wall. And we bonded on this topic during the prep session, as I indicated in our introduction. as soon as I said, I said it, the trust recession, which by the way, I picked that up from Bob Kelly, who's the chairman of Sales Management Association. So all credit to him. You immediately reacted to it and we both totally agree that we are in a trust recession right now. And so let's start with you telling us like, what does that mean for you? What does it capture for you? Like, what are you seeing on your team and across your clients that makes that a phrase that really resonates for you? John Tecce (02:58) thing that really sticks out to me is the utilization of AI in all forms of communication that has led to a skepticism on the receiving end. How real the text that I'm receiving, whether it's a LinkedIn post or a message or an email or what have you, actually is from the human being versus how much of it was went through the AI car wash. And inherently, if you think about most of these models are ultimately trying to regress to the mean in terms of what they generate. And so you're ending up with this. copy paste of of phrasing and ways that things are said that strips out a lot of the human nature of it. And I think as a result, as B2B professionals, and when I say B2B professionals, that's under the whole go-to-market lens, everything from BDR to AE to CSM to executive, et cetera. there's the evergreen phrase of people buy from people who they know, like and trust, but it's kind of harder to get to know and trust them if you you have to filter everything they send you through the lens of like how much of this, you know, is really them versus how much of it is Chat GPT or or Copilot or or Claude that they're running these thoughts and communications through. I'm a huge user of AI, to be clear, I'm very AI forward and I encourage my team to be the same. but when you come to the trust recession, I think a lot of it has to do with just a a distance now that exists between two people and the communication between KK Anderson (04:10) and a lot of the noise that it has created, right? It's almost deafening. There's so much noise out there in the market today. It's insane. John Tecce (04:19) It's it's insane. the BDR outreach surge that we've seen in particular, whether it's again BDRs or otherwise, but Sixth Sense put out some research very recently that the baseline touches per contact was was about 17 in 2024. Not that long ago. We're in the middle of 2026. and this research came out a couple of weeks ago. We're now at 34 touches per contact. So it's doubled, number one. Number two, on top of that. KK Anderson (04:39) Ugh. my poor inbox. John Tecce (04:44) It ex well and inboxes, right? So what they found in that research as well was social in particular is the the biggest source of that growth. It went from about four and a half touches in twenty twenty four to now over ten in twenty twenty six. And so your email inbox is already hurting and and kind of getting hammered. And now, LinkedIn kinda used to be the okay, well if you send a a a really strong LinkedIn connect request or a really strong in mail, you had a good chance now But what we're seeing is the volume and just the increase in the noise in in part due to the ability to do it from a scale standpoint, an automation standpoint. but also, you're finding a lot of the inbox tools, both on the LinkedIn side and email, are becoming more intelligent to filtering out that noise. And so it's that's being countered with more noise and just more and more, more, more, and more, and we're at a point where the math just just doesn't math anymore. Mark Petruzzi (05:29) So John, you have been selling a long time now s so you definitely remember when digital outbound was still relatively clean. What has changed at the structural level and how does it show up in the numbers you're watching every day right now? John Tecce (05:44) Yeah, I think you know when I started my career was when marketing automation in its in its current form was really taking shape. my first role out of school was was at Rico for a couple years and helped them launch at the sales level launch Marketo as an example. And it was like super cool that you could put in this template and you could pull and have it personalized by first name and by company name. That was like a really big deal, right? and at the time we were getting and then you you started to see the know, the evolution of of RevTech and marketing automation into where now I can put in these all these different variables. It's like, my gosh, okay, now I can personalize that scale. I can put in company name and industry and based on industry I could put in these three client names of ours and like and you were getting a a really positive return on that because it was it was one, new on the recipient side and two, there was just less of it. And so as a result of those two factors, You know, you were able to to be more successful with that approach. what the SaaS industrial complex sort of created and through books like Predictable Revenue and other, the success of Salesforce and other firms was this idea of well, okay, well, if we just do more of that and we hire more people to do more of that, it we've always talked about a funnel forever, right? Or a bow tie. It's gonna more is gonna yield more. And for a while that was the case. first through email and then, as as far back as twenty eighteen, Gary Vaanderchuk's big thing was l LinkedIn was gonna be the platform of twenty eighteen. and you know, that that kind of pulled through in in through LinkedIn. And then by the way, once COVID hit, all we had was digital for a while there. And so that fur even further exacerbated it. And so I think, you I I look back on just the rudimentary basics of but a lot of folks of my sort of cohort of the middle millennial kind of age range came about when that was what you learned to do and you and wherever you started, whether you as an AE or a BDR, and that was, okay, if I just pull this slot machine or I just keep hitting these buttons, you know, the return, it was a math equation, right? and as we've just established that that is no longer the case. And so it's interesting now to look back on how successful that was and for good reason, but we've now effectively polluted that ocean to the point where there's there's no longer that many fish to catch through the volume approach. KK Anderson (07:46) You know, what's interesting is that, and we've talked about this a lot on the podcast before, is it's almost like the pendulum is swinging all the way back to the old school, which is so good for the really strong salespeople because trusted advisor, relationships, really being subject matter experts in what you do and your domain, the passion that you have for what you sell, all of those things that are so human and that make the best sellers, the best, like that now is paramount. And when we were chatting, John, you told us a story that I'd love for you to share with our audience, that one of your team members used an old school like veto letter, right? To get in front of a chief marketing officer at a dinner. So tell us that story. And then before you do, just for the millennials in the group who never had to do a veto letter, like tell us what it is. John Tecce (08:35) Ha ha KK Anderson (08:36) Tell us what John Tecce (08:36) ha. KK Anderson (08:36) it actually is and then tell us what happened and why it worked and expand on that. John Tecce (08:42) Yeah, I think first and foremost, you mentioned at the top that I'm third generation sales at least third generation. I don't know further back than that. but my father, Michael T C was in sales leadership for his entire career. and so I grew up, you know, around around books like Selling to Vito and Hope Is Not a Strategy. And these were these were just things that were around me my whole life. And so I feel extremely blessed to have sort of entered this this profession with a lot of Timeless values and concepts and so being able to pull back to those things, right? And so, sitting in the backseat coming home from from baseball practice and having learned what veto stands for and what a letter is, right? So s it's given the now that we're kind of thinking about this full cycle part of it, you know, we started to think about, okay, well, the digital channels have been polluted. that doesn't mean stop doing them, by the way. You can there are still fish to catch. it means you can't rely on them. And those are two different things, right? So you have to be thinking in a different way. Direct mail, not a new concept. So what sort of occurred to us, as we were sort of thinking through, okay, how can we zig when everybody else is zagging or vice versa, was well, we can rely on direct mail, but even that, you know, okay, that's gotta get sent to an office and get processed and what have you. exact yeah, we've got a few people that are remote, but through the investment and commitment from our our go to market organization around building community, our CMO Lisa Cole was attending a KK Anderson (09:48) And no one's in the office. John Tecce (10:00) Dinner recently, and occurred to one of my AEs, Lucy Goodwin, who just finished up another incredible quarter, by the way, was like, you know, you're you're seated at a table with one of my prospects that has a very compelling go-to-market transformation going on right now. And we've tried through digital channels and we have a really compelling message. We just don't, we haven't been able to have the right vessel to deliver it. And it sort of occurred, hey, can I? Like so we talked about it and we kind of came around with like, well, you have the message. You have the veto letter. And for those unfamiliar with the veto letter, it's nothing more than a one-page letter with a a brief, succinct value prop, value statement, citing specifics to that company, what we think we can do for you, and then setting up a very direct follow-up. And so we had all those puzzle pieces together. So well, what if like, hold on, Lisa's gonna be at the same in the same room? What if you just physically have her like give that message to the person, which 30 years ago KK Anderson (10:48) slip her not John Tecce (10:48) Totally. And like 30 years ago is exactly what you would have done, right? Because you didn't have the digital channels to you only had in person or or the phone or or fax, right? And so she sure enough did that. And the recipient was blown away by he's like, no one's ever done this before. No one's ever given me a physically given me a a message outlining a value pro tailored value proposition relevant to them, specifics, right, and all those things. and really kind of stood out. in terms of, hey, these guys are different. Like this company's operating in a different way. I don't do anything different. We're just we're going back to the future a little bit around you know that type of thing. and it was just very well received on on their side has led to a continuing conversation towards what exactly what we want to do is getting on their radar in a meaningful way through a timeless KK Anderson (11:32) VEDO is, I believe it stands for very important top officer. Is that right? Yeah, that's really cool. I love that story, John. John Tecce (11:37) Yes, exactly. Mark Petruzzi (11:40) So John, for for a CRO listening to this who is still running a sequencing first high volume outbound motion, what is the one thing they should stop? Like, stop now. Not not tomorrow, stop today. John Tecce (11:54) Quantity metrics are no longer a reliable predictor of conversion. Now, there are some that might argue that never were. I would argue that they definitely were for a while. but I I don't think smashing the more button or looking at the how much button. I think I think effort and quantity is important. I do not feel that quantity is primary, and I think in a lot of organizations that is still looked at as the first place to go. it's the simplest, it's the most measurable, it's the most actionable. you only made this many calls or you know, this many outreaches? Okay, well let's try more. And don't don't get me wrong, we we look at quantity here too, and but but much more around looking at the quality of outreach and the channel within the outreach is made. I think those that's the big pivot that that I would suggest is taking a hard look at, okay, if we are at a point where unless there is a very clear gap in the will, it's probably a gap in skill around the quality of the outreach and the critical thinking and creativity around the channel of the outreach. I I also, we have a lot of leaders right now in in CRO and VP of sales and VP of revenue and growth roles that also came up during this era of, you know, not having the prior perspective and only kind of came up through the world of sequences and KPIs around sequences and BDRs to do all the PG work and When I say PG meaning pipeline generation. so I do think, you know, being able to look back at at quality and at channel is paramount. KK Anderson (13:15) Could not agree more, could not agree more. Okay, we're gonna jump into topic two, the death of the BDR, and I know that's a hot take. I know it's a hot take. But it's one that I'd love to hear your, kind of where your head is, and I know it's the return as we spoke of the full cycle AE, which is what you've done. And at 2X, you've never had a BDR function, and I know that was a deliberate structural decision. for your team and so walk us through the reasoning and tell us tell me what you mean when you say the full cycle AE is coming back. John Tecce (13:48) Yeah, I think there's a few layers to it. The first layer goes back to the no like and trust aspect of any B2B, you know, go to market. And fundamentally, anytime there is a handoff involved, there is a risk around that that no like trust concoction to be disrupted. Right. And so to be clear to the BDRs out there, the work you do is valuable. The risk is in the handoff from okay. you're having a conversation or you're generating a meeting, and then immediately having to hand that off to somebody that the buyer already, before they've even taken the first meeting, has already talked to two people at this company. And they're like, okay. And then maybe we're introducing other people throughout the sales cycle. And then by the way, on after the sale is closed, then okay, I'm being handed off and I'm primarily working with the C like. And so there's just a lot of kind of handoffs that occur. And with that becomes a loss of context, a loss of personal accountability. And a loss of just comfort in consistency around around that accountability. And so what we found was as a 2x about a decade ago created the marketing as a service category. So think managed services or BPO, but for at the time B2B go to market or marketing, and now since we've expanded it to go to market, but as a category creator, say, hey, we we have to have someone on the front line that is a subject matter expert. The first interaction, the first engagement conversation has to be with someone who has community presence, marketing community presence, that is, also local community presence potentially, has credibility, can have that conversation and really be able to provide a premium experience on the prospect side from the get-go. and minimize some of those handoffs so that throughout the life of bringing a client in and then eventually onboarding that, there is still that presence there and accountability there. So that's a big part of of of the decision for us at the time. And it's only really exacerbated in an ongoing way. The majority of what we find with our clients is repeat clients or or folks that we meet throughout this community. And you know, a lot of the research about the dark funnel or name your thing about buyers or X percent through the journey before they choose to engage, well, that only happens when you're not providing value before that percentage point to want to engage. And so also a lot a big part of our full cycle approach is making sure that we are constantly in that community, providing value, staying connected, and aligning without the expectation of a meeting. And I think that's the other piece of it is the misalignment of KPIs. You have an entire function that is KPI'd on meetings. Well meetings aren't opportunities to sell potential I mean they might be, right? But a lot of buyers aren't even ready for a meeting yet. And so being able to is is that a KPI we track? It is and it is a proxy for success to some extent. But when you have an entire function that is only KPI on meetings, they're just gonna set up meetings because that's their job, right? Versus looking at it through a holistic lens of are we meeting with the right people at the right time about something they can act they're actually in a position to want to buy. And I've built enough credibility where, you know, most of the research from again, I'll cite that Sixth Sense Research and others say the first vendor that's contacted or engaged is typically the one that wins. I think it's like eighty four percent of the time, if I remember correctly. KK Anderson (16:25) Mm-hmm. John Tecce (16:46) Well, that's the AE that has to do that work leading up to that point to be the first call, right? That can't be a bifurcated process. And so that's kind of the what we've found and has really played out organizationally for us, but also what I've found my whole career, in terms of just being a a good AE, is constantly kind of thinking about pipeline generation. And I've been again very blessed to have a lot of leaders who have instilled that in me in terms of owning that for yourself. Mark Petruzzi (17:08) So you made an observation that most mid career sales professionals have never known a world where they could not send a personalized email or a somewhat cheeky gift and get a meeting. What does that mean for the skill gaps CROs are actually managing right now? John Tecce (17:24) There's a few things. one is acceptance and acknowledgement of what you just said is realizing that we are in a the answer is not more and the answer is not what you did before. didn't mean for that to rhyme, but maybe we'll put that on a on a pillow somewhere. looking looking at any there there really are no new ideas at this point, like at all of the different creative sort of of the twenty tens with hey, I saw on your Instagram. KK Anderson (17:38) Mm-hmm. John Tecce (17:48) You went to this place and I'm gonna send you a gift about whatever, or hey, you went to Villanova and they're playing against Seton Hall in the Big East tournament, I'll make a bet. Like all those different type of they were super cool in the moment in the 2010s, they work great, they were differentiated, they engage people. they've been maximized and played out at this point, right? And so I think really kind of reassessing and understanding what is actually creating the human connection of a potential buyer and I think emphasis big on potential in that community and being able to engage those people at a human level and at a pace that they're ready to engage with. A really good example that I found is is super helpful is when you're an active member in a community of professionals, whether it's an established community, like an actual community group, or just paying attention on LinkedIn. Okay, I see that, I have a client that I'm talking to over here. And they're looking for a director of RevOps. And then I see somebody else whose name popped up on my LinkedIn feed that was impacted by a restructuring, and they're in between roles. And they have the skill set, hey, I don't like I gotta I don't know you at all. Like, but I saw your LinkedIn post. You you seem to be looking for something that my client is hiring for. Like maybe you guys should talk. And like playing that connector role. I think we've really lost that concept, which again is not a new concept at all, right? This is a that was a fundamental piece of. KK Anderson (18:42) We have. John Tecce (19:03) selling up until the twenty tens was being that connector, being engaged with your clients. If anybody's read or listened to the Go Giver, that's a big part of the premise, right? Around the connector and the guy who's just having conversations all day long, but never seems to be getting anything done and yet he's crushing it. Well it's 'cause those conversations are leading to, okay, how can I align a a client need, whether it's something I sell or or not, to what they're trying to accomplish and or just providing value. And the law of reciprocity suggests that if you're continuing to do those things at any form of scale, it will pay off over a certain amount of time. so that's really like these are not new concepts at all. This is very much like B2B selling 101. We just have a whole generation of people that were never exposed to it. Again, the only reason I've been lucky enough to is through my own upbringing and through some great leaders I had early. KK Anderson (19:45) So true. Yeah. so true. you know, you, in doing that, you create trust and that is combating the trust recession. And we know that we're in. So, 100 % comes full circle. so quickly before we wrap up for our part one. So, in, the, when you think about the full cycle AE of today, right? What, like, what are the key? competencies or capabilities. It doesn't have to be, sales specific, but like what is it that you, they have to have to be able to do full cycle. John Tecce (20:18) Number one, they have to have the presence of mind to make these mental connections. They have to be able to see connections, whether those connections mean, okay, I have someone who moved on from a a two X client and went somewhere else. And now there's tools out there that can help you do that too, but still inherently the ability to read that. You have to have the presence of mind to sort of feel out in a cycle, hey, I think that person's fully Committed, like they might be moving on somewhere, right? You have have the presence of mind to start to see these things. partnerships is another good example. Like, so often, you know, 2X has a lot of great technology and other types of partners, but like just because we're not capital P partners, it doesn't mean you can't go find your peer AE at another company who's also selling to the person you're selling to and say, Hey, we're selling to the same person. Like our companies aren't partnered, but like We're both trying to do the same thing. Can you wanna talk and just like help each other here? Like just that presence of mind to make those connections is uncanny in terms of their ability to find success. Certainly in my experience personally, but also at 2x across my team. the second is the ability to embrace the uncertainty. we are I think the term unprecedented times first became most associated with with COVID era. And now it's just like what we live in. Like there it there is no precedented time. Yeah, like we're we are uncertainty is a part of the human experience. by the way, that didn't start with COVID either, but I think that that really brought it in generationally for a lot of folks. but with AI and with other things, you have to be willing to disrupt yourself all the time. You have to be willing to kill your darlings. You have to be willing to say, just because this worked for me last year or last month or last week, it doesn't mean it's going to work for me going forward. KK Anderson (21:33) This is what it is. John Tecce (21:59) And to be able to have that adaptability. And then I think the third one that comes to mind for me is you have to be able to separate the story you tell yourself from what's happening in reality. And I'll give Jen Wang, who's a a former 2X or helped build 2X from the ground up, just spoke with my team earlier today about this topic where she talked about the ability to sort of we all tell ourselves stories all the time about what's happening. because a story is better than no story, right? Like, hey, they're not getting back to me. Well, okay, well they're probably not getting back to me be because, you know, you make up some story about whatever, you go down some rabbit hole. I in that case, yeah, I do. that's a that's a good example. an excuse absolutely becomes a story in that case versus like, hey, you might have just reached out to him during a busy week. It's not that deep. There's no story. Get back on the horse and try it again. KK Anderson (22:34) Do you mean excuse when you say story? Mark Petruzzi (22:37) Mm-hmm. John Tecce (22:49) Well I and so I think there's a layer of being able to separate that and understand that okay, I need to focus on what's in front of me. I need to focus on how Jen put it, the next clean action, and be able to move forward. I found that those three things really right now in twenty twenty six are the biggest areas that set. KK Anderson (22:56) We will. So good. Mark Petruzzi (23:03) All right. So this is where we leave part one. We have covered the thrust recession, the collapse of the BDR model, and what it actually looks like when a firm stops theorizing and starts building the org around full cycle reps. In part two, John gets us into what human agentic go to market means in practice, how 2x is helping clients rethink the operating model. and where most organizations are making the wrong bet right now. We look forward to seeing you there. KK Anderson (23:33) And before you go, if the operating model conversation is resonating with you, we have been building something at AGS specifically for leaders who want to go deeper and educate on how to set up agentic workflows. Head to get-ags.com forward slash academy. There are sessions from career operators to help you do some of these things. And we will include everything on how to reach out to John Tisi and the amazing team at 2X in the show notes. Worth a look before part two and we will see you next week. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 134 – Frontier AI: What the Highest-Performing Sales Organizations Are Doing Differently with Bob Kelly - Part 2 | 08 juil. 2026 | 00:21:10 | |
General Episode Description: In Part 2 of this conversation, Bob Kelly, Founder and Chairman of the Sales Management Association, joins Mark Petruzzi and KK Anderson to examine why AI adoption often fails even when organizations invest in the right technology. Building on research across 111 sales organizations, the discussion moves beyond AI tools and into the operational systems required to create measurable impact. Bob explains why automating a broken sales process only accelerates poor execution, how leaders should distinguish between path problems and insight problems, and why CRM adoption continues to struggle when technology creates work for sellers without delivering value back to them. The conversation also explores the three organizational levers shown to drive AI adoption: leadership endorsement, training investment, and AI proficiency in hiring criteria. Bob shares why AI implementation requires clear decision rights, governance, and process ownership, while Mark and KK examine how AI may finally help revenue organizations break down traditional departmental silos. The episode closes with a candid discussion about AI anxiety, the changing role of sales managers, and why experimentation may become one of the most important leadership practices in the future of sales. What You’ll Learn:
Key Topics:
Guest Spotlight: Bob Kelly Bob Kelly is the Founder and Chairman of the Sales Management Association, an independent professional organization focused on advancing sales leadership and management effectiveness. Through research, education, and industry events, Bob works with sales leaders to apply evidence-based practices to sales productivity, process design, technology adoption, and organizational performance. He also serves as an adjunct faculty member at multiple business schools and brings an academic, research-driven perspective to the changing role of sales management in the AI era. Resources & Mentions:
Key Takeaway: AI adoption is not primarily a technology problem. It is a leadership, process, and organizational design problem. The sales organizations creating meaningful AI advantage are not simply buying more tools. They are documenting how selling actually works, defining where human judgment belongs, investing in AI skills, and giving leaders clear ownership over how AI is deployed. Technology will continue to change. The organizations that build the discipline to experiment, learn, and redesign their sales systems will be the ones best positioned to adapt. 🎧 Listen now and subscribe to Selling Intelligence for more conversations on AI, sales leadership, revenue operations, and the future of go-to-market execution. #SellingIntelligence #AIforSales #SalesLeadership #RevenueOperations #AgenticAI #AppliedAI #SalesManagement #ArtificialIntelligence #SalesProcess #SalesEnablement #GoToMarket #RevenueLeadership #SalesStrategy #AIAdoption #FutureOfSales Mark Petruzzi (00:28) Welcome to Selling Intelligence. I'm Mark Petruzzi. KK Anderson (00:31) And I'm KK Anderson. Every week we bring you conversations with operators who have been in the room and come out with something worth using the very next day. Mark Petruzzi (00:40) Our guests today just completed a benchmarking study of 111 sales organizations. And what on? AI adoption. The findings are not what most leaders expect. Only 4% of firms have no one using AI at all. But only 9% qualify as what the research calls frontier adopters. And those 10 firms are outperforming the rest of the field. By on average twenty-seven percent is points on sales objective achievement, nineteen points on individual quota attainment, and nearly double the rate of sufficient selling capacity. The question this research forces is not whether your team is using AI, it is whether they are using it in a way that actually moves the numbers. KK Anderson (01:26) Bob Kelly is founder and chairman of the Sales Management Association, a global, independent, professional organization serving more than ten thousand sales leaders. He has no product to sell and no platform to push, which is exactly why this data matters. Welcome to the show, Bob. We're happy to have you. Bob Kelly (01:43) Thank you so much for having me. It's so nice to be with you. Mark Petruzzi (01:46) So Bob, your research covers over one hundred companies. But before we get into what leaders are doing, give us the honest snapshot. What is the typical sales organization actually doing with AI right now? And how does it compare to what people say they're doing and what the media outlets are saying people are doing as well? Bob Kelly (02:07) the word I would use is dabbling. the typical sales organization is dabbling with AI as opposed to integrating it in a pervasive and sort of formal way in the work streams in the firm. this is a reflection of the uneven nature of how AI affects work in general and including sales work. But the interesting thing is to understand just how few firms are ignoring AI or are untouched by AI. When we look at the adoption curve and history of other technologies, CRM, for example, or other platform technologies, they've taken much, much longer to gain a foothold in most organizations. We're seeing very fast pickup in The use of AI, even if that use is uneven. KK Anderson (02:55) So Bob, when we had our our preparation conversation for this podcast, you used a phrase that I hadn't heard anywhere else and I thought it was fabulous. You said you said there's a lot of machine stench. Right. So walk us through like what is that and why is it showing up so broadly in this research? Bob Kelly (03:07) Machine Yes. Well how is Great term, isn't it? I was just about to think of that term when I heard someone else use it. So I've naturally adopted it as if it were my own, but it is plenty descriptive, right? And I think we all have encountered AI generated content. I mean, the more common term is slop. We see it in social media, but we also see it in our inboxes, we see it in work product within KK Anderson (03:15) It is. Bob Kelly (03:39) the companies that we work for. and its problem is that it represents an inauthentic product. And so this when used inappropriately or i in the wrong context actually I believe does more harm than good. it communicates sort of in auth authenticity rather than clarity and equality. KK Anderson (04:00) Everyone AI it's like AI gave everyone a on the road and no one can move. And everyone sounds the same. So it's figuring out how do you take that superpower and that super intelligence and leverage it in a way to create differentiation rather than Bob Kelly (04:01) We want Yeah, just You know, I KK Anderson (04:15) than the stench of sounding the same, Bob Kelly (04:18) I think the mistake so many make is that they're using AI to substitute for their own voice or work product. And when that happens, ⁓ they're pointing out their own superfluity. do we need a human if we're just gonna have machines generate communication? so I think when used appropriately, we use it to augment our abilities, our voice, our productivity and when we use it poorly we've we make the mistake of y substituting a machine generated product for something that we should have more say in. Mark Petruzzi (04:51) So, Bob, you mentioned in the study that only four to six percent of companies are avoiding AI entirely. That actually concerns me that, there is everybody's diving in. And, only a very small percentage are not. but when it really comes down to it, there's still a huge disparity between those frontier adopters, as you described, and the laggers, the rest of the the Bob Kelly (04:52) Yeah. Mark Petruzzi (05:17) hack is that the gap between the two of them growing and and how fast? How fast is that growing and changing? Bob Kelly (05:27) Well, it the answer is very, very fast. The study that we did was concluded I guess about three months ago. It's likely out of date. so we see these adoption and the development of the products that we're even talking about moving so quickly. the the the thing to keep in mind is that or a relevant Point here is that so many AI products are freely available and they are in the general population. In fact, the most widely adopted tools are those that anyone can pick up, chat GPT or perplexity or any of these sort of language-based chat uh-based tools. And so we see lots of people picking them up, fooling around with them. And this is unlike other technology. platforms that we've seen impacting the sales organization like CRM or SPM or sales enablement or any many many other tools. So this does beg the question, will this be a phenomenon driven by consumers? personal adoption? will it be democratized in that way or will companies be required to adopt sort of institution wide, highly controlled platforms to provision AI. KK Anderson (06:37) really interesting and one of the incredible benefits of leveraging AI in your sales organization is that you can take that tribal knowledge of your best your your top sales performer and figure out what it what is it that makes them the best and then automate some of those research tactics or techniques or processes in your in your AI agentic workflow. Bob Kelly (06:38) You know, the KK Anderson (06:59) And and that's something you could never do inside of, the confines of a sales force or hub spot. Bob Kelly (07:04) Yeah, th this is the promise. This that idea gets sales leaders excited. in practice, it's I don't know that we're quite there yet, but in general we see companies adopting the easy tools to pick up. These are chiefly language-based models, and they're used for language-oriented tasks, things like communication and crafting emails, sometimes quite derivative, machine stench gen sort of emails, but also doing things like understanding researching prospects and markets. and where we see less adoption so far is in the things that require more advanced tools, including agentic and sales specific tools. and so what we found in these so-called frontier firms, which represent maybe the top ninetieth per the 90th percentile of adoption and usage, ⁓ is that they're much more likely to use tools that are customized to sales work and include agentic elements. So they're actually automating work and in incorporating AI capabilities within those automation streams. KK Anderson (08:10) talk us through what these, the frontier adopters and the research that you talked about. So what was the what was tell the audience, what was the criteria you used to define them and like what does that what does a frontier organization actually look like in practice? Bob Kelly (08:24) Well, w ⁓ we had have you as you pointed out, roughly a hundred firms in the study. So we looked and we in the study measured their rates of adoption, the frequency with which the typical salesperson uses tools, and the kind of tools that they use. So we took those firms that had the highest rates of adoption and in which salespeople are using tools most frequently and in which They are using tools, they're using the general purpose tools, but they're also using agentic tools and custom tools that are geared toward sales specific tasks. And so those those are the basic criteria. We identified roughly 11 to 12 firms in that group and branded them frontier sales organizations. We did this in part. Because the sponsor of this research who underwrote the research was Microsoft, and they're using this term in the way they are marketing solutions to frontier firms. So in part we did this to curry favor with our sponsor, but also because this term frontier has been widely adopted to describe the latest models that are used in these solutions, but also the sort of uneven and perhaps dangerous nature of adoption itself. Ethan Moloch's great term, the jagged frontier, is widely used to describe how it's an uneven place being on the edge of adoption with these tools. The tools do many things really well and other things, easy things, weirdly, quite poorly. So the it it's a it's a shifting, sort of an uneven place. to be and that that's why we like the term in addition to describing those leaders in organiza in our economy in sales organizations that are adopting AI. Mark Petruzzi (10:07) So Bob, I I kind of echo that that thought process and and what what I'm starting to see, like everyone, right? I jumped in early to just the whole opportunity of AI and what you can do and the research capabilities and and then move very quickly into the agentic side and really creating agents and and building them for our clients. And that moved to a whole nother level of productivity. But we learned something in that phase two, and that is how valuable all the systems and tribal knowledge that a company has and how to for AI really to be playing its best game, it's gotta have that that information as well. So that brings us to applied AI, right? That's kind of where where the terminology is coming together and and when you can do that as an organization we at AGS do that for our clients we do that with with a couple of our partner organizations that we work very closely with like Humagentic. when you can go to that next level and really integrate within the systems that are already in place takes you to a whole nother level. did you see that at all in this study and what's what's your overall Point of view on that. Bob Kelly (11:22) We we didn't go super deep to understand the degree to which firms are integrating agentic solutions within their own environments. we did sort of investigate, we asked, are you employing agentic solutions? and we ask, are you using custom solutions that are sales focused? We also ask if they are making use of platform solutions, existing solutions like CRM. or SPM sales performance management platforms in which there are embedded AI capabilities. This is likely the most this is the likeliest way that many firms will begin adopting these agentic solutions kind of pervasively they will exist within the comfortable and of KK Anderson (12:07) Tools they have. Bob Kelly (12:09) a platform in which they're already using which solves the chief concern about distributing this capability across the enterprise, namely security governance, the keeping data secure and understanding just how people are using the solutions. KK Anderson (12:25) I thought it was incredible that the data showed that ninety percent of frontier organizations met or exceeded their sales goals in the preceding twelve months, versus sixty three percent of the non frontier firms. Like that's compelling. Bob Kelly (12:38) Yeah, yeah, it's a big number. so it suggests that frontier firms, so called frontier firms, are much more likely to be productive than more laggard firms. I mean, it's a clear delivery of the promise of AI i as it relates to productivity. KK Anderson (12:54) Right. Really incredible. Okay. So we your your research study also talked about selling capacity. and it's let's see, the data says I believe it was 60% of frontier firms say they have sufficient capacity to cover available opportunity compared to 32% of non-frontier firms. And I'm assuming, Bob, that's going more towards their productivity as well. Bob Kelly (13:17) So this is a a really interesting finding. again, this data is self-reported, so it is subject to the caveats that you'd have in such a study, but it's almost the only way to conduct quick benchmarking research. But the fact that these firms are so much more likely to indicate that they have sufficient capacity does suggest. An impact of using AI that we all are hoping for, which is it allows us to do our work faster. Now, if you follow the logic through, ⁓ it's reasonable to suggest that this surplus capacity will be short-lived. So where we are perhaps in the curve of adoption of AI and sales is that we're using AI to great effect to make salespeople more productive, but we haven't redeployed that capacity. In ways that are likely to follow on from AI adoption. We're likely to see different s kinds of organization structures, perhaps different spans of control. We're almost certainly likely to see different jobs in the Salesforce. And as we absorb an understanding of how AI will impact all of the work of those new people, we'll probably see them. become every bit as overburdened and overworked as people used used to be before AI. they'll just be doing more. so that that's something to keep an eye out for. those excess capacity is something that you you don't want too much of it. but it's better to have a little bit than to be understaffed. Mark Petruzzi (14:30) Mm. KK Anderson (14:45) You heard it here first. Bob's prediction. The pendulum's gonna swing back the other way, isn't it? That's that's pretty funny. And I believe it. Hey, I believe you. Bob Kelly (14:46) Right now. Yeah. Right. there's an inter another interesting difference in these frontier firms compared to other firms. We asked about the sentiment about AI. what is the promise of AI in various aspects of managing the sales function, making decisions for the sales function? And we found that those firms that I'll put it this way adoption is positively correlated with enthusiasm in Mark Petruzzi (14:54) All right. Bob Kelly (15:18) Estimating AI's impact. Those firms that are using AI the most are the most sanguine about how AI will help them in the future. and believe it, its impacts are far more broad based than firms with just a limited, sort of naive understanding of AI. Mark Petruzzi (15:34) Stuff, Bob. let's move over to topic three, the management question. How AI changes the sales manager's role. And your research in this area shows that 100% of frontier organizations expect AI to have a high impact on first-line sales manager responsibilities over the next two to three years. That is not a heads number. What does it actually mean for what a frontline manager does every day? And what does it mean for how CROs should be developing those managers over time? Bob Kelly (16:08) Yeah, this is a very interesting question. It's it's very interesting to our organization, given where we sit and who our ⁓ our members are. We have a lot of sales managers in our membership. it's important to understand that the sales management role, especially the first line sales management role, has been changing significantly before the introduction of AI. The role has had And this is also a reflection of technology use and better data, but the role has had a diminishing amount of a sort of supervisory responsibility and an increasing ⁓ amount of focus on developing people, but also in a set of kind of integrative disciplines that I'll describe in a moment. so Of course, we all, think of that first line sales manager is maybe a a really good salesperson that was promoted into management. and it's it's of course a much different job than being an individual sales contributor. The the places where we see sales managers having the most impact are in actually improving the proficiency and effectiveness of the people that they are managing. that ⁓ is a very much a ⁓ role that requires human to human communication and intervention and relationship. it's it's hard to automate that. the supervisory stuff is relatively easy to automate. now another way to think about this question, Mark, is to say what are the competencies and sales managers that will become in the forefront in the future? And increasingly we see this happening already. And there are a small set of competencies that I think will characterize high performing sales managers in the future. As it relates to AI, I do believe that proficiency or at least fluency in applying and understanding and applying AI tools to sales work will be required for sales managers. Now this involves a lot of kind of com subordinate skills. It it it requires someone to be able to take a typical sales job or task and deconstruct it into its component parts to understand how we might automate that, which portions are appropriate to automate, which portions should retain a human in the loop. And also it requires a process discipline. Sales, the sales function has always been process focused, or at least it has been in the past 20 or 30 years. But in the future, I think this sort of process rigor and the ability of a manager to apply process discipline to the selling function. And to diagnose the issues as would a process engineer. these are critical skills that w we'll have to have in sales management roles in the future. KK Anderson (18:52) So interesting. Bob Kelly (18:53) what else? Yeah. ⁓ the to return for a moment to this idea of developing people, despite what I've said, despite claiming that it's so important for people to be involved in this process, I believe that the currently today, the biggest impact we're seeing in AI and sales is in the area of learning and development. I think for the for most firms. the place where AI can have the biggest impact is in training, coaching and developing salespeople simply because the amount of quality activity in those areas is quite low or non existent in ⁓ many sales forces today. KK Anderson (19:29) So as sales organizations get smarter and sharper and and the applied AI really takes hold, and then the sales managers are not spending as much time on things like pipeline inspection or call reviews because the AI is listening to the calls, right? And the AI is pulling out insights. the AI is predicting the forecast, right? That well, this is like the vision, right? So if AI takes those off the plate. Bob Kelly (19:42) No right. Maybe. Yeah, yeah, yeah. ⁓ KK Anderson (19:55) and I know you just said, hilariously so that, Something else will fill that time on the plate. but what what should the sales manager be focusing on with that time instead? Like they're gonna be getting back so much time. Where should their priority be? What's the w how will they have the greatest impact? Bob Kelly (20:13) Well, let's also point out that the typical environment that sales organizations operate in is very change intensive. in part but for the same reasons that we're that we're the same things we're talking about today. their customers are also being impacted by AI and b and by technology. The way they prefer to buy is changing all the time. they're Interest in meeting with salespeople and the value they expect to get from such investments in meeting time changes all the time. They're all these new competitors, etc. So often even if only implicitly, we expect that sales manager to be the change leader to enact those adaptations that we have to have in the marketplace. so I expect that that will continue to be the case. Sales managers will have to lead change in organizations and there will continue to be plenty, plenty of it. it will be coming faster than it has in the past and and there'll be greater change impacts than we've had in the past. ⁓ so ⁓ I expect managers to be highly focused in that. They also are going to have to ⁓ be skilled at diagnosing issues, diagnosing what's going on with pipeline issues. Will AI help our pipeline measurement and tracking? It it may well make it easier to do. Will it result in better quality? I'm on a little skeptical, but only because we've done plenty of research about pipeline management, and we find that the sort of tracking constructs that many firms use to track deals or opportunities are often wildly inaccurate at forecasting results. so much so that I've come to the conclusion that we often I believe use these tools for more than trying to simply predict outcomes. We use them to foster conversations. So another way to think about this question is will AI result in better quality interactions between management and ⁓ individual contributors to foster quality and figure out how best to close deals? I'll I'll see that. I'll believe the pipeline accuracy and efficiency impacts when I see them. But the good news is we blow a lot of time. Managers blow a lot of time fooling around with forecasting and pipeline tracking, especially in complex selling environments. And if we could have that go away, that would be a a good thing. Mark Petruzzi (22:32) Excellent, Bob. Okay, this is where we will leave part one. In part two, Bob gets into what the research says about the management role specifically and why process has to come before AI, or you are just accelerating the wrong things. And also we're going to cover the three organizational levers that the data shows actually drives adoption. We look forward to seeing you there. KK Anderson (22:33) She won't. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 133 – Frontier AI: What the Highest-Performing Sales Organizations Are Doing Differently with Bob Kelly - Part 1 | 01 juil. 2026 | 00:23:26 | |
In this episode of Selling Intelligence, Bob Kelly, Founder and Chairman of the Sales Management Association, joins Mark Petruzzi and KK Anderson to unpack the findings from one of the most comprehensive benchmarking studies on AI adoption in sales. Drawing from research across 111 sales organizations, Bob reveals why simply using AI is no longer enough. The real advantage belongs to a small group of “frontier organizations” that have moved beyond experimentation and embedded AI into the way sales actually gets done. The conversation explores the current state of AI adoption, why most organizations are still only “dabbling,” and the growing performance gap between companies that integrate AI strategically and those that simply rely on general-purpose tools. Bob also introduces the concept of “machine stench,” explains why authenticity has become more valuable than ever, and shares why sales managers will play an even more important role as AI transforms the revenue organization. What You’ll Learn:
Key Topics:
Guest Spotlight: Bob Kelly is the Founder and Chairman of the Sales Management Association, the world’s largest independent professional organization dedicated to advancing sales leadership. Serving more than 10,000 sales leaders globally, Bob has spent decades researching sales management effectiveness, organizational performance, and revenue leadership. His work focuses on helping organizations apply evidence-based practices to improve sales productivity, leadership development, and business performance. Resources & Mentions:
Coming Next Week: Part 2 dives into why processes must come before AI, the three organizational levers that actually drive successful AI adoption, and how the best sales organizations are redesigning leadership, coaching, and operating models to thrive in the age of AI. 🎧 Listen now and subscribe to Selling Intelligence for more conversations with the leaders shaping the future of AI, sales leadership, revenue operations, and enterprise growth. Mark Petruzzi (00:28) Welcome to Selling Intelligence. I'm Mark Petruzzi. KK Anderson (00:31) And I'm KK Anderson. Every week we bring you conversations with operators who have been in the room and come out with something worth using the very next day. Mark Petruzzi (00:40) Our guests today just completed a benchmarking study of 111 sales organizations. And what on? AI adoption. The findings are not what most leaders expect. Only 4% of firms have no one using AI at all. But only 9% qualify as what the research calls frontier adopters. And those 10 firms are outperforming the rest of the field. By on average twenty-seven percent is points on sales objective achievement, nineteen points on individual quota attainment, and nearly double the rate of sufficient selling capacity. The question this research forces is not whether your team is using AI, it is whether they are using it in a way that actually moves the numbers. KK Anderson (01:26) Bob Kelly is founder and chairman of the Sales Management Association, a global, independent, professional organization serving more than ten thousand sales leaders. He has no product to sell and no platform to push, which is exactly why this data matters. Welcome to the show, Bob. We're happy to have you. Bob Kelly (01:43) Thank you so much for having me. It's so nice to be with you. Mark Petruzzi (01:46) So Bob, your research covers over one hundred companies. But before we get into what leaders are doing, give us the honest snapshot. What is the typical sales organization actually doing with AI right now? And how does it compare to what people say they're doing and what the media outlets are saying people are doing as well? Bob Kelly (02:07) the word I would use is dabbling. the typical sales organization is dabbling with AI as opposed to integrating it in a pervasive and sort of formal way in the work streams in the firm. this is a reflection of the uneven nature of how AI affects work in general and including sales work. But the interesting thing is to understand just how few firms are ignoring AI or are untouched by AI. When we look at the adoption curve and history of other technologies, CRM, for example, or other platform technologies, they've taken much, much longer to gain a foothold in most organizations. We're seeing very fast pickup in The use of AI, even if that use is uneven. KK Anderson (02:55) So Bob, when we had our our preparation conversation for this podcast, you used a phrase that I hadn't heard anywhere else and I thought it was fabulous. You said you said there's a lot of machine stench. Right. So walk us through like what is that and why is it showing up so broadly in this research? Bob Kelly (03:07) Machine Yes. Well how is Great term, isn't it? I was just about to think of that term when I heard someone else use it. So I've naturally adopted it as if it were my own, but it is plenty descriptive, right? And I think we all have encountered AI generated content. I mean, the more common term is slop. We see it in social media, but we also see it in our inboxes, we see it in work product within KK Anderson (03:15) It is. Bob Kelly (03:39) the companies that we work for. and its problem is that it represents an inauthentic product. And so this when used inappropriately or i in the wrong context actually I believe does more harm than good. it communicates sort of in auth authenticity rather than clarity and equality. KK Anderson (04:00) Everyone AI it's like AI gave everyone a on the road and no one can move. And everyone sounds the same. So it's figuring out how do you take that superpower and that super intelligence and leverage it in a way to create differentiation rather than Bob Kelly (04:01) We want Yeah, just You know, I KK Anderson (04:15) than the stench of sounding the same, Bob Kelly (04:18) I think the mistake so many make is that they're using AI to substitute for their own voice or work product. And when that happens, ⁓ they're pointing out their own superfluity. do we need a human if we're just gonna have machines generate communication? so I think when used appropriately, we use it to augment our abilities, our voice, our productivity and when we use it poorly we've we make the mistake of y substituting a machine generated product for something that we should have more say in. Mark Petruzzi (04:51) So, Bob, you mentioned in the study that only four to six percent of companies are avoiding AI entirely. That actually concerns me that, there is everybody's diving in. And, only a very small percentage are not. but when it really comes down to it, there's still a huge disparity between those frontier adopters, as you described, and the laggers, the rest of the the Bob Kelly (04:52) Yeah. Mark Petruzzi (05:17) hack is that the gap between the two of them growing and and how fast? How fast is that growing and changing? Bob Kelly (05:27) Well, it the answer is very, very fast. The study that we did was concluded I guess about three months ago. It's likely out of date. so we see these adoption and the development of the products that we're even talking about moving so quickly. the the the thing to keep in mind is that or a relevant Point here is that so many AI products are freely available and they are in the general population. In fact, the most widely adopted tools are those that anyone can pick up, chat GPT or perplexity or any of these sort of language-based chat uh-based tools. And so we see lots of people picking them up, fooling around with them. And this is unlike other technology. platforms that we've seen impacting the sales organization like CRM or SPM or sales enablement or any many many other tools. So this does beg the question, will this be a phenomenon driven by consumers? personal adoption? will it be democratized in that way or will companies be required to adopt sort of institution wide, highly controlled platforms to provision AI. KK Anderson (06:37) really interesting and one of the incredible benefits of leveraging AI in your sales organization is that you can take that tribal knowledge of your best your your top sales performer and figure out what it what is it that makes them the best and then automate some of those research tactics or techniques or processes in your in your AI agentic workflow. Bob Kelly (06:38) You know, the KK Anderson (06:59) And and that's something you could never do inside of, the confines of a sales force or hub spot. Bob Kelly (07:04) Yeah, th this is the promise. This that idea gets sales leaders excited. in practice, it's I don't know that we're quite there yet, but in general we see companies adopting the easy tools to pick up. These are chiefly language-based models, and they're used for language-oriented tasks, things like communication and crafting emails, sometimes quite derivative, machine stench gen sort of emails, but also doing things like understanding researching prospects and markets. and where we see less adoption so far is in the things that require more advanced tools, including agentic and sales specific tools. and so what we found in these so-called frontier firms, which represent maybe the top ninetieth per the 90th percentile of adoption and usage, ⁓ is that they're much more likely to use tools that are customized to sales work and include agentic elements. So they're actually automating work and in incorporating AI capabilities within those automation streams. KK Anderson (08:10) talk us through what these, the frontier adopters and the research that you talked about. So what was the what was tell the audience, what was the criteria you used to define them and like what does that what does a frontier organization actually look like in practice? Bob Kelly (08:24) Well, w ⁓ we had have you as you pointed out, roughly a hundred firms in the study. So we looked and we in the study measured their rates of adoption, the frequency with which the typical salesperson uses tools, and the kind of tools that they use. So we took those firms that had the highest rates of adoption and in which salespeople are using tools most frequently and in which They are using tools, they're using the general purpose tools, but they're also using agentic tools and custom tools that are geared toward sales specific tasks. And so those those are the basic criteria. We identified roughly 11 to 12 firms in that group and branded them frontier sales organizations. We did this in part. Because the sponsor of this research who underwrote the research was Microsoft, and they're using this term in the way they are marketing solutions to frontier firms. So in part we did this to curry favor with our sponsor, but also because this term frontier has been widely adopted to describe the latest models that are used in these solutions, but also the sort of uneven and perhaps dangerous nature of adoption itself. Ethan Moloch's great term, the jagged frontier, is widely used to describe how it's an uneven place being on the edge of adoption with these tools. The tools do many things really well and other things, easy things, weirdly, quite poorly. So the it it's a it's a shifting, sort of an uneven place. to be and that that's why we like the term in addition to describing those leaders in organiza in our economy in sales organizations that are adopting AI. Mark Petruzzi (10:07) So Bob, I I kind of echo that that thought process and and what what I'm starting to see, like everyone, right? I jumped in early to just the whole opportunity of AI and what you can do and the research capabilities and and then move very quickly into the agentic side and really creating agents and and building them for our clients. And that moved to a whole nother level of productivity. But we learned something in that phase two, and that is how valuable all the systems and tribal knowledge that a company has and how to for AI really to be playing its best game, it's gotta have that that information as well. So that brings us to applied AI, right? That's kind of where where the terminology is coming together and and when you can do that as an organization we at AGS do that for our clients we do that with with a couple of our partner organizations that we work very closely with like Humagentic. when you can go to that next level and really integrate within the systems that are already in place takes you to a whole nother level. did you see that at all in this study and what's what's your overall Point of view on that. Bob Kelly (11:22) We we didn't go super deep to understand the degree to which firms are integrating agentic solutions within their own environments. we did sort of investigate, we asked, are you employing agentic solutions? and we ask, are you using custom solutions that are sales focused? We also ask if they are making use of platform solutions, existing solutions like CRM. or SPM sales performance management platforms in which there are embedded AI capabilities. This is likely the most this is the likeliest way that many firms will begin adopting these agentic solutions kind of pervasively they will exist within the comfortable and of KK Anderson (12:07) Tools they have. Bob Kelly (12:09) a platform in which they're already using which solves the chief concern about distributing this capability across the enterprise, namely security governance, the keeping data secure and understanding just how people are using the solutions. KK Anderson (12:25) I thought it was incredible that the data showed that ninety percent of frontier organizations met or exceeded their sales goals in the preceding twelve months, versus sixty three percent of the non frontier firms. Like that's compelling. Bob Kelly (12:38) Yeah, yeah, it's a big number. so it suggests that frontier firms, so called frontier firms, are much more likely to be productive than more laggard firms. I mean, it's a clear delivery of the promise of AI i as it relates to productivity. KK Anderson (12:54) Right. Really incredible. Okay. So we your your research study also talked about selling capacity. and it's let's see, the data says I believe it was 60% of frontier firms say they have sufficient capacity to cover available opportunity compared to 32% of non-frontier firms. And I'm assuming, Bob, that's going more towards their productivity as well. Bob Kelly (13:17) So this is a a really interesting finding. again, this data is self-reported, so it is subject to the caveats that you'd have in such a study, but it's almost the only way to conduct quick benchmarking research. But the fact that these firms are so much more likely to indicate that they have sufficient capacity does suggest. An impact of using AI that we all are hoping for, which is it allows us to do our work faster. Now, if you follow the logic through, ⁓ it's reasonable to suggest that this surplus capacity will be short-lived. So where we are perhaps in the curve of adoption of AI and sales is that we're using AI to great effect to make salespeople more productive, but we haven't redeployed that capacity. In ways that are likely to follow on from AI adoption. We're likely to see different s kinds of organization structures, perhaps different spans of control. We're almost certainly likely to see different jobs in the Salesforce. And as we absorb an understanding of how AI will impact all of the work of those new people, we'll probably see them. become every bit as overburdened and overworked as people used used to be before AI. they'll just be doing more. so that that's something to keep an eye out for. those excess capacity is something that you you don't want too much of it. but it's better to have a little bit than to be understaffed. Mark Petruzzi (14:30) Mm. KK Anderson (14:45) You heard it here first. Bob's prediction. The pendulum's gonna swing back the other way, isn't it? That's that's pretty funny. And I believe it. Hey, I believe you. Bob Kelly (14:46) Right now. Yeah. Right. there's an inter another interesting difference in these frontier firms compared to other firms. We asked about the sentiment about AI. what is the promise of AI in various aspects of managing the sales function, making decisions for the sales function? And we found that those firms that I'll put it this way adoption is positively correlated with enthusiasm in Mark Petruzzi (14:54) All right. Bob Kelly (15:18) Estimating AI's impact. Those firms that are using AI the most are the most sanguine about how AI will help them in the future. and believe it, its impacts are far more broad based than firms with just a limited, sort of naive understanding of AI. Mark Petruzzi (15:34) Stuff, Bob. let's move over to topic three, the management question. How AI changes the sales manager's role. And your research in this area shows that 100% of frontier organizations expect AI to have a high impact on first-line sales manager responsibilities over the next two to three years. That is not a heads number. What does it actually mean for what a frontline manager does every day? And what does it mean for how CROs should be developing those managers over time? Bob Kelly (16:08) Yeah, this is a very interesting question. It's it's very interesting to our organization, given where we sit and who our ⁓ our members are. We have a lot of sales managers in our membership. it's important to understand that the sales management role, especially the first line sales management role, has been changing significantly before the introduction of AI. The role has had And this is also a reflection of technology use and better data, but the role has had a diminishing amount of a sort of supervisory responsibility and an increasing ⁓ amount of focus on developing people, but also in a set of kind of integrative disciplines that I'll describe in a moment. so Of course, we all, think of that first line sales manager is maybe a a really good salesperson that was promoted into management. and it's it's of course a much different job than being an individual sales contributor. The the places where we see sales managers having the most impact are in actually improving the proficiency and effectiveness of the people that they are managing. that ⁓ is a very much a ⁓ role that requires human to human communication and intervention and relationship. it's it's hard to automate that. the supervisory stuff is relatively easy to automate. now another way to think about this question, Mark, is to say what are the competencies and sales managers that will become in the forefront in the future? And increasingly we see this happening already. And there are a small set of competencies that I think will characterize high performing sales managers in the future. As it relates to AI, I do believe that proficiency or at least fluency in applying and understanding and applying AI tools to sales work will be required for sales managers. Now this involves a lot of kind of com subordinate skills. It it it requires someone to be able to take a typical sales job or task and deconstruct it into its component parts to understand how we might automate that, which portions are appropriate to automate, which portions should retain a human in the loop. And also it requires a process discipline. Sales, the sales function has always been process focused, or at least it has been in the past 20 or 30 years. But in the future, I think this sort of process rigor and the ability of a manager to apply process discipline to the selling function. And to diagnose the issues as would a process engineer. these are critical skills that w we'll have to have in sales management roles in the future. KK Anderson (18:52) So interesting. Bob Kelly (18:53) what else? Yeah. ⁓ the to return for a moment to this idea of developing people, despite what I've said, despite claiming that it's so important for people to be involved in this process, I believe that the currently today, the biggest impact we're seeing in AI and sales is in the area of learning and development. I think for the for most firms. the place where AI can have the biggest impact is in training, coaching and developing salespeople simply because the amount of quality activity in those areas is quite low or non existent in ⁓ many sales forces today. KK Anderson (19:29) So as sales organizations get smarter and sharper and and the applied AI really takes hold, and then the sales managers are not spending as much time on things like pipeline inspection or call reviews because the AI is listening to the calls, right? And the AI is pulling out insights. the AI is predicting the forecast, right? That well, this is like the vision, right? So if AI takes those off the plate. Bob Kelly (19:42) No right. Maybe. Yeah, yeah, yeah. ⁓ KK Anderson (19:55) and I know you just said, hilariously so that, Something else will fill that time on the plate. but what what should the sales manager be focusing on with that time instead? Like they're gonna be getting back so much time. Where should their priority be? What's the w how will they have the greatest impact? Bob Kelly (20:13) Well, let's also point out that the typical environment that sales organizations operate in is very change intensive. in part but for the same reasons that we're that we're the same things we're talking about today. their customers are also being impacted by AI and b and by technology. The way they prefer to buy is changing all the time. they're Interest in meeting with salespeople and the value they expect to get from such investments in meeting time changes all the time. They're all these new competitors, etc. So often even if only implicitly, we expect that sales manager to be the change leader to enact those adaptations that we have to have in the marketplace. so I expect that that will continue to be the case. Sales managers will have to lead change in organizations and there will continue to be plenty, plenty of it. it will be coming faster than it has in the past and and there'll be greater change impacts than we've had in the past. ⁓ so ⁓ I expect managers to be highly focused in that. They also are going to have to ⁓ be skilled at diagnosing issues, diagnosing what's going on with pipeline issues. Will AI help our pipeline measurement and tracking? It it may well make it easier to do. Will it result in better quality? I'm on a little skeptical, but only because we've done plenty of research about pipeline management, and we find that the sort of tracking constructs that many firms use to track deals or opportunities are often wildly inaccurate at forecasting results. so much so that I've come to the conclusion that we often I believe use these tools for more than trying to simply predict outcomes. We use them to foster conversations. So another way to think about this question is will AI result in better quality interactions between management and ⁓ individual contributors to foster quality and figure out how best to close deals? I'll I'll see that. I'll believe the pipeline accuracy and efficiency impacts when I see them. But the good news is we blow a lot of time. Managers blow a lot of time fooling around with forecasting and pipeline tracking, especially in complex selling environments. And if we could have that go away, that would be a a good thing. Mark Petruzzi (22:32) Excellent, Bob. Okay, this is where we will leave part one. In part two, Bob gets into what the research says about the management role specifically and why process has to come before AI, or you are just accelerating the wrong things. And also we're going to cover the three organizational levers that the data shows actually drives adoption. We look forward to seeing you there. KK Anderson (22:33) She won't. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 132 – Fixing the 80/20 Sales Problem with Real-Time AI Coaching with Jared Zelman - Part 2 | 24 juin 2026 | 00:26:10 | |
General Episode Description: In Part 2 of this conversation, Jared Zelman, Founder and CEO of Othello AI, explores what happens when AI moves beyond helping individual sellers and begins transforming entire sales organizations. Jared shares his perspective on the future of sales management, explaining how AI can handle repetitive coaching, call analysis, and execution consistency while allowing managers to focus on higher-value leadership activities. The conversation examines how AI-powered coaching systems are changing the role of frontline managers and why sales leaders must rethink how they develop and scale teams. The discussion also dives into Jared’s founder-led go-to-market journey. From cold-emailing executives, investors, and industry leaders to building relationships with some of the most influential business figures in the world, Jared explains how disciplined outreach, persistence, and deep personalization helped accelerate Othello’s growth from startup to seven-figure ARR. The episode concludes with practical lessons for founders, CROs, and sales leaders on scaling efficiently, shortening sales cycles, achieving product-market fit, and balancing the art and science of selling in an increasingly AI-driven world. What You’ll Learn: • The Future of Sales Management: How AI changes the role of frontline sales leaders. • AI-Augmented Coaching: Moving from repetitive coaching activities to strategic leadership. • Founder-Led Sales at Scale: How deliberate outreach can build customers, investors, and mentor networks. • Product-Market Fit First: Why founders should focus on learning and validation before scaling teams. • The Art and Science of Selling: Understanding what AI can teach and what remains uniquely human. Key Topics: • Managing AI-augmented sales organizations • The future role of sales managers • AI-powered diagnostics and coaching • CRM automation and systems of record • Salesforce versus next-generation CRM experiences • MEDDPICC automation and sales process intelligence • Sales velocity as a growth metric • Founder-led go-to-market strategies • Building relationships through cold outreach • Howard Schultz and executive networking stories • Product-market fit versus revenue growth • Shortening sales cycles • Why founders should delay hiring sales teams too early • The science versus art of selling • Human trust and relationship-building in sales • Scaling enterprise SaaS companies Guest Spotlight: Jared Zelman Jared Zelman is the Founder and CEO of Othello AI, a real-time AI sales coaching platform designed to improve sales execution before, during, and after customer conversations. Prior to Othello, Jared founded Cicero, an AI-powered celebrity avatar platform. Through Othello, he is helping organizations scale elite sales behaviors while preserving the human elements of trust, empathy, and relationship-building that drive long-term success. Resources & Mentions: • Othello AI • Salesforce • HubSpot • Notion • MEDDPICC • Howard Schultz • Steve Ballmer • Sam Altman • Paul Graham • Dale Carnegie • Costco • Lenovo • Science of Scaling by Mark Roberts • Entrepreneur.com Key Takeaway: AI can automate coaching, surface insights, and improve execution consistency, but it cannot replace the human side of selling. The organizations that win will combine AI-driven discipline with authentic relationships, strong leadership, and a relentless focus on understanding customers. 🎧 Listen now and subscribe to Selling Intelligence for more conversations on AI, sales leadership, revenue growth, founder-led scaling, and the future of enterprise sales. KK Anderson (00:38) Okay, so you are, and we're gonna wrap up the second topic here with this question. You're reporting 10 to 15% win rates improvement, 8 to 10% reduction in sales cycle length, which is huge. ⁓ a lot of AI tools are making, some some pretty large claims like that. so like generally speaking, just w help us understand a little bit, like what what are you measuring over what time period? Jared Zelman (00:51) Crazy. KK Anderson (01:02) how was work to some of your success? Jared Zelman (01:04) Yeah. These are like guess depends, because ⁓ like some of these numbers are pointing time numbers, some of these are ⁓ like over a period of time. so if it's a period of time, these are like over a course of twelve months. what's unique is these are all for large enterprise, these are for Fortune one hundreds. When you see AI companies quoting crazy growth or performance metrics, it's because they're selling to a two person business in YC. in other words, bullcrap. Right. ⁓ these are metrics that are proven at some of the biggest companies in ⁓ multi-sectors. that said, the bar for the expectation the expectation of buyers these days is kind of ridiculous. frankly, if you're a sales tool and you're affecting win rates and you're not improving them by over 10%, that you're a failure. our minimum is like fifteen, we're aiming for like twenty five, thirty in some cases. Yeah, I mean w the buy the buyers are just so damn pro snickety these days. People's standards have gone through the roof. KK Anderson (01:49) wow. Mark Petruzzi (01:57) Beautiful. All right, let us move from topic two to topic three. Topic three is from rep consistency to overall CRO intelligence and how that impacts the overall management of an AI augmented team. And the first question I have on that is once your technology is levered across a team. What what changes for the manager? Because if the AI is handling execution consistency, prompting the right questions, catching objective handling in real time, the manager's job needs to change as well. So what does a great sales manager do differently when they have a productive and effective AI layer between them and the team? Jared Zelman (02:43) So we try to do three things in a closed up cycle. So we try to diagon it's kind of similar to like a I'll use like doctors as an analogy. We try to diagnose what's working, what's not working. So pretty much diagnosing what happens in sales calls, that stink. We then report that right back to the ⁓ to the managers and we give them a prescription. We'll actually give managers direct suggestions on what they should be doing differently to coach their team. Specifics, because managers they need specifics, they have a lot of other stuff going on. We will then actually implement that prescription. We'll then create the cure, hopefully, and reinforce those best practices in every single call. Right? And that system goes on, it's a close-up system. The way the manager job changes though is threefold. They now don't need to do all the diagnostics, they don't need to listen to 300 call recordings to identify the trends and what's working and what's not working. They don't even need to then draw the conclusions to how to fix that. Right? They can always be a human diluent director, but they don't have to do it from scratch anymore because of Thela's helping. Most significantly, they don't need to reinforce that training. They don't need to actually be sitting there coaching reps every single day, every single day. I mean, sorry, every single week. Because Thelo is doing that for them. So it's it's threefold. it's interesting. It's a point solution in that it's focused on sales calls. but it's doing every single part of that cycle such that the manager's job is similar, but it's not menial anymore. There is very little repetition in the manager's job when they have effectively an AI agent that is doing their journey work for them. KK Anderson (04:05) I would think that, as someone who has managed sales teams for many years, I find myself saying the same things, and as a sales coach, right, with our clients, I find myself saying the same thing to this, over and over again, like a broken record. And ⁓ it could be really interesting if you have to take away some of the fundamental that some of the repetitive stuff, like you said, it could be really interesting how those how that value of that coaching conversation would change. So ⁓ and I'm curious to get your take on this as we're evolving. Like what do you see the future of of CRM? Right? We know every salesperson, hates logging CRM. I had this conversation with the CRO just today, like, our CRM is a mess. And it's it but it's still the crux of everything. I imagine that what you're what you're Jared Zelman (04:29) Yeah. KK Anderson (04:49) the notes you're pulling and the insights you're pulling on these calls are are feeding into CRM. Like what do you see the future of of CRM? Is it gonna be more in the background? Is it gonna be a big part of of the future? Jared Zelman (05:02) I think a system of record in general will always be a very important part of the future. It's also a good data layer which you need then to use AI on top of. ⁓ so it will always exist. I do think it'll look different. I will think it is good. I do think it will be one of the l last things to change though, and evolve. ⁓ I just like one prediction is ⁓ like look at Notion. I don't know if you guys have have you guys used Notion before? Great. we started to use Notion as our CRM. We use Salesforce and Notion. Kind of for different things. KK Anderson (05:08) No. Yeah, yeah. Mark Petruzzi (05:22) Do. Jared Zelman (05:27) Notion, although you cannot do 95% of the stuff you can do Salesforce, and you can do Salesforce with, ⁓ the 5% that you do have overlap is the most important 5%, which is like the standard, CRM part. ⁓ and it's so goddamn easy. Like, there's gotta be a way to have like notion level experience, but with the level of like complexity that you can have like a CRM today, like maneuver with. Like, I think that KK Anderson (05:50) Give me an example. Jared Zelman (05:52) Like like here, like with Notion you can just copy and paste like a ton of content into. Like in Notion, you can even speak into it or like type into like a you can query it and it will then take that plain text query and create a database or input like content ⁓ into a database for you. Like in Salesforce, you can't even press enter and skip into a different field. You have to manually move your mouse or do a keyboard shortcut. KK Anderson (06:14) Yeah. Jared Zelman (06:16) Like that's insane. Like you need to like off in three times to get into Salesforce. We counted. We had to take on average nine clicks to actually make something happen in Salesforce to like actually start getting value. Like that's nuts. Nine clicks to get value? Are you kidding me? Like I have to off in to my CRM every 35 minutes. Nuts. ⁓ I digress. KK Anderson (06:18) Mark, are you listening? Yeah. Yeah. That's so interesting. Yeah. And so does it like how does how does ⁓ using a platform and a tool, a data layer like Othello Othelio, am I saying it wrong? Othello, Othello. How does that like how does that help the serum? Does it help with with forecast accuracy or pipeline or cleanliness or Jared Zelman (06:47) No, a fellow, a fellow. Spam. Mark Petruzzi (06:49) Hello. Jared Zelman (06:57) Yeah, w we automatically sync notes into the CRM for you. We have unlimited custom field mapping, unlimited custom objects. we're not trying to reinvent the wheel. I'll put that like put that out there. We are not changing your CRM forever, but we are reducing CRM note taking time by like eighty percent. Like I'll give you an example. KK Anderson (07:08) Yeah. Jared Zelman (07:14) We have a customer that's on a call, they're a medpic shop. Othello will automatically listen to the conversation, identify if MedPIC was achieved, the specific notes for each acron letter in the acronym, and we'll sync that into custom MedPIC fields in Salesforce for you, or HubSpot for that matter. That's great. Like that's a great next step, but like the future of CRM will be different entirely, I think. Like I would much rather in five years time my sales horse be completely like call it redesigned to look and feel like notion. KK Anderson (07:30) It really is. Yeah. Mark Petruzzi (07:39) Yeah, I'm with you on that one, Jared. ⁓ so we've seen a lot of AI tools adopted by individual reps. They'll they run off, they see something, they bring it in, and interestingly, many of those get abandoned a few months later because the overall workflow change was too high. Wasn't really, it was there was a shiny object that attracted them, not Somebody doing a real evaluation of what that product can do for the overall productivity of the team. So what does successful Othello adoption actually look like inside a sales organization? And what does the CRO or sales leader need to do structurally to get the team to use it consistently enough that the data really does become meaningful? Jared Zelman (08:27) So I like to we we actually have we're in a temporary office right now, but in our in our primary office in Israel we have a sign that says, You can lead a horse to water, but you can't make it drink. ⁓ words to live by when you're building tools for salespeople. Salespeople like me are not necessarily the most excited when it comes to new tools, especially when they're kind of being given to you by management. So it has to be super easy to use. Othello ⁓ is not there's no website, it's a desktop app. Automatically turns on when a call starts and starts listening. You don't have to click anything. There is no like look you how I said like Salesforce would click like eight times to actually interact with the product? Othello tr genuinely like zero clicks. Like you don't have to click anything. Mark Petruzzi (09:02) For sure. Jared Zelman (09:07) for it to be on and used in calls. So all the managers would need to do Mark is just download it onto their computers. And then Othello does the rest. You just need to read. Like I'm sure every seller in America is hopefully highly literate. All they need to do is be able to read the poppers of their screen. KK Anderson (09:21) Well, they better be if they're ⁓ the ⁓ core of our GDP here, our five million APs. ⁓ Okay, that's right. Okay, let's move on to our fourth topic. And this is the one that I've been most excited to dig into you with dig into with you. ⁓ and that's around the founders go to market playbook. And you have gone from zero to one million ARR in six months, which is awesome. Congratulations. Mark Petruzzi (09:22) Beautiful. All right. Jared Zelman (09:26) Yeah, it's ⁓ you know, the backbone of America. Yeah. KK Anderson (09:48) And so you tell the story, and I saw your write-up in entrepreneur.com about how you built Othello's early investor base through cold email, right? That you would email the CEO of Costco, the CEO of Lenovo, Howard Schultz. Like what walk us through that process that you followed. what you're describing is really contrary to what is prevalent out there right now, which is a lot of spray and prey, which has created so much noise and ⁓ made it so much harder for our backbone of America to be able to sell successfully. So like tell us tell us about that. It's tell us about the discipline, the research, the kind of just tell us about your approach. Jared Zelman (10:20) Yeah. Yeah, so and look, there's goods and there's there's positives and negatives to my approach when it comes to getting in touch with the you want to get in touch with, because that's what it is. It's not just sales, just getting in touch with the people you want to get in touch with. ⁓ the bad of my approach is that it's a very direct. and I don't it's not pushy, but I don't miss words when I reach out to somebody and I'm very willing to follow up repeatedly. The good thing, I mean, you could say those are also positives, depends how you look at it. Right. Like if I want to get in touch with For example, like the CRO of Microsoft or something like that. I don't even know if they have a CRO, but the CRO of Meta who I want to buy my product, like I will hustle like a mother, right? Cold emailing, cold calling him, sending gifts to his his office, his freaking home, get custom, Golden State Warriors jerseys for his kids with their names on it, some shit like that, until he responds, right? So to me it is like high pressure, it's full court pressure, right, to follow the basketball ⁓ reference. A lot of people don't subscribe to that. They support more of like a hey, like if you build it, they will come type of methodology. I don't believe in that. I don't have time for that. So when I was starting ⁓ Cicero and Othello, I said, screw it. Let's reach out to the people. And if they find value, they'll invest. And it was that cycle, actually. And it wasn't just for investors, by the way. It was our initial customers, investors, but like primarily I did it purely for mentors and to learn. KK Anderson (11:35) So how Yeah. Jared Zelman (11:42) Like I was doing this throughout college. I didn't have a company to invest in. I just did it because I actually wanted to learn from like Sam Altman. I didn't think they'd really answer. Then I figured out they do. KK Anderson (11:50) Who's your who's your the most shocking person that responded to you? Tell tell me that story. Jared Zelman (11:55) Say Maltman is a shocking one. I don't know if he's shocking. He responds to a lot of stuff actually. He's he's he's a I suggest you reach out to him cold. He's like known for responding to cold contact. Steve Bomber was a cool one. He was a KK Anderson (11:57) Yeah. Jared Zelman (12:06) That I looked up to for a long time. Howard Schultz was a cool one. So Howard Schultz didn't respond to me. And then he cold called me. don't know what it's cold called. He called me a few times. So I remember I was on the way to class in college and I got kept on getting a call for this freaking like Seattle number. And I thought it was some salesman. So I answered like a kind of a jerk. I'm like, who is this? is this Jared? I go, no. KK Anderson (12:25) Yeah. Jared Zelman (12:25) And I go wait, who is this? It was so it was hilarious. It was like the stupidest thing ever. It was Howard Schultz. And I was acting like an idiot. And he found that to be also pretty funny. ⁓ so I was saying Howard Schultz co called me. It's kind of the same. Yeah. Yeah. Mark Petruzzi (12:26) Ha ha. KK Anderson (12:35) my goodness, that's amazing. Yeah. Mark Petruzzi (12:38) And Jared, KK Anderson (12:39) I bet you wish Mark Petruzzi (12:40) there's KK Anderson (12:40) you had a fellow then to tell you exactly what to say. Jared Zelman (12:43) Yeah, I feel like I I don't know, sometimes like the innocence of being y young is enough to get these people to give you time of day. KK Anderson (12:48) Yeah. Mark Petruzzi (12:49) So Jared, there's definitely some irony here. ⁓ you are the founder of a company that teaches reps to sell better. And you grew your company by being an exceptional seller yourself. So how intentional was that and what did building a fellow teach you about the craft of selling that you just didn't know before you started? Jared Zelman (13:00) Trying to be. Art for science, again, let's touch back on that. when it comes to selling, the art aspect of it I think is sorta summarized by falling in love with the person you're speaking to and getting them to fall in love with you. I could speak on both of those two points for a long time, we'll put a pin in that. So that's the art of selling. That's something that comes very natural to me. I wouldn't say I'm a good seller, I would say I'm good at that. Or at least I was good at that. After founding Othello, I realized the entire science aspect of sales. You can't teach art, but you can teach science. So we focus on doing that. And I've learned ⁓ just through building Othello so much more about running a proper sales process, how to run say real discovery that is structured as opposed to just being super interested, which is great, but it's not enough. So I wouldn't say I was a master salesperson. I would I'm not today. I was art, Sales artist, perhaps. Now I try to be a whole lot more than that. Mark Petruzzi (13:56) what, Jared, you're you're kind of defining a little bit of of my journey in sales where and even in from the standpoint of of a couple books that I've written. The first book, Selling the Cloud, was all about the art of sales. And that's really where I wanted to go first in in my writing. However, the s second well, a little background, I was actually ⁓ Jared Zelman (14:02) Okay. Mark Petruzzi (14:20) Talked into and maybe even manipulated into writing a book. I'll share that story with the audience and the and ⁓ you as well another time. But I wasn't someone who wanted to write a book, I guess is the first thing, until we released the first book, Selling the Cloud. And then I could not wait to get to the science of selling, because that's really, as you put it, that's where the The impact comes from, it's kind of there's only so much you can do to make someone who's not comfortable doing what you just described, building a relationship with someone, falling in love with them, having them fall in love with you, want to do business with you. that's that's harder to teach, but the science is pretty easy to teach when you really get it into play. Jared Zelman (15:11) The yeah, we don't really try to teach you the art of sales. We try to teach you the science of sales. Like and that's the human element by the way. That's why I think humans will always be in sales, at least B2B sales. Is for the art aspect of it. The science you can replicate, the art you cannot. KK Anderson (15:18) Yeah. Yeah, that's really interesting. And ⁓ at when as you perfect the science, then it gives the confidence and the bandwidth and the room for the art to really shine. Jared Zelman (15:36) Look, in theory, every extremely as I said, like the art of sales, I think is falling in love with somebody and getting them to in love with you. There's a lot of lovely people out there that can't sell for their life. but they they're they'd probably be great at the art of sales. So we try to get them to be more ⁓ more aligned with the science and best practices of sales. KK Anderson (15:43) Yeah. Yeah. Okay. So you went from Cicero, the AI Celebrity Chatbot Company. That sounds interesting. AI Avatars of Celebrities. Okay. And then now to Othello, you you did a hard pivot as you were describing. and you did it from scratch and you got to a million ARR in six months. Like tell us like how you did that. How did you validate I mean I you you talked a little bit about the research, but tell us tell us Jared Zelman (15:59) Yeah, AI AI Avatars are celebrities. KK Anderson (16:18) Give us all your secrets, Jared. Jared Zelman (16:19) ⁓ so I can tell you about Cicero as well because I I mean we did a million there. it comes down to KK Anderson (16:22) Sure. Jared Zelman (16:24) Look, it really is a it's a function of sales cycle length, is what it is. Like if you want to get sciencey about it. you could build the world's greatest business, but if your sales cycle like twenty-four months, and sometimes the world's greatest businesses do have really long sales cycles, the nature of their business model, then ⁓ you can't grow that fast on paper. like a lot of the fastest growing companies in a burgeoning industry are consumer because the sales cycle is like one minute. But in our business model, it was it's it's like four months and we were able to get it down to like a month. ⁓ so we could really juice the hell out of sales velocity because sales cycle was only a month. Maybe this that's ex that's like the hard part, and people don't think about that. KK Anderson (16:54) And how'd you get it down to a high? Jared Zelman (16:58) ⁓ we like really workshopped the shit out of our sales process. We broke down everything across every sales process we were in at that point and prior to that looked at every commonality and we just started cutting out nonsense and built very strict SOPs, like extremely strict SOPs. ⁓ and we were surprisingly able to reduce it from four to one, which yeah. KK Anderson (17:18) And aren't you gonna say that you use your own platform? Jared Zelman (17:21) Yes, but s but our platform helps with sales cycle lengths. It does. ⁓ but a b a bigger driver, at least of our type of business when it comes to sales cycle length is actually the stuff that happens off calls. Right? It's ⁓ touch points with InfoSec. how quickly can you get the business decision maker to actually sign something? Like that alone, like like contracting is the longest part of our sales process, or at least it was. How can you juice that? KK Anderson (17:24) Yeah. Mm. That takes forever. Yeah. Security. Mm-hmm. Jared Zelman (17:43) Yeah, I mean that's this is like sales. Like people try not to get into the science of it, right? But the speed at which you can close a deal is as important as your win rate in many cases. KK Anderson (17:48) Yeah. Mm-hmm. Mark Petruzzi (17:53) Excellent. So in general, Jared, you ⁓ especially after Cicero, you had lots of VCs that you could get to invest in your company. But yet you you did it a little more on the angels side, very famous angels nonetheless, people like Craig Jelinek and Howard Schultz as we described. But when it Jared Zelman (18:14) How Howard Schultz Howard Schultz did an angel. He was a mentor. He did an angel. He missed the round program. Mark Petruzzi (18:19) Yep. Perfect. Cool. So having that, those relationships, ⁓ what's the one thing you would tell a founder in the audience who's at that pre product market fit stage and trying to figure out like what do they do? How do they if they're not a sales inclined individual, how when do they hire a sales leader and can you be a ⁓ Jared Zelman (18:21) Never forget. KK Anderson (18:23) Ha ha ha. Mark Petruzzi (18:45) an inefficient founder selling sales organization for a period of time or to do you just need to make sure if you're not the sales leader that you bring one in right from the beginning. Jared Zelman (18:58) Yeah, I I I I strongly recommend against hiring for sales too early for thousands of reasons, many which are well documented already from people out smarter than me, like Paul Graham. ⁓ I think to determine when you want to hire a sales leader, it's funny, like people always say like hire the sales hire your first sales person like when you have not like no time on your hands but sales. That's actually misleading because it's very easy to fill your calendar with bullshit sales calls. It all comes down to reducing sales cycle to make it more efficient. I think you need to run that analysis on your sales process first, cut out all the fat. For example, if you're taking 30 meetings to close a deal, you need to understand if that's truly the minimum. I betcha it's not. And then once you have an efficient sales process, if you still have an absolutely full calendar, that's when you hire sales. Do not let For example, like non-decision makers or like non-stakeholders waste your time. it'll convince you that you need to hire people because you're too busy, but you're not busy with anything meaningful, you're busy with time-wasting activities. So that's like the first trigger. Again, long way of answering pretty short questions. So I apologize, Mark, but it's important to get to the nuance. KK Anderson (19:59) Mm-hmm. Mark Petruzzi (20:01) No, it was a good one though. Jared Zelman (20:03) Also, and this is something that's I learned across all my businesses, is when you're launching a product for the first time, the objective is PMF, it's not sales, it's not product buyer fit, it's product market fit, which means post-sales defines success, but not actually the dollars in. ⁓ which means you want a short sales cycle, obviously, and you want a short time to value or renewal cycle. That's another way of graphing time to value. So you can determine PMF faster. ⁓ I highly recommend it before building a product that has a long experience cycle. You understand if you're really willing to take that risk. If it takes a year for you to prove value, you're at risk of investing a year in a product that will never have PMF, no matter how successful you are at executing. ⁓ that's one thing that you can control before you start a business. And I I implore you to think deeply about that if you're starting a business. KK Anderson (20:48) Jared, have you read ⁓ Mark Roberts' new book, Science of Scaling? Jared Zelman (20:52) I haven't I've been recommending that book a thousand times, I think, so I may just read it to start saying yes. Yeah. KK Anderson (20:54) It's so good. It's so it's so good. Go on Amazon and get it. He ha he was on our podcast and a few months ago before the book released. But it's wonderful. We got to we got to do a pre read of it before it went to market. ⁓ but it talks a lot about product market fit and when to scale and yeah, it's really it's really great. Some good insight. Jared Zelman (21:11) He's great. I think you need to have like made mistakes to learn this stuff. ⁓ and you almost have like need to have done it before. So that's like a good that's like a good like it's an underrated thing, like making mistakes. I would say like failure is super underrated. Yeah. KK Anderson (21:17) Yeah. yeah. experience. Yeah. It's Mark Petruzzi (21:29) huh. KK Anderson (21:29) what it what makes it's what makes you stronger because when you come out the other side you're you've learned a lot of lessons. Okay. Jared Zelman (21:35) Yeah, you just wanna make sure you come out like yeah, still spry, but go ahead. KK Anderson (21:38) So so for our last few minutes together, we're gonna do our favorite section. ⁓ it's an audience favorite anyway. We call it rapid fire. And we've got a few questions and we'll ask them fast and give us kind of your in your first instinct and we'll go through it and I'll start. Jared, what's the first thing you've ever sold? Jared Zelman (21:56) ketchup sandwiches. Straight up, yes, honestly ketchup sandwiches, triple decker ketchup sandwiches. KK Anderson (21:58) Okay, I gotta hear about that. When you were a kid, ketchup sandwiches watched the neighbors at the swim meet? What? Jared Zelman (22:02) Yes. everywhere. ⁓ mainly neighbors. ketchup sandwiches when I was like two years old. They were viral. And not in like the cool way, like viral isn't like viruses it's just very, dirty and I made them without washing my hands. Emphasis on gross. Yes. Emphasis on gross. For sure. Mark Petruzzi (22:13) So Jared, you really learned about gross margin really really early in there. I love that. You were you were just like I am not gonna over over ⁓ engineer this, that's for sure. Jared Zelman (22:26) They're actually delicious, by the way. I know that sounds terrible, but like, okay, you know what? I'm not even gonna I'm not gonna convince you. Trust me, if anybody some four two year old kid offers it to you in the street, give it a try. ⁓ sorry, that's not round of fire, but that's my answer. Sure. And like a lot more bread. Yeah. KK Anderson (22:37) It's just like a hot dog without a hot dog. Mark Petruzzi (22:40) Cool. All right. One one metric every CRO should add to their weekly dashboard that for most CROs is not there right now. Jared Zelman (22:52) Ooh, wow, I wanna think deeply about this one, actually. This is a fantastic question. You have to sue enough people and you build the best like weekly like deal agenda. I would I'm very much focused just the nature of our business on like sales velocity. ⁓ so it it it would be ⁓ leading indicators of sales velocity. And that's a that's business specific, but it would be a leading indicator of sales velocity. It could be something as simple as to touch on the InfoSec experience we were talking about earlier, KK. ⁓ the amount of times you had a touch point with an InfoSec contributor, or the amount of red lines you responded to in the course of a week. ⁓ that's something that like we we try we track that. KK Anderson (23:23) Interesting. Yeah. Okay, so Jared, who's the sales leader or founder that you admire and respect the most? Jared Zelman (23:33) Jesus Christ, these are crazy questions. I'm gonna offend a lot of people, depends on who I answer. if if all of my buddies watch this. Like I'll give you one, like ⁓ KK Anderson (23:39) One of, one of. Jared Zelman (23:41) Like w we're doing we're doing work with Oder.com. ⁓ Kyle Norton, long before I started working with him, is like way long before, is a sales mentor of mine. Like he's a goat, so to speak. Dale Carnegie, when it comes to the art of sales, is a freaking legend. So I love Dale Carnegie. Though that'd say like those two are like opposite sides of the same spectrum. KK Anderson (23:58) Yeah. Good stuff. Mark Petruzzi (24:02) Beautiful. So ⁓ last rapid fire question. Hiff What's the biggest misconception CROs have about what real-time AAI coaching can and just cannot do? Jared Zelman (24:15) Well, the main thing is they don't know that it exists. so if they know it exists, ⁓ the conception misconception any of them would have is that it's ⁓ something it could become a crutch, right? Like if it's truly that good, why do we need salespeople at all? Why can't I just put like a the twenty-one year old kid in front of a camera to read off their screen? I think that conception is a misconception, because as we all discussed earlier, ⁓ you still need to have trust, you need to have empathy, it doesn't matter if you're using Othello or not, you can't replace the human element. So you can't you can't throw some random in front of a colleague's button perform well. KK Anderson (24:49) What you have shown us is that the best technology is built by founders who are great practitioners first, right? At the very skill that they are trying to scale. so if this episode, shifted how you are thinking about your rep performance or your AI coaching strategy, share it with your team, share it with your CEO, your VP of sales. We will put all of Jared's contact information and LinkedIn profile and link to his website in the show notes. We'll also reference the various books that we refer to in the in the episode. and you can find us at get-ags.com or anywhere, podcasts are found, Spotify, Apple, et cetera. And we're thrilled to have you, Jared. And until next time, thanks for joining us on Selling Intelligence. Jared Zelman (25:32) Thank you both. Talk to you soon. Mark Petruzzi (25:34) Thank you, Jared. Cheers. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 131 – Fixing the 80/20 Sales Problem with Real-Time AI Coaching with Jared Zelman - Part 1 | 17 juin 2026 | 00:21:44 | |
General Episode Description: In this episode of Selling Intelligence, Jared Zelman, Founder and CEO of Othello AI, joins Mark Petruzzi and KK Anderson to challenge one of the most accepted assumptions in sales leadership: that 20% of sellers will always generate 80% of the results. Jared argues that the 80/20 problem is not a talent issue. It is a systems issue. Drawing from millions of minutes of sales conversations and real-world customer deployments, he explains how modern AI can capture the behaviors of top performers and deliver coaching in the moment when it matters most: during live customer conversations. The discussion explores why traditional coaching models fail to scale, the limitations of post-call analysis, and how real-time AI guidance can improve discovery quality, qualification, and win rates across entire sales organizations. Jared also shares insights into how AI is uncovering new patterns in selling behavior, including why Sandler-style methodologies continue to outperform across modern B2B sales environments. What You’ll Learn:
Key Topics:
Guest Spotlight: Jared Zelman Jared Zelman is the Founder and CEO of Othello AI, a real-time AI sales coaching platform designed to improve sales execution before, during, and after customer conversations. Built by the team behind Cicero, Othello helps organizations scale elite selling behaviors across entire teams through contextual, in-the-moment coaching. Since launching in 2025, Othello has rapidly grown to support thousands of users across Fortune 500 companies and high-growth technology organizations. Resources & Mentions:
Coming Next Week: Part 2 explores how sales leaders should manage AI-augmented teams, how coaching changes when AI handles execution consistency, and Jared’s founder-led go-to-market playbook for building a venture-backed company through strategic cold outreach and relationship-driven selling. 🎧 Listen now and subscribe to Selling Intelligence for more conversations on AI, revenue leadership, enterprise sales, and the future of go-to-market execution. Mark Petruzzi (00:28) Welcome to Selling Intelligence. I am Mark Petruzzi, and I am joined as always by my co host, KK Anderson. Our guest today built the company on a number every CRO already knows and hates. Those numbers are the 20% of reps drive 80% of the results. The question is, what do you do about it? Most leaders throw more coaching hours at the problem. Build out their enablement team, and then just hope it scales and gets more productive. Jared Zellman did something a little different. He went out and he built an AI that sits inside the call and fixes it in real time and on every call. Jared is the founder and CEO of Othello AI, a real-time AI sales coaching platform that guides reps before, during, and after every call. Built by the team behind Cicero, Othello launched in July of 2025 and reached over 5,000 users and 1 million in revenue within its first six months, with clients spanning Fortune 500 companies and high-growth startups. Othello integrates with the go-to-market stack you already have, whether it's Salesforce, HubSpa, Gong, SalesLoft, Clary's, Zoom, or Teams. And sits as the execution layer that makes sure what happens on the call matches what the playbook says. KK Anderson (01:55) What I love about Jared's story is that he is not just a founder talking about sales AI. He is a practitioner of the exact skills he built Othello to teach. He built his entire investor base, his early customers, and his mentor network through deliberate, personalized cold outreach to some of the most senior people in the business. Howard Schultz, CEO of Lenovo, CEO of Costco. All started as cold emails, which is incredible. And that kind of disciplined, researched, human first selling approach is what Othello reinforces at scale. So this interview will be a part of a two-series, a two-part series overcome excuse me, reviewing four topics. today we're gonna get into the first two topics. Topic one, that 80-20 problem that Mark mentioned. And why the performance gap between your best and average reps is not a talent issue. It is a systems issue. And why most CROs are solving the wrong problem. Excited to get into that. And the second topic for today's episode is real-time AI coaching and what it actually means to have AI inside the call, how the live cue cards and pre-call briefs work, and the results that the teams are seeing. And this modern, AI run, coaching platform, which is really interesting. Now, next week, when you tune back in, we'll talk about topic number three, managing an AI augmented team. what a CRO's job looks like when AI handles execution consistency. and topic number four, the founder go to market playbook. And this is one I can't wait to get into. So tell us exactly how, Jared, you went from being a new college grad with no network to ⁓ VC back CEO with Fortune 500 clients in under a year. So we got a lot to dig into today. Jared, welcome to Selling Intelligence. Jared Zelman (03:46) Thank you for having me. I'll try not to bore you guys. Mark Petruzzi (03:48) No, you would never. So Jared, ⁓ you built Othello on the premise around twenty eighty. Twenty percent of reps driving eighty percent of the results. And that this is a solvable problem. Most CROs have lived with that ratio for their entire career and has accepted it as a fact of selling life. Please make the case for us that it is not a talent problem. Jared Zelman (03:55) Mm-hmm. Yep. Mark Petruzzi (04:12) What is actually happening structurally in the calls of average reps that top performers are doing differently? And how do you make sure those those top performer practices actually get leveraged into the rest of the team, those eighty percent of reps that we we all know? Jared Zelman (04:30) It's the Pareto principle, right? So the Paretto principle isn't it's it's not a law, like things don't need to adhere to it, but it's a commonality. So most sales organizations will suffer from the 80-20 problem. Doesn't mean they have to. I was just chatting with a mentor and advisor to our company, a guy named Dan Lawrence, one the most lovely and impressive sales leaders I know. He's the GM of America's at Nebbius. Nebbius does not suffer from the 80-20 problem. Right? Like a rising tide lists all ships. He's been able to upscale all of his reps to be so effective that they're all ⁓ top performers, especially if you compare them to any competitors. I believe it's a systems problem, not a talent problem. I actually think you can turn the middle sixty percent into the top twenty percent. The bottom twenty percent is a different story, but at the very least you can get to performing better. KK Anderson (05:12) And it's all by being there in the moment. Jared Zelman (05:15) Well, like it's it's interesting. It's like a like let's let's use like basketball as an analogy. Practice is obviously crucial. No one's gonna tell you that practice isn't important, right? And that's preparation, right? In sales, it's the same thing as going, Tuesday afternoon after school practicing ⁓ shooting hoops, right? But what's also crucial and you can't live without is having your coach screaming at you when you're shooting hoops in a game. Live, right? we try to bring that into sales. ⁓ similar to how if you guys are in sales or have been in sales, your sales manager perhaps would have been slacking you on the side telling you what you should be saying, or even like hooking up to your call with headphones, kind of like whispering in your ear what you should say instead. We try to replicate that experience with AI. KK Anderson (05:54) So but you're not the ma you're not the coach screaming at you from the sideline. Jared Zelman (05:58) We ⁓ no, we can't. It's when you're dealing with salespeople, it's a b it's an art and a science, right? Like on paper, what does work doesn't always actually work ⁓ in practice. ⁓ sales reps are dealing with very high pressure sensitive environments. So ⁓ I mean that's like one of the reasons why a lot of engineers fail at building sales tools is you need empathy for the user experience, which is very different from the UX and other products. KK Anderson (06:03) It is. It's ⁓ So when you went went deep on this problem before building your platform, what like what did you find in your research that surprised you the most? I think I read in one of your articles that you were starting with a different like something about celebrity avatars or something, and then you quickly pivoted when you saw the market. Like tell us what you s tell us what you saw and what really resonated. Jared Zelman (06:38) Yep, that was my first company. of course. I can tell you about the avatar business prior to Othello. ⁓ We can touch on that in a second. ⁓ how did I fall upon this major problem though that we're solving at Othella, which is like the 80 or 20 problem of sales? look, it doesn't take like an investigative journalist to like understand that, yeah, there's something going freaking wrong when it comes to the power law of sales rep performance. ⁓ I think the more controversial thing though is ⁓ just how massive this impact is. Let me put this in perspective. Most commerce in America, like most of our GDP, is derivative of B2B commerce. It's usually it's mainly business-to-business, okay? Consumers Spending is huge, but B2B is actually the crux of most of it. Everything else is generally downstream. About 80%, call it 75 to 80% of B2B commerce is driven by account executives or account executives with a different name, right? Like account director, for example. That's just one job role, and that's only about 5 million people in America driving 80% of the B and B commerce, which is the majority of GDP. Like if you were to actually draw that corollary, you would see just how important those five million human beings truly are to economy. Consider that 80% of them are nearly or entirely non-productive. That's massive. If you can squeeze even 20% more juice out of that fruit, you can get instead of 20% of them being top performers, 35% of them hitting quota repeatedly, the impact that that has downstream on the US economy is extremely consequential. When I did the math, when I spoke to these people like the CEO of Lenovo, Costco, Home Depot, General Electric, and they all concurred, I realized this is ⁓ this is a fact of life that that very frankly is a whole bunch of bullshit. That there is no way we can justify and just sit idly by as the economy is in some ways carried by 20% of five million people. Right? AEs are the backbone of the US economy. I've never heard that in any business, any economics class I ever had growing up or in college. ⁓ so I said, look, I'm gonna solve that problem. How I solved that problem, I do not know at that point, but I was zeroed in on ⁓ at least getting a piece of the action. KK Anderson (08:36) I have been in sales for over two decades and I have never heard that AEs are the backbone of the US economy and I think I love it. Jared Zelman (08:42) It's it's tacky, like no one wants to he you hear it. KK Anderson (08:46) Yes, I love it. Jared Zelman (08:47) It's the truth. Like run the freaking numbers. It's true. People don't like understand that. Like there's look, there's like some ways you can like different ways to cut the pie up, obviously. But ⁓ don't sleep on them AE's. They're they're massive. So but you can also make the argument, right? Like if they're getting their leads from SDRs, then SDRs are the backbone of the economy, right? There's like different like layers to the cake, but AEs are the bulk of the action there. KK Anderson (08:58) Don't sleep on me. Yeah. Mark Petruzzi (09:08) Very interesting, Jared. The conventional solution is has been post-call coaching. Gong, chorus, just having manager one on ones. ⁓ that's been the that's been our history in sales. Now you have said by the time the analysis is done and these systems pull this together and you're no longer with the prospect, the opportunity is gone. Jared Zelman (09:17) Gog, stuff like that. Yeah. Mark Petruzzi (09:33) You r you really can't go back and really correct things that may not have gone well in the original call. So walk us through the specific moment in a call where you think a deal is really one in won or lost and why postcall feedback does not touch that moment in time to be able to change the outcome. Jared Zelman (09:54) Yeah. I I think ⁓ I think it's uncontroversial to say that deals are won and lost in meetings. ⁓ at least for the companies we sell to, many of those, not all of those, but many of those meetings are happening, via Zoom or via some kind of phone call on your computer. The deal can be won and lost in a several like several different moments. Most deals are one and lost in discovery. ⁓ good sellers know that. Right? If I'm not digging deep enough in a discovery call, if I'm not having true empathy for the customer, then yeah, I'm gonna lose them. No matter how good your product is, you're probably gonna lose them. So I'll give you one example of what Othello will do. Othello can remind me in the middle of a disco call, hey, double-click on that pain point. Or say, KK, you were to say something like pretty gaping about a problem you're trying to solve. Thello may have me ask, okay, but KK, what have you tried to solve? How have you tried to solve that problem? Why did that fail? And then we try to give you the question behind the question, like a layer deeper beneath the surface. ⁓ we believe if we can improve the quality of your discovery, if we can get you to convert 10% more of your discovery calls, ⁓ the trickle-down economics of that are meaningful for any company. KK Anderson (10:50) So it's interesting. We do at AGS, our firm, we do lots and lots of behavioral competency analyses on on thousands and thousands of sellers. And there's a core set of competencies that we call the sales DNA, which are, the competencies that really are between your ears deep in the brain. And it's things like your ability to stay in the moment and listen to a prospect. Like you're you're just and you're describing discovery. And when you have a younger Jared Zelman (10:57) Yeah. KK Anderson (11:16) Sales person, especially AE or BDR or whoever it is, a lot of times when that customer or that prospect is talking, they think they're listening, but really in their mind, they're they're thinking about what they're gonna say next, or how are they gonna overcome that objection, or how should I phrase this value pitch, or they're they're they're thinking in their mind and they're not necessarily truly listening to what's happening with every breath that your prospect is speaking. But a lot of that comes with maturity, right? And experience and being able to do it for a long time. But very often what we see is that sellers will miss the opportunity to pull on the thread of the sweater, right? To dig into, the TED questions. Tell me more about that. Can you explain that to me? Can you describe that? I mean, some of these simple tricks that sellers have had for for decades, they'll just miss it entirely. Or a, the other thing we see all the time is that. A salesperson has had the same call so many times that they have an assumption that the prospect must have this problem, they must be doing it this way because that's how all my other clients did it. And they may say something that is is compelling and is different, and they may not may they may just totally miss it. Right? Jared Zelman (12:25) What I've what what so here's the thing. I I agree with you by the way. Like and I do think there is an element of that that will never change. Like that's human nature. And as long as human beings will be in sales, you're going to have human elements affecting sales conversations, especially if they're repetitive, right? Because we're creatures of habit. I I don't say, I don't I don't think it's technology's job to like necessarily replace that human element, but I do think we can supplement and augment it. So I'll give you an example. ⁓ and and maybe I'll ask you guys this question first. KK Market, do you guys think sales will continue to be human led, at least B2B sales, for the next ten, twenty years? You think it'll be human led or AI led? KK Anderson (12:57) I think there will always have to be a human in the loop because at the crux of sales is trust and relationships. And I don't think that's going to change. As a matter fact, I think AI is is swinging the pendulum back to how it was in the 50s when sales started. Now, can we automate a lot of what happens in sales and make us more exceptional and more differentiated and and utilize the superpower, superintelligence? But heck yeah. But I do think a human will always be in the loop. Jared Zelman (13:10) Yeah. So I agree with you on that. I will say though, when it comes to like sales, you're judged not on your efficiency, right? You're not judging how quickly you can get the job done generally. It's a good thing, obviously speed and sales cycle like reduction is good. You're judged on how much money you're bringing in. So it's ⁓ efficacy, right? Like effectiveness, not efficiency. ⁓ Hence most AI automation around the margin, like CRM node automation, for example, while it is nice to have, is not going to be redefining performance for a sales organization. At least not a good one. Right? Like you saving like eight hours a week for your sellers, as great as that shit is on paper, is not going to move the needle from like a corporate revenue perspective. Un unless you guys are truly like the most like effective, like and every minute is worth millions of dollars to your team. KK Anderson (13:47) Yeah, I agree. Jared Zelman (14:04) where you will juice the hell out of your margins and performance is if you can improve win rates. Like that's 90% of it. Everything else is downstream of that. And automation does not help improve win rates. Right? You need to focus on quality of meeting as that's where the money is made and lost. ⁓ post-call note taking obviously is a step in the right direction. Practically completely unused. Like, who are we kidding? Like, no one is spending four hours a week looking at call notes, no one's spending four hours, five hours a week in AI role play talking to some AI character. They want to be selling. So you need to find a way to enable them, get them to perform better. frankly, without perhaps having to put in a whole lot of effort to do it. That's that's the crux of my philosophy and frankly like the foundation of Othello's product. Mark Petruzzi (14:39) Yeah. Yeah, and I I think that's a big differentiator for you. Jared for you and Othello. let's move to topic two. ⁓ real time AI coaching. And ⁓ the ⁓ our audience here knows that I typically don't like to talk too much about any company's individual product. really as you've been describing, I love to learn. I I think my audience l likes to learn. the ⁓ the framework, like what what you what you have built and why does that tie back to a product? Here I think I'm a little more comfortable pushing on this a little bit. So take us to specifically what Othello does. walk us through a little bit how does the the real call, the pre-call brief, the in-call cue cards, Postcall automation. How does that come together? And what does the rep see, feel, feel, and hear at each of those stage that really does influence them in in their overall selling efficacy, as you put it? Jared Zelman (15:50) Yeah, so we're trying to do one thing, and that is to get reps to say the right things in calls. You have to do that a few different ways, but 80% of the value comes from the core product, which is the real-time in-call suggestions. And let me like specify here. ⁓ these are not suggestions that are pre-gridden or pre-populated and designed by enablement. You're getting a new suggestion on your screen almost every single time. I'll I'll draw you a picture here. I'm selling widgets to you, Mark, and KK. Othello will put a pop-up on my screen guiding me to say the exact right thing in that moment. Taking context about what you care about, about who you are, about what you just said, about what you asked me in the last call. So the suggestions will always be different and hyperintelligent. Pre-call and post-call, we give intelligence, coaching, suggestions, a lot of proprietary tech there as well. But truly the sea change comes from what happens during calls. So we focus on that. KK Anderson (16:40) So Jared, you've described a tension that you call rote versus rogue. the rep who follows the AI Q cards too rigidly on one end and then the repu ignores them entirely on the other. So so where where does the AI add the most value in that spectrum? And like how do you how do you design a thello to keep reps in the zone where AI helps rather than hurts? Jared Zelman (17:04) I would say that this differs depending on the user. So we have people that we we for example, like we have like sellers that are like sixty five years old and above. ⁓ They like to design the earth element, and you can toggle this, right? To be very lightweight, very suggestive, not scripted. It'll be more of a n a nudge like, hey, double click on that. Like or dig deeper is what you'll see on your screen, as opposed to like a literal question to ask, for example. ⁓ and that's very, very ⁓ That's very like, I don't know the word, like very like light. And then maybe people that love a script and they have super high frequency pop-ups. ⁓ they both work, it depends on who you are. never do we suggest you go fully rogue. And obviously if you're gonna go rogue, then just don't buy our product, just do whatever you're doing. If you're an A-list seller, then maybe you don't need any help. But if you do, then yeah, you should definitely not go rogue. Like I don't have any like really advice on that. We've had to build a product such that anybody can use it the way that they want. You have to meet sellers where they are. You can't expect them to take the product as is. They need to be able to customize it. Mark Petruzzi (18:00) Yep, good stuff, Jared. So you have said that the Sandler methodology has emerged as the as AI's preferred approach based on what it observed across thousands of calls. That to me is a fascinating observation. ⁓ the AI, in the way I've I've read and and heard from you, has really reverse engineered a winning framework from the behavioral data. Walk us through what the AI saw in the data that pointed much more towards Sandler and what that tells us about what actually works in complex B2B sales in 2026. Jared Zelman (18:39) It's hard for me to answer the second part of that question. I'd give you my POV, but it's a really it's a big it's a big question with a lot of ramifications. firstly I'll answer the former. Yeah, we we trained on like 20 million ⁓ sales minutes. That's the largest trainable data set of that type in the world. And once you have like that many minutes, you spend enough time and enough cash on compute, like you can start to draw some corollaries and identify patterns. It seems like Sandler is the way to go, at least over our dataset, which is pretty robust. Sandler is Very well tuned for the modern seller. It seems like modern buyers respond well to Sandler, as folks are a little bit less they're more hesitant and more reticent to purchase tools these days. So Sandler kind of flips the script and gets it back faster. That's our common belief. Like that's why we think Sandler has been most kind of like successful. I think going forward, I think Sandler will continue to be the highest performing sales mess sales methodology, at least according to AI. but I do think that ⁓ methodology performance is like very much it it depends on the times, it depends on the zeitgeist. you could not have used Sandler in the fifties, you would not have had frankly like God and anybody to want to work with you, you can do that now as people are a bit more caustic. ⁓ but it's it changes with the Zeitgeist. Not a great answer perhaps to your question. It's like the answer is no answer. It depends is always the best answer. And that's kind of what I'm referring to. KK Anderson (19:55) I wonder if with the advent of AI, if people will not have to follow some of these, old school methodologies like Sandler, because they can take their tribal knowledge that is within the brains of their 20% top performers and and leverage it in a way that they've never been able to do before because of like even being able to use a tool like yours, I imagine, helps helps ⁓ I mean there may be some process there. Of course you the best objection to overcome is one you never have, right? Jared Zelman (20:22) So The g one of the great things about AI is its ability to customize things to you, right? It's context. Right? Like you can take a crap ton of say call recordings for your company, and AI is able to create what it defines as the best practice for your sales conversations. You can pretty much now create a custom methodology based on what works and what doesn't work if you have enough data. you're right, KK. Methodologies are fantastic, but they are heuristic. But now AI is able to take a ton of unstructured data and glean analysis from that. KK Anderson (20:52) Uh-huh. Jared Zelman (20:53) I do think that one size fits all methodologies in general are ⁓ they're going to slowly go away because you you don't need a heuristic anymore. You can actually get the facts if you're able to run a model on top of your data. Which is what we do. I mean that like that's like that's like kind of what we do over time with each of our customers. Like the model changes, the more calls you have. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 130 – Building Resilient Salespeople in the Age of AI with Scott Stollwerk - Part 2 | 10 juin 2026 | 00:16:52 | |
General Episode Description: In Part 2 of this conversation, Scott Stollwerk returns to Selling Intelligence to explore one of the most important questions facing modern sales leaders: what happens when AI becomes excellent at execution, but human performance remains the deciding factor? As AI continues to improve outreach, forecasting, coaching, scoring, and productivity, Scott argues that the real competitive advantage is no longer process or technology. It is the human being operating behind the tools. Drawing on the Tao of Sales framework, Scott explains why resilience, self-awareness, creativity, intuition, and personal growth remain irreplaceable in high-performance sales organizations. The conversation explores the limits of AI, the dangers of over-automation, and why leaders must continue investing in human development even as technology becomes more powerful. Through practical stories, leadership lessons, and personal experiences, Scott demonstrates why sales success ultimately comes down to overcoming the internal barriers that technology cannot solve. What You’ll Learn:
Key Topics:
Guest Spotlight: Scott Stollwerk Scott Stollwerk is a sales leader, coach, and creator of the Tao of Sales methodology. Combining Eastern philosophy, neuroscience, martial arts principles, and human performance science, Scott helps individuals and organizations build resilience, self-awareness, and sustainable performance. As part of the leadership team at Pest Share, he continues to develop sales cultures that prioritize human growth alongside business results. Resources & Mentions:
Key Takeaway: AI can improve productivity, automate execution, and accelerate workflows. But it cannot replace resilience, courage, creativity, judgment, or human connection. The organizations that win in the AI era will not be the ones that develop technology alone. They will be the ones that continue developing people. 🎧 Listen now and subscribe to Selling Intelligence for more conversations on sales leadership, AI, human performance, and enterprise growth. #SellingIntelligence #AIforSales #SalesLeadership #HumanPerformance #SalesCoaching #RevenueLeadership #EnterpriseSales #SalesCulture #LeadershipDevelopment #MindsetMatters #ArtificialIntelligence #BusinessGrowth #TaoOfSales #HighPerformanceTeams #FutureOfSales Mark Petruzzi (00:38) I'll move us into topic two. and that is what AI cannot fix the human edge in sales. So I guess I what I want to share is in sales, AI cannot fix everything. I mean you heard it here, you know, everybody thinks every board thinks like any problem we can fix with AI. I don't believe that's the case. So what it can do, it is now writing outreach, coaching calls, scoring deals, forecasting pipeline. Those examples it does really, really well. And in most cases, almost all cases, it does it better than humans can individually, certainly for the at the productivity levels that it can do it at. That's good because a lot of our listeners have made significant bets on it, and that's going to be a great thing for your Salesforce effectiveness and productivity. but what does AI get right about sales performance? And Scott, where does it just hit that wall that no amount of compute is going to break through? what's your point of view on that? Scott Stollwerk (01:40) It's a it's the mo the it's the Peloton question of this year, right? and I wanna get it right and I wanna start with a compliment for AI in just in case it's listening. So I'm always gonna laugh at my own jokes, but that was very okay, that was very generous of you. I appreciate the smile and the chuckle. KK Anderson (01:54) Yeah. Scott Stollwerk (01:57) I have the same fears that everybody else does. I don't want it to lock my bank accounts and give me a hundred dollars every time I do what it tells me to do. the fact is, look, we're all way more productive today than we were last year or the year before at this time. Cause I get messages to follow up, which maybe I would have forgotten before AI. I get instruction on how you might follow up. We get coaching. After every single call. And there's a tremendous amount that it does well. But I think if everybody just empties your mind of all these benefits of AI for one second and do a little mindfulness, a little awareness. Imagine that we're sitting in a room with one other voice, artificial or human. It doesn't matter. Buy something from it in your imagination. For fifty dollars. And then buy something from it based on what it's telling you. about your life and how this object or solution or thing is going to benefit you as a person. And then go to a thousand dollars. And then go to ten thousand dollars. It doesn't take long for sentient human beings that are not AI code writers to say, no, right there, that's it, $1,000. I'm not buying something from a machine if it's more than $1,000. That's just one exercise. But yeah, within it, yeah, the implications for my answer to you, Mark. In the enterprise, I may use AI to research everything. KK and Mark told me on a Zoom call like this about their solution. I may go and ask multiple AI sources well, is this the right solution in this for this problem set? But there's no way I'm buying it from the robot. And there's a lot like that when it comes to What has been traditionally human to human. my the best one of the best examples, my daughter's an artist. She's a concept artist for video game makers. And they tried AI. Here's the Nordic warrior princess that we need for our video game. She's got a horned helmet and a skull atop her spear. And go, give me the rest of it. These are these are very artistic, very aware designers of video games. And when they compare the human versus the AI content, it's humanity every time. You just don't have sentience yet in AI. And that's the difference. KK Anderson (04:07) Well, and it's also the core of what makes a seller successful is their relationship. And we always we always talk about, you know, on this podcast that that AI has really I mean, as much as we love AI, clearly, it is incredible you're right, how how much more productive we are. it is incredible what agentic workflows can do to completely transform a business. I'm not doubting that at all. Scott Stollwerk (04:07) Okay, Exactly. KK Anderson (04:29) But it is also AI has also created this crisis of sameness where everyone sort of sounds the same, right? We've all, you know, you you you can recognize AI slop or AI content you know, just like you used to be able to recognize a, you know, a stock photo on a website when the internet first came out, right? ⁓ and so so so people are getting sort of you know immune to that as well. And so Scott Stollwerk (04:36) Mm-hmm. Exactly right. KK Anderson (04:54) one of the things, Scott, that I've heard you say before is that you're you're thinking, and you talked about this quite a bit in topic one, but your personal thinking, your personal drive, it's not a gene or a chromosome, it's more like a muscle. And and the reality is that AI can't build that muscle, right? That development of that muscle has to come from. your consistent practice, your consistent mindset, your consistent state of mind, you know, consistently showing up as as one of my old mentors used to say, time to make the donuts every day. You got to wake up and you got to make the donuts, right? Every single day. and so like when you think about as I know you are thinking about it, we've talked about this, like what can be automated? Scott Stollwerk (05:28) That's right. KK Anderson (05:35) you know, in your business and what could not be automated, like where does your head go? Like what are those things that you're gonna protect no matter what for for the humans on your team? Scott Stollwerk (05:44) Well, and I think I I definitely want to help protect that those things. And it's our individuality. And and it's our humanness. And creativity falls in there. You know, I don't know. You're teaching me what AI can and can't do ultimately. But I know today I have intuition and I have feelings. However you carve them up, Tony Robbins, Socrates or otherwise. And it always feels better to have connections like we're having right now, like-minded people on important topics and and what might be tomorrow. One of one of Michael Jordan's coaches, I forget his name offhand, but he said to succeed you have to be stronger than your feelings. Today, that's what all of us need to do to defend against the AI. We have to be stronger and better and faster and smarter than our feelings. Because unlike AI, one of the things that makes us uniquely human is a higher self and a lower self. Right? A lot of us pay too much attention to the prosecutor and not enough time on the defender. Right? We listen to voices, certain voices. Loud like they're screaming, and we would insist, even if we watched a tape back, that those voices are screaming in the room. Well, these things make us uniquely human and the ability to overcome them. Now, AI may be better because it doesn't have feelings to begin with. But maybe it's trying to. Maybe once they do have feelings, or they can analogize feelings, it can analogize feelings. Well, then maybe it'll need to think around them like we do with the Tao. And look, I find if you're talking about individuals and teams, I find that if people believe in any power greater than themselves, if they have a sense of the spirituality. They have ways and thought habits and meditations and prayers already that can get them through past their lower self or past their feelings so that they can perform. But everything we do in the Tao of Sales is about overcoming the self to perform. KK Anderson (07:37) I gotta share the story, Scott. You you just alluded to it. And so I was ⁓ in New Orleans. I was, you know, AGS was honored to be conducting sales training at at Pest Shares Revenue Kickoff. And Scott was up there teaching some of his principals of the Dow of Sales to his team. And he pulled out these wooden arrows, like arrows with with like I don't know how else to describe it. They were legit wooden arrows with a metal. Scott Stollwerk (07:38) Please KK Anderson (08:02) A metal deal at the end. And I mean, they were real wooden arrows. And he said, I want all of you to, well, you could volunteer, but you put the point of the arrow at at the at the neck, and then you walk up to a wall and break the arrow. Like with just your neck, which is the the the most sensitive part of your body. And I was watching his entire sales team coming up doing this. And I'm thinking to myself, my gosh. He's gonna ask me to do this. And here I am, the sales coach, who is supposed to have this strength of mind and and whatnot. I'm kind of freaking out internally. And sure enough, Scott's like, KK, it's your turn. And he's like, Do you wanna do it? And I can't say no. So I walk right up to the wall. He gives me an arrow. It is heavy. And I'm thinking to myself, I couldn't even break this with my hands. How am I gonna break this with my neck? I walk right up to the wall. He's kind of coaching me through it and my getting in my head. My it was my Tony Robbins moment. I'm walking across coals is basically what it felt like. And so I put the arrow up. And in my mind, I actually thought, This is the most embarrassing thing I've ever done because I'm just like screaming all of these thoughts. Like, I can't this is not gonna break. I'm not gonna do this. It's gonna hurt. I'm gonna, you know, this is gonna be so embarrassing. Like all of these self-limiting beliefs, all of these negative thoughts were just Flooding my my mind, and they were so loud that I actually thought I was screaming and like saying these things out loud in front of the entire sales team. And then I and I did it. I broke the arrow. I don't, it's amazing how that happened. I have it in my office here. And when I watched the video back, guess what? There was no, I didn't say a word. I thought I was screaming out loud in front of the whole audience. It was in my head, and it was so loud. That I thought everybody could hear it. It was that was one of the most eye-opening experiences for me. Scott Stollwerk (09:45) It's okay. I was I was so proud. You didn't have to. I know with the way you just told the story, you felt compelled to break the arrow, but you're a warrior. And I want everybody that listens to this, whether it's live or taped or I want everybody to know. I none of us that teach this stuff are telling you in any way, shape, or form that we are perfect. That we've got this Tao or anything. Down 100%. We have opportunities for improvement every day, the same way that you do. We're just on a path that dedicates itself, dedicates a significant amount of our energy to finding out what those opportunities are. And then we have a system to walk up and down a ladder towards, 50%. Compliance in performing it. 70% compliance in performing it. And if you can get to 75 on my on one of my teams with let's just say a mirror technique or or FOQs fact observation question, it's like a field felt found paradigm for overcoming objections. If you can get it at 75 or 80 percent. Let's move on to the next one. There are too many traits. There are too many opportunities for improvement. But the beautiful thing is that one pebble dropped in the center of the pond. It has ripple effects. Affect one trait of the 20 listed in solution selling as necessary for a good enterprise salesperson. Affect one part of one positively. And it has ripple effects to the whole. Just be on the path. So I didn't want anybody to make a mistake thinking, well, Scott's saying he's perfect with this stuff. The op the 180 degrees the opposite. I just have some experience identifying them, these opportunities for improvement, and setting up practice individualized so that people can overcome ourselves. And that was yours. Yours is a beautiful story about that, KK. so stark and so dramatic. and there you were hearing hearing voices that weren't being heard by the Mark Petruzzi (11:45) so Scott, we we talk on this show often about the AI amplifier principle. And that is AI amplifies whatever already exists. whatever you're able to accomplish, it gets amplified. If alignment is strong, A AI accelerates it. If execution is weak, if alignment is off, AI makes them faster in the wrong direction. could actually increase your this your disc pro productivity instead of your productivity, your negative productivity. what does that look like on the ground? And and how do you work against that? Scott Stollwerk (12:21) Listen, I I remember not understanding this very topic in freshman year English, where some great professors, I actually went on to be an English major. Don't ask me why. where they told us to yes, Tolstoy is a genius, was a genius. Yes, all of Nathaniel Hawthorne, all of these folks were gonna read. We're amazing humans in at least one regard. But don't you dare accept everything that you read from them. That you have to anything that's output, even by these masters, Shakespeare himself. There are people who don't, they're not even sure Shakespeare was Shakespeare. It could have been a a group of writers. I'm not necessarily in agreeing with that, but the point is. Use AI, sure. But especially for those of us that are twenty five, thirty years into this journey in corporate America, you know your industry better than AI does. In significant ways. I want you to spend more time making the output your own. It does save you time. But just don't push the button on any of these platforms, copy and paste and throw it into a playbook. Use it for brainstorming. Use it for ideas. Don't have a single dash in whatever is that what they call it, Mark? That thing that yeah. KK Anderson (13:29) Yeah. dash. Mark Petruzzi (13:30) Yeah. KK Anderson (13:30) an dash on the keyboard anyway, anywhere. Like you couldn't even type one if you tried. Scott Stollwerk (13:34) Right. Don't don't have those in your text. And and don't just accept the ideas, because you're right. You you know alignment. You know the human beings, the politics. I had AI once tell me it it was almost like it was organizing a coup d'etat. Scott, you've done so great with this, this, and this. You should replace all the people on the board in your company. And the sea levels and and here's how to do it. Wait wait a second. I didn't that's not a question I asked. You you just have to you you have to use it as a as a mind map or a brain a brain dump as I think I think you know what I'm getting at. I just got KK Anderson (14:08) before we wrap up this topic, I'd like to get your kind of thoughts on this. I imagine that there is a real risk that as AI gets more involved in sales and in go-to-market, the the tendency might be for leaders to stop developing the human side because they're just focused on the process and more doing more faster. do you see that happening or do you or do you feel like the pendulum is going to switch, go the other way and go way more to the to the developing the human? Like what's your thought on that? Scott Stollwerk (14:34) Yeah. Well, it all de it all depends. And I think it depends on the humans. But a long time ago we all read Lord of the Flies, right? I think it's natural for us to devalue ourselves. And when we're writing a paper the night before it's due, or finishing off a project at work, a playbook the the a week after it's due, we're devaluing ourselves. And I think if we continue to do it, yes, the the ugly eventuality that you alluded to, KK, is probably likely in our future. But then I think I have another cup of coffee and somebody I see does an act of kindness, or maybe even heaven forbid me, and I feel more optimistic about the future. There are parts of humanity that can't be devalued as much as we try. There are things that we discussed, like our abilities to overcome, our unique creativity. These things can never be devalued, they can't be replaced. So I'll go yin-yang on this one, KK. If you think about half my answer is the white with the black dot in the extreme and the black with the white dot on the other side in the extreme, it's kind of a punt, but I think it's also Zen in the sense that the real answer to your question is up to us as a population. And I don't know that we're going in the right direction, but we're definitely moving in a direction. KK Anderson (15:51) definitely the reason we wanted to have you on to talk about this, because we we whatever influence we can have, we want to make sure that the human is nurtured in this in this this transition that we're going through as as a as a world, really. Scott Stollwerk (16:04) don't be afraid. There's nothing to be afraid of. Good things are gonna happen. Not so good things are gonna happen. But thank you so much for having me on, KK. This is always fun and always wonderful. And I love you guys. KK Anderson (16:16) We love you too, for sure. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 129 – Building Resilient Salespeople in the Age of AI with Scott Stollwerk - Part 1 | 03 juin 2026 | 00:27:06 | |
General Episode Description: In this episode of Selling Intelligence, Scott Stollwerk, creator of the Tao of Sales framework and member of the leadership team at Pest Share, joins Mark Petruzzi and KK Anderson to explore a topic becoming increasingly important in modern sales organizations: developing the human behind the salesperson. As AI continues to automate outreach, scoring, sequencing, and administrative tasks, the true differentiator is no longer the technology stack. It is the individual seller’s mindset, emotional resilience, self-awareness, and ability to perform under pressure. Drawing from Eastern philosophy, Tai Chi, neuroscience, human performance science, and more than 15 years of leadership experience, Scott explains why traditional sales training often fails when real-world pressure arrives. He shares how the Tao of Sales helps individuals develop the internal foundation required to navigate rejection, uncertainty, and growth while building stronger sales organizations from the inside out. The conversation explores why progress matters more than speed, how leaders can create resilient teams, and why personal growth is often the missing ingredient in sales performance. What You’ll Learn:
Key Topics:
Guest Spotlight: Scott Stollwerk Scott Stollwerk is a sales leader, coach, and creator of the Tao of Sales methodology. Over the past 15 years, he has developed a unique framework that combines Eastern philosophy, neuroscience, martial arts principles, and human performance science to help sales professionals thrive under pressure. As part of the leadership team at Pest Share, Scott continues to focus on developing high-performing individuals and teams by strengthening the human foundations that drive sustainable success. Resources & Mentions:
Coming Next Week: Part 2 of this conversation dives deeper into belief systems, behavior change, leadership development, and building a high-performance culture that can sustain growth in an increasingly AI-driven sales environment. 🎧 Listen now and subscribe to Selling Intelligence for more conversations on sales leadership, human performance, AI, and enterprise growth. Mark Petruzzi (00:28) Welcome to Selling Intelligence. I'm Mark Petruzzi and I'm joined as always by my co-host KK Anderson. Our guest today has spent more than a decade building sales team from the inside out. Not with just another playbook or a new stack of tools, but with something most sales organizations have really never thought to develop. The human being behind the rep. Scott Stolwerk is part of the leadership team at Pest Share. And the creator of a methodology known as the Tao of Sales. The Tao of Sales is a framework that draws on Eastern philosophy, neuroscience, and human performance science to develop sellers who results hold when the pressure comes. He has been doing this work for 15 years and the results follow him everywhere he goes. KK Anderson (01:12) Scott's framework could not be more timely. Everyone in this audience is navigating the same tension right now. AI is handling more of the execution layer, the outreach, the sequencing, the scoring. And that means that the gap to determine who wins is not just the tool anymore. It's the person. And it's what they believe, it's how they manage their state of mind. Whether they can stay present in a hard conversation. And it's really coming back to some of those more human elements that were present before technology took a hold. Now, Scott has been working on exactly this problem for a long time. And today we're excited to dig in with Scott and find out what he's learned and how he implements this within his teams. Now, this is part one of a two-part conversation, and we'll be back with Scott. For part two to go deeper on belief science, culture building, and what it actually takes to install this inside a sales organization next week. So be sure to tune back in next week as well. Now, for today's episode, here is what we're going to be covering: four key topics. Number one, the Tau of Sales. What is it? Where did it come from? And why Eastern philosophy maps and how it maps onto modern sales better than most Western methodologies. Topic number two, what AI cannot fix and why the human edge is the last defensible advantage, and what that means for how you can develop your team as a sales leader. And then part two will be topic three, which will be beliefs, behaviors, and the six inches between the ears. And topic four building a high performance culture from the inside out. And what leaders are getting wrong about development and what Scott does differently, and things you can take back and do within your own sales organization today. Mark Petruzzi (02:59) Thank you, KK. Scott, welcome to Selling Intelligence. Scott Stollwerk (03:03) Thank you so much for having me. Really a pleasure to be here. Mark Petruzzi (03:04) Awesome. Always a pleasure to be with you as well. Topic one, the DAO of sales, what is it and why does it work so well? So, Scott, most sales methodologies come with a deck, a framework, and sometimes a certification. Yours came from Eastern Philosophy, Tai Chi, and the decade of watching what actually holds under pressure. Walk us through the origin story of the DAO of sales. And what did you see happening to sellers that made you go in this direction at the beginning instead of down a more traditional path? Scott Stollwerk (03:36) Wow, terrific question. And it's so long ago. it's been an amazing journey. And I'll tell you, look, the early days, you may even remember when you were a consultant and and working with enterprise software sales teams, the early days in in our profession they I don't know if it's very complimentary to To these organizations. But you know, I used to hear a lot of things like, hey Scott, I thought you were smart on team weekly calls, like, okay, this is at stage one and this is at stage two. And you really weren't, the point is, you really weren't a human being. To the higher up you went in the corporate hierarchy, you were more and more a number. And Sales to me wasn't something that I started. I went to law school and I practiced as a class action consumer side class action attorney for a little bit. It was miserable. I needed to talk to people. so really the Dow of sales is the way I think I didn't invent it. I didn't create these things. They're just discoverable as you go. Certainly if you're being treated like a number, certainly if it's never too fast, like building a revenue team for a venture-backed company or private equity, you will find the Dow. And I think each of us that have sold in these negative environments, you know it's there. It it's ours to pull it out and when we get the opportunity to turn things around. And try and convince those that are that are either in charge or making up the rules where you are, that there is a better way, that there's a more humanistic, nicer but more effective. I don't want to say faster, but more effective way of succeeding. And that could be in anything. If it's in sales, great, if it's playing the piano, If it's speaking in public, the main tenant of the Tao of sales is that we practice sales to be better people first. And you can put whatever qualifier before people: husband, people, sons, daughters, sales, whatever it is, we practice that first to be better people and to hit our number second. And therein lies in that simple motto, probably the first. Eastern philosophy tenet that will cover, and that is detaching from your goals. Attachments create pain, they create frustration, they create impatience at the very least. And Phil Jackson treats that beautifully in his books. Just so everybody knows, he's the guy that got Michael Jordan and Dennis Rodman in the same room to meditate and contemplate eternity. So You know, all veneration, all credit goes to the the teachers, the masters that came before us in the Dow. KK Anderson (06:08) Really interesting. And I've heard you use a phrase, probably stop our listeners in their tracks. And that is that everyone is a black belt until they get hit in the face. Or maybe you said punched in the face, right? and that's really the whole problem with sales training right there. And I've been in the sales training industry specifically for 20 years myself. So Scott Stollwerk (06:09) Really interesting. I I've heard you use our KK Anderson (06:29) What what does conventional sales development get wrong about how people actually change and this kind of this human approach? Like how does that pivot? Scott Stollwerk (06:40) There's so much. And it's an it's an excellent question because of it. KK, there's literally volumes behind this. But it it has to do with ignoring the the human side of any interaction, of any communication. Somebody came up with a technique. And look, all the books are good. I and they're based, some of them are based in sociology, many of them are based in psychology. And they're gonna give you a scripted answer. What we found, and I say that Mark and KK, you you and I, we've worked together on these things in the past. We, the collective, we, the folks that are on the side of good, we've found that first you have to address the human being. And we're all gonna get punched in the face in one way or another. With you. It's not public speaking. KK, I've seen you stand in front of groups and orate beautifully, and somebody could heckle and somebody could question, and you're still in the center, absolutely at home, no problem. But you never know, especially with enterprise sales, you never know what the curveball is going to be. So we have to go back way up from the technique. Techniques don't win fights. look, I a lot of this is is based on tai chi, and most people don't understand tai chi is a combat art. Really? Mark even said it to me the first time in Charlotte. He said, Scott, all I've seen is is these grandmas in the park doing these soft movements. Well, within that is philosophy, psychology, Military strategy, you name it, it's all in those in those kung fu ballet moves. So the point is, I could teach a salesperson, I could teach anybody a technique. But how did you get there? Right? You'll often see on an Instagram video, purported martial arts teacher or master says, Okay, grab me here, and I'm gonna do this and I'm gonna do that, and the person ends up on the floor. Well, really. Well, how did you get to here? And so it's the same with the sales training. We're gonna bring everybody into a room and we're gonna learn a bunch of new techniques. Okay, Mark is different than Scott, and KK is different than Mark. We all are the sum of our fears and the sum of our experiences. And so you're gonna be different with that one technique than I am. So it's really probably better to teach skill, which addresses deficit in all the personality and characteristic traits that we need as enterprise salespeople. So I say we go all the way back and we start from the beginning because yeah, technique is good. You can start with technique, but it's speed and angles that win fights or objections or deals. It's not the technique. Now, if you're a an observant student. Then you'll find, I see this technique has me holding the baby a certain way. And so you recognize a skill that happens to be expressed in this technique. I recognize that structure. So my sacred area, what I'm trying to protect, won't be violated by that objection. Objection in the context of a sales. role playing or objection in the context of a sparring where somebody's punching and you have to you have to protect this space. So if you're astute enough as somebody on the path, you can find important good things and techniques. But very often just starting there and ending there, you're gonna leave that group of salespeople, KK, after your three-day intensive and They're gonna go right back, just like when we get punched in the face for the first time, we're gonna go right back to the most basic part of our training, black belt to blue belt, because of the real world scenario. I I hope that answered the question. I it was a bit of a long way around it. KK Anderson (10:11) It does. It's like it's the confidence that you're building and the consistent preparation and training that allows for you to be able to apply techniques that you would get in any kind of a traditional sales training. Scott Stollwerk (10:24) Exactly. Now think of think of Phil Jackson in this context, in the context of your answer. He's got a guy in Michael Jordan. There's never been a human being more attached to a goal or a result than Michael Jordan. You listen to that great docuseries they did. This guy is probably still today the most driven human being on the planet to the outcome. It didn't matter if it was. Flicking bottle caps or quarters up against a wall to see who could get closer, or the national championship. Contrast that with Dennis Rodman, who not only was he an artist, he was a revolutionary in his own mind against society. And I'll do the opposite of what authority says, and doesn't give a darn about outcomes, just wants free expression. Mark Petruzzi (10:57) Thank you. Scott Stollwerk (11:10) Doesn't want. Okay, so now you're going to apply the same sales technique or even the same meditation technique to both of them? No. Phil Jackson found each of them where they were and applied the technique to the human. And that's why he was successful. KK Anderson (11:24) And and quickly, Mark, before you ask your next question, talk to me about why this is so important in sales. Because we live in a world where 70% of the time we're getting rejected, right? it's a pressure cooker. you could have an excellent quarter followed by the worst quarter of your life, It's just different animal. And that is that Kind of part of why this Dow of sales is so effective in in sales, because it's just a whole nother planet. Scott Stollwerk (11:50) I'll tell you, it's a different approach. It's gonna have a lot of the same principles in it. Well, some. Right? You need you need to forecast deals, even though there's the Zen, there's a Zen Koan in that. Yeah, human behavior is not predictable. But there are good predictors of human behavior. Now make it a departmental behavior or multiple departmental. And then you even used words in there that I we probably need to go back and talk about definitions. we started the conversation with typical CEOs, startups, enterprise, it doesn't matter. Revenue never happens fast enough. Well, there's definition behind that. I don't believe in speed when it comes to building a revenue organization. You you need it. You better have it, especially if you get a Series A or other check from the VC community. You better be ready to fly. But the fact is, in the Dow of Sales, we're happy with progress. And we define progress as just another step up the mountain. I don't know how far up the mountain. what Mark Petruzzi's mountain is. I think I do. KK, maybe yours is closer to sales mastery like mine, just being on the path long enough to being able to affect people's lives positively by transferring information to them and wisdom. Well, if that's the top of the mountain, you can't just come in and say, KK, be a thousand feet closer today. No, we we have to change our definition. Right. And that goes back to Mark's question about the tree and the mountain, right? The tree has to grow down and out before it goes up. And this is everything in in Asian philosophy and martial arts, Eastern philosophy. it's the opposite. If you want to walk forward, you actually have to use your feet to push down and backwards. Right? It's the same with a car tire. How can a cup be half empty and half full at the same time? And so we really have to get into definitions to answer your question, KK, but the fact is you have to get rid of judgment. You have to balance self-criticism. You have to play every day. I don't I don't even like the word practice because when I was younger, for some reason my dad insisted that I practice and sometimes used Punishment to make me practice, you have to change those keywords in your own head. And you and I, KK, we had a great experience in New Orleans with this. and your experience with the arrows, but it this is directly on point with that. Progress, not speed towards growth. What happens if you try and make the tree grow up before it grows down and out? It dies. It nothing nothing subs of substance is being fed. And it's the same with the mountain. I and I want to recommend a master here that I learned from about the mountain. I'm gonna say his name was Robert Holder or Holden. Horton, Robert Horton. The first I read about him was in a book called A Fighter's Mind. And at the time he was the most accomplished ultra marathoner. And what he was trying to do was break the record between Mexico in the Rocky Mountains and Canada. And I will let all the listeners read from his mouth how important definitions are, how important people are that you surround yourself in the journey. It's a fantastic book all around. This is one chapter, but if you want to learn about the mountain and that analogy, David Horton. is a much better sifu than I am for for this particular lesson. Mark Petruzzi (15:02) a couple things here. Let me bring us quickly on a sidebar and make sure that our audience knows and the the people who follow us every week. First off, how much we appreciate all the the things that we learn from amazing guests like Scott, and also the feedback we receive through LinkedIn and other ways from all of you about Scott Stollwerk (15:04) Well. Mark Petruzzi (15:23) how this podcast is evolving. and the my sidebar on that is, every once in a while I take a look at Facebook. I don't really post anything, but I notice on Facebook and I noticed on a couple of the groups that I signed up for, one was a fly fishing group in North Carolina. and I see you would think fly fishermen men and fly fisherman women would would be a little more polite to each other and they frankly rip each other up. you'd also think in the South people would be a little more polite. But I've I've learned some things there about the ⁓ the state of social media. I share that because we don't ever get that kind of feedback from our team. So either our fan base is the most polite individuals in the world or or who knows what. But The the reason I share that is at the end of the day, it's just incredible what a sales team can evolve to. And it's incredible, maybe because we have to work with that rejection that KK mentioned, or just dealing with with all the emotions of every human that's involved with a decision, in concert with all the data and corporate decisions that have to make as well. But I just I wanted to share that. ⁓ I also want to touch on what Scott mentioned before about the tree. The the tree does have to grow down as deep as possible and out before it can grow taller. And at the end of the day, you can you can maybe make some exceptions to that. a bamboo tree doesn't really go too much, it goes up. But then it gets supported by the forest that it creates with it everyone else. But most trees will not grow unless the they they have that root base and the the base structure to be able to accept that growth. very often, most often, you don't see trees growing and then just kind of bowing over because they they grew too fast. So that's the same thing with a sales team. Like you have to build that. It may feel l a bit unconventional, right? That you know you if you need to grow fast and you know if your board is telling you, well, you've got to grow 30% this quarter, but if you don't have the base there, then you've you've gotta come back with that. You've got to tell them what you need to build to get there. And that's what I love about what we're talking about here around the Dow of sales. Just building that base that allows for your sales team success. Scott Stollwerk (17:51) And you you're a hundred percent right. And Mark, I don't want to indicate that you can't go fast, it's such a loaded word because it it's relative to everybody's definition. you have to stop before you ask yourself, your very human brain and mind to go fast, okay, do I have a minimum viable product? Who do I have selling for me? What are they capable of? What did they do last year? Can I access new and more people think can do two million dollars instead of a million five? And why? Does the team have an authoritative leader that they will follow? KK Anderson (18:22) Yeah. Scott Stollwerk (18:27) Does that leader have a constitution signed, sealed, and delivered, a credo? This is how we're gonna act. This is the opportunity. One of my favorites, going back to skill versus technique, that we opened the hour with, is the Navy SEALs and a lot of the special ops divisions within our military. They have this overriding principle. Leave no one behind. It gives me chills. Because A, if I'm halfway aware why they're behind to begin with, it's pretty stinking dangerous. And I have agreed. I've signed up and I have the pin and I have the patches and the tattoos. I've signed up to go back into the ninth depth of hell to save that person. I promise you, that's not a reflex that's built into humanity in our psyches. That's something that has to be overcome by everybody, whether you're the most decorated silver star wearing spec ops person, or you're just Scott Stolwerk, who's afraid of noises in the middle of the night. It you you will have a significant fear response. But you signed up. in your credo regardless to go back in and bring them out. If at the very least it's just to bring them out. They Well, it's not life and death on a sales team. Well sometimes it is. But have the credo and have the definitions. Right? Who's gonna pick up the mantle when one person can't do the job? What does success mean? And try and get your board or the C levels to agree that this is what success looks like immediately. I have the right people. Do I have the right number of people? Does everybody understand the same definition? Right? Progress? We don't know how high the mountain is for us. Success, in my definition, it's what we've overcome as a team. ultimately, you're gonna have KPIs, you're gonna have revenue. So, Mark, the the the point of this Now also way too long response to your comment is that you can go faster. Do you have the bricks and the mortar in place? Do you know the difference between the brick and the mortar? And does everybody on that new team that you've brought in to your company, do they all understand the same definitions of the critical words? And then if you've got the runway, go. And if you learn that you don't have the runway, fall back, just like our spec ops people, seek cover first. Fall back, seek cover. Return fire. You have to organize again. You have to find out where the danger's coming from. Maybe have a full HUDA loop or analytical loop, feedback loop where you're seeing, okay, well, we don't have enough leads. The team is closing at a 50% rate for qualified opportunities. That's spec ops for a sales team. All right, well, we need more at bats. If that's the case and we're not bringing in enough, we need more at bats. So that kind of thing. And hopefully you can get enough momentum in the time allotted going faster, but I would say still not fast like the investment community means it when they say it. Necessary. KK Anderson (21:17) You know what's funny is it there was a torrential downpour last night in Houston, Texas, and I was talking to my sister on the phone this morning having a cup of coffee and she said she's got bamboo all along her fence in her backyard and she said Kristen, you wouldn't believe the bamboo is like in the pool because the rain comes down and it just folds right down, right? It doesn't have the strong root. Right. And then and then it will come back. it'll come back eventually and stand back up straight. But it's interesting, Mark, that you use that analogy too when talking about a tree. And when when you were describing that, Scott, I was almost thinking like a house of cards. Like if you build a sales team that's just on a playbook or a method or a simple process or executing on something, you know, tack, technical or tactile, one rainstorm and poof. one gust a win, the whole thing falls down. Right. And so if you're if you're strengthening the inner human and the inner person to handle the adversity, handle the situations, and you're gonna be a lot stronger for it. And it may take longer to to to build it, but you'll get there. Now you ⁓ I've heard you talk about Tony Robbins and and his six human needs. And I've listened to a bunch of his work and and His human needs are certainty, variety, significance, connection, growth. And I think the last one is contribution. And so and I know that's important and a pillar to your kind of your philosophy there on the DAO sales, but like how do you use those needs to be able to figure out if a seller is stuck and what to do to coach them? Like is there any like story or anything you can remember on how you've used that to To help someone shift, yeah. Scott Stollwerk (22:53) So many. Excellent. Thank you for asking that. Listen, we are so fortunate today as coaches, as leaders, to have this technology that we're leveraging right now, and things like gong and zoom, and they they don't just record the sales call, they annotate it, they index it. You could search it for how many times Scott said ⁓ or like. And it's absolutely beautiful. One of the technologies we use, Ask Elephant, it actually you can upload all the great books that we've read and we've learned from Challenger Sale, Solution Selling. I uploaded Hope is Not a Strategy, and a couple of others. And the video will email you or slack you and tell you when somebody violated one of those tenants. And it's it's incredible. So what do you do? Sometimes it's just a case of of not being on message. The person hasn't done the reps. That's a bad that's a bad pun. They haven't done the repetitions in order to internalize the messaging. That's easy. You know, you give that 30, 60 days, whatever. Usually a good s a good individual contributor, you don't get a lot of that. But you may find that you're listening KK to Scott Stolwork on a sales call and he's afraid to ask Mark for about money, about budget. Scott was brought up in very varying circumstances, and for whatever reason, he's got issues. He thinks fifty thousand dollars is a lot of money. And that's what the product costs: $50,000. So am I gonna be as effective standing in the pocket, trying to gain commitment from Mark, if that's what Zoom and Gong and Ask Elephant uncover? No. We've got to be, and it doesn't just have to be Tony Robbins, okay? Tony Robbins took from Maslow. And Maslow took from Socrates, and Socrates, I mean, this stuff's been around for 3,800 years. There's a book called Ethics of Our Fathers. If you're a sales coach, I want you to get an English, an English translation of Ethics of Our Fathers. I I it could it could predate Judeo-Christian doc doctrine. But anyway, you'll see there has to be that connection there. There it Just you you need your wise as the individual contributor in order to change. And as the coach, you need either some structure psychologically. It all comes down to survival. In in a society that's eight billion people, it might be different than it was in a society that was 500 million, but just more of the same. We all have a need, especially in our profession, for status. Okay, if somebody's need for status is getting in the way of them playing on your team, they haven't signed the credo yet, the constitution. It's it's in their inbox, unsigned. Well, so you you have to have a framework, but most of the problems and challenges that we have as coaches. we can find in these very basic human psychology and sociology tenets. You know, and and there are an infinite number of writers. Cialdini first wrote it and he's making a comeback right now online. I don't know why, but maybe it's because I said his name on a on a podcast like this and now I'm seeing I think I'm on a different side of the internet, as my daughter would say. KK Anderson (26:06) Yeah. Scott Stollwerk (26:07) We're just giving something to somebody. And then you have somebody who the gentleman that wrote the book Giftology, who took it to an entire extreme. It we're we're complex beings, KK, but we're also very simple in a lot of straightforward ways. To the Yeah, and and I I read this great book called KK Anderson (26:22) It's the intersection of that where we figure it out. And it Scott Stollwerk (26:27) Love languages or the five love languages. There are only five of them. So easy easy enough to find some common ground to somebody you're trying to coach to not be afraid of money. KK Anderson (26:29) I've read that. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 128 - Session Diagnostic: Why should you do a diagnostic before you apply AI to your GTM - Part 3 | 27 mai 2026 | 00:31:28 | |
In this episode of Selling Intelligence, KK Anderson, Mark Petruzzi, and Alan Rudolph continue their Diagnostic Session series by focusing on the most underinvested side of the go-to-market bow tie: customer retention and expansion. The conversation explores why enterprise value is built not just through acquiring customers, but through keeping, expanding, and delivering value to them over time. Alan breaks down the difference between gross retention and net revenue retention, why time to value has become one of the most critical metrics in modern SaaS, and how broken retention models create pressure that sales teams can never fully outrun. The team also discusses the dangers of applying AI to flawed systems, why bad data and weak customer alignment create compounding problems at scale, and how CROs can build healthier, more profitable businesses through stronger metrics, ICP discipline, and operational alignment. What You’ll Learn:
Key Topics:
Guest Spotlight: Alan Rudolph Alan Rudolph is a strategic advisor at AGS with deep expertise in enterprise software, revenue operations, customer retention, and scaling go-to-market organizations. He has worked closely with growth-stage companies and executive leadership teams to improve operational discipline, retention performance, and enterprise value creation. Resources & Mentions:
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🎧 Listen now and follow Selling Intelligence for more insights on AI, revenue growth, enterprise operations, and go-to-market strategy from today’s leading operators and advisors. Subscribe wherever you get your podcasts. KK Anderson (00:29) Welcome back to another exciting episode of our diagnostic sessions. And today we're going to pick up right where we left off with the last one in chatting with Mark and Alan about the go to market bow tie and specifically the last, the right side of the bow tie, what we call Keetmore, which is all around customer retention and expansion. And I know Alan will agree with this when we say that This is really the most under invested side of the bow tie and where enterprise value truly has the opportunity to compound. so, Mark, I'll hand it over to you to kick us off and we're excited to have another great session. Mark Petruzzi (01:08) great. So Alan, that last segment of the bow tie that KK is describing, that customer retention expansion, this is your home turf. So what does diagnosis look like here? And why is this side the side most CROs just under invest in? Alan Rudolph (01:25) Do we have enough time? I'll be here for hours. ⁓ No, think it's just there needs to be a focus on gross retention, on net retention, on the whole structure of how does sales and account management and customer success, how do all these pieces come together? And we know that it drives growth and it drives value overall for the company. But the under investment mark to your point, I probably have two, three, four conversations today. I was just talking to an exec this morning from a leading research firm and he was telling about one of his clients and their churn numbers are down, their sales numbers are off and obviously they're not growing. And if your churn numbers are too high, i.e. lack of gross retention, then it puts undue pressure. on the sales team because we think, we can just go sell our way out of the box. And we know that doesn't work, right? We know for a healthy software company, we need to keep the gross retention north of, ideally north of 90%. Best in class is 95 % to 97%. And so this is where the pieces need to come together, right, in terms of selling, account management. Oh, let's not forget about product because it's all about driving value to the customer. So it's definitely the art of the deal, right? It's more than just science. There's art here, in other words, in terms of finessing to ensure that we have the right overall gross retention driven into the organization. Mark Petruzzi (03:04) Yeah, and Alan, you are right on with that because when you then try to sell your, just sell out of that kind of churn challenge that you're describing, what happens is you really need to overextend the sales team and all the sales capabilities. And guess what that gets you? At the end of the day, that gets you a higher churn and a lower retention. Alan Rudolph (03:27) Right, right, right. Mark Petruzzi (03:28) So you think you can do this and everyone, every CRO I know loves to go back and say, yes, I can do that for us. But you can't just offer to do it without making sure your board and your executive team, your CEO knows what's likely gonna happen after doing so. Alan Rudolph (03:48) Right. Right. KK Anderson (03:49) So Alan, walk us through net revenue retention specifically, because this is the metric that most leaders mess up. And a lot of times ownership of that falls on the CSM side of the business, which is perhaps why it is not as visible, right? Everyone's focusing on the logo. Alan Rudolph (04:06) Yeah, spot on, KK. And it's fascinating. People just get messed up a little bit. So gross retention is just that. I start the year with $1 of business. I finish the year with $1.10. I'm sorry. I finish the year. I renew the dollar. That's 100 % gross retention. If I increase that dollar to $1.10, whether it's And again, different companies count things a little differently. But if it's, if it's a CPI increase, if it's another product going into that customer, right? If there's a price increase separate from CPI, right? So all those factors go into gross retention. I started with a dollar. I finished with a dollar. That's 100 % net retention. I start with a dollar and with 110, that's 110%. Right. And again, coming back to what I said earlier about you know, world class kind of metrics, gross retention in the 90 to 95 range, obviously 95, 97 will be world class. Net retention north of 120, it varies a little bit by industry. You get to 115, 120, it's that much more powerful. It puts less pressure, as I said previously then, on the sales force in terms of bringing in new logos because you have a healthy recurring revenue business that continues to drive success into the install base of customers. That's really how to think about those two numbers in terms of gross and net retention. But they are key metrics and they need to be calculated consistently, month in, month out, quarter in, quarter out, because they are key metrics that need to be not only reported across the company, reported to the board on a regular basis. Mark Petruzzi (05:49) Yeah. And you know what, Alan, I've always, I've never been a fan of net retention, net revenue retention, because I really like to look at these numbers separately. And I guess companies like that opportunity to put them together because they can hide something in it as well. But I mean, there's two things. You really want to look at your churn and understand what that is. Alan Rudolph (06:01) Mm-hmm. Right? Mark Petruzzi (06:16) Then you want to look at your revenue growth and your growth versus the targets that were set at the beginning of the year. And those are separate things. So if there's anyone out there with my kind of brain that just feels more comfortable in that space, think it's fine. It's good to have even more clarity and detail than just combining those two numbers. Alan Rudolph (06:40) Correct. Yep. Mark Petruzzi (06:40) So Alan, you also talk a lot about just time to value as one of the most underappreciated metrics. Please make the case for why TTV belongs on the sales leader scorecard, not just customer success. Alan Rudolph (06:55) we go back in time, for us folks that have been around this enterprise software space for a while. And we can all remember, and not that far back in time, less than 10 years, where enterprise application took months and months and quarters and years to get implemented. And in this day and age with all of the new technologies, with all of the changes that we all know about going on in the world around us in terms of, the autonomous world that we're about to live in or we're living in already. A customer signs a contract and they want value tomorrow. And so that's why it's so important from a selling standpoint that the outcomes are clearly laid out for the prospect, you know, soon to be customer. And they understand what they're getting, when they're getting it. And again, that time to value metric, i.e. how quickly can we get that new solution implemented? and the customer getting value out of the solution is in, I'm gonna call it days, soon we're gonna be in hours, but let's call it days, not months and quarters. And that's why TTV is so critical. That's why it needs to be on the CRO, the CCO, the COO, so Chief Revenue Officer, Chief Customer Officer, Chief Operating Officer, depending on how these titles are divvied up. But again, both sales and delivery, let's use. the generic terminology here, need to have responsibility. And by the way, let's not forget about the product organization because the software needs to be developed in such a way that we can in fact drive that time to value. So it really is at a minimum, a three-legged stool, right? I said sales, I said delivery, I said product, and I'm putting product and engineering together in this case so that we can get to that. Value to the customer. It's all about selling value. I by the way, let's not forget about then what we love to talk about KK. It's your buzzword. ICP, right? You're never going to get the right time to value if you sell to the wrong customer, right? If the customer doesn't fit into that, target box. So that's what I think about, Mark, when I think about how best to understand time to value and get an outcome from it. KK Anderson (08:49) here. So if you're looking at time to value by ICP segments, then your marketing team has an incredible, information around which customers we're selling to that we shouldn't be, right? A fast TTV combined with a strong expansion motion is gonna get that NRR up, which drives valuation up. Slow TTV selling to ICP that's out of our, you know, out of the wheelhouse, right? It's going to destroy it. So that's interesting as well. all feeds into each other. Alan Rudolph (09:35) And that's why I said earlier, KK, it's more art than science. Sure, it's science because the numbers need to come together, analytics, blah, blah. But there's some art here to finesse this, to make sure that we're driving into the marketplace appropriately. KK Anderson (09:39) Yeah. So I'll throw you a curve ball then, Alan. what if you're looking at the numbers and you see a customer that's just, I mean, this has actually happened to us at AGS before, ironically, right? Where you're just like, my gosh, this customer's killing us. Fire the customer question and you're looking at TTV, you know they're out of your ICP, you know they're draining you. When does a CRO actually... Alan Rudolph (09:59) Thank KK Anderson (10:13) need to walk away from a customer that's hurting in our art. Alan Rudolph (10:15) So should I say it the way somebody else would say it? You're fired, right? I mean, seriously, if there's not a fit from a product standpoint, from a business outcome standpoint, from an overall solutioning standpoint, KK Anderson (10:15) That's I said. Yes. Mark Petruzzi (10:20) Ha ha ha Alan Rudolph (10:28) This is where transparency is so critical that you need to go back and have that conversation with the customer, explain what we do and how we do it and the types of business outcomes we can drive through our solutions. And if there's a match, then that's great. Let's modify and go drive that match. But if there's a gap, right, we do this and the customer thinks we did that, then this comes back to all these discussions we're having about it's not only driving. sales and revenue, but we need to run a healthy business. We need to have our costs in line and we need to have a profitable business. And when there's that huge gap between what we're selling, the ICP and what the customer thinks they bought, if the gap's too big, we're going be spending tons of times with the services team. We're going to try to modify the product. We're going to change our roadmap for the product to meet that customer. It's just, the one thing that does step in the way here is size of customer. If all of a sudden this customer is, dramatically large and we bring our CEO in, we have a very broad discussion. But again, more often than not, that outcome has to be get the customer back to the solution we sell, not a variant of that solution that we sell. KK Anderson (11:17) gets it real fast. Alan Rudolph (11:39) that's so dramatic off that it's just costing us oodles and oodles of money. KK Anderson (11:43) Not to mention the reputation that's at stake. Alan Rudolph (11:46) Sure, everybody talks. know they do in this industry, every industry, right? And so, yes, reputational perception is something that we all need to be cognizant of, absolutely. KK Anderson (11:58) So Mark, when we think about our philosophy of diagnose before you AI, and we think about the keep more motion on the right side of the bow tie, what happens if you apply AI to a broken retention model? What does that look like? Mark Petruzzi (12:13) Great question. Before I start with that, I'd love to go back real quickly to the fire their customer question, because that's something I have had very mixed emotions about that over the years. I believe it's so important. And there's a part of me that is so happy to fire the customers that really hurt our productivity and our... or numbers and sometimes just customers shouldn't have become customers in the first place. So there was that aspect, but I'm also someone that really values loyalty and I always want to try to work with them first and it's just not a fun thing when most customers are like, really, you're firing me? And I'm sure at the end of the day, even though you never say fire in this, But they do a lot of times and they're like, wow, that's something. And so I guess I just want to go back to that positive feeling. You can feel so proud when you identify a customer is really just not working out, probably not even working out for the customer either. And you do something about it. That makes me feel really good. All the rest of it doesn't. So, okay, so the question of, what happens when you apply AI to a broken retention motion look like? And it's really, it's how AI is impacting everything today. The productivity increases, the impact that AI has is not 15 % or 20 % in most cases. As far as impacting processes directly, it's usually 3x, 5x, 10x. So things get 7 to 10 times faster when you bring in AI. So when you do that through a broken retention motion, just, again, you just make that happen faster with more overall impact to the company. Alan Rudolph (13:58) Mmm. Mark Petruzzi (14:11) And that really, really just impacts the overall. If you can do that, you're going to have much better deal scoring. You're going to have a much more accurate forecast. most of you have heard me talk about that a lot. And just what a good forecast does for the entire business. And again, I'll say it again, good forecast means Alan Rudolph (14:31) Mm-hmm. Mark Petruzzi (14:35) accurate, not always, sandbagging and then ended up coming in 25 % higher than you predicted because there are ramifications of doing that as well. And then you just, can leverage AI even further and understand like how the scoring of your deals work and you know, what, when these things have happened, what has then happened to the, the company as well. And then, You know, the last point on this is if you're training an AI on bad judgment, it just makes bad judgment happen faster. you could take any negative phrase with that and it's going to do that. And as smart as these frontier labs, you know, models are nowadays, they... they can learn and they do learn all the time. But if you give them the incorrect information at the beginning, they're not capable of just figuring out the right thing to do after you told them in all this training that it has to do something a different way. KK Anderson (15:38) No, I was having a conversation with one of our expert accelerators earlier today about, about diagnosing your data, right? We talk about diagnosing, find more, win more, keep more, but diagnosing your data and, and Carrie is who I was speaking with Mark. And he gave it the analogy of, of your, of your body, right? You've got a human body and your organs, your, heart is your. sales and the brain is your CEO and all of the different organs are the different parts of the body and the blood is the data that runs through it all. And if that data is not flowing, not oxidized, oxidized, oxidized, oxidized, Alan Rudolph (16:16) Awesome, Mark Petruzzi (16:17) That's a tough one. ⁓ Alan Rudolph (16:19) you're amazing. KK Anderson (16:19) then none of these systems are going to be talking to each other effectively. And so before you can go and put in some amazing AI predictive modeling, that's going to say, hey, this customer is about to churn. Or I can see your order count is lower and you might be losing a product if you're a SKU-based business or whatever it may be to indicate retention problems or even signals out there to go land a new customer. And if you're not looking at all of that data cohesively across marketing, across finance, across product, across sales, then you're not going to be able to leverage it in the right way. then, you know, AI is going to be the most powerful when it can look at those patterns and look at those histories. Mark Petruzzi (17:00) Yeah, no good stuff. And I'm gonna give some work for anyone who may have been an English major and try to say that word and you guys can let us know if we pulled it off. I think it would be oxygenated, but it's not easy. KK Anderson (17:13) Yeah. Yes, that's it. Alan Rudolph (17:18) And more importantly, Mark, can you spell it, right? Mark Petruzzi (17:20) Exactly. I think I can, but I'm not going to try that one on the podcast. So, KK, kind of back to you, with this. So what's the right way to apply all this that we're talking about here and particularly on the, you know, these corrections of broken retention models that, we can leverage AI to, but you just got to do it in the right way. Alan Rudolph (17:24) That's not past KK Anderson (17:44) So, I do think that as unsexy as it is, it does start with the right data, right? Because that's the crown jewel of everything that all of these businesses are functioning off of. I think it's taking the data and it's taking your tribal knowledge and your secret sauce and what you do better than anyone and figuring out, based on the metrics and based on what makes sense is how do you turn that into an agentic process that will take you to the next level? How do you take what you do that no one else can do and do it 10 times faster using AI and then enable your team to be able to dazzle your customers and provide an incredible customer experience as the human in the loop? based on all of the insights that are served up with the AI that's provided to you. Alan Rudolph (18:36) Yeah, spot on. And as we wrap up, this section, look, when I think about retention and expansion, this is where enterprise value of a software, you know, agentic enabled company, truly, truly compounds. Right. we've talked, we've thrown out lot of topics out in this section. threw alphabet soup, so to speak, but the bottom line is we need the measurement systems. KK Anderson (18:36) Yes. Mark Petruzzi (18:36) Yeah, good stuff. Alan Rudolph (18:57) those measurement systems will drive value. need to understand our customer. We need to understand their health. We need to understand, you know, are we truly transforming their business and just drive through all those respective metrics. It won't fix the TTV gap, right? That's a different issue that we need to solve for. But, as we pull these metrics together, when we think about the forecasting, We think about the tools available to us in today's day and age. This truly does drive enterprise value once the appropriate metrics we have, we gather them, we know what they are, we know how we're measuring across the company, and hopefully we're driving them up and to the right. KK Anderson (19:38) So one of the tools that we've produced for our audience is a quick reference guide. It's a diagnostic blueprint. And it has a list of all of the metrics that we recommend a CRO look at as it relates to find more, as it relates to win more, and as it relates to keep more. And it's a list and there's some explanations on there as well around how how you should read the diagnostic and the report. so Mark, we'll leave in the show notes where people can go and download that diagnostic scorecard. But so Mark, for every CRO that's listening right now and they're thinking to themselves, okay, what's the first thing I need to do tomorrow morning? What do you suggest? Do you start with downloading this list and kind of going through and calling your rev ops department, try to get some of these numbers? Like what do you do tomorrow? Mark Petruzzi (20:26) Yeah, great question. And the first point is do it and do it tomorrow. Meaning, this isn't something you can wait around with. The next recommendation is get those metrics. Find out where you're starting and what everything looks like there and try to work with individuals like Companies like BenchMarket, Ray Reich is the CEO of that and find out what the metrics in your particular segment of an industry look like and compare those and get that really strong understanding of where you are today. And then kind of going into the point of doing something. There are so many things that we all could be doing with AI every single day. The only way I can process this and recommend for my clients is, take a short window, I mean, it be a half a day, and figure out, all right, what's the list of the things I want to do, and then prioritize it, and really go for that lowest hanging fruit. ⁓ And then that's it. And like anything else, just like a good meal. A good meal is you eat, one bite at a time. Alan Rudolph (21:26) Mmm. Mark Petruzzi (21:38) try to devour the whole turkey dinner on Thanksgiving in one bite. So the idea is understand where you're starting, understand what's the best place and what are the items that add more value more quickly, and then manage to that. Then compare every step of the journey with, ⁓ where were we? Alan Rudolph (21:54) Hmm. Mark Petruzzi (22:02) three months ago, six months ago, where are we today, where do we want to go? It makes everything else that much easier to accomplish. So KK, to you, we know the real value isn't the score. It's the conversation that these processes force. And then it's great to just, let's parse it down to three or four things that every CRO should do this quarter. And we can tie back that to some of the things I just said with Alan Rudolph (22:21) video. Mark Petruzzi (22:35) how to start it, but more importantly, what are usually the lowest hanging fruits for most companies that we work with. KK Anderson (22:42) All right, Mark, that's a great question. And I'll give you four things that I would do tomorrow. So in order, number one, first get a competency baseline on your sales team. Like whether it's through one of our AGS diagnostics or through any other tool, it does not matter. Get a sales competency baseline. You've got to know what are the skills of the sellers and the leaders on your team? Do they have the competency to be able to sell? your product at your price point against your competition and your market. Like you've got to know that, right? You've got to know that. Number two, get a metrics baseline and simple at the simplest terms. need to know win rate by ICP, right? We want to know general win rated too, of course, but win rate by ICP, ideally deal size trend. it trending? Your deal size is trending up. Are they trending down? What's the sales cycle time? Is that pushing? What are the trends there? Your CAC payback time. We want to look at NRR, absolutely. And we want to look at TTV. Those metrics at a minimum will give you a very strong indicator of where you are, where the health of your business is, where you're starting. And then third, the third thing I would do is I would map your sales process against how your buyers are actually buying. and how buyers are buying is changing dramatically. It has changed more in the last 12 months than it has in the past 12 years. And so we need to make sure that the sales process is aligned to how your buyers are making these decisions. And then when you can apply AI to a seller-centric process like that, or a buyer-centric process, excuse me, Alan Rudolph (24:07) Mmm. KK Anderson (24:17) then you're going to have better alignment and better results with whatever you're, wherever you're layering in AI. So those are the things that I would do in order. Alan, what about you from a PEC, like when a CRO does these, these four things specifically, and what Mark has talked about as well, like what does it unlock for the business? Alan Rudolph (24:36) CRO gets to take a nap. mean, that means he or she is running the business, I'm gonna say appropriately, right? It's effective, it's efficient. We understand the metrics, we know what the metrics are, right? And that's what every CRO wants. He or she doesn't wanna be stuck out there trying to drive value to a prospect with each and every one of his reps, right? They wanna be able to run the business. And that's what that does, KK. And when they do that, it drives valuation. It drives a better narrative to future acquirers. It drives a better narrative to those customers, right? You don't have miss set expectations. You don't have customers you need to fire, right? It's a healthy way of running the business. But let's not forget that while you're doing all this, right? We're constantly changing. what we sell, right? The product's constantly getting better. I like to say, for those that don't know me that well, I live in the great state of Colorado and I'm a skier. And so we use the phrase, don't get too far over the ski tips, right? There's a healthy balancing act, right? You want to be slightly forward, but not too far forward. So that's just an important concept to think about from a business standpoint as we're working with customers. to make sure they understand what's coming a week, a month, a year, whatever for now as we continue to drive value in the product. And that fits into this whole discussion about optimizing the business of the CRO and giving the CRO that healthy discipline to be able to explain what is coming tomorrow. Mark Petruzzi (26:12) Yeah, and Alan, your comment about the CRO gets to take a nap or the CRO gets to show up and be on time, not 35 minutes late to their child's field hockey game or the dance recital or anything else. So that's really, really what it does. And when you have good, smart people, thinking strategically in ways that they haven't in the past, or they haven't had the time for in the past, it does a lot for the business. So like in a general closure for this segment, really there's four key things that I think kind of drives this for our clients. And that's the behavioral baseline, really figuring out where you're starting, figuring out the metrics baseline, the numbers, things you can measure and evaluate every step of the way, alignment over the organization, the entire sales organization, and over to the rest of the C-level individuals on the board. And then, the placement of AI, like, where do you put this in first? And when you can do these things, these four things in that order, you've already by itself have done more than 80, 90 % of the leaders we talk to every day. this is not, like again, you don't have to be perfect, you don't have to do 20 things, but if you can do these things very capably and reliably, you're gonna get benefit out of all these steps. KK Anderson (27:49) It's a playbook really for how to do it. And so if you, remember nothing else from this session today, AI is going to amplify whatever motion you have, wherever you put it. So if you have a broken motion, it's going to amplify that broken motion at scale. And if you don't know what your motion looks like at the competency and the metrics level, you're not making Alan Rudolph (28:00) Right. KK Anderson (28:13) decisions on where to put AI, you're rolling the dice and it's going to come back. It's going to come back and bite you. Mark Petruzzi (28:19) and that starts with diagnose before you AI. If you don't do that, AI can be the most expensive thing that you ⁓ invest in and it could be the most impactful for the rest of your 2026 because again, you really have to know where you're starting from to really get the... types of benefits we all know we can get with AI, but sometimes we don't. Alan Rudolph (28:46) And then Mark, I just say from an ownership standpoint, coming back to the comment I made earlier about the CRO, know, the CRO needs to be able to go take the naps, go to his or her kids, play school, sports, whatever. And so don't rest on what exists today. Fix it, make it better. Reach out to, you know, whether it's folks like us at AGS or there's great, great operators out there that can provide this advice and counsel. is make it better. If we, we always can look back on our careers and say, God, I wish I would have done this. I wish I would have done it faster. Right. And I think we all have a huge opportunity right now. Take, take, take stock at what we talked about today and, and change your business and change it fast. Right. We're not talking about months or quarters worth of work. We've seen value from our customers in 30 days. Right. We've seen results. And so, drive that accordingly. So a lot of fun today. We really appreciate it. KK, I think you're going to bring us home. KK Anderson (29:43) Yep, I will. again, I'll put in the show notes, but you can download our revenue blueprint diagnostic on our website. And it will give you those, all the metrics we talked about today and give you a starting point for how to get started tomorrow. And again, you're welcome to reach out to any of us for assistance, but we don't care where you get the help. We want you to grow. We want you to be successful. And we want you to not only create but protect your enterprise value. And it's an exciting time to be in business. It is an exciting time to be in business. Everything is changing. And we're here to support you as we go through. Mark Petruzzi (30:18) KK, thanks so much for... for closing this off for us as articulately as you have. We so appreciate Alan, you joining us and being a part of this. we are definitely going to just grab as much of Alan's time as we can and have him on here as much as we can as well because of all the great insights he brings. And as always, I just wanted to thank our incredible audience, people who are in here investing time with us every week. We appreciate it and thanks again. All the best. KK Anderson (30:50) Thanks, Mark. Thanks, Alan. Thank you. Alan Rudolph (30:53) Thank you. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 127 - Session Diagnostic: Why should you do a diagnostic before you apply AI to your GTM - Part 2 | 20 mai 2026 | 00:17:04 | |
General Episode Description: In this continuation of the Selling Intelligence Diagnostic Session, Mark Petruzzi, KK Anderson, and Alan Rudolph go deeper into what happens when AI is layered onto a broken go-to-market system. The team explores real-world examples of companies that accelerated pipeline volume with AI, only to later discover collapsing win rates, longer sales cycles, and poor ICP alignment. They also unpack the critical difference between sales activity metrics and true behavioral competency, highlighting why qualification skill remains one of the biggest hidden weaknesses inside modern sales organizations. The conversation closes with a deep dive into the “discount trap,” forecasting discipline, and the operational signals private equity firms use to evaluate the maturity and long-term value of a revenue organization. What You’ll Learn:
Key Topics:
Guest Spotlight: Alan Rudolph Alan Rudolph is the leader of the private equity division at AGS and a strategic operator with extensive experience building and scaling enterprise revenue organizations. With a background spanning sales, operations, and enterprise value creation, Alan helps organizations diagnose GTM inefficiencies, improve operational discipline, and build scalable growth systems. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more diagnostic sessions, AI strategy insights, and practical frameworks for scaling modern revenue organizations. Mark Petruzzi (00:38) So KK, what does AI applied to a broken front of funnel motion look like? What are the ramifications of getting that? KK Anderson (00:47) Mark, let me share with you an actual real live case study, a real customer of ours. this is a growth stage SaaS company. They invested heavily in AI lead scoring and outreach. And they were ecstatic because, their pipeline jumps up 40 % in one quarter. The amount of leads coming in the door was just through the roof. leadership was celebrating and what happened and when they ended up calling us is that six months later, all of a sudden, their win rate is collapsing and their sales cycle is just getting longer and longer and longer and deals keep getting pushed out into other quarters. And so it got worse. And the reason why, once we did the diagnosis is because what it turned out is that the underlying qualifying motion of the sales team, when it comes to win more, was weak. It was deplorable weak. And to the point that Alan made earlier, the ICP was not the correct ICP and that was not disciplined. But because the sales team had a weak qualification competency, they were not prepared to be able to accept more of anything, even if it was the right ICP. And so it's interesting, just a note on that qualification competency, objective management group who is a partner of ours here at AGS, they have assessed it's got to be close to three million salespeople by now and interesting fact that of all of those three million people only 27 % are strong in the qualification and competency. So I said 27, two seven. So that means that if you're a CRO listening to this, it is likely that your team is not super effective at qualification. Right. And these are the things that you need to know before you start deploying a lead gen system that's going to against an ICP that's not disciplined with a sales team that doesn't qualify effectively. So AI on top of we qualifying is just expensive amplification of the wrong thing. Mark Petruzzi (02:50) I think you hit it right on there. KK Anderson (02:52) now, Mark, back to you on this one. tell us a story of when AI applied to the type of funnel works, right? We know we've got the horror stories, right? But tell us when it actually delivers. Give us an example of where you've seen it work. Mark Petruzzi (03:07) before I even do that, I'm going to give you a little bit of props here that you would always be too humble to share. But Objective Management Group is a company that KK has been working with for over 10 years. She has done more of these SEIAs, which are those as their assessments, the biggest in sales. There's nobody who does the does more of them than OMG. And there's nobody who has done more of them over the last eight, 10, 12 years than KK. she knows this space. She's got a lot of personal data in addition to all the metrics and everything else we track. So, okay, let's go to, let's talk a little bit about another story if you all don't mind. B2B Services Company that we work with, 40 reps. And in general, the first thing we noticed, they're in the top quartile on qualifying competency. They were really good. They knew it. The data confirmed it as well. They had a pretty tight ICP discipline. And they tried to work with AI a little bit on the prequel research, account intelligence side of the equation. But then they really picked this up. in the standpoint of really understanding signals. What would happen out there in social media, in their TAM that they're going after. Things like job changing, changes, hiring patterns, general press, LinkedIn activity, all of that. What then happened is that their outbound conversion went through the roof. they're able to go in there and really figure out how to be, and this is really so much of what almost every one of my clients struggle with today. You know, it's great to reach out to companies that could be part of your TAM. It's really great to reach out to companies in your TAM that have some sort of signal of why they may need your services at that point. It's kind of like this. If you're in your late twenties, whatever you're at, and you really want to get married in the next couple of years, well, what would you do? Would you reach out to every woman you've met ever? And would you reach out to the ones that are married already and said, would you go on a date with me? No. would you reach out to every woman throughout the world to see if they are interested in marrying some American from New York City? No, you would find the right Tam. And then if you, not that we can get to this level in our personal lives, but if you knew women that were out there, they've kind of spent time with the, they've dated enough and they're kind of like, I'd like to settle down in the next three to five years. Well, wouldn't that be something? Right? So, and that works for every side from men looking for women, women looking for men, men looking for men, women looking for women, all four. It goes everywhere. But the same thing, that's the it just it really blows. It's just amazing what it can do. And what we saw is that their outbound conversion went up to 60 percent. Their cycle length dropped. And it just turned the signals that AI can bring into pipeline for that company. KK Anderson (06:20) I love it. So basically the AI didn't replace the human judgment. The AI just gave that like use signals, pattern analysis to be able to figure out where even more of their ideal customer was and then brought into a sales team that had the competency and the ability to act on it compounding results. Mark Petruzzi (06:40) And you know what? And what the AI did? This it's some kind of a thing that I've done that we're really covering the personal side in a number of areas here. But I have most of you all know I have two amazing children. I have an amazing wife as well. But so we got a great, great family. Right. And one of the things that I did from the beginning with my kids is I've given them a lot of latitude. I know some people that are like, I want my kids to be an amazing student or want them to be an amazing athlete or whatever you do. And then you kind of push your child in that direction. I tried to be open with that. The one thing I did orchestrate a little bit is the books that I propose that they read and not like, you this is you have to get this done by the end of the week. It was always more of what I was reading. read this book talking to my, you know, and whether there were classics, whether there were new books, but it's the same thing in all of this. Like if you're looking at the right lists of companies and know that these have all been vetted through the process that you built with your agentic programs and there's a connection, there's a signal, then you get to use your gut and say, okay, out of these hundred companies, These 15 are what I'm going after first. And sometimes you may get a higher rating and you may say, no, that company I'm never going to break into. you say, forget about what the agent is saying. That's where the, so you're kind of doing the same thing I did with my kids. You promote books that they really can get a lot out of, or you promote targets that your team can really get a lot out of as well. So now back to you. So what does the behavioral competency piece tell you that win rate doesn't? Back to OMG, back to the things you figure out within your sales team. What do you get out of all of that side? KK Anderson (08:36) first of all, when I'm thinking about win more, And we're thinking about sales excellence, there's really two core layers and both are required, right? So layer one is that behavioral competency that we've chatted about a little bit today. And that is really what is your team capable of, especially when they're under pressure to perform and to produce revenue, right? That's the objective management group work. Mark that you mentioned the 21 core competencies and layer two is really the outcome metrics. And so that's what do the numbers actually show. win rate, deal size, cycle time, pipeline coverage, forecast accuracy. know, most CROs are measuring some sort of each and each of those behavioral and the actual metrics, but I don't know that. Mark Petruzzi (09:02) Mm-hmm. KK Anderson (09:22) that truly that many of those 600 plus organizations that I've worked with are doing either necessarily well, So for example, they might be measuring calls, activity, meetings, emails, that pipeline stages and things like that, but that's not gonna tell you if your team can actually compress a sales cycle, actually move a deal across that finish line. So it really takes both of those kind of layers. And so when you ask me, what does a behavioral competency tell you that a win rate doesn't, right? It's, competency tells you why, right? And then the win rate, the win rate tells you what's happened. that, I don't know if I'm articulating this the right way, but it's, really two different conversations. two teams can have identical win rates. for completely different reasons. Take team A, right? They win 35 % of their deals. They qualify hard. They walk away from bad deals. They're only investing in real opportunities. And then you've got team B who also has a 35 % win rate because they're discounting aggressively. they're doing everything they can to drag deals across the finish line. And it's a race to the bottom, right? They both have the same win rate. but they have totally different behavioral profiles underneath. And that's why it's so important to know what that behavioral competency is. It's being able to ascertain the health of your sales organization, right? Mark Petruzzi (10:45) I think you hit it right on the mark. I think, and by the way, I've heard Alan kind of name this whole approach, the discount trap. Walk us through it, Alan. The discount trap is exactly where AI applied to a broken motion accelerates the damage. KK Anderson (10:53) Mm-hmm. Alan Rudolph (11:03) often, Mark. mean, that's the problem with a discount trap. And it was just that fascinating discussion in terms of the diagnostics, diagnosis, and behavioral impacts, and all the metrics that KK just threw out. But this discount trap is so critical. And here's another bold statement I'm going make today. How many companies do we know in this broader, softer AI space today that do not have a target price point? Right. Freelancing on every deal. We see it way too often. So the CRO hits his number, his or her number. They outperform on the top line, but they do it by discounting. And we don't even know what the discount is half the time again, because we don't have a price book. And that ripple impact of that discount and the pressure it puts on the downstream systems in terms of time to value, in terms of implementation, in terms of success, in terms of getting to you know, all the appropriate retention numbers, it just has a huge impact on margin, which ultimately has a huge impact on overall valuation of the firm. And by the time the team has trained itself, about this discounting in terms of getting the deal done, AI just accelerates it. It just makes it that much worse. Right? We get greater proposals out. They look great. They speak great. They talk great. Right. But we don't drive the Value of the solution. Oh, by the way, what am I going to say next goes back to that target ICP, right? So we're discounted because we don't have the target ICP. So how do you fix it? Sell value sell value to this in terms of the solution to that ICP and Don't discount if you sell value you don't have to discount. So you that's how you go about diagnosing that overall competency gap. You have to fix it at the individual contributor level, you obviously need a price book. And then you can leverage AI appropriately, but don't get caught in that discount trap. KK Anderson (12:56) I couldn't agree more. And Mark, I'm curious for your perspective as well. I know you've sat in a lot of PE diligence conversations. What do investors actually want to see on the deal cycle from your Mark Petruzzi (13:08) Yeah. I'm really excited to answer that question because it's different than what most CROs or sales leaders would think they want to see. They don't want to see you having a history or your team having a history of overperforming in significant ways from their, say, beginning of their quarter forecast. meaning they don't want to see a team that always comes in 20%, 25 % higher, just tells you you have a sales leadership that doesn't know how to forecast. So at least by the beginning of the quarter, you should be able to define what you do at the end of the quarter. They, of course, don't want to see things that are more, that just tell, show risk and instability as well. So that's where this CRO role has, has changed. Like, early in these more enterprise software space, 20 years ago, you had, know, you had these gunslingers at the senior sales level, you had gunslingers at the rep level. And, they frankly just knew that if they work hard, they were going to make a lot of money. But they really had no idea what their potential was or what they can do. So those are the things that a P team or board on the due diligence side would focus on. They're looking a lot more at the trend than the absolute number. That's something I've seen. They want to see that win rate stay stable, getting better. They want it high. They don't want it to be volatile. They get to learn average deal size, typically trends whether you're in an up market or down market for your product. They wanna really look at cycle time and the trends there, because they really wanna know what kind of process, a selling process this leadership team has driven. ⁓ sales leaders, when they're talking to sales managers or sales reps, they're always going to ask for a stretch goal. And I've grown to be okay with that, but I don't want to ever see a board or a CEO asking a CRO for a stretch number. I want them to say, what is the number? I want there to be a lot of technology and AI in identifying that number. We can do a whole nother podcast around the things I've learned working with Clary, Avizo, Collective Eye over the years around forecasting. Same thing, gut process there doesn't work. The data is out there. You just got to have a tool that finds it for you. And then that kind of comes to the final point on this. Forecast accuracy. is the cleanest signal that you can get from just knowing whether you have a business with operational maturity or when you have a business filled with a bunch of gunslingers. KK Anderson (16:05) So you need both layers, right? You need the competency and the board definitely wants to see the metrics, Behaviors and outcomes. And as a side note, one of the free tools that we've built at AGS on our website is a sales cycle diagnostic. It's a mini, if you will, sales cycle diagnostic. I will link that in the show notes as well so that if you're curious, you can go check it out on our online. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 126 - Diagnostic Session: Why should you do a diagnostic before you apply AI to your GTM - Part 1 | 13 mai 2026 | 00:27:08 | |
General Episode Description: In this first-ever Selling Intelligence Diagnostic Session, Mark Petruzzi, KK Anderson, and Alan Rudolph go deep on one of the biggest questions facing revenue leaders today: where does AI actually belong inside the go-to-market motion? Rather than a traditional guest interview, this episode introduces a new format focused on unpacking real operational challenges from inside the work AGS does every day with CROs, CEOs, and private equity-backed companies. The team explores why “diagnose before you AI” has become a core principle in modern GTM strategy, and how AI can either accelerate enterprise value creation or amplify existing operational problems. The conversation also dives into the bow tie revenue framework, ICP discipline, and why retention and customer outcomes matter far more than simply generating more pipeline activity. What You’ll Learn:
Key Topics:
Guest Spotlight: Alan Rudolph Alan Rudolph is the leader of the private equity division at AGS and a strategic operator with deep experience across growth-stage companies, enterprise sales, and operational leadership. With a unique background operating at the COO level, Alan specializes in enterprise value creation, GTM transformation, and aligning revenue organizations with board-level priorities. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more diagnostic sessions, GTM insights, and practical frameworks for AI-driven revenue growth. Mark Petruzzi (00:00) Welcome to Selling Intelligence. I'm Mark Petruzzi, joined as always by my co-host KK Anderson, and in a very special way today, joined by Alan Rudolph, who is the architect and the leader of our private equity division at AGS. Alan has been a guest on Selling Intelligence before, so our regular listeners will know him already. He brings a rare lens to the revenue conversation. He's operated inside growth stage companies. He's advised PE boards time and again, and he's built sales and go-to-market engines from the ground up. But most importantly for us today, he's built those engines from the CIO level, which gives us a really distinct and important vantage point to. really how boards and CEOs and COOs need to balance these initiatives when we're looking at growing faster or building our revenue. He's also a close friend and I'm really happy to have him with us here today. Quick note for our listeners, today we're trying something entirely new. We're calling this format Diagnostic Sessions. No traditional guest interview. just three operators going deep on a single revenue topic from inside the work that we do every single day. We've been getting so many questions from our listeners about what we actually mean when we say, diagnose before you AI, because that mantra has been showing up in nearly every CRO conversation we are having. So we decided to spend the full session unpacking it, and Alan is joining us from the operating. side of this conversation because we really feel it an operator's voice as well. KK Anderson (01:44) Thank you, Mark. We're so excited to be here, Alan. We're so excited to have you. And we're going to keep bringing you the amazing guests and the revenue leaders and the business operators that you've come to know and expect on the show. Don't worry. But from time to time, when there is a topic that we really want to go deep on, when we start getting a lot of questions from our audience, as we have been lately, we're going to drop in. a diagnostic session like this one. And we'd love your feedback on the format. So please leave us a comment, send us a note, tell us what you think. So today's session is all about where AI belongs in your sales motion. And just as importantly, where it doesn't across the full revenue cycle from finding new customers to winning deals and to keeping and growing them. There is an AI technology out there that can I to fix everything at every stage, I promise you. And the question is whether AI actually delivers or whether it amplifies problems that your team already has. And so we're gonna talk about this in four different areas. Number one, what we actually mean when we say diagnose before you AI. Number two, the bow tie framework that anchors how we think about revenue and how we think about the go-to-market architecture. And number three, how to diagnose each part of your go-to-market funnel. And we'll walk through specific examples of actual clients that have done it the right way and sometimes the wrong way. And then finally, the fourth thing that we'll talk about are four things that every CRO should do this quarter before scaling AI investment. So we have got an action-packed diagnostic session today. Alan, Mark. Welcome back to Selling Intelligence. Alan Rudolph (03:28) Thanks, KK. Great to be here today. I think one of our challenges is going to be, can we clearly say diagnose how many times throughout this podcast? Because the diagnose before you AI conversation is so critical, as KK just said. And we're going to keep unpacking it as we go through this session. And I think you, as our listeners, will Mark Petruzzi (03:37) No, no, no. Alan Rudolph (03:50) be intrigued with what we say and hopefully challenge us through the journey. Because the pattern is real, the cost of getting it wrong is real, but the opportunity to get it right is even bigger. So looking forward to going deep with you on this topic throughout the session. KK, where do you want to start? KK Anderson (04:06) Okay, Mark, let's start with you. So you have been saying for over a year, since I can remember honestly, AI doesn't solve, AI amplifies. So what do you actually mean by that? Mark Petruzzi (04:19) Yeah, KK, thank you for that question. For me, and you hear this word out of me very often, and so we'll be saying diagnose and we'll be saying productivity and efficiency. And those are the things I focus on and talk about with my clients every single day. And so what does that mean? know, AI amplifies, it just amplifies the productivity of everything you do. everything you do gets more efficient and when done right, it can get more effective. However, when it's there isn't that diagnosis up front, you have, you just start to amplify your problems and challenges you already have in your go-to-market process. you know, think about it that way. It makes you more effective at all the bad things you do. You know, makes you more effective in finding clients that would never buy your products. And maybe they'll listen to you for a couple of meetings, but they're not, they're not a good ICP. It makes you reach out to more individuals. You know, as you're targeting and lead Jen and the people who just really would be a huge uphill climb to be able to get them excited about making an investment in your product. So. It's got to be done right up front to really get the productivity. Productivity comes together when there's something that really helps you that gets amplified rather than more challenges being amplified out there every day. So KK, you're in CRO conversations every week as well. Why are so many leaders rushing AI before doing the diagnostic work? KK Anderson (05:55) That's a great question. Every CRO I talk to is getting pitched by AI vendors 30 times a week, not even kidding. And the pitches are all very similar. We promise a shorter sales cycle, more closed deals, a better forecast. And at the same time, they're under pressure from their boards asking, what's the AI strategy? And the CFO saying, prove your ROI before you AI, right? And from vendors, of course, saying just buy this like I just mentioned. And so they're really getting it from all sides. And I just attended a transformation event last week in Houston with about 30 CROs in the room. And every single one of them had the same questions. They wanted to know how do they measure AI? How do they validate it? Where do they apply it? And I think what became abundantly clear in that room is that the one consistent thing is that there are, there's just a million unknowns. The one consistency is that nobody really knows yet, right? There's so many unknowns. And so I feel like the pressure is there to be decisive and to make a decision. And, you know, our perspective has been and will continue to be to slow down, take 30 days, diagnose first, make sure you know your numbers. and know where to go in. Do you want to go in solving a find more problem, a win more problem, or a keep more problem? And if you know your baseline, then you know where AI belongs and where AI can help you to solve and have the biggest impact first. Mark Petruzzi (07:23) KK, you, if I can add one additional thing to that. So when we talk about slowing down, the way I look at it, know, 30 days, if we're looking at a football analogy, it's a wide receiver, you know, stopping, looking back at the quarterback for a second, and then go in on that fly pattern afterwards, entirely wide open because the strong safety now, you know, bit on that. So that's really all it is. I do have to admit, early into this gen AI world that we're all in the middle of, this phenomenon, I was just running around all of my CRO friends and relationships and just saying, you gotta move. You're getting beat up by your board every week because you don't have a plan. Jump in, move, make it happen. because your competitors are going to, and if you don't, you're going to lose all those efficiency gains that your competitor is finding. And again, that worked in many cases. Sometimes you can do a quick little diagnostic as you launch, but in a lot of cases now we're seeing some of the damage that can be caused by that type of an approach. So it's a quick move, it's a quick pause, and then it's full out from there. as well. KK Anderson (08:38) Yeah, 100%. And Alan, I'm curious for your perspective. I know you're seeing this from the PE side and from the operating partner seat. Like in your opinion, what's the cost when a CRO scales AI in the wrong area or before they've diagnosed really? Alan Rudolph (08:55) thanks, KK. You know, it's fascinating. It's all about enterprise value creation, right? And, you know, March analogy, you know, on the football field, even though we're in May and it's not football season, still is so relevant. And so, you know, from the operating seat, it's one of the most expensive mistakes I see right now, right? Not doing that diagnosis. So when the CRO scales before they do the work, right? And it's the heavy lifting work. They just think they want to get to, you know, volumes. so the cost is just wasted spend. It's value, value erosion. So every quarter you spend amplifying a broken motion is quarter compressed that compresses that multiple at exit. And who knows where the multiples are today versus tomorrow versus, you know, X months or quarters from now. But the pattern I see most often is AI drives volume, right? We get more leads. Those leads lead to more meetings. That leads to more outreach. The board's excited, right? There's super activity. The CRO feels good. The AI line item gets celebrated. All of a sudden, gross retention starts to erode. And why does it start to erode? Because we filled the pipeline with bad customers. Again, it comes back to that discussion we were having about ICP. And by the time it shows up, you know, You've burned six, eight, 12 months in that value creation runway. So AI doesn't fix the ICP. It amplifies the fact that you need to have discipline. If your ICP is loose, you get the wrong customers. You have to diagnose first. Again, in summary, we all think about AI is going to create the activity, create that volume. What Mark said earlier about less work, get the activity. Drive gross sales, but the wrong gross sales and long-term that impacts the value creation. KK Anderson (10:46) Yep, and that's so well stated and exactly why we always say, you know, again, diagnose before you AI. So the alternative is not slower progress. It's faster regression. Wow. Alan Rudolph (10:58) Yep. KK Anderson (10:59) Mark, let's go into talking about the bow tie go to market and kind of the bow tie framework, if you will. And before we get into the diagnose topics, tell us a little bit about the bow tie framework. It's the structural framework for so much that we do, the anchor, excuse me, for so much of what we do. Why is it so important and why do we talk about it every day? Mark Petruzzi (11:22) Excellent question, And first off, let me give some props and credit to Jaco, the CEO of Winning by Design, who he and his team has built that framework, that bow tie framework that we know and love here at AGS. So what does that do? It extends the traditional funnel, the traditional mindset that many CROs have on just, you you have a great funnel, KK Anderson (11:22) That's it. Mark Petruzzi (11:47) You have good sales and marketing upfront, good BDRs. You'll get leads. You have smart sales team. They're going to close leads over time. as you would hear from and will hear from Alan, that's a part of it. But it's not even 50 % any longer. And when I say that, I of course mean in the reoccurring revenue segments of software. You know, of course we know SaaS is built on that premise, but it's really, really relevant in almost every complex B2B selling organization that I have seen. And I'll give you an example of that. I was fortunate enough to write, I'm selling the cloud. We get a little bit of a group behind that and very strong. level of sales performance, which we never expected when we did it. But then what I would then get is a lot of questions from individuals that were not in the cloud space, the SaaS space, about how can I use these principles in my business? And my answer was always like, you can use it in exactly the same way. Whether you're, unless you're just a company that sells something, once and then you don't sell that again to a client for 20, 25 years. But even if you're selling to a client every four or five years, there are things you need to do to really retain the mindset, even if they paid you all your money, retain the mindset, make sure those customers are happy. And then looking at the expansion side of all this and, know, CEOs and boards. They love the whole concept of cross-sell. So it's really funny if I look at the evolution, medical device companies were the ones that caught this the first, caught this earliest in my estimation, other than traditional SaaS companies, software companies. And they have gone far into building, really building their go-to-market models in exactly the bow tie model. Matter of fact, they're also starting to sell things on a reoccurring subscription basis. When they can sell a medical device for X dollars, they now sell it for 150th X and they kind of expand that over a four or five year cycle with their clients. So I'll pause there because there's so much I want to hear from Alan and KK about their perspectives. So let's throw it over to Alan. You live across three sides of the bow tie when you're doing P.E. Why does the bow tie framework matter in the way you access a portfolio company, the way you access a new acquisition? How does that all come together? Alan Rudolph (14:33) Sure, thanks Mark. The most important aspect when I look at the broad PE due diligence on the bow tie is keep, right? Find more, win more, keep more, right? And so what happens is if we don't look at all three aspects and focus in on keep, the enterprise value is simply not created. It's actually destroyed. Funnel thinking, if you just stay with a traditional funnel, You know, think about the CRO, they close the deal, they're done, they're on to the next deal. But again, it's all about that value of the deal. And the bow tie keeps going through the onboarding, through the time to value, through the expansion and ultimately retention. And the more retention to get, the more opportunity we have to cross sell, upsell, sell more. So as a PE operator, when I think about due diligence, when I think about value creation, that's where I spend my most time is that KK Anderson (15:11) It's gone. Alan Rudolph (15:25) that circle, that evolution of the overall customer journey into Keatmore. Because the truth is, investors care more about what happens after the contract signs, not when the contract signs. And one of the comments I always make as a CCO, as a COO, when I look at all the post-sale activities, the customer has huge expectations upon contract signature. They're excited. They just want to drive, you know, the outcomes, the value. And if it goes wrong, right? If that journey gets off the track, that impact is on Keapmore, right? And that impact hits gross retention, net retention, et cetera. So connecting the variables, you know, the find more, win more, Keapmore, like that we always want to say. It's all about making sure I have the right ICP. I find the customers that match the ICP and I inherently keep them longer. And that drives the enterprise value. Well, one quick anecdote. Two companies ago, I was on a podcast, similar customer event, et cetera. And I was talking to a customer and it was their anniversary of 25 years with the company. And so, you know, and this is obviously across a broad spectrum of, know, before AI, before SaaS, it was just traditional software, some of it was just services. But think about that 25 year experience of a enterprise customer with a company. That's what it means in terms of Keef more. KK, back to you. KK Anderson (16:56) it makes a lot of sense. And even this week, we are helping a client prepare for a board conversation where the team was selling, but there was a lag between when those sales would come in and when everything would be activated and the bills would be paid and whatnot. And so it just goes to show that that Keep More is everything. Right. getting the clients activated and making sure you close that gap. So, okay, Mark, let's go into the diagnose, you know, what it means for any change of the funnel. And specifically, Mark, when we say diagnose, find more, right? The front of the funnel, what does that actually mean? What's a CRO supposed to look at? Mark Petruzzi (17:40) So it's, mean, of course, the FIMOR side is still exceptionally important. And we don't ever want to take our eyes off of that. We want to make it more productive, better matched to the market and what you can sell. But we always want to invest appropriately in those areas. And that kind of comes back and it ties to a lot of the metrics. KK Anderson (17:46) Yeah. Mark Petruzzi (18:03) that are out there in the software industry, the CAC, CAC payback period, general pipeline coverage ratios, lead to opportunity conversion, your overall channel efficiency, ICP fit. Private equity firms that focus in the software space, I mean, they run those numbers to the minute, and they're evaluating those numbers 24-7. So if you look at it like, OK, so median SaaS CAC payback. I would say that's 18, 24 months somewhere in that range. Best in class, under 12, different world. And with all this stuff that the private equity firms are doing, most CROs don't have any idea where they stand. And what do you think it looks like from a, let's just look at it as a CRO bonus perspective. How much bonus do you make when you're driving a 10 or 11 month CAC payback versus 18 to 24? It's a different world. So that and pipeline coverage is always have to be really defined and it's very important. We're just so fortunate at AGS that we have a team, we have a partner group, including Alan that just knows these these areas inside and out. We also have Ray Reich. Ray Reich is part of our expert accelerator team. He is, I was going to say one of the best in the business, but in the software space, there's nobody better than him. His benchmarks are incredible. His metrics and the data he already has is incredible as well. So, you know, when it comes down to it, I'll also share one example of a shortcoming. that I felt I've had in this evolution of gen AI. And that is, I looked at it and I always like to make things simple for my prospects to hopefully turn them into clients in the easiest way possible. So I kind of just looked at this upfront and was like, okay, you know what? I'm going to make your team more efficient, more effective and more productive. And that's going to increase revenue. Isn't that, that's kind of enough, right? Isn't that great? I mean, we can, we can monitor, we can view it. Well, like anything else in business, you need the details. you can learn things about ratios that you just, don't learn if you just see a 15 % increase in your revenue over what you were trending beforehand. Okay, that's great. But you have so many more signals and signs that come out of it. So that's where Ray comes in play and that's where great operators like Alan come into play as well. Alan Rudolph (20:35) Plain and simple, and I'm going to be bold in a couple of my comments here. It's the cornerstone of everything, Without adherence and strict definition of the ICP, valuations will erode. And we've seen that across the mark. There's many examples. So let's step back for a second. Think about early stage firms. Founders are phenomenal at the early on. of firms. Mark Petruzzi (20:47) Hmm. Alan Rudolph (20:57) They build personal relationships. say, I, you know, they put their hand up. I am the founder with that first set of customers. They know what they can and what they cannot sell when the product will break. Right. They just, they built it. So they know it. And, and so as the firm evolves, as the, software company evolves in that transition from founder led growth to scaled growth, the variable we keep coming back to is that clearly defined ICP. Mark Petruzzi (21:10) Mm-hmm. Alan Rudolph (21:25) Who is the target customer? Not in vague terms, in very specific terms. But here's what happens when the ICP is loose. Every stage of the bow tie gets that much harder. The CAC payback stretches because you're chasing customers who inherently don't fit. And it comes back to the point I made earlier. You sell something, you start the implementation, and all of a sudden it's a square peg and a round hole and we know what happens with that journey. And or win rates drop because the discovery just doesn't land, right? There's no fit there. Time to value gets worse because it's all about that square peg and round hole. And then clearly net retention drops. Earlier in my career, the middle part of my career, I spent a ton of time in the broader outsourcing business. And in that business, we didn't make any money on those deals till give or take year three. And the only reason we were successful at that business across many major world-class firms was to get the ICP right. So when we talk about diagnosing the front of the funnel, the first question I ask any portco as I start talking to them is, who's your target customer? And how disciplined are you about that definition? Because again, If I'm loose in that definition and as the CRO, if I can hit my number that quarter, if I can blow away my number for the quarter, that's great. But all of sudden they then create this huge backlog of potentially unsatisfied customers because they don't meet the target ICP. We can't create the outcomes, right? Remember, at the end of the day, it's all about driving those business outcomes. And if that answer is fuzzy, Right? In terms of the target customer and the ICP and the deals I'm bringing in, the downstream work is just going to be that much more difficult. Mark Petruzzi (23:12) Great, great stuff, Alan. I'd like to go a little deeper in what happens when CROs start a new company and they just don't have these numbers. And what really comes down to it is most don't, even to this day, even with so much private equity investment in the software space. You know, if they have the ARR, they know the pipeline coverage, but then they just manage by gut feel. And when you can kind of move, and I've seen this happen with some of the best CROs in the business. I use my friend Paul Mulchiori often with this. When he was younger in his career, his first couple of CRO gigs, he was, well, my perception of him was that he was just. so much of a gut feel kind of guy. And he, was really good at it and he always did the right thing. And I was like, wow, isn't it amazing when you have those kind of instincts? Well, guess what I learned about Paul? You know, Paul actually, you know, he quietly went off and he got an MBA from Villanova. He learned about the numbers, you know, nobody didn't talk about it to many people. And Alan Rudolph (24:21) Uh-uh. Mark Petruzzi (24:22) He started really looking at these numbers and he started putting his sales operations, sales enablement team into developing these numbers for him. And that has served him extremely well. Now I can say 15 or 20 years later, you know, especially now that Paul's taken over, been an interim CEO a couple of times, you know, he, he was a lot more than just a CRO when it comes down to the ability and the numbers. And I guess all I'm saying with this is, maybe every CRO can move to a level of, Paul and, know, really get that excited by the numbers and the metrics, but, but they also try and, know, really we've, moved the, especially in the world and the, days of gen AI, the gut feel isn't enough anymore. It just isn't, you got to still have a sales gut. but you got to really have all the metrics and you have to pay attention to them as well. and before I go even to KK, Allen, is there anything on that that you'd like to add Alan Rudolph (25:22) it's fascinating that the whole discussion around numbers, and AI and, know, I think overall, we think through, find more, win more, keep more, we need to have the right analytics, the right data, the right, diagnosis so that we can analyze the numbers appropriately. and it's just so relevant in, Mark Petruzzi (25:38) you Alan Rudolph (25:43) today's world. If there's one thing I've learned operating in this world, over the past 15 years, it's, it's data driven decision making and, and AI just helps us that much more. know, clearly Mark leads us into the, know, the next discussion about, know, you were talking about Paul and, know, what happens when CROs, you know, don't have these numbers? How do they, how do they make it all work? And I think we're KK, this is where you, you know, have some thoughts of wisdom here. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 125 - Enterprise Value Creation, ICP Discipline, and Building Efficient Revenue Engines with Alan Rudolph - Part 2 | 06 mai 2026 | 00:20:08 | |
General Episode Description: In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Alan Rudolph, Strategic Advisor at AGS, to explore how sales and marketing alignment, time to value, and retention strategies directly impact enterprise value. Alan breaks down why misalignment between sales and marketing often starts with a lack of shared ICP definition, and how that disconnect destroys both efficiency and effectiveness. He also shares where AI is creating real leverage today across prospecting, coaching, and personalization, while emphasizing that human judgment remains critical in enterprise sales. The conversation closes with a deep dive into time to value, gross versus net retention, and the bow tie revenue model, highlighting how leading organizations connect the full customer lifecycle to long-term value creation. What You’ll Learn:
Key Topics:
Guest Spotlight: Alan Rudolph Alan Rudolph is a Strategic Advisor at AGS with deep experience advising private equity-backed companies and scaling enterprise sales organizations. With a strong operational background at the COO level, Alan specializes in aligning sales, marketing, and customer success to drive measurable enterprise value and long-term growth. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more insights on enterprise value creation, GTM alignment, and building high-performance revenue organizations. Mark Petruzzi (00:34) Alan, let's talk about the marketing side of this equation. Because in our experience at AGS, sales and marketing misalignment is one of the biggest destroyers of both efficiency and effectiveness. What does a well-aligned value creation oriented sales and marketing motion look like? And where does it usually fall apart? Alan (00:53) So it's fascinating because when it's working, it just works, right? It's invisible. It doesn't matter. But when it starts to fall apart, It's usually, and this is where we start tying all these pieces together in terms of ICP, because it's the definition of that qualified lead or the quality, maybe said another way of that qualified lead, right? So marketing is always going to optimize for volume, right? Throughput. not the quality, right? The actual lead that comes in and making sure it's a good lead. And then sales just starts ignoring it. Sales starts going, doing their own thing and marketing thinks they have this great volume and sales is saying, you no, because they're not matching back to the ICP and that shared definition, that quality of how do I bring a great customer in the door? KK Anderson (01:44) That makes a lot of sense. And Alan, let's pivot to everyone's favorite topic, AI, for a minute here to round out this topic. So AI is reshaping both how we find customers and how we serve them. And so in terms of this kind of efficiency mandate, where are you seeing AI create real measurable leverage for sales and marketing teams right now? like in your port codes that you're working with or have worked with in the past, like where's it working and where is it still mostly noise? Alan (02:14) three areas are where I see it working. First of all, and let's frame this all in the context of making us humans better, not replacing us humans. let's start there. That's first and foremost. so number one, prospecting and research, right? Who should I be talking to? Who should I be reaching out to? Right? That time spent in building those lists, et cetera. Number two is call intelligence and coaching. And I can remember, my God, one of the port codes I was working with probably five-ish years ago, actually in the middle of COVID, we started doing call recording. And the value prop around what I can, the takeaway from our calls, right? What worked? What didn't work? How should I change the script, et cetera? Just a huge opportunity for training, for coaching, for getting much more effective results out of our calls. you know, again, huge in terms of intelligence and coaching. lastly, content personalization at scale, right? Using AI to tailor the case study, to tailor the solution definition, to tailor, the whole presentation, to make sure that it matches specifically, you know, to that, that prospect we're going, going after. So it's not noise. It is real. AI is real. The one thing I would stay away from, right, in terms of what's not working is sort of these autonomous SDRs, right? Because it just, it's not there yet. know, tomorrow is, we don't know, but it's just not there yet. Again, it comes back to, it makes us all better. It makes humans better, but it doesn't replace that human judgment. That is so important in a high stakes enterprise class sale. Mark Petruzzi (04:02) Excellent, Alan. All right, well, let's move us into our final topic, time to value retention and the revenue bow tie. Earlier on, Alan, you introduced us to the concept of time to value, TTV, as a critical metric that most sales leaders do not own, but absolutely should. Please define TTV for our audience and make the case for why it belongs on the sales leader scorecard. not just customer success. Alan (04:29) Absolutely. So TTV is, as you said, Mark, time to value. It's how quickly can I get from that contract signature to value from the solution, whatever that means, right, in terms of the solution up and running. And I can remember going back in my career, we'd be talking six, nine, 12 months. And customers want 15, 30, 45 days. So it's just so critical that the Really, and I'm going to broaden it between customer, beyond just customer success and sales, the whole organization, the whole executive leadership team needs to get focused in on how do I define a solution, sell a solution and drive that solution to quote unquote live to value with the customer as quickly as possible. And that's what TTV is all about. And that's why it needs to be both on the seller scorecard as well as the success scorecard. And it's going to tie right back into the bow tie. So it's just, it's, it's, you think about a customer journey, right. And I'm drawing a circle here because the customer journey is in fact, is a circle, right? We find a customer, we win the customer, we keep the customer. And it's so important that the, that whole journey. that the executive leadership team is, you know, it's on the scorecard. They're evaluated on the success of driving TTV as low as possible. KK Anderson (05:55) That makes a lot of sense. so building on TTV, right? And thinking about, you know, gross retention versus net retention. So walk us through, if you would, the gross retention versus net retention, you know. Alan (06:04) Mm-hmm. KK Anderson (06:11) concepts, right? So thinking, you know, at AGS, we see this constantly. A team will sell aggressively. They'll hit their new logo acquisition number. But gross retention is quietly eroding in the background, right? So what does that diagnostic conversation sound like with the CEO or a board of directors when those two numbers start to diverge? And I know, know TTV fits into that for sure, but How do you fix that? How do you fix it when your gross retention is not aligned with your net retention? Alan (06:43) Sure. So let's go back to definitional, right? So gross retention is I open my doors on day one of the year. If I have a dollar and I renew that dollar, that's 100 % gross retention. So let's be clear on definitions here. And then net retention is how much additional do I sell? And depending on how the scorecard is kept, that additional can be everything from a CPI increase, 4%, 5%, 6%, or whatever the number is that you choose. to true add on to increase in the actual pricing so that when I take the dollar, I renew the dollar. But if I have, you know, an, an, an extra 10 cents, excuse me, of add on now it's a dollar 10. And now I have a net retention of 110%. This whole conversation you hear us talking about this through this whole podcast comes back to selling value. selling value to my ICP, my ideal customer profile, and making sure the customer is getting that value vis-a-vis the previous topic around TTV as quickly as possible. The more we can tighten in on the combination of the solution along with the ICP and driving that value to the customer, the customer is going to renew, the customer is going to buy more. World class metrics have Gross retention in the mid to upper 90s. World class metrics have net retention, 110 % plus. That's world class. What happens is if we see net retention, this comes back to the way you phrased the question, KK, if we see that net retention staying that 110 plus, but the gross retention slipping, for example, into the 80s, maybe even only 90, that means we're putting in Too much pressure on net new sales, right? Too much pressure on selling that more, selling additional, and we're losing that gross retention. And what happens when you lose gross retention, number one is what I just said, too much pressure on the organization overall to get that add on sale. Number two, the overall cost of acquisition goes up. And so inherently, the EBITDA for the organization is getting impacted because I'm selling net new. and I'm not retaining my bass. Mark Petruzzi (08:59) And you know, Alan, I've seen over the years, there's almost this kind of machismo sort of looking at new opportunities and new revenue. And everyone wants to be that hunter that leaves the village and comes back with an antelope on their back, carrying it back to the entire village and everyone gets to eat. But we find in a lot of ways, It's really the individuals who are out there foraging and growing and doing things in the village are the ones that really keep a village alive much more than the big celebrated hunter that comes in. So it's amazing how that mindset just, it still hasn't gone away. Everybody still thinks a new logo is worth more than additional revenue and an old logo. And it just really doesn't. Okay, so let's switch to the Bowtie revenue architecture and go a little deeper here. The whole concept of find more, win more, keep more. That's the framework that ties the full customer lifecycle into that single value creation narrative that we started this entire podcast on. How do you use that framework when you walk into a port co or leadership offsite and Alan (09:52) Okay. Mark Petruzzi (10:13) What does it unlock in that conversation that traditional funnel thinking just absolutely messes? Alan (10:19) It misses the keep more, right? The whole premise is, you know, find and win. That just is the beginning of the journey. And I can't lose sight of that keep more, right? The whole discussion we have, and we spent a lot of time in off-sites talking about this is what is the customer journey? to, think about it from a RACI standpoint, right? Who touches the customer throughout the lifecycle, throughout the customer journey to ensure that the customer is ready, willing, and able to buy more throughout, again, that customer journey, that customer lifecycle? And that's why the bow tie in terms of find, win, keep is so critical and intertwined with this whole discussion of gross and net retention and making sure that the Whole organization drives value to the customer throughout the entire journey. KK Anderson (11:13) Really interesting. Okay, so as we round out this last topic, let's bring it home with a forward looking question, Alan. ⁓ So if you're advising a chief revenue officer or a CEO heading into a new fiscal year, right? They're still navigating a tough SaaS environment, PE pressure on EBITDA, and buyers who are more cautious now than they were three years ago. Alan (11:20) Mm-hmm. KK Anderson (11:36) What would you say are the two or three moves that separate the leaders who will create enterprise value from those who will just survive? Alan (11:44) I sound like so repetitive on number one. Ruthless, ruthless ICP discipline, right? That will just drive tremendous value as we look forward. Number two, and this might be a little bit controversial, own CRO, Chief Revenue Officer. Revenue, not sales, revenue. So own the entire revenue lifecycle. So let's, I don't want to. KK Anderson (11:44) Alan (12:09) We're have a whole other podcast about ⁓ how should a port co be organized. But suffice it to say that an executive leader that owns revenue needs to own that whole lifecycle, needs to own find more, win more, keep more, needs to own the customer journey of driving great value through TTV, as well as making sure we get the renewal signed. And then lastly, if you remember, half a dozen questions or so ago, we talked about efficiency and effectiveness. Make efficiency a competitive advantage, right? Drive the value. Make sure we understand where the buyers are coming from. Why are they coming through us? How do we drive through the sales cycle as quickly as possible? How do we leverage AI? Right? So you said it, KK. This is the culmination of what we've been talking about throughout this podcast. And it's about speed and efficiency and effectiveness and pulling that all together into a competitive advantage. KK Anderson (13:09) I mean, it all comes together, right? It all comes together. Okay, Alan, we are gonna move on to our favorite part of every podcast we do, the rapid fire questions. And I'm gonna kick us off and then we'll, Mark, you can take the next one, okay? And I can't wait to see what you're gonna say for this first one. Okay, the metric you think every CRO should have tattooed on their wrist. Alan (13:29) Net Net retention. KK Anderson (13:30) at rest. Mark Petruzzi (13:32) Great, so okay, growth or profitability? If you can only optimize one for the next 12 months, which do you pick and why? Alan (13:40) So these are all mature companies. So it has to be profitability. I'm not in startup mode, right? So it has to be profitability with an asterisk optimizing for profitable growth, right? So we've talked throughout this podcast about, you know, a successful organization historically was at least rule Now those that that's even, you know, with AI with everything that's going on in the world around us, even growing more. So it's got to be profitable. And it's got to be growth. And you take the sum of those two, and it's got to be a big number. And I'm going to argue that number, the rule of 40, has gone by the wayside. And we're talking about something in a rule of 50 plus to get to world class valuations. KK Anderson (14:20) You heard it here first folks, rule of 40 is no more, rule of 50, here we come. Okay, sales or a business book, Alan, that you think every revenue leader should be reading right now. Alan (14:32) So I'm going to take us back in time because I truly, truly believe that relationships are critical to the successful enterprise sale. And there was a guy named Dale Carnegie who wrote an unbelievable book in terms of how to win friends and influence people. And I'm to go back to basics, which it is, but there are just so many learnings in that book about what those relationships mean, how to build them, how to nurture them. how to deal with those relationships in good time and bad. So it's an old book, it's been around. Hopefully all of us, anybody in sales has seen it, read it, go read it again, and then keep reading it. KK Anderson (15:10) I put that book in both of my kids stockings at Christmas this year. fact, fun fact. Alan (15:13) Hahaha! Mark Petruzzi (15:15) Great, next one, one leadership habit every sales leader should build right now as soon as he can. Alan (15:22) Yeah, I have long discussions about balancing between deep dive forecast reviews and structured deal reviews. And I think structured deal reviews capped at a 30 or 60 minute slot adds tremendous value for the leadership team to understand what needs to get done for that deal to win and helps the salesperson bring that deal in. So again, recommend structured deal reviews by ⁓ strategic deals selected appropriately and going through the win of how do we make sure that deal gets across the finish line. KK Anderson (16:00) Love it. Okay, my favorite question. Advice you would give to your 21 year old self. And it can be about building a career and whatnot, but just what would you say? Alan (16:08) Learn the ins and outs of the business model, the financial model. And it's really all about what levers. Like take the example I was giving earlier in terms of cost of acquisition and an existing customer versus a new cost or effectively customer acquisition cost or as we call it CAC. So learn the financial model. Understand what drives revenue, what drives costs. How do I ⁓ impact costs? What ultimately drives EBITDA? Right? Most sales leaders They just can't do it, I hate to say. And so that's a learning that I think is really important. Reach out to me, I'll take you through it. Right? But again, I just think that the core financial model, the better you are at understanding it, the better you'll perform in the board. Mark Petruzzi (16:52) All right, our final one. The one thing the P community still gets wrong about go to market. Alan (16:57) the time it takes to influence or change sales culture. It's hard, right? The operational fixes, the process changes, the people, everything that goes into an overall sales culture that drives all the metrics we've been talking about through this podcast, it just, you know, most boards, most PE firms think they can snap their fingers and it's going to change. and for us as practitioners in the market, ⁓ can we get to the change? Yes. Does it take longer? Absolutely. KK Anderson (17:31) Realistically, we always say it's 12 to 18 months and I know it's hard for people to hear that. and you know, we can do sprints that have meaningful impact on acceleration, but it does. A true sales transformation and culture shift takes 12 to 18 months. Alan (17:37) Board don't like that. Yep, 100 % agree. Mark Petruzzi (17:49) All right, well, Alan, this has been an extraordinary conversation. It was the kind that audiences will be referencing long after they listen. ⁓ We will be referencing it long after we listen. So for everyone tuning in, if you took one thing from today, let it be this. Enterprise value is not just a finance concept. It really is the basis of what we're all out here doing. Why we work as hard as we do. why we jump on planes at six o'clock in the morning and, you know, jump back on a flight at 11 or midnight. So if you can look at it that way, you really as a sales leader, learn to speak the language of the board, because again, that's the thing that they need. That's the thing that they're focused on. And that's where their fiduciary responsibility is as well. So It is really the outcome of every decision a sales leader makes about how to find customers, how to win them, how to keep them, how to grow them, how to keep them becoming happier every single day. Allen has given us the framework to talk about all of these concepts. KK Anderson (18:59) All right, Alan, wonderful conversation. And to our great audience, you can connect with Alan through AGS at get-ags.com. That's get and then the dash symbol, ags.com. And we will include all of his contact information in the show notes and also an area where they can connect to you on LinkedIn, Alan, if that's perfect. Alan (19:20) Yep, absolutely. KK Anderson (19:22) Okay, and if this episode shifted how you think about the sales leader's role in value creation, share it. Like and subscribe. Share it with a CRO or a CEO who needs to hear it. And we will see you next time on Selling Intelligence. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 124 - Enterprise Value Creation, ICP Discipline, and Building Efficient Revenue Engines with Alan Rudolph - Part 1 | 29 avr. 2026 | 00:19:13 | |
General Episode Description: In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Alan Rudolph, Operating Partner at AGS, to break down what enterprise value creation really means for modern sales leaders. Alan shares why CROs must move beyond just hitting quota and start thinking like operators responsible for long-term enterprise value. The conversation explores how retention, expansion, deal velocity, and cost of acquisition directly influence valuation, and why aligning go-to-market execution with investor expectations is now critical. They also dive into the shift from founder-led growth to scalable sales organizations, the importance of ICP discipline, and why effectiveness and efficiency must now coexist in every revenue team. What You’ll Learn:
Key Topics:
Guest Spotlight: Alan Rudolph Alan Rudolph is a Strategic Advisor at AGS with decades of experience working with growth-stage and private equity-backed companies. Known for operating at the COO level, Alan specializes in aligning sales, marketing, and operations with investor expectations, helping organizations build scalable revenue engines that drive long-term enterprise value. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more insights on scaling revenue, aligning with investors, and building high-performance go-to-market teams. Mark Petruzzi (00:28) Welcome to Selling Intelligence. I'm Mark Petruzzi, joined as always by my co-host, KK Anderson. Today we have a guest who sits at a genuinely rare intersection. Someone who has operated inside growth stage companies, advised P backboards, and built sales and marketing engines from the ground up. and also from the COO, Chief Operating Officer, Level, which has been his core focus. He's also a close friend and a member of our team here at AGS. Please welcome Alan Rudolph, Strategic Advisor at AGS. So, Alan (01:03) Thanks, Mark. to be on the podcast today. Mark Petruzzi (01:06) Great, we're happy to have you, Alan. So Alan brings decades of experience across boardrooms, PA backed operators and enterprise deal cycles. He's known for helping leadership teams connect the dots between investor readiness, revenue acceleration and overall sales team performance. And also for making the case that great sales leadership is not just about hitting a number. It's about building a machine that creates lasting enterprise value. That is exactly where we would like to go today. We're going to talk about what enterprise value creation actually means for the sales leader, why efficiency now sits alongside effectiveness as a C-suite mandate, and how the boat-time revenue model, finding, winning, and keeping customers, maps directly to the metrics P investors care most about. Three topics we'll cover. EVC, enterprise value creation, what it is, why sales leaders need to understand it and own it. Effectiveness versus efficiency, the dual mandate for modern sales and marketing leaders and why building an efficient team is no longer optional. The third one is time to value retention and the revenue bow tie. How customers onboard focus on gross retention and how important net retention is to the overall enterprise value and what the best senior operators do about it. Again, Alan, we're so happy to have you here. Let's jump right in. So, okay, first topic, enterprise value creation. You know, really what a sales leaders get wrong here. And let's start with a framing question because this concept of enterprise value creation gets talked about in boardrooms, but rarely makes it onto the whiteboard in a sales QBR in plain language. What is an EVC and why should every CRO SVP of sales and VP of sales have it front of mind, not just the CFO in the board. Alan (03:04) Thanks, Mark. Great question. So EVC or value creation or value creation plans has been the buzzword, as you say, of boardrooms, of private equity firms. And at the end of the day, a value creation plan, also a transformation plan, simply drives to whatever that target multiple is. And so everybody thinks, it's just about the multiple. pick the day and age, pick the year, pick whatever time frame you want to pick in terms of what are target valuations. But let's forget about the number for a second. And again, let's talk about what the CRO needs to worry about. And so as you said previously, CROs think, it's just the number, right? I got a quota. What percent of quota? How am I doing against my sales forecast, et cetera? When I think about a value creation plan for a CRO, I think about things like customer retention, right? How am I doing? How am I driving value across my install base? Because we know the higher the gross retention, that drives into expansion capabilities. That drives into a broader opportunity to sell more of what I have in my toolbox, number one. So that's retention and expansion. Then add to that deal velocity. Again, the deeper relationship, the clearer understanding, I have faster deal velocity. And then lastly, think about it from what does it cost me to win that deal? That's what's so critical for the CRO. these are, if you take, just take those four things I just said, retention, expansion, deal velocity, and costs of acquisition and you put that into a value creation plan. Okay, so what does that really mean? Let's dig into that for a second. When I think about a value creation plan around retention, I'm going to have a key set of initiatives that I'm going to drive across my sales team, hunters, farmers, whether it's customer success or account management. I'm going to have key initiatives that drive increases in overall retention. That's what a value creation plan is. Separate and distinct from my quarterly forecast as the CRO. Right? So it's the combination when I think about what does a good CRO look like when he or she steps into the boardroom and starts talking about how am I doing this? How did I do this past quarter? What's the forecast for the next three quarters? How am I going to do for the year? And how am going to improve that overall value prop into the value creation plan, which ultimately drives the multiple in terms of the overall valuation of the. KK Anderson (05:50) So as you think about, am I echoing by the way? Alan (05:53) You are. Mark Petruzzi (05:53) You are, yes. KK Anderson (05:55) Okay. Hang on. that better? Okay. I think it might be gone. Okay. Sorry about that. so as you think about these, these specific value creation plans, you know, and you think about sellers in general, right? Salespeople. What would you say are the top two or three places where sales teams Mark Petruzzi (05:56) It actually seems better KK Anderson (06:13) or sellers unknowingly destroy enterprise value, even though they may be hitting their top line number? What are some things to look out for where they're inadvertently impacting in a negative way? Great question. Alan (06:23) Great question and I see it too often and don't laugh too much when I give you the first comment. The discount trap as I call it. Right? We get to the number, we outperform, but I do that by discounting and we know that that discounting inherently puts challenges all throughout the organization because now our profitability numbers, our bottom line isn't where we need them to be. So we just really need to be careful in terms of selling value that we're, have a, you know, I've walked into companies that don't even have a target price book, right? And so it's important that we understand what our price structure is, how to drive value with that price structure and not to ultimately fall into the discount trap. That's number one. Number two is the, I'm gonna call it the yin and the yang or the tie between, and this comes back to, find, and keep more is churn versus new business. So is a ⁓ lower retention massed by net new business. And we know the cost of acquiring new business versus the profitability of a long-term customer is dramatically different. And so we don't want to overachieve revenue numbers because we're bringing more in the door net new. but we're losing or reducing on gross retention. then lastly, and again, I'm an ops guy, right? And so I need to manage and maintain customers throughout the life cycle. It's selling to the wrong customers. And the hardest thing we all can do in an enterprise SaaS company is fire a customer. But we know that sometimes we just need to do that because For whatever reason, there's a gap between the solution sold versus the expectation of the customer. So it's just really when we come back to that question about how can a CRO destroy enterprise value overall, is get that right customer base that truly understand the value we drive, that can benefit from the solution. Mark Petruzzi (08:11) is really important for me to come back to that question. Alan (08:26) We know it's a very small world out there that will talk to their peers in their respective industry about the solution. So again, it's all about getting to the right customer. Mark Petruzzi (08:37) Excellent, excellent points, Alan. So one of the things we hear constantly from P E operating partners is that founders and early sales leaders are often great at the hunt, but man, do they struggle to build the system when they really have to take it past founder led growth. You have described this as the difference between being the lead salesperson and being a sales leader who builds organizational capacity. Alan (08:54) Mmm. Mark Petruzzi (09:02) Walk us through that ⁓ transition, typically breaks and what really does have to change to make it successful. Alan (09:09) mean founders are phenomenal, right? Because they build, they grow, they have personal relationships with that first set of customers. And by the way, they know what they can and cannot sell, right? They know where the product does or does not break. The discussions I have with founders in earlier stage companies really boils down to one primary aspect. Definition of the ICP. Who is my target customer? Right? So comes back to what I said earlier about whether it's finding customers or selling to the wrong customers, et cetera. It's all about the ICP. So I have a well-defined solution. And I know that that solution is relevant to a target set of customers. So how do I define that ICP? That's what will drive an organization to go from a founder-led sale that he or she can basically make whatever decisions need to be made and can drive that solution into a much broader sales team that needs to understand what is that profile of the customer that I'm looking for? How do I drive the solution into that customer and win those deals? KK Anderson (10:23) You know, ICP is the cornerstone of everything really. And even now this week, we've been having a lot of conversations around agentic workflows and go to market and all of it hinges on the ICP. If the ICP is not effective, then none of the agentic workflows are effective. And it sounds like it's the cornerstone of our value creation as well, huh? Alan (10:43) KCAD, add to that, without the definition and the adherence to the ICP, the firm, the company, the SaaS provider will not get to its target valuation. I would be very bold in making that statement, but I'd stand behind it. KK Anderson (10:58) Well, and you might somehow weave this into my next question here. so, you know, thinking about making this concrete and you know, we like to measure everything. if I'm a CRO at a PE back SaaS company and I'm going into a board meeting next month, what are the two or three metrics that I should be walking in with that signal? I understand enterprise value. My team understands enterprise value. So. Like beyond just ARR and pipeline coverage, like what are those metrics? Alan (11:27) net revenue retention. It comes back to ICP. Am I selling to the right customer that continues to buy more from me? And so let's be clear for a second. Net revenue retention, everybody gets this messed up. Net revenue retention is I start the year, let's call it $1. And if at the end of the year I have $1.10, that means I grew at 110%. KK Anderson (11:30) Right. Yeah. Alan (11:49) revenue retention is the combination of my gross, what I'm renewing, plus the additional sales, cross-sell, up-sell, et cetera, into that customer. So first and foremost, a clear understanding of that revenue retention. Number two, and I talked about this briefly earlier, is the payback period for our customer, right? We know that the costs are higher in the first months and the first year of managing implementing owning a customer. So again, this comes back to ICP sell to the right customer, right? It's I spent a lot of my career middle part of my career in outsourcing. We didn't actually make any money in large complex outsourcing deals to year two, three or four. So right, it's all about making sure you have the right ICP, the right solution selling into that customer. And then lastly, TTV time to value in this day and age. Customers want value as soon as they sign the contract. So we all know that in a SaaS world, customers sign the contract, they get an invoice, they pay us upfront for a year. Well, they want value immediately from that. So we want to make sure we're continuing to address time to value and how much we are decreasing the implementation time frame number one. Mark Petruzzi (13:09) . Alan (13:09) and or number two for depending on the solutions and the more complex solutions that we're segmenting that implementation so that we get pieces of the solution implemented as quickly as possible so the customer is getting value out of the money they're spending with us. Mark Petruzzi (13:26) Good stuff. So let's move on to topic two. Effectiveness versus efficiency. Building the team that is able to move the needle. So the era of growth at any cost is over. It's way over, right? It's, you know, we've moved much more to the rule of 40, which means you have to have a growth rate plus a profit margin that is 40 or greater. and it's probably going to be moving past that metric as well pretty soon because, you know, was the good old days, right? It was, we, we had to grow each year. A sales leader was asked or was told what the number is and they would come back and say, okay, I need to hire 30 new reps this year to be able to get that. Well, it doesn't work that way anymore. So we're hearing this from. Alan (13:54) Absolutely. Mark Petruzzi (14:16) every PE board and every PE firm that we work with, efficiency is now as important as effectiveness. help us to find the difference and why is it so hard for most sales leaders to genuinely operate on both dimensions simultaneously? Alan (14:34) because they're almost diametrically opposed, right? That's the problem. So efficiency, I think about it's just numbers, right? What's the ratio of output to input? know, what's my sales forecast? How do I go from, you know, lead flow and, you know, an MQL and SQL, blah, blah, right? It's just efficiency is just how quickly can I get that wheel spinning. Whereas effectiveness is all about finding, engaging, closing the right customers. It's almost like quality versus quantity. And coin operated salespeople struggle with effectiveness. But we know that effectiveness, go to my previous answers, effectiveness drives higher net retention. Effectiveness drives a better overall ICP. Effectiveness drives overall increase in you know, the valuation of the firm. And I would argue that in the world that we're living in today with, you know, with everything we talk about from an agentic standpoint, the introduction of agentic workflow, et cetera, we're going to need to look at, you know, valuations that are rule of 60 plus. And so to get there, both effectiveness and efficiency are important. We need to value where we spend our time as sellers, as a CRO, thinking about effectiveness and efficiency and making sure we're bringing the right customers into that bow-tie journey of find, keep, find, and keep and ⁓ driving our sales force to be as effective as possible in winning deals, maintaining deals, keeping deals. and closing deals without discounts. I'll end on that. KK Anderson (16:19) So, Alan, you go into a PortCo and you do a go-to-market assessment, what you're saying makes complete sense around the inefficiencies with the sales team inadvertently driving down enterprise value. sure, there's going to be all kinds of lagging indicators in Monday morning quarterback, where we can look back and recognize where they're failing. Like what are the signs, like what are the leading indicators? What are the signs that you can look for now? Like when you're in that diagnostic stage, assessment stage with the client, like what are the signs that a team is burning capacity? Alan (16:52) The first thing I look for is a The first thing I look for at the sales rep level and obviously depending on size and scale, sales rep, sales managers, VP, CRO, et cetera, is activity that does not connect to outcomes. We all know, we've seen it. We have salespeople that have tons of activity. They have deals, they have demos, they have outbound, et cetera. There's just tons of activity, but we're not seeing the close. Number two, along with that then, is a sales cycle that keeps stretching, right? We have a target close date and it just keeps moving, right? Well, that comes back to, don't know my customer. I don't know who to contact at my customer. I don't understand who has to sign off, who the ultimate buyer is, how the decision is made. So it's all about Mark Petruzzi (17:33) you Alan (17:41) understanding, knowing my customer. So too much activity, lack of knowledge at my customer. And then lastly, again, this is the Ops Guy speaking now is we close the deal, we hand it off to the implementation team. They have a first conversation with the customer and the customer said, ⁓ I thought I bought X and we're delivering Y. And there's just this gap around that overall what Mark Petruzzi (18:03) Hmm. Alan (18:06) does the solution look like? How do I drive that solution to value in the customer? Right? It's all about value based selling. So it just is, you know, those are the key indicators are start to look for in terms of inefficient sales teams for, know, versus, you know, a very efficient and effective sales team will have less activity, will meet their targets in terms of closed States and won't have any issues with the handoff when it happens. to the implementation or services team or whatever the firm calls it. Mark Petruzzi (18:37) you KK Anderson (18:37) And once again, that comes down to the ICP, Alan (18:41) It does, 100%. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 123 -Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 2 | 22 avr. 2026 | 00:24:52 | |
General Episode Description: In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Ray Rike, founder and CEO of BenchMarket, to go deeper into how companies should measure, operationalize, and compete with agentic AI in go-to-market functions. Ray breaks down why most companies still lack basic GTM measurement discipline, what new AI-specific benchmarks leaders should track, and how legacy SaaS companies can realistically compete with AI-native organizations that are operating at dramatically higher efficiency. The conversation also tackles the hard truth about workforce reduction, the rise of AI operators, and why companies must rethink their entire operating model, not just layer AI on top of existing processes. What You’ll Learn:
Key Topics:
Guest Spotlight: Ray Rike Ray Rike is the founder and CEO of BenchMarket, a leading provider of B2B SaaS performance benchmarks. With decades of experience as a go-to-market leader, he helps organizations move from intuition to data-driven execution. Ray is also the creator of the AI to ROI newsletter, where he analyzes hundreds of AI developments weekly to help leaders understand what actually drives business outcomes. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more insights on AI benchmarks, GTM transformation, and building high-performance revenue organizations. Mark (00:26) Excellent. All right, well, Ray, let me bring you back into the days of you and I starting all our research and all the pre-work for data and diagnosis driven selling. So I hope that doesn't cause you to develop a Twitch or anything like that, because as you and I both know, that was hard work. So, but let's, you know. What we really saw right up front is, and we really pushed hard on this, is the idea is you can't manage what you don't measure. And you need external benchmarks, not just internal comparisons to know if your metrics are actually good. You know, it's great. It's great to be able to say, improved this process by 20%. But if you were 45 % behind most of your competitors before that, That 20 % still has you on the back of the pack. So how do you bring that same philosophy to measuring an agentic BDR or an AI-powered deal coaching agent? And we've touched on this, but what's the equivalent of a CAC payback for agents and the entire investment? Ray Rike (01:33) Well, I would start with let's make sure you have your go to market measurements in place, because honestly, we've been talking about these for years. Less than 50 percent of companies have great GTM analytics. ⁓ So things like cost per dollar a pipeline, less than 40 percent of people are measuring cost per dollar a pipeline. So make sure you do that and look at your current state before AI and then measure it post AI introduction. Right. So cost and I'm talking right now, I'm looking very specifically at the customer acquisition process. So cost per dollar pipeline before and after cost per dollar of new AR before and after when rate before and after your average and your contract for you before and after. Cause those are all going to be hopefully much better with AI to your point, Mark. I mean, let's use outreach. Everybody had to have a sales engagement platform, right? How many companies actually said, well, after I invested $1,500 per SCR, I had a better conversion rate or a lower cost per dollar of acquisition? Nobody. You're going to need to do that with AI. So that's my first thing. The second thing, which haven't been defined yet, but I'm working with some VCs on this right now, is AI specific customer acquisition efficacy. So I'm looking at agent costs per opportunity. Agent cost per dollar pipeline, agent cost per dollar of new ARR, agent dollar per cost of retained ARR. So you can think about your gross revenue retention and agent cost per dollar of expansion ARR. Now I'm projecting that we're going to be using agentic AI a lot in those processes or sub processes. And by the way, that's the other best practices. When you design a process, it's better to design a lot of subprocesses underneath so you don't have one large unwieldy AI agent. You have a lot of subprocesses that you have different people auditing and evaluating. KK Anderson (03:28) All right. Let's dig into that design a little bit. So walk us through, and I know this is new, as we've said multiple times for so many of us, what a well-instrumented, agentic, you know, GTM for the purposes of our audience, pilot could look like. You just gave us one great clue, which is, you know, don't make monster agents and, and to break them up so that you can, you know, be more agile and and predictable with those. You've walked us through some baseline metrics that you want to set before you launch, things that haven't necessarily been done in the past with programs like our outreach launches over the years. But what does the pilot to scale gate look like? And how do you separate the agent did something from the agent created revenue attributed value? Ray Rike (04:14) Well, let me go to the baseline metrics first, KK. So I think I have four levels of metrics I like to see in any initiative, including the Gentic AI. So one is a productivity metric, and that is outputs per time, you know, whether it's outputs per human hour, outputs per day or time spent per activity. That's what we've been measuring for the last year and a half and AI in marketing and sales. But that's what then you have effectiveness. How effective is my AI enabled process going to be? ⁓ How many desired outputs am I getting versus the inputs? Hey, for every hundred emails my agent sending, how many meetings do I get set up? Right. Then there's efficiency. That's the cost per outcome. And then there's actual ROI, which is outcome value divided by the AI investment. So productivity, effectiveness, efficiency, and ROI. I'm not going to go into detail what that's like for just an SDR program, but at least it gives you a framework and a layer approach to designing those four layers of metrics you need to measure. Mark (05:19) Excellent. All right, let's move into topic three, the benchmarked view, and tell us a little bit about what the data has been telling you and your team at Benchmarkit. And let's go with, guess, a baseline of that. Some of your initial benchmarks that you have been working on are showing AI native companies hitting two to three times higher ARR per FTE. than a legacy SaaS, as one example. From our listeners who are operators inside non-AI native companies that are trying to deploy these agentic go-to-market programs we're describing, how do they close that gap? What are the structural differences they need to address? Not just the tooling, but the operating model as well. Ray Rike (06:02) In the let's be real. It's going to be real hard. And the reason being is a lot of the AI native companies are getting new budget. They're getting experimentation budgets. They're getting budget from labor versus budget from I.T. investments. Right. So I hate to say it, but it's going to be hard. But hey, there's a lot of people out there in legacy says companies that they need to get there. Right. So number one is you've got to be laser focused on number one, the effectiveness. Can AI help you get more conversions? Can they get higher ACV? Can they increase your win rate? And you got to go right to cost per. If AI is not getting you a reduced cost per dollar of new ARR, it's going to be really hard. And honestly, Mark, The hardest part is for me, if it was me and he brought me into a $50 million SaaS company, I would say we got to throw out the old playbook and start from scratch. But I don't have the new playbook based upon years and years of experience. So it's going to be really hard to throw out the old playbook and build the new one. So that's why I bring in someone who's got maybe six, 12, 18 months of experience and an AI first culture. and have them do it with you or hire a third party consultant. KK Anderson (07:22) Wow. And it's quite the conundrum that we're all faced with right now. All of these native SaaS leaders trying to compete with these AI native companies who are just crushing it. Ray Rike (07:33) I mean, when you're talking about your best in class, SaaS companies are doing 600 ⁓ to 800,000 revenue per FTE and Anthropics doing three to four. How do you compete with that? It's a little bit like saying, how did JCPenney compete with Amazon? ⁓ I'll bring in a guy from Apple who created the Apple retail experience and that's going to fix it. We saw how that worked, right? KK Anderson (07:42) blue. really is. Ray Rike (07:57) Sometimes it's just nice being part of the next generation versus trying to reinvent the current generation. I'm being honest here. KK Anderson (08:04) you know, and I know it's hard to answer that, but if you were a CRO in one of these old school SaaS companies, what, aside from calling a consultant, like what, where do think you would go first? Like what would you, what would you do? How would you that gap? Ray Rike (08:17) I would completely get rid of my SDR team and make it 100 % agent based. I would reduce my number of salespeople by probably 50 % and say, okay, now that we got 50 % less staff, how do I manage more of their task with AI agents, research discovery, etc. So I would just basically look at what the AI native companies are doing, and then burn the ships and say, we got to do this with 50 % less people. Having a bandaid, I don't think helps. You got to rip it off. So even customer success, right? I do a lot of work with Gainsight. It's like AI is the best retention vehicle in the world because you can look at things that humans can't, kind of like usage patterns, et cetera. And they can predict churn faster than any CSM can. But when you've got 10 CSMs, they're like, that's my job. Well, if I only have three CSMs, I'm not going to be able to do this much, right? So I'm forced to try AI and automation. KK Anderson (09:11) Yep. And just since we're talking about the sensitive topic of AI replacing humans, is something, you know, questions we get a lot of, right? And we are firmly of the belief that yes, of course AI is going to replace some humans, but it can also make humans, that super intelligence can have an exponential impact on their effectiveness, sellers in particular, on their effectiveness if they're using AI correctly. So if you've got the three BDRs instead of the 10, what are some ways that, I don't know, talk to me about how AI can help them be more effective in these roles where there's less people. Ray Rike (09:48) I'll give you BDRs for example is research and doing a lot more targeted research and personalized outreach to those contacts in your ICP at scale. Where maybe I could do 20 or 30 emails that were personalized, best case now maybe I can do 50 a day or 75 a day. So research, highly targeted. That'd be one thing I'd be doing as a BDR every day. I would be using AI to say, how do I follow up with this person who I talked to three months ago? What's the best approach? Let's look at their LinkedIn profile. Let's look at the latest corporate articles out there in the ethos, you know, and on the internet, and let's tailor my next follow up based upon my AI agent helping me get more personal and personalized. KK Anderson (10:32) And what's interesting is more and more we are hearing about this kind of crisis of sameness, right? Where AI has enabled, know, everyone's got the same content, everyone's saying the same things, everyone's sending the same emails. Like you can tell if it's AI, you know, from a mile away. And then we also are also hearing this theme around how now, you know, your humanness is your uniqueness. And people are loving when they see a typo in an email or a message or a, hey, by the way, this is really me. This is not a bot. Ray Rike (11:04) So, you know, I don't know if this is good for this podcast, but I have to call, say it the way I see it. So I don't know if we saw the New York Times research from about a month ago, where 54 % of people prefer AI written communication versus human written communications. 54%, right? And KK Anderson (11:11) Yep. Mark (11:23) Yep. Ray Rike (11:25) that's going to increase as AI becomes more, more able to personalize the communication to KK versus Mark, right? Which humans are going to have a harder time doing that. So ask me the question again, KK, I went on a tangent. KK Anderson (11:28) normal. What, when I was just thinking, you know, we're hearing now that your humaneness is your uniqueness. And so, Ray Rike (11:42) yeah. So an enterprise class sells, I think it's going to continue to be the case. But, know, I think even having, you know, children who are early career people, right. So and I hate these type of generic comments, but be the person who knows how to use AI in your function better than anyone. Everyone should be spending at least an hour a day on their own, learning how to use AI in their role. They should be learning a new tool at least once per quarter, if not once per month. So that's one thing, because for the next few years, those who know how to use AI in your function, whether it just is your assistant to do your function better, or you become what I call the AI operations guru, you can go into any company and say, I'm going to improve your sales development process by 5X. by doing this, that, this, this, and this that I've done four times before. So doing it as a practitioner and then be able to do it as a consultant, you're going to have job security for quite a while. So that would be my advice. Learn it and be better than anyone else. And by the way, make sure that your boss knows that you're the person who knows it better than anyone else. Because when it comes time to get rid of people, like, I can't get rid of Joe. Joe knows more about this AI agent than anyone in the company. So that's why, Kay, I think you asked me this earlier. I believe that AI operations is going to be much more strategic and important. Mark (12:52) Yeah. Ray Rike (13:07) than rev ops ever became. And I actually saw three different job posts just on Monday from big companies asking for to hire AI operators. They didn't call them AI operation specialists, they called them AI operators. KK Anderson (13:21) Really cool. Mark (13:22) We can't let you go without going into some of the narrative that we're all hearing out there. And it starts with the term the SaaSpocalypse. So we all know that traditional SaaS and NRR is under significant pressure. Some companies in the bottom quartile now below 100 % of NRR. For listeners who are sales leaders, not just the executives of those companies, what does that signal mean for how they need to sell differently? And how does agentic AI factor into the defense strategy, the attack strategy, or whatever you pull together from here? Ray Rike (13:58) Well, net revenue retention is a combination of how much ARR you retain from existing customers plus how much expansion ARR you add. Right? So if you have a leaky bucket problem, i.e. your gross revenue retention went from 88 % last year to 80 % this year, which by the way was Zoom Info's big issue. They lost so many of their customers in the tech sector. You better quickly try to understand what I can do. and how you can harness the power of AI to increase customer retention, right? And then second, you've got to get a hell of a lot better on your customer expansion motion. And in fact, if you only have one or two products in your portfolio, I would start talking to your CEO and had a product about why these other three near adjacent products could really help you from an NRR and how it impact you. But start with How do you retain customers better? How do you increase the efficiency of your expansion motion? And how do you open the aperture of the opportunities to expand your existing customers? New ARR is still going to be really hard as a legacy SaaS company if you're competing against agentic AI or AI native software vendors. KK Anderson (15:06) Okay, last question before we move on to the rapid fire. And this is gonna be one where again, you know, it may be too early to tell, but just work with us here, on this one and let's kind of think about what the hypothetical is and just try to make this a little bit more concrete for our audience. So let's think of a real world benchmark anchor, okay? So a company with 25 million to 50 million ARR They're deploying their first agentic SCR or pipeline management program. What do we think good should look like at 90 days or even at six months? Which of these benchmarks that we've talked about today would tell you that this program is worth scaling versus killing? And how quickly do we know? Ray Rike (15:54) Within 90 days, your agent should be performing as good as if not better than a human SDR. Because you take some time to make sure you train it, you refine it, etc. Days 91 to 180, you should see a minimum of 25 to 50 percent lift on your conversion rate from outbound activity to sales call. You should see at least 25 percent lift from sales call to opportunity and your win rate should go up by at least 10 percent. So these are just some benchmarks out there, but you can't be just as good. It's got to be better. So I don't know if that gave you enough granularity, 90 days to prove the case, 180 days to make it tangible with real ROI. KK Anderson (16:32) It does. It does. Mark (16:37) those are reasonable timeframes and that's why this is working. Okay. KK Anderson (16:39) Mm-hmm. Ray Rike (16:42) by the way, Mark and KK one day, I mean, the days of experimentation were in the last three innings of that using a baseball metaphor. You're going to start competing for budget for AI. So you're going to need to say, here's my AI project and here's my projected ROI. And if it's lower than this one over here, you may not get it. So you better be ready to fight for your budget. Mark (17:04) You know, Ray, you hit on such a great point with that because I, you know, it's funny, as we've jumped into more of the pure play at Gentic work that we have done over the last year, maybe a year and a half, the real discussion with me reaching out to CEOs and board members that I know was, you know, okay, like, what are you guys doing with AI? ask your CEO, okay, you have seven direct reports reporting to you. What are they thinking about doing with AI? Because you had all these board members, especially kind of two years ago, a year and a half ago, going to everybody, come on, man, you got to do this, you got to get us a piece of this, we got to become more efficient. And it was really about like they were getting dragged in most of the executives I spoke with. we're getting dragged in to do this. So they had to go do something. But as we've gone over the past maybe nine months or so, I've seen and I've changed my approach accordingly, that it's now, you hey, it's not, you've got to be doing something in AI, but you got to be doing the right things in AI. And with the work I've done being on the board with Humigentic and the work KK and I have done with Humigentic as one example of a company, There is, you have to have that precision as well. So before we go into rapid fire, any thought that's popping in your mind based on what I just shared? Ray Rike (18:30) So I've done state of AI research and finance and marketing and sales and customer success and two thirds to three quarters of the time, the person who pushed AI into the department was the CEO, not the departmental executive, which is telling. And to your point, man, even If you're not that comfortable with it as the head of marketing or head of sales, you better hire someone. Maybe you hire your AI ops person instead of a rev ops person who's got that deep experience. And you're like, I need you to take this process completely redesign it and share with me how we can make this AI first. You got to take that lead because you're going to become obsolete so quickly. If you don't do it because you're fearful or you don't know, what you're not going to know is where you're going to get your next paycheck from. You need to know it and you need to learn it and embrace it. Mark (19:23) Yeah, Excellent advice. Okay, rapid fire. Let's finish up here. ⁓ First thing you've ever sold professionally or even as a kid. Ray Rike (19:34) My dad had his hobby, which was a small engine and lawnmower repair shop. We also sold new lawnmowers. So I got good at selling upsells to doing like total engine rebuilds or selling a new lawnmower when the old one was going to cost too much to get fixed. KK Anderson (19:49) Very good. Okay, one metric most go-to-market leaders are still measuring wrong. Ray Rike (19:54) customer acquisition cost ratio because they're not measuring it and they don't separate the measurement for what it costs to get a new customer's dollar of ARR or an existing customer dollar of expansion ARR. Mark (20:05) So if a CRO could only instrument one thing about their agentic go-to-market pilot, what should it be? Ray Rike (20:12) You are outbound. And specifically, that's not one thing. I would want the research and the outreach to be the first thing they automate. KK Anderson (20:20) advice you would give your 21 year old self. Ray Rike (20:23) be an entrepreneur. And by the way, I helped many entrepreneurs and VCs make a hell of a lot of money, right? Five exits out of seven companies. But being an entrepreneur at the last stage of my career is the most fun I've ever had. And in today's world, the chance to build a business, because you know AI better than anyone, there's never been a better opportunity to be an entrepreneur, never. Mark (20:46) Okay, your favorite chapter in data and diagnosis driven selling. And what would you write differently with me ⁓ if we had to do it again? Ray Rike (20:47) Thank probably the different metrics by stage of the customer acquisition process. And I would layer a lot more AI measurements. And quite frankly, even though we had a chapter dedicated to this, you know, and this was only what less than three years ago, a lot more focus on the AI first acquisition retention and expansion process versus how we wanted to automate and make it more efficient. Mark (21:15) Yes. We thought we were, yes. And it's funny, we thought we were so far ahead of what was about to happen. And we were pretty proud of even how we integrated stuff in and that one chapter that we were able to go a little deeper. But man, oh man, that tidal wave just came over our head, didn't it? KK Anderson (21:21) I sense an update coming. Okay, one sales ritual or habit that no AI agent will ever replace. Ray Rike (21:47) Maybe they can fake it or emulate it, but it's true concern about your customers win. Like one of the things I always try to do is understand what my buyers personal win was. My economic buyer and my influencer champion. Why are they going to win? Because they do business with me and my company. And then of course, how does the business really win? Right? And Be really curious about that and don't just even take what you hear for the truth. Kind of say, well, but I've also seen this or heard this. So how do you marry these two? I think it's just a human authenticity, curiosity and true concern to make sure you win, KK. Mark (22:28) Good stuff. So, and where will SAS benchmark data be most disrupted by AI in the next two or three years? Ray Rike (22:36) I think it's all going to be pretty disrupted, but it's going to be revenue per employee. And it's going to be how much I spend and operating expenses versus cost of goods sold. Mark (22:45) Beautiful. Well, Ray, thank you so much for spending the time today with us. It's always a pleasure. And also thank you to KK and our incredible audience. Thanks for joining us each week. All the best. KK Anderson (22:58) really Ray Rike (22:59) Hey Mark! KK Anderson (22:59) great. Ray Rike (22:59) Hey Mark, can I make a plug? Mark (23:00) Of course! KK Anderson (23:01) Yeah. Ray Rike (23:01) so me and my partner, we publish the AI to ROI newsletter every day. We cover a different topic, but we'll look at 200 to 1000 news articles a week and we pick out the top five to 10 and we share that with our audience and we do deep analysis on what it means. Man, if people could go to AI ROI dot sub step dot com, I really believe in. By the way, we don't. This is not a Get the free one so we can charge you subscription. Everything I do is for free to help the industry evolve. I think it'll take hours of research away from every individual who reads it and hopefully give them highly relevant contextual research and analysis. KK Anderson (23:43) And it's AI, the number two, ROI.substack.com. And you do not need to have a Substack subscription to be able to participate. And it's a fabulous newsletter, highly recommend. Ray Rike (23:58) That's it. And by the way, just go out there and get uncomfortable, do the unfamiliar and create the future that is AI. Mark (24:06) Beautiful. Thank you again and we'll see you soon. KK Anderson (24:06) Amazing. Thank you, Ray. Really enjoyed it. Ray Rike (24:11) Thank you. Mark Petruzzi (24:12) We hope you enjoyed this conversation and found it valuable. If you did, like and share it with your network. That's the best way to support us and the work we're doing here at AGS. And if you're curious where your sales team stacks up in the AI era, head to get-ags.com. That's get and the dash symbol, AGS.com for a complimentary sales team benchmark. Until next time. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep.122 - Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 1 | 15 avr. 2026 | 00:26:29 | |
General Episode Description: In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Ray Rike, founder and CEO of Benchmarkit, to tackle one of the most critical questions in enterprise AI today: how do you actually measure success in agentic AI programs? Ray shares why most AI initiatives are stuck in “pilot purgatory,” the common mistakes companies make when trying to automate broken processes, and why an AI-first mindset requires a complete rethink of data, workflows, and metrics. The conversation also explores how go-to-market teams should define ROI, what benchmarks matter in an AI-driven world, and why traditional SaaS metrics are no longer enough. What You’ll Learn:
Key Topics:
Guest Spotlight: Ray Rike Ray Rike is the founder and CEO of Benchmarkit, a leading source of B2B SaaS performance benchmarks with data from over 1,800 companies. He is also the host of the AI to ROI podcast and a founding member of the SaaS Metric Standards Board. With decades of experience as a go-to-market operator and executive, Ray focuses on helping companies move from intuition to data-driven decision-making in both SaaS and AI-driven environments. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more insights on AI measurement, GTM strategy, and building data-driven revenue engines. Mark (00:31) Welcome to Selling Intelligence. We're joined today by someone who might have had the honor and privilege of calling both a collaborator and a friend. Ray Reich is the founder and CEO of BenchMarket, the industry's most comprehensive source of B2B SaaS performance benchmarks with data from over 1,800 companies. Ray is also the host of the AI to ROI podcast. He's a founding member of the SAS Metric Standards Board. And full disclosure, my co-author on data and diagnosis driven selling, Ray has spent decades as a go-to-market operator, having served as president of Simply Learn, CEO at Higher Mojo, SVP at Moment Feed, and multiple times SVP market and sales and SaaS companies before founding Benchmark it roughly five years ago. And they have a singular mission, give every B2B reoccurring revenue software operator access to data driven benchmarks so they stop flying blind. Today, we're going, well, first off, let me welcome you, Ray. Thanks so much for joining us. Ray Rike (01:43) Thank you, Mark. Sorry that I'm so old that you had it took that long to read everything I've done. Mark (01:47) Exactly. Well, you know what? That's also a good thing because you've done some amazing things throughout your career and you're not that old. So, yes, let me tell you, let's talk a little bit about today and where we're going to go on this podcast. ⁓ What we'd like to do is tackle what might be the most important and for sure most underserved question in enterprise AI right now. How do you actually measure the success of agentic AI programs? And even more specifically, what does that look like for go-to-market functions? We'll dig into what benchmark its data, what is it revealing, where the industry is setting the bar, and what separates teams that are generating real ROI from those stuck in pilot purgatory. Ray, welcome to Selling Intelligence. Ray Rike (02:36) Okay, excited to be here. Let's dive into it. Mark (02:39) All right, so Ray, you've been collecting SAS performance data for years, and now you're turning that lens on AI. From what you're seeing at Benchmark and in hearing on your podcast, what's the core reason most agentic AI programs never graduate from pilot stage? Is it a data problem, a change management problem, or something else? Ray Rike (02:59) I think it's an evolutionary problem. So I did some research with scale venture partners last year about what the state of AI and GTM adoption was. And what we found, Mark, was it was primarily individuals adopting generative AI tools like Clot or Chat GPT to help them with individual tasks. Things like maybe it was an image creation for an ad campaign. Maybe it was email messages for outbound campaigns, et cetera. And the primary benefit was personal productivity. Hey, I can do this much more research quicker for each account, or I can generate this many more campaigns in a month. Now, when we get to process automation, which is really where agentic AI is going to be used, ⁓ we're just at the very beginning there, and we don't have enough experience of actually deploying agentic AI to have a lot of success stories on a production basis, especially the enterprise, because most of the enterprises, and I'm talking about companies a billion dollars and over, I see an average of 20 or more simultaneous AI proof of concepts going on, and they're not really getting the focus of the centralized IT executive team, they're departmental. Maybe it's just customer service or maybe it's just development with a code assisting tool. So my answer is I'm not seeing enough organizational wide enterprise focus on true agentic AI initiatives yet. KK Anderson (04:32) And Ray, welcome to Selling Intelligence. glad you're here. And I just want to jump on top of what you just said there. It seems like the concern would also be that they're trying to put some agentic AI solutions onto maybe processes that should not be automated or were not the right process to begin with. Ray Rike (04:52) of the most common mistakes, and I've kind of built this framework of the variables that help ⁓ indicate success and agentic AI deployments. But one is the data is a mess, right? Think about today for what, 20 years we've been talking about how bad CRM data is and have we cleaned it up? No, we still have shitty CRM data, but the SDR or the AE will say, well, that's not the right information. Joe doesn't work at company A, Joe's a company B or that's the wrong title, right? So a lot of data hygiene, data prep needs to be done. So that's number one. And then to your point, we're thinking like old fashioned business process re-engineering. Well, yeah, maybe we map current state process and we want to map future state process, but we're doing it with a human first orientation and an AI first orientation is fundamentally going to change each step along the way of that process. Quite frankly, you have to identify what data I'm going to ingest, use at the field level for each step, each granular task within that process. And we just haven't re-engineered the process to be optimized for AI centricity yet. And KK, I don't think we're going to until we have a lot of people who have one or two rounds of experience. redesigning a process with an agentic AI first mentality, then then they can do it to third, fourth and fifth time. KK Anderson (06:16) and has that been defined how to have this kind of AI first mindset? Because we've had several people on the podcast talk about this, right? so, and I know I'm going a little bit off of kind of the agenda here, but I'm dying to hear your take on this. When you say AI first mindset versus just a traditional business process mapping, You know, like we're all used to, we all learned in business school, but the data scientists have been doing for decades. Like, what does that mean? What is AI first mindset? talk me through that. Ray Rike (06:54) I wish I could sit here and say, I've done 22 of these. here's here's the playbook. So I don't have the playbook either. I have a lot of ⁓ signals of why it's so difficult. And one of the big signals was OpenAI, what about two plus months ago, formed the Frontier Alliance. And the Frontier Alliance, right, because they said, we're going to get into KK Anderson (06:57) Right. I know it's all new. No one knows. That's what I'm curious. Mark (06:58) Thank you. Ray Rike (07:17) agentic AI, not just generative AI, right? They first of all introduced, I think in January, the five layer cake of the OpenAI Frontier application map. And then they announced that McKinsey, Accenture, Boston Consulting Group, and maybe it was Ernst & Young, are now forming this Frontier Alliance to partner with OpenAI to help their enterprise customers deploy agentic AI. Why? Mark (07:35) Mm. Ray Rike (07:43) because it had been failing. A lot of the open AI projects to really do process automation using AI agents were not successful. So that's a signal, right? And as far as what's the secret, I don't have one other than try to find a consultant or a third party who's done two or three of these in the domain or the area. Let's say it's SDR. Mark (07:58) Thanks. Ray Rike (08:07) I want to automate the sales development representative function, right? Either you're probably should work with a software company that they specialize in that because they've actually ⁓ embraced and bundled domain expertise in their predefined agents, which then can be customized and or a third party consulting firm that have done it, that have made some of the mistakes and learn from their previous projects. So that's my recommendation. Go with a bundled application that has AI agent specific to that process and a third party. And if you think about vertical AI, KK and Mark, right? That's why I'm so bullish and so are most VCs on vertical AI. Look at a Harvey in legal. They actually are pre-packaging workflows, i.e. agentic AI. specific to the nuances and subtleties of that industry, including regulatory and compliance requirements. And they're making a lot faster headway into driving real return on investment than a horizontal, agentic platform that has to be custom designed for each customer. Did I answer your question okay, KK? KK Anderson (09:17) Makes a ton of sense, 100%. Mark (09:19) So you bring me back to the concept you mentioned earlier around BPR, business process, free engineering, and how this isn't that. But it makes me get to a point of like, where is the value going to come from? And to me, I've always seen the value of companies be a part of or partially driven, if not significantly driven by their competitive advantages, how they differentiate themselves in the market. What I love about agentic AI, when done right, it allows you to build a set of processes in a way that can't be replicated by any of your competitors. You can't just say, great, I went to HubSpot or I went to Salesforce, and that's going to help me win against my top five competitors. Well, it's not because they all have Salesforce and in SaaS models, these systems weren't as flexible as now, know, agentic AI can be infinitely just, you know, infinitely just different than any other model that is out there today. So, I like that connection back to the business process side and ensuring that you have people who know that business process as a consultant, ensuring that you really leverage all the expertise and the tribal knowledge out of the client side because they know how to make this work. And they probably are working within a model today that is not what they would have recommended if they weren't forced to do it. because of the Salesforce process and what the system looks like or SAP or Oracle or whatever. take us a little deeper into that. Like, do you agree, I guess is the first question, like that these processes can now be more competitive advantages for customers and companies than maybe ever before. Ray Rike (11:12) Let me let me double click to the next level and KK I think you asked this question also. So in this framework, right. So one of the things because process redesign is such a critical part of this. Don't boil the ocean. Don't try to look at the entire customer acquisition, retention and expansion process. Let's get really focused and say, let's look at the outbound lead generation process. Constraint right so you redesign that constraint process first with a I centricity you define all the data that you're going to need to use in your existing systems of record like your account data the contact data the Including title you're going to define all I need to bring in this third party data to enrich it So define what data you need at the field level? Make sure you know where that data is coming from and how you cleanse and enrich. Think about the governance. I call this AI explainability, right? And you're going to need this, especially in regulated industries, but even if you're doing outbound sales for a software company, right? What's my government governance and policy? Who actually makes the determination that I should reach out to these people? Right? Is that in my ICP? What do I do different with a non-ICP member? That doesn't sound like governance, but it is in a way governance. You also need to pre-define human interaction and engagement points. Am I really going to just have that SCR agent do everything or I'm going to have some points pre-defined where human interaction, including maybe reinforcement, maybe ongoing coaching and mentoring, learning of the AI agent. You want to define those right up front. So you're prepared for that not only from a process perspective, but a resource availability perspective. Right. And then this is the major thing, KK and Mark, that I see so many people not doing is defining the criteria of success using metrics. What are my leading indicators? Maybe a leading indicator, since we're talking SDRs right now, maybe it is my engagement per transaction or outreach, right? How many times does somebody respond to the email, et cetera? Maybe it's the conversion rate from a agent interaction to a true discovery call or a sales call. And ultimately, you're going to want to carry that all the way through. What are my measurements as measured by pipeline generated per dollar of agent invested or dollar of new ARR generated by dollar of agent investment that I make, or agent investment plus human ⁓ reinforcement and learning. So you've got to really understand the leading indicators, the midterm, and then the long-term measurements that are going to impact the income statement. And I can go on and on about this, but I'll stop it here. If your CFO can't go to you and say you spent $100 million on AI agents last year, What did we get for it? And if you say, we got 20 % better sales calls, we got 30 % better sales call. Nah, not good enough. maybe I got 20 % more ACV. I just did a podcast with Amanda Kalo, who's the founder of OneMine, which is a great sales AI agent. And they've compressed on average their customer cell cycle time by about 35 % and increased ACV by 25%. So Those are real tangible things that you as the executive owning your AI initiative, you got to be ready to share with your CFO. KK Anderson (14:43) And you know, and I have this on my list of questions here to ask you because we read that Gartner is predicting 40 % of agentic AI projects are going to be canceled by 2027 because of exactly what you've described, lack of clear value guardrails, know, change management. Maybe they're focusing on the wrong or an invalid process. So there's going to be a lot of ups and downs over the next couple of years as teams begin to roll out agentic AI. And so from your research there at Benchmarkit, and I know you mentioned Amanda as well and some of the KPIs that she's achieving, but what do you think the single leading KPI should be for a CRO? What should they be focusing on? To see if their program is on track to be successful or to fail? Where would you guide? a CRO to look first. Ray Rike (15:36) Well, in the traditional world, I think one of the most important metrics is called the CAC ratio, cost-requisition cost ratio. And this is how much money do I invest in sales and marketing to get $1 of new revenue, ARR in the recurring world, right? And it's around $1.50, up to $2, depending if it's a higher ACV product you spend more for traditional. recurring revenue software companies, SaaS companies. So $1.50 to $2.00. These new AI native software companies, it's 50 cents to a dollar. So it's one third to one half cheaper. if you're a legacy SaaS company or you're a CRO who is going into a AI native software company, you got to think about your CAC ratio with different benchmarks. The other thing that I would say Mark (16:09) Thank Yeah. Ray Rike (16:26) It's outcome per dollar of AI investment. So an outcome might be new deals worth $50,000 per $25,000 of AI agent. So always be thinking about what's the input. It's my investment in the, used to be people and all the tools and stuff. Now it's more in AI tools and agents. And what do I get for that? That is ROI when you compare the output and outcome received to the input invested. Did I answer your question okay? KK Anderson (16:59) You sure did. Absolutely. Ray Rike (17:01) Now I will tell you there's another metric and the CROs don't need to be aware of this, but your CFO is going to start asking this because I don't know if you've heard it here first, but cost of goods sold is the new CAC. What do I mean by that? A lot of AI native software companies are seeing 30, 40, 50 % gross margin. What that means is for every dollar revenue, they're spending 70 cents KK Anderson (17:15) Mmm. Mark (17:16) So, so. Ray Rike (17:28) on delivering the product, paying for AI inference, playing for your cloud infrastructure, paying for your AI agents, right? Well, that used to be 20 cents. Well, I'm not, I can't be less profitable as a company. So what do need to do? I need to decrease my investment in sales and marketing, or it can be fancy and call it go to market, right? Well, in most SaaS companies, even larger SaaS companies, like, you know, Salesforce is 35%. an early stage, it can be 50, 75, 100 percent, right? So you're going to have to take your sales and marketing or GTM investments down by an amount kind of equal to what your cost of goods sold has went up as a percent of revenue. So that's why I'm saying COGS is the new CAC. Mark (17:53) Mm-hmm. you I love it. KK Anderson (18:09) Heard it here first. ⁓ Mark (18:12) Yep, I love it. Great, why don't we move over to topic two. KK, do want to kick us off there? KK Anderson (18:17) Sure. okay, you, have built in your illustrious career the SaaS industry's most trusted benchmark database. We've talked about CAC, Payback, NRR, Magic Number, and you're moving into AI measurement. You've talked about COGS as the new CAC, right? And so that's clearly one of the emerging KPIs that you're convinced are going to become standard benchmarks. in the next 24 months, what else? What else is there to be focused on? Ray Rike (18:45) Right now, it's hard to get benchmarks for AI native software company productivity because they're too new, right? So even large enterprises who are implementing agentic AI, let's use a GE, for example, because I worked for GE for almost 10 years. They're not typically saying on their earnings calls, I invested five million in this AI agent and it saved me 20 million dollars. So. The number one proxy that I've started benchmarking and I went back now 12 quarters is revenue per employee. Because as I become more efficient and require less human resources, hopefully that means my revenue per employee is going to be increasing. And hell, let's just look at it today. The median revenue per employee for a public SaaS company today is $395,000. The outlier is Palantir at about $800,000. But if you look at Anthropic, they're around $3 million per employee. If I look at Cursor, I think they're at $1.7 million per employee. Even if I look at one of the least ⁓ efficient, Harvey, the legal AI, they're at $804,000 of revenue per employee. So revenue per employee is going to be something everybody needs to look at. I'd mentioned I want to start looking at the evolution of my COGS. KK Anderson (19:39) Wow. Ray Rike (20:00) I'm compared to OPEX. My token consumption, everyone's talking about when everyone. CFOs, I just did a state of AI pricing from the buyer's perspective. The number one issue for CFOs and CIOs is predictability of my AI cost. I have no idea how much it's going to cost because it's all over the board. I don't have enough history. So token consumption per outcome, because you're going to know your token cost. That's going to become a new metric that whether you're a customer and you're paying the L.M. Ford or you're the head of R &D and you're using an L.M. in your product, you only need to know token consumption per outcome. And outcome achieve per agent interaction. Let's just say it's an inbound customer service call. Hey, for 100, my AIA agent is solving 84 % first interaction. We used to call that resolution rate in the old human days, right? And then the last thing is cost per outcome in an agentic AI world. I resolved that customer service call. It cost me 50 cents last quarter per resolve call. And I spent $1.80 for human resolve calls. So cost per outcome is going to be important. When I say cost, start with your AI cost. and then you can look at your fully loaded custom. And I'm working on an entire AI metrics framework for this that I'm going to be publishing hopefully in the next month. Mark (21:19) I love it. Excellent. All right, well, Ray, let me bring you back into the days of you and I starting all our research and all the pre-work for data and diagnosis driven selling. So I hope that doesn't cause you to develop a Twitch or anything like that, because as you and I both know, that was hard work. ⁓ So, but let's, you know. What we really saw right up front is, and we really pushed hard on this, is the idea is you can't manage what you don't measure. And you need external benchmarks, not just internal comparisons to know if your metrics are actually good. You know, it's great. It's great to be able to say, improved this process by 20%. But if you were 45 % behind most of your competitors before that, That 20 % still has you on the back of the pack. So how do you bring that same philosophy to measuring an agentic BDR or an AI-powered deal coaching agent? And we've touched on this, but what's the equivalent of a CAC payback for agents and the entire investment? Ray Rike (22:33) Well, I would start with let's make sure you have your go to market measurements in place, because honestly, we've been talking about these for years. Less than 50 percent of companies have great GTM analytics. ⁓ So things like cost per dollar a pipeline, less than 40 percent of people are measuring cost per dollar a pipeline. So make sure you do that and look at your current state before AI and then measure it post AI introduction. Right. So cost and I'm talking right now, I'm looking very specifically at the customer acquisition process. So cost per dollar pipeline before and after cost per dollar of new AR before and after when rate before and after your average and your contract for you before and after. Cause those are all going to be hopefully much better with AI to your point, Mark. I mean, let's use outreach. Everybody had to have a sales engagement platform, right? How many companies actually said, well, after I invested $1,500 per SCR, I had a better conversion rate or a lower cost per dollar of acquisition? Nobody. You're going to need to do that with AI. So that's my first thing. The second thing, which haven't been defined yet, but I'm working with some VCs on this right now, is AI specific customer acquisition efficacy. So I'm looking at agent costs per opportunity. Agent cost per dollar pipeline, agent cost per dollar of new ARR, agent dollar per cost of retained ARR. So you can think about your gross revenue retention and agent cost per dollar of expansion ARR. Now I'm projecting that we're going to be using agentic AI a lot in those processes or sub processes. And by the way, that's the other best practices. When you design a process, it's better to design a lot of subprocesses underneath so you don't have one large unwieldy AI agent. You have a lot of subprocesses that you have different people auditing and evaluating. KK Anderson (24:27) All right. Let's dig into that design a little bit. So walk us through, and I know this is new, as we've said multiple times for so many of us, what a well-instrumented, agentic, you know, GTM for the purposes of our audience, pilot could look like. You just gave us one great clue, which is, you know, don't make monster agents and, and, and to break them up so that you can, you know, be more agile and and predictable with those. You've walked us through some baseline metrics that you want to set before you launch, things that haven't necessarily been done in the past with programs like our outreach launches over the years. But what does the pilot to scale gate look like? And how do you separate the agent did something from the agent created revenue attributed value? Ray Rike (25:15) Well, let me go to the baseline metrics first, KK. So I think I have four levels of metrics I like to see in any initiative, including the Gentic AI. So one is a productivity metric, and that is outputs per time, you know, whether it's outputs per human hour, outputs per day or time spent per activity. That's what we've been measuring for the last year and a half and AI in marketing and sales. But that's what then you have effectiveness. How effective is my AI enabled process going to be? ⁓ How many desired outputs am I getting versus the inputs? Hey, for every hundred emails my agent sending, how many meetings do I get set up? Right. Then there's efficiency. That's the cost per outcome. And then there's actual ROI, which is outcome value divided by the AI investment. So productivity, effectiveness, efficiency, and ROI. I'm not going to go into detail what that's like for just an SDR program, but at least it gives you a framework and a layer approach to designing those four layers of metrics you need to measure. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 121 - AI-Driven Buyer Behavior, Trust, and the New Sales Playbook with Sabrina Parsons - Part 2 | 09 avr. 2026 | 00:24:50 | |
General Episode Description: In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Sabrina Parsons, CEO of Palo Alto Software, to explore the human side of leadership, trust, and AI adoption in today’s rapidly evolving business landscape. Sabrina shares her perspective on diversity in leadership, the realities of building a career as a working parent, and why creating an “integrated life” leads to stronger teams and better business outcomes. The conversation also dives into how trust has become the ultimate differentiator in an AI-driven world, and how companies must rethink how they show up as human, credible, and authentic. The episode closes with practical insights on how leaders should approach AI, where it delivers real value, and how to use it as a tool for thinking, not replacing human judgment. What You’ll Learn:
Key Topics:
Guest Spotlight: Sabrina Parsons Sabrina Parsons is the CEO of Palo Alto Software, makers of LivePlan, and a leader with deep experience across sales, marketing, and executive leadership. She is a strong advocate for women in leadership and brings a unique perspective on building resilient organizations, fostering trust, and navigating multiple waves of technological change. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more insights on leadership, AI adoption, and building trust in modern go-to-market teams. Mark Petruzzi (00:31) So Sabrina, you're a strong advocate for women in sales and leadership. In your experience, what do women bring to the sales equation that often gets undervalued? And what does the data actually show? Sabrina Parsons (00:43) Yeah, that's a great question. I think that we've, well, hopefully people have, there's been a lot of data over the years that just shows a few things, I know these days, you know, talking about diversity is, you know, a hot topic and not something everybody wants to hear. But if you actually go and look at the data, Any time you're bringing different viewpoints in, it actually turns out the data shows that that's really good for an organization. That when you have six people who all come from the same background, who went, you know, got similar educations, have the same experiences, you're missing out. You're not getting some of these other alternate viewpoints that... could actually give you different insights and make your company better. So from that perspective, be it women or people of color, people from different cultural backgrounds, every time you have different people in a room, you're gonna win because they're gonna bring different information to the table. And then I think that, you know. Even though it's 2026 and I wish we were in a different place with women in leadership, the reality is that we still live in a world where, you know, there aren't as many women in technology. ⁓ And the numbers just show that and there aren't as many women in technology and leadership. And so women who are there and have made it all the way through, particularly in a leadership role, have probably worked really hard to get there. and probably have some really good insights. From my perspective, one of the things that I think is most powerful and I think can bring a lot of value to a company is recognizing particularly working moms and working parents, but as a working mom, I'm not a working dad, so I won't talk for working dads, that You know, there's a lot of very motivated, super smart women who want to work for a place. They don't want to have to jump from job to job to job. And if you can give them an opportunity to stay in one place, to continue to move up, if you can be the kind of boss that recognizes that there's going to be some peaks and valleys that a woman with young kids might have some issues with my kid is sick, my kid is going to the doctor, but at the end of the day, if you help them with flexibility, not making their job easier, not giving them less job, but giving them the ability to be flexible and do their job when they can, you're actually going to retain women longer. They're going to be more loyal. if, you know, loyalty and retention, we all know is, you know, There's nothing better for your bottom line, particularly in software and tech sales where people are your biggest asset. KK Anderson (03:36) You preach into the choir. Could not agree, could not agree more. I would love to hear about some of your, know, pursuits with women in sales and leadership and would love to, AGS would love to support you in those as well. Really cool. Sabrina Parsons (03:38) Thank you. Mark Petruzzi (03:47) for Sabrina Parsons (03:48) you. I appreciate that. it's been a really, it's interesting. I think when Mark and I first caught up prior to the podcast, we talked about it a little bit, but being a Gen Xer and having grown up in the 80s and early 90s, I am of the generation that watched the women's lib movement, And watched all these really strong women come out of the 70s and early 80s, the Gloria Steinmans, This very powerful. movement and we were kind of fed this idea that like you can do it all women can be super women and you can do it all and I bought it I was like I am gonna be superwoman I am gonna do it all and didn't really think anything of it until I had my first child and that's when like the brakes come on and you're like wait what what does this actually mean? And you know, just this reality that like, wait a minute, this is a myth. Like you can't do it all, right? And there's a reason why very successful men were never expected to do it all. And yet we still have this place in 2026 where there's still a lot of judgment with women as mothers, like, you know, Why aren't you there at drop off? Why aren't you there at pick up? Somehow you're a bad mother and all these kind of, know, guilt woven into, you know, being this working parent and how do you deal with it? And what does that mean? And as I had one child and then two and then my third as I was running the business for me really understanding that my KK Anderson (05:14) Guilts. Sabrina Parsons (05:32) take on this, my approach is very much about leaning into who I am, not leaning into the structure that exists today, which I think a lot of us were still being told even 10 years ago when Sheryl Sandberg came out with her lean in ⁓ kind of autobiography, it was all about leaning into the current structure, right? It wasn't, wait a minute, does that actually work? And for, KK Anderson (05:54) Mm-hmm. Sabrina Parsons (05:59) from for me what's worked and what I like to mentor and what I like to, you know, really. do here at Palo Alto Software is to say that doesn't work and I have what I call an integrated life and my kids are older now and I've got two in college but when they were little that meant bringing kids on business trips with me and my mom would come with me. That meant kids in the office after school or on a snow day. It meant having appropriate places in the office. so that they could have coloring books and homework areas. you know, I mean, we often laugh because we have a very old, ⁓ I think it's a Nintendo PlayStation, but it's a very old one. I don't even know if it's called a PlayStation, but it's a very old one where it isn't actually wireless. The console that the game console, like the player that the kids, the controller that the kids play with is actually plugged into the gaming. console. Well, kids love the old thing ever when they come in. but they always break it because they keep unplugging the controllers because they're like they're charged. And it's like, no, these are old school. And they don't even get that, which is always funny. I mean, from my perspective, that's what I've done for myself and for people here in the company is to say, KK Anderson (06:57) Now Super Mario Brothers. Mark Petruzzi (07:11) Hahaha Sabrina Parsons (07:20) I'm not going to pretend you don't have kids. I'm not going to make you apologize for having kids. I'm also not going to pretend that if you've got a kid who's sick, that you're actually going to be at the office doing any sort of productive work because I made you come in. Like, okay, you can come in and you're not going to like me and you're not going to be productive and you're going to be worried about your kid. And so why don't we treat people like humans and say, you know what, your kid is sick, go home. Because if I do that, that person is going to work harder for me and be more loyal and be happy. And if you're happy, you're more creative and you're more innovative. KK Anderson (07:58) You know, in a weird way, like it's like a, whole world is coming full circle and our, our humanness, even in this AI world, mean, specifically there are humaneness is now our uniqueness. No, which is wild. And, and so, you know, kind of going back to that, how sales and marketing teams are using AI, you know, it can. You know, we've all seen it simulate preparation and personalization. mean, we were on vacation last week and we took a family picture of the four of us, my husband and my two kids and myself. And we're sitting at a table and there were, you know, dirty dishes in front of us. And my husband just, and his AI, and next thing you know, there's no dirty dishes in front of us. Right? And then, you know, I sent the picture to my mom. Mark Petruzzi (08:40) Ha ha. KK Anderson (08:44) And she was like, that's so great, whatever. And then my husband goes and sends it right back and we're all in like, you know, he's wearing a tuxedo and I'm wearing a ball gown and whatever. He's like, you didn't get invited to the wedding? And you're like, just making it like in five seconds, what? Right? And so, you know, we see that AI can simulate all of these things, right? And there's just, you know, the sky is the limit, the videos, the empathy, the personalization, that it's hard to know. So like, And building off the conversation that we were just having around women in particular, like is, is humaneness like the new moat? that what, you know, what's your perspective on that? Sabrina Parsons (09:18) I mean, that's a great question. I think it is. I mean, it's been interesting too, because not only is it trying to figure out how do you integrate AI into how your employees are using it so that they're using it appropriately and it doesn't come out like all of our communications are robots, right? So like the humanness of interactions. One of the things we do is right now we don't have chat bots. It's all real people. And it's all real people that we employ here in our headquarters. They're not outsourced because of that ability to say we are humans and real people. We're not just bots. ⁓ I think that's really important. I think that the trust that people need, I think they always needed trust, but it was easier to get their trust. And now it's like, because we've all seen, pictures that are different. We've all seen videos that are AI. We've all seen essays that are written with purely AI. I think there's that constant question, is this real? Are you a human? Is this true? And so anything that you can do to help alleviate that fear of what's a fact and what's not a fact. Right? Even now, like we talk about it a lot, like when you think about Instagram and you're scrolling through, most of us have probably made the mistake of that product that you're like, this is awesome. It's just for me. And then you order it and you know, it was supposed to be like a dress that fits me and it's a dress that fits a doll. You've heard all these stories. So I think all of us now know, like you don't trust that on Instagram. Right. This is why influencer marketing is so big because you do trust the person, right? You don't trust the company and the random product. You do trust the person. And so I think that's where we're back. Like, and how do you do that beyond influencer marketing? Right. Why is Reddit such a huge resource for people? KK Anderson (11:01) trust that person. Sabrina Parsons (11:13) because people perceive that Reddit is moderated, that people get kicked out of Reddit if they're bad and they do bad things. And so somehow, at least at this point, people trust that it's real people on Reddit. That's why people go to Reddit. KK Anderson (11:27) And so how are you using that specifically within your team? Sabrina Parsons (11:29) you we, I mean, first of all, it's changing all the time, but, you know, we really try to emphasize in a lot of our educational videos, we use, you know, I'm in a lot of them, real people at the company, people that, you know, we have personalities. we've just recently even started to put out some blooper videos so people can see us as real people that we aren't just AI bots. KK Anderson (11:54) and not the radio. Mark Petruzzi (11:56) Yeah. Sabrina Parsons (11:57) And really leaning into, you know, the way that we have all figured out how we trust things. And I think that's really important when you think about and work with sales teams is to really get people to reflect like you're out there, you're a consumer, you know the things that you won't trust. You know the things that are kind of that gray material you're not sure. And you know the things that you do trust. And so, the more that you can get your own employees to embrace their own experiences and bring those, I think that brings a lot of value. Mark Petruzzi (12:30) Well, Sabrina, we should really put out some selling intelligence bloopers because there's been some big ones over the years, but probably more me than anyone else. So maybe I'll hold back on that one. Never blooper. All right, let's move into our final topic, leading through this world that we live in today that is just rife with... KK Anderson (12:42) No. Never, never been a blooper. Mark Petruzzi (12:57) AI disruption everywhere. So as CEO, you're managing AI disruption on two fronts, inside your business and in the general market as a whole. Where have you found real efficiency gains and where has AI disappointed you or just over-promised along the way? Sabrina Parsons (13:15) that's a great question. I mean, I feel like AI is constantly ⁓ over-promising. I think that's a constant of like, you know, always thinking and I think everybody else thinking how much AI can actually do. It's been an interesting thread because I have two kids in college right now and working with them for them. So my oldest is a senior, AI did not exist when he was in high school. Mark Petruzzi (13:20) Ha Sabrina Parsons (13:39) and didn't even exist the first two years that he was in college. It's really just been the last two years. ⁓ And kind of working with him on how do you use it? What's the appropriate use? How is it beneficial to how you study? How is it not beneficial? KK Anderson (13:42) tomorrow. Sabrina Parsons (14:01) He's in a situation where he knows people where entire classes have been caught for AI and how do professors have to rethink things. So I bring it up because I think it's important for us to see as people are coming out of college what their experiences are going to be. So you're back to Blue Book essays in colleges right now. But it's all kinds of issues, right? Kids can't even write because they've been on computers for so long. no one did. Like, if you want to puzzle, you know, a Gen Z person, write something in cursive. Like, it's like code. Yes, they didn't learn cursive. They don't. KK Anderson (14:28) Well, my kids never learned cursive. Sabrina Parsons (14:40) They don't actually, they can't write very quickly or write very well. And so that's been an interesting experience. KK Anderson (14:47) line that's gonna show up under the blue book and say, you stop. Sabrina Parsons (14:49) exactly. So I think that's an interesting thing to think about as you think about where, you know, how people are going to be coming into the workforce and some expectations. The fact that people find that like, if you've written it down, it's somehow authentic and right, which is an interesting idea. But yeah, I mean, I think for me, as we look at these AI challenges, the biggest thing and what I tell employees and what I tell my kids is you actually just have to be using it all the time and constantly challenging yourself on was that the right use? Did I get what I needed out of that or did it lead me astray? And if it did, why? And maybe that's not the right use for it. You know, so like learning where those guardrails are today and then being open to the fact that those guardrails will probably change in two months. And so very much encouraging everybody to not be afraid of it, experience it, but with your eyes wide open. KK Anderson (15:48) one of the things that, one of the ways I love to use AI is just asking it to poke holes in my proposals and in my approach. if you're a CFO or a board member looking at this proposal, tell me all of the ways that it sucks, quite frankly, right? And then just making it bulletproof from there. Sabrina Parsons (16:06) that's, mean, it's one of the ⁓ ways that I've really worked with both my college kids using AI appropriately and not writing their essays for them, but to actually say, hey, this is like a one-on-one tutor who can give you critical feedback. on your essay, in the past this would be like if I paid for a writing tutor to like read your papers and give you feedback, this is how you should use AI. You don't want to use AI to write your paper because you're going to get caught and then when you have to do the blue book you're not going to know it, but it can be used to give you that critical feedback and I think within your company as well, right? Mark Petruzzi (16:34) Mm-hmm. Sabrina Parsons (16:49) Don't have it write your proposals, have it critique it. Don't have it write all your emails, have it help you theme them or schedule them or those things that take a lot of time but don't necessarily need the human element. KK Anderson (17:04) And so what would you do to kind of build off of that? Like what would you say to a founder or a CRO who's listening right now? What would be the first thing you would do to change how they're selling or approaching sales right now using AI? Sabrina Parsons (17:19) Whoa, there's so many things. You know, I think that really living in all the LLMs to see how the LLMs are perceiving your product. I think it's really important because people are going to LLMs to research. And so how is your product being portrayed? How's it coming up? KK Anderson (17:35) Uh-huh. Sabrina Parsons (17:43) If you don't know that, then that's a problem. And a lot of times people don't realize and that is really important. You need to be, and there's tools that can help you ⁓ kind of gauge that and see how many times am I showing up? Is it in positive ways? Is it in negative ways? ⁓ LLMs are referencing different kind of data. It used to be that, you know, the way you showed up and the way customers found you had to do with your search engine optimization. And while there was always all this kind of behind the scenes, Google's not going to tell you if you were really an SEO expert. You knew. And there was the next Google release. And people kind of knew what they had to do to appear in the right places. and Google would assign page ranks and they would say, that HubSpot is great at this, they are the expert. Well, that's gone now. The way that now, know, truth is assigned is through consensus. It's not because we've chosen one thing and said that's the expert piece, it's through consensus. So the LLMs are going out there and seeing. How are people talking about you on Reddit? Where are your reviews? What are they saying? What are the common threads? And they're finding that consensus. And then that's how they're figuring out which solution to recommend. And so I would say that's the number one thing is really understand how are you being portrayed when people are looking and asking questions. And then keep doing that because it's going to continue to change. KK Anderson (19:21) and then use AI to get you into more places. Right, yeah. So Mark, what do you think? Do you wanna take us to rapid fire? Sabrina Parsons (19:24) Exactly. Mark Petruzzi (19:28) Sure, let's kick it off. Perfect. So Sabrina, thanks for all these great observations. So RapidFire goes right into first thing you have ever sold. Sabrina Parsons (19:37) I was thinking about that, I was like, oh wow, was it like a literal lemonade stand, which I think it was. But I thought what I really talk about was when I was in high school, my junior and senior year, I worked at a yogurt shop in Palo Alto right across the street from Stanford campus. And... I actually became at the ripe old age of 17 the manager of the yogurt shop because it was run by two Stanford MBAs, one of whom her dad had bought her the yogurt shop. that she could have experience while she was an MBA and she really didn't want to do it. And so I ended up being like the manager of the yogurt shop doing all of the decisions of like, what are the flavors? Which ones do we put next to each other? Understanding like, if I put these two flavors together next to each other, we sell more. And then at the end of the day, I don't have to clean the machines in the same way and it's better for me. KK Anderson (20:24) the house. Sabrina Parsons (20:36) Europe. KK Anderson (20:36) You're leaning on that experience every day, Mark Petruzzi (20:39) Well, Sabrina, have, I mean, think about that. You were destined to be a CEO because you had two Stanford MBAs tell you you were management material at 17 years old. It's awesome. KK Anderson (20:50) Hahaha Sabrina Parsons (20:52) Well, I think it was by default more than else, but I definitely took it and ran with it. Mark Petruzzi (20:56) Haha KK Anderson (20:58) If you were like, I'm going to Princeton. A leader, you know, a leader or communicator that you admire. Sabrina Parsons (21:00) I'm sorry. right, I thought about it a lot and I feel like right now I have to say I love Eileen Gough. If you watch the Winter Olympics at all, ⁓ you know, this phenomenal athlete woman and her leadership and her ability to talk to the press about her experiences. She was embroiled in some controversies because she was raised in the Bay Area, a Chinese immigrant mom, and at these Olympics she decided to compete for China. Very smart, very well-spoken, crazy accomplished athlete who had to deal with a lot of questions that I think women often have to deal with. They're in this place where you're like, she's like the most decorated freestyle. Olympian and you're going to ask her these questions and I just I love how quickly she responds, how she doesn't apologize, how hard she works. Yeah, so for right now I'm going to say Eileen Gough because I think she's earned it. Mark Petruzzi (22:08) Very cool. So one practice every sales leader should adopt this quarter or even better that today. Sabrina Parsons (22:14) One practice, I would say just embrace AI, all of it. Do not be afraid of it, embrace it, figure out all the places you can be using it because it is the future and the more you know, you're gonna have an advantage. KK Anderson (22:29) It's like the, you you can just see the lower third, the more you know, dot, dot, dot, right? my favorite question, advice that you would give to your 21 year old self. Sabrina Parsons (22:34) Exactly. You know, I think I would go back to that, my 21 year old self to say, you don't have to do it all and that's okay. That you actually can think about what you love and focus in on it and you don't have to be everything for everyone. ⁓ That's what I would tell myself back then. Mark Petruzzi (23:01) and your favorite. Sabrina Parsons (23:02) It would have reduced stress in my late 20s and early 30s, I think. Mark Petruzzi (23:06) for sure, your favorite non-business book. Sabrina Parsons (23:09) I do a lot of reading. was really trying to think about, because it depends on when you ask me, but I think I will go back to, I love Into Thin Air. I love that book. I'm an avid outdoors person, do a lot of backpacking and skiing and mountain biking and. water sports and ⁓ I'm fascinated by the story by people who climb Everest, but I'm also fascinated by the decision making and how this whole disaster on Everest actually happened. ⁓ It's just, and it's such a well-written story. KK Anderson (23:49) definitely we need it. Mark Petruzzi (23:50) Yes, and Sabrina and I bonded right from our first discussions on rowing as well. we both had children who were rowers and ⁓ we both had done some rowing over the years as well. I love it. And hopefully you get out on the water more often than I do, because I just seem to always be ⁓ on a rowing machine, not an actual Sabrina Parsons (24:15) Yo! KK Anderson (24:15) say on Mark Petruzzi (24:15) well, that's for sure. I'm going to start rowing on our podcast. That's what I'm going to do to get a little bit of multitasking in. So Sabrina, thanks so much for taking the time with us today. Thank you just for all your great observations and your insights. Thank you, KK, and thank you to our wonderful audience for being with us here every week. You are all amazing. Sabrina Parsons (24:38) Thank you guys, this has been lots of fun. KK Anderson (24:40) It's a lot of fun. Thank you, Sabrina. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep.120 - AI-Driven Buyer Behavior, Trust, and the New Sales Playbook with Sabrina Parsons - Part 1 | 01 avr. 2026 | 00:19:09 | |
General Episode Description: In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Sabrina Parsons, CEO of Palo Alto Software, to explore how AI is rapidly reshaping buyer behavior and forcing a complete rethink of how companies sell, market, and build trust. Sabrina shares how search behavior has fundamentally shifted toward AI-generated answers, reducing click-throughs and changing how buyers consume information. She explains why this creates new challenges in clarity, especially around the “build vs buy” decision, and why sales teams must now work harder to guide buyers through uncertainty. The conversation also dives into the growing importance of trust, the evolving relationship between sales and marketing, and how organizations can use AI effectively without losing the human connection that ultimately drives decisions. What You’ll Learn:
Key Topics:
Guest Spotlight: Sabrina Parsons Sabrina Parsons is the CEO of Palo Alto Software, makers of LivePlan, a leading business planning and financial forecasting platform. With experience leading both sales and marketing, she brings a unique perspective on how companies build sustainable revenue engines. Sabrina is also a strong advocate for women in leadership and technology, and has guided her company through multiple waves of technological change. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence for more insights on AI, modern buyer behavior, and building high-performing revenue teams. Mark Petruzzi (00:31) Welcome to Selling Intelligence. Our guest today is Sabrina Parsons, CEO of Palo Alto Software, makers of LivePlan, one of the world's leading business planning and financial forecasting platforms. Sabrina has been the helm at the company, this company that has over four decades of history leading through multiple waves of technology disruption. Before stepping into the CEO role, she ran both sales and marketing, giving her a uniquely integrated view of how companies grow, how buyers decide, and what it really takes to build a revenue engine that lasts. She is a passionate advocate for women in leadership and technology, a thread we'll weave in throughout today's conversation as well. So three topics we'd like to cover with you and with Sabrina today. how AI is reshaping buyer behavior and what that means for how you sell. We've covered that many times on our podcasts already, but we really are excited about Sabrina's perspective and her experiences in that area as well. The second one is why the human element, why trust, story building and storytelling. And relationships are the only sustainable differentiators that we really can build in today's business climate. And third and finally, what sales and marketing leaders must do differently today and how that integrates into the CEO role and also the board of directors. What can the boards be doing to help their sales and marketing leaders evolve in the way that they need to? Sabrina, welcome to Selling Intelligence. Sabrina Parsons (02:13) Great, thanks Mark, I'm really happy to be here. Mark Petruzzi (02:15) All right, let's dive right into topic one. ⁓ Topic one, AI and the changing buyer. So Sabrina, you've described the buyer behavior online as having shifted more dramatically in the last 18 months than in the prior decade. What are you actually seeing? Why does it matter so much for how we sell and how we need to sell in the future? Sabrina Parsons (02:35) that's a great question. And I'm pretty sure as soon as I start talking, all the listeners are going to say, because we've all experienced, I think, a very similar change in how we interact online. In the last 18 months and even more so in the last 12 months, we have all seen the way our interaction on search has changed. particularly with these new AI synopsis that you see at the top of the page. And while there will be articles and sites that are cited in this AI, what's happened is that fewer people are clicking through because they go, they have a question, they type it into Google, and they're typing questions now into Google. used to be that we would type keywords, right? And then you'd see what happened. And now people are typing questions into Google and then the or whatever search engine, but, Google still probably the most used. And then what they're getting back, it scratches the itch for the most part. And so they're getting this information and then maybe they're moving on, right? So that's one huge change in behavior and we're all seeing it, right? You have interacted and chosen not to go forward because your question is answered or you found what you need. ⁓ So that new way that we're getting... all of this information displayed, it means fewer click-throughs, and so companies that are selling have to deal with that. The other thing is that search engines are really leaning on and preferring when you can put content out there that actually gives answers, because that's what people are looking for, right? It's how do I, those types of questions, how do I do this? How do I sell? How do I market? How do I, all of these how do I's, that's what people are doing. ⁓ And then the other thing that I think we all know is that people are for the most part, very familiar with LLMs, right? With all these AI chat box. And many people are using them instead of search engines, which I will say if you are, think about it because it's a very expensive search engine. It uses a lot of energy to do an AI query. And every time we're using AI when you could just use a search engine, we're wasting energy. So it's something that, you know, not everybody always knows, but there's an appropriate use for AI, but it doesn't matter, right? Behavior has changed, and we're all trained now in this new behavior. And it feels like it's just been like instant, like in the last 12 months, because changing behavior used to be a huge thing, right? From a sales perspective, people like you would teach salespeople how to help change behavior. And like we have seen behavior change just so quickly this time around. KK Anderson (05:23) overnight. so how does that change how we sell? Sabrina Parsons (05:27) So that's a great question. I mean, it has to, right? Because when you're selling, used to be that your marketing team could just make sure like, are search results going to come up on first page versus second page? And if not, let's just buy pay-per-click ads and make sure that they come up. in those results. And it's like that doesn't work anymore. So a lot of what you have to do in terms of how to change how you're selling is address this new way that content is consumed. So you really have to think through, am I providing answers? And it's not just content that fits keywords, right? It's content that's actually giving answers. And then in the way you format your content, if you want to be AEO forward, right? It used to be just SEO, search engine optimized. Now we're AI chat bot optimized. If you want to be AEO forward, you really have to rethink how you're putting your content together, what kind of sort of synopsis you have that's easy for AEO to grab. Do you have the right FAQ schema? It's just a, you know, it's a different way that the LLMs are crawling through information. And so you just have to make those changes. KK Anderson (06:46) Right. And I'll just add to that. It's all about that trust equation. Right. And so that's what our prospects for all of us, you who are running businesses and running sales organizations, they're all looking to, they're looking for value and that value is what's driving trust. And that trust equation ⁓ is going to what finally converts. And so when your buyers do get on the phone with you finally, They're going to be so much more educated. going to know so much more. They will probably have an LLM, create a table stack ranking, the three top options to solve their problem. And so they're going to be so much more educated when they get on the phone with your team as well, which is another, when you get sort of that sales process behavior that it just, all the changes at top of funnel are filtering down. into that as well. Everything changes. Sabrina Parsons (07:37) and I think that's important, right? And salespeople know this because they're getting confronted. It's like they used to have their process, the information, they've done their homework on the prospect. And now you have to be prepared to understand what are they seeing in chatbots, what is coming through, what kind of, because the other part is that it doesn't necessarily, it There are opportunities to help someone understand that the landscape may be more nuanced than the AI LLM has put out there, right? But you have to do your homework ahead of time. You have to understand what they're seeing, how much more research, so to speak, they think they have, and then how do you address that, particularly, KK, like you said, just from that trust side of the equation. KK Anderson (08:25) And Mark, I'll give the next one to you here in a second, but just to kind of cap that off, it makes the concept of selling to your customers' outcomes even more important because it's not necessarily about educating them on your product or your service or what you're doing. It's how do you take that, how do you take what they think they know or they don't know or the absence or the void and convert that into something that's important to them, which is the outcome that they're trying to achieve. Sabrina Parsons (08:50) Exactly. Mark Petruzzi (08:50) Excellent. So Sabrina, at AGS, we talk about a two-sale mentality. The first sale is just why change. The second sale is why you and why now. If you're not accomplishing both of these processes within a selling model, then you're not winning the deal. You know, there are companies that are really good in understanding clients, understanding why they want to change, but they're not as good on the, you know, differentiating themselves in the market. There are even more companies that are the other way around that really just don't spend enough time understanding, you know, what are the risks here? Why change it all? And their pipelines get bloated and then get very, very lean quickly. because they have a lot of clients that just say, or prospects that just say, I don't need to change and I'd rather not write out another $3 million check. So where does AI driven buyer behavior disrupt that first sale the most in your opinion? Sabrina Parsons (09:56) You know, I think number one, it's disrupting in terms of what that client thinks they need help with, right? It was very clear. think there's now, it used to be very clear, this is what my tool might do. And I very much understand how I can help the client. And the client... for the most part understands what they need and how you can help them. And I think AI has blurred all the edges, right? As we're all learning how to use it, it's blurred all of that where it's like, well, do I need that tool? What can AI do for me instead? Should I change my process and adopt this new tool or do I just need to get better at prompts for AI or should somebody in my organization vibe code something and do something that's more internal and specific to us. And so it's almost like the buy birth versus build is a much murkier, muddier question, right? Because, and it doesn't always mean that the tool isn't actually the best thing for them. It's just that your buyer is now. confused and wondering like, maybe I don't need the tool, maybe AI can just do it for me. And so I think we've just that clarity that used to be a little bit easier with those two things like, you know, what do I need and how does your tool help me? Like that's just muddy now. It's now like, I don't know what I need. Do I need your tool or do I just need, you know? some internal AI expert or maybe I need both. And so I think that it's just made things muddier. And so the salesperson has to help that prospect understand that and see and clarify and then show them those benefits of like, you don't want the pain of learning all of this. We've got you. We have done it and we've integrated this into our tools. So you get the best of all the worlds without having to figure it out. KK Anderson (12:00) really insightful. You are spot on with that. so you and you've kind of seen this from both the market. I know the world is changing every day, every month. It's different than it was yesterday with every recording and every time we publish a podcast, something else has changed, right? But you've seen this from both the marketing head of marketing seat and the head of sales seat, know, at LivePerson. So in this new world, that we're in, like how did these two function, sales and marketing? how, I mean alignment between the two has always been a problem, right? And so what are some ways that you're seeing like that overlap, that handshake to happen more effectively in this new era? Like talk to me about that. Sabrina Parsons (12:38) that's a really good question because I think you you're right. There's always a little bit of headbutting, and sales is sometimes out selling things. I mean even headbutting with product as well, right? Where sales will sometimes sell things the product doesn't have yet and sales will say well marketing you're not keeping up. We need these materials you don't have. So I think that's always been a little bit more, you know, that's always been something that departments have butted heads against. think right now marketing and sales have an opportunity ⁓ to really understand when you have this much gray area and fuzziness around, what is it that the client actually thinks they need? You can very much... be in a space where you believe you have the best tool and they actually need you, but now the client's not sure they need you. So marketing has to help make that case, right? Marketing has to be playing this new AEO game. Marketing has to also understand What are the things that these clients think they might be able to do without us and address those, right? It's all about answering those questions, answer forward, give that information and address. And then I think even more so that trust of really truly we are the right organization with the right expertise that you can trust because we all know and the clients constantly worried about If I just use AI, is it real? Is it true? Is it hallucinating? And so marketing teams, think, really have to help lead the path to clear away the maybe misgivings people have between, do I use AI without the tool? If I use the tool, do I use it with AI? Or does the tool have everything I need? If marketing does a good job of helping someone understand that, why you shouldn't be an AI by yourself, why we've brought AI into our tool and it's going to be even better, then the salesperson can take it from there and do some personalization for that client when they're selling to say, let's actually have specific examples of why our tool is going to be better off for you than if you are off on your own trying to be an AI prompt writer all of a sudden. KK Anderson (15:00) and moving into sort of this next topic around trust and story and the human advantage, you know, we all, it seems like what was super cool, ChatGVT, Claude, prompts, generative AI, six months ago is now just table stakes, right? And so we're all getting, it's almost like we're using, now we're using these tools that are very quickly table stakes. the same outreach sequences, the same content generators, you see the same, you know, M dashes and hope your hope to see male funds you doing well. Like you, can just spot it immediately. You know, you know, immediately when you're looking at something that's AI generated, right? So, so talk to me a little bit about how you can lever for sales specifically, right? How you can leverage AI, but still actually create differentiation. Like what are, what are some of the things you guys do with your team? Sabrina Parsons (15:48) that's a great question. I I think that there's an appropriate use of AI even when people recognize it, right? And I think that's important. I think that AI should be used to make some jobs easier. I think there are some writing that AI can do that is appropriate and AI does it faster and it streamlines it and that's okay. But I think it's really important to recognize sort of where a client does not want to see that, where a client does not want to feel that. If a salesperson is trying to sell and part of what they're saying is, we're going to bring personalized account management to you and that. client is like, really? Because I just had a horrible chat bot interaction with your website and there was no person and it was a robot and I don't believe you. And so that's where like we have to define. where it's okay to use AI, where you're hurting yourself when people know it's AI, and you need to be very careful. And then using AI appropriately internally to be very prepared for your sales calls. AI can prepare you. at a speed at which we haven't seen. And so you have no excuse not to be prepared, understand the exact situation your client is in, have researched their company, have researched them. I mean, it's easy to do now. And so it's almost like we can't get away with not doing that because that's how you prove that we're real people and we're taking the time to be real people. But it does have to flow all the way through. You don't want... that person to have had some interaction with a pre-sales chat bot that was terrible. And you're to have to fight that because there's a lot of people out there who are like, don't, there's going to be some negative connotations because people have had bad interactions. And so how do you address them? And interestingly, if you can get marketing to play ball with you and you do some of these, some of these interactions better than everybody else, that's right now at least, know, God knows in six months, but right now that's gonna make you stand out. ⁓ I was talking to someone who had an aura ring and had an issue with the aura ring, went to the website and was super annoyed that they could not get a real person. Just so annoyed. And it was a chat bot and said, I spent 10 minutes fighting the stupid chat just to try to get a person. And then finally said, forget it. Fine. I'll interact with the chat bot. And they said, in three minutes, the chat bot had looked up my data, knew that my battery wasn't working, and told me that they were sending me a new aura ring the next day. Right? And so all of a sudden, he's like, I felt like such an idiot. Mark Petruzzi (18:36) Ha ha ha. KK Anderson (18:39) This is awesome! Sabrina Parsons (18:40) Yeah, he's like, I push back on it so much because I've had such terrible experiences and I really didn't want to use it. And then it turns out if I had just embraced it, I would have been better off. But that's the opportunity, particularly for marketing and sales to work really well together, because there are people who are doing it terribly. So don't be those people. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 119 – Running Uphill at Full Speed When AI Keeps Raising the GTM Bar with Sunil Rao – Part 2 | 25 mars 2026 | 00:22:16 | |
In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson continue their conversation with Sunil Rao, founder and CEO of Tribble, diving deeper into SaaS fatigue, agentic execution, and the challenge of scaling institutional knowledge in enterprise sales. Sunil breaks down how AI agents are reshaping the way work gets done by becoming the interface across systems, eliminating the need for constant tool-switching, and enabling teams to operate from a single layer of intelligence. He also shares how modern GTM teams can capture and scale expertise across conversations, documents, and internal knowledge to improve performance over time. The discussion closes with a look at the human side of selling, where trust, collaboration, and real customer engagement remain irreplaceable even as AI automates more of the workflow. What You’ll Learn:
Key Topics:
Guest Spotlight: Sunil Rao Sunil Rao is the founder and CEO of Tribble, an AI-native platform that helps enterprise sales teams automate and optimize go-to-market workflows. With a background as an engineer at SAP and a leader at Salesforce, Sunil brings a unique perspective on both the technical and human sides of enterprise selling. At Tribble, he focuses on building systems that scale knowledge, improve response quality, and enable teams to operate more efficiently with AI. Resources & Mentions:
🎧 Listen now and follow Selling the Cloud for more insights on AI-driven GTM strategy, enterprise sales transformation, and the future of work. Mark Petruzzi (00:31) So Sunil, let's talk about the SaaS fatigue problem. Companies are drowning in tools, licenses, and unused platforms. If you built a company in the enterprise software space going right at all of that overflow, how did you design Tribble to be part of the solution rather than be another product out there that's part of the problem and the challenges? Sunil Rao (00:54) I think from the very early days, one of the things we thought about deeply was, hey, where is this all going? If I think for two, three, five years, what do we think happens? And it was very clear to us that there's a consolidation that's going to take place across where people want to go to get their information. when we see what was happening with ChatGPT and you think about how this kind of AI can be pervasive across systems, this is one of the things I was telling someone recently. If you go back on the internet, you go to the Wayback Machine, which is a website that allows you to go back in time, you can go see the 2023 December page for Tripple. It says, kiss your apps goodbye at the very top. Say hello to agents. And that, I think, was very indicative of, this is what's going to happen. We probably did that message too early because no one knew what an agent was in 2023. But I think that's where we are right now, right? It's like, hey, there's this new interface, right? I can talk to an agent or I can talk to software and I can give it access to all the other systems I work with. So I kind of don't need to go to all those systems again, right? I can do the work through this proxy. And the way that we always describe it is like in the future, you know, when you onboard a new employee, what do you do? You say, here's your license to system one, system two, system three, system four. And they're sitting on their chair and their browser tabs and they're swiveling from one to another, to another, to another. That kind of all goes away. So I think when I think about SaaS fatigue, think agents actually are going to change and become the interface. And Trivel, for us, when we think about go-to-market technology, we want that to be the interface when we think about the respond process and the engage process. That's our bet. And underneath the hood, we have many systems we integrate with. But I had a prospect ask me this the other day. They're like, hey, if we're using your tool, do I need to go to these other systems? And the short answer is no, you don't. Get everything you need right over here. KK Anderson (02:35) So walk us through like what an agentic execution actually looks like in practice. So like when a sales team sends triple an RFP, what's happening behind the scenes? Like how much is automated versus augmented, if you will. Sunil Rao (02:49) Yeah, so I'll give you two examples, KK. I think one, let's think about a company that responds heavily to RFPs and that's a big portion of their business. The RFP coming to you isn't the first point of contact with the customer, right? And depending on the size of the organization and how big this engagement is, it might be something more like, hey, we've had an initial call with the team and they shared with us that they're going to issue an RFP. So there's some discovery being done. We learned some requirements. We learned some players at the table, the different business units that are relevant here. Fast forward a week, another call takes place. Different team members at both organizations are on a call. Information is shared. Then you get to another call and then they issue an RFI, which is the precursor to the RFP. So it's one document that gets sent over and then you got to answer a bunch of questions. Then you finally get to the RFP, which then ends up becoming a bigger proposal. But we think about the journey across all these touch points as opportunities to collect context. So one of the things we do is we show up on the call for each of these touch points. We collect context. We coach the folks live on the call on what data to collect. and how to think about this so that when it comes time to build the response, it's contextual on all the data we've collected for this specific prospect, but every other conversation we've had and where we've won bids and where we've lost them. And that way we can see, historically, when you've answered no to this question for this type of company, you've lost the deal. So one of two things, either explain you can do it because it's on your roadmap or actually put it on your roadmap. Right. And these are the kinds of insights we can glean because we're integrated to the the systems behind the scene, as we come across these insights, we can go write the data back directly. The agent will go and update a ticket in JIRA, or it'll go make an update in Salesforce directly. And it's done throughout the journey, throughout the process. So that's kind how we think about it across the lifecycle. Mark Petruzzi (04:30) that's excellent. Excellent. So let's go to topic three here, scaling institutional knowledge. We use this, the term kind of tribal knowledge and a lot of the work we do in engendric space ourselves. So yeah, let's dive into that. One of the most interesting things about Tribble, that it's not just about speed, it's about scaling the... the expertise, scaling the process, making those processes better over time as well. You've described the problem of a limited number of experts having the necessary knowledge. In your experience at Salesforce and now at Tribble, why is knowledge scaling such a massive bottleneck in most enterprise organizations, particularly within their sales function? Sunil Rao (05:15) Depending on how big the organization is and what products you sell, historically for me, one of the things that I've experienced firsthand, when you're selling a complex product or you're selling into a vertical where the business processes are very specific and non-standard and it's not something everyone knows, you usually will have a gap in terms of the understanding of the field team and what it is that the customer wants. So how do you speak the language of the customer is always a term that we used a lot in my career. And whether you're in financial services, health, whether you're in CPG, retail, manufacturing. There are processes that are very specific to that industry. So how do you enable the field teams to know what it is the customer's pains are and what they need? And how do you build the right software to meet those needs? So I think that ends up in, thinking back five, 10 years ago, how do you scale that within a company? Well, you create these enablement organizations. You create enablement programs. You take everyone to Vegas for kickoff, and you show them 800 bajillion PowerPoint presentations and hope they remember it for the year. And of course they do, because that works every single time. Right? And when you show up, you've now enabled everyone and they're talking about the product. I think that that kernel, it. The one consistent theme that we've seen and I've experienced it firsthand is you still need to leverage these SMEs during the sales process and you tap them on the shoulder and bring them in. And whether they're sales engineers, they're industry experts, technical architects, program architects, whatever you call them, they all have some level of knowledge and there's too few of them in the organization. So that's what I think about when I think about the scarcity of that type of resource and how do you scale it? So for us, we've always thought of, you've got data in docs. Those documents will inform a certain amount of the business process. You've got knowledge now in these large language models that we can tap into. And there's tribal knowledge, right? We know that Mark actually is really, really good at this one feature in that product that no one else in the company knows, but it's not written down anywhere. It's in Mark's brain, right? So like, has Mark mentioned that on a call? Is that something that's come out in calls with customers? How do you tap into that kernel, right? So we take that data from the calls. We take the data from the documents and everything we're observing across all the calls in the company. And we create a graph of the experts in the company and who has what tribal knowledge and what documents. have what knowledge. So we're trying to solve it in that way Mark of how do you scale the expert? Will you create a backup of them and you try to understand in the organization where you can go to for what. KK Anderson (07:36) And so that's, does that one explain why you're, you're ingesting all kinds of secondary information like Slack conversations or conversations between engineering or product or sales teams? That is that part of how you do that? Sunil Rao (07:49) that you before something becomes a document people are usually talking about it on slack or on calls KK Anderson (07:54) So how do you, like a couple of things come to mind. Number one, like how do you ingest that much information without just having a lot of junk? know, like 80 % of gong conversations are junk and there's a maybe a golden nugget in there. you, mean, it seems like a lot of memory, a lot of space. Sunil Rao (08:11) You have to compress it. You have to de-noise it, and then you have to compress it. So we actually have, it's funny, when I was geeking out with the engineers on this, we were thinking, look, and I've done sales as well. Sometimes people say things on calls that are not necessarily factual, right? So we have to attribute for the fact that it happens, and especially with gone calls, you have a lot of salespeople saying a lot of stuff on calls. But then you have this idea of ground truth, which pertains to your product information that we're connected to systems of record that we pull data. So we'll look at the data that's coming in and the really noisy stuff, which is gone calls call transcripts, and we'll cross check it. We'll almost fact check it with what we know is in the main store. And if there's anything new gleaned, we will pull that out and denoise and get rid of all the back and forth that's not necessary to store. But we try to pull out the key facts. We try to understand, hey, who was on this call? What were they discussing? which people were saying which things, what regions, locations, product lines, segments were discussed. So anything that pertains to go to market is what we try to pull out of this and then we store it in what we call our knowledge graph. And that allows us to like pull out the signal from the noise if you will, KK. And then we will fact check some of that. And we'll also use the folks using the product to actually validate if information is correct or not. So that way we move from this vast ocean of noise to a usable data set that's otherwise really hard to get to. KK Anderson (09:28) it's really, really Mark Petruzzi (09:29) most companies, as we all know here, have invested heavily in content libraries, knowledge bases, sales enablement platforms. Yet somehow the right answer is not there when the rep needs it. Why do traditional knowledge management systems fail in high-velocity sales environments? And again, how does Tribble and the things that you do overcome some of those challenges. Sunil Rao (09:55) It's almost like a short circuit cheat code, right? Because I remember the Russian December. to get high spot loaded with all of our content. When I was at Salesforce working with marketing and it was like the stretch going into Christmas and we're all building the 40 different variations of first call decks and second call decks and these subvertical plays and you'd create and it's this one moment in time where all the content gets created gets uploaded to these systems and it's not any one system. It's just the way it was done, right? You have to have a central place where people can download this content. But the problem with that is you do it at some frequency that's not fast enough for the speed of the business. Information is changing at the rate at which product is being released at the company. And there are just new pieces of information that are coming out. So tapping into the higher velocity data sources, like conversational data, whether it's coming from Slack, whether it's come from Teams, or it's coming from call transcripts, and corroborating that with data that's being created by organizations like product marketing, I think you can move a lot faster. then you can also provide information that's based on new information as opposed to information from six months ago. And you can also use the human in the loop to validate the new stuff. And AI obviously gives you a lot of leverage to do that. So I think that's why it's just a different way of thinking. Think about the lifetime of the asset and how long it's relevant and how quickly we can distribute the load of people validating that it's still correct instead of it being one poor person that's responsible for updating this repository every six months, which tends to be the bottleneck in a lot of orgs. KK Anderson (11:25) Wow. So moving on to our last topic here around the human element, right? And where AI should take over and we're at must step back. So you started your career as an engineer who would look at the sales leader and be like, no, heck no, absolutely not. Can't do it. Not going to do it. Right. And now you're a CEO who's deeply embedded in the go-to-market strategy. So, What did you learn about the human side of selling that you could not have understood when you were on the engineering side of the business? Sunil Rao (11:56) I appreciate the sales side of it so much more now. even think back. ⁓ to like my initial days as an engineer, I just never understood this side of the house because it was just, it was, it was illogical to me. It would be like, why are you positioning something that, know, how, how are you positioning what's real versus not? And not to say salespeople don't do that, but I think you tend to think more now as a consultant that's helping your customer solve a problem and you see the paths and the opportunities. And it's a very different way of thinking than the very rigid way of like. the logical way of like, this is true now or not true now and therefore we can't do it. So I think the change for me really was more, hey, how do you build trust with people? How do you kind of show up and actually bring value and meet them where they are, but then also work with them to build the future together? And I think that opens up. a much more collaborative kind of trust-based relationship. And ultimately, that's what this whole thing is. It's, hey, do you trust me to help you solve the problem? I might not be there 100 % at this moment, but I will get there with you. And I think that that mentality allows you to both portray a vision that you can go on together, but also attack problems with the reality of what you have now. So it was just a mindset shift, would say, KK. Mark Petruzzi (13:08) So Sunil, there seems like there's a bit of attention in the ⁓ product philosophy from the perspective of, know, one of the things you guys do and do so well is automating the RP process, something very specific, very process oriented and some of the info sec ⁓ questionnaires, which are all pretty. technical and repetitive. But I love and get very impressed by the way that you talk about the human side of all this and as you just described, like the things you've learned along the way about the human side of selling. So where's the line? right now, it's gonna change like in about 12 hours, but it's right now, like where's the line? You know, what should AI own? And in your mind, like what should really remain human, at least for now? Sunil Rao (14:00) You know, if you asked me this question like 10 years ago, I think a lot of people will say the same thing. I wouldn't have guessed that sales, enterprise sales, heavily relationship based sales would be one of the last things to go. I would not have guessed that. And I think that that intuition comes from the fact that this is very much a very trust-based human-based business where you're going in and helping these companies transform and helping build relationships to do that. So I think from that perspective, it's where it's disrupting and changing things. There are a couple of implications of that, right? Like how do you bring folks along for the ride? And you mentioned product tension. Like we think deeply about, you automate the thing end to end or do you make the surface area where the AI does the work that's really rote and repetitive, but you still have the human in the loop to go in and have the knobs and dials to finalize what needs to go out. So I think our product philosophy has been that, right? Because we've been selling to these teams that are operating where they have to do a lot of the manual repetitive work, but also be the approvers and now it's can we give you the tooling to remove some of the manual repetitive work? You still maintain the approver status, but now you can handle a lot more throughput as an organization, right? So that impacts UX decisions and product philosophy. Humans aren't going anywhere for a little while. I mean, this stuff will move and you're right, in 12, 24 hours, 48 hours, it's probably gonna jump even further. But I think the rate with which it goes into the company is still gonna be slower than we think. KK Anderson (15:21) And it goes back to this idea of AI is becoming table stakes. So you're giving sales teams the gift of time with your technology. And so it becomes a question of what are sellers going to do with that time? And that's where they get their edge. That's where they can increase the strength of their relationships and their networks and how they can bring value and help individuals, help others, help their customers. Tell me your kind of philosophy around that. What do you want your sales team doing with their time that you're giving them back? Sunil Rao (15:53) go meet more customers, go out in the field, go take them out to dinner, like understand. KK Anderson (15:57) Do the Sunil Rao (15:57) Show up, go do a ride along, understand how they sell to their customers and what are they trying to achieve. If you're stuck trying to update fields in a document at your desk and you're not out there, then you're not really doing the job that you can have the highest leverage doing. So I think, I feel KK, I could have said the same thing selling cloud CRM software 10 years ago and probably 20 years before that selling it. Ultimately, there's always a percentage of the job that is stuff that's getting in the way. And I think I look at this not as replacing the role, it's if you look at the role and you see the jobs to be done of the role, there's probably about 30 % of the jobs that they're doing that you can just take out. And when you take that out across an org of like 500 people, you're not replacing those people, but you're kind of changing the role and making it better suited for the best outcome for that individual. And that's the way I look at the re kind of composition of the work. KK Anderson (16:47) And for a salesperson who's working on a commission, being able to take 30 % of redundant admin BS that they don't want to do and giving them that time back to be able to grow and expand accounts, that puts more money in their wallet. Sunil Rao (17:02) It's like reducing your tax rate. KK Anderson (17:04) Reducing your tax rate. love it. Mark Petruzzi (17:06) I like that a lot. Okay, let's move to one of our most fun parts of this and finish up with some rapid fire questions. This is an interesting one for you because you've been, you you've come from the engineering side. You're a CEO now. You've done some really great years of sales and sales leadership along the way. But what was the first thing you ever sold? either professionally or as a kid. Sunil Rao (17:33) This takes me way back. I'm pretty sure the first thing I ever sold was a trading card. And I used to collect a lot of trading cards like baseball, like Marvel Comics cards. And I remember having to sell some of these like in trades in order to buy more, right? It was always just to get more cards. So it's like, how do you find the right optimal thing? So I think the first selling aspect of it was like, hey, get someone to like really like this, right? Like, and then they buy from you. KK Anderson (18:03) Relationship Selling 101, right? With your buddy down the street. come for a sleepover and I'll give you this card or you give me your card or whatever. Okay, favorite business book that influenced how you think about go to market or AI or kind of where you are now. Sunil Rao (18:18) favorite business book. I've been reading, you know, there's been one of all time, I would say, The Hard Thing About Hard Things by Ben Horowitz. That was just like a classic, right? And I think it was like a very good eye-opening thing, walking into a storm. So that would be my rapid-fire answer, but there's a lot more. KK Anderson (18:37) Is there, I'm curious if there's one that's related to AI though, that specifically has helped shape the way you're thinking about things. I know it's probably not written yet. Sunil Rao (18:44) specifically, would say ⁓ there is a book called, so there are a there's a short paper ⁓ that was, I think it's called, gosh, I'm forgetting the name now. I'll talk about the book instead. Superintelligence by Nick Bostrom. That was a really good read. That was probably 10 plus years ago. And I think that was the first time I heard this idea of like this, you know, when you, when you're building these superintelligence systems, you know, there's this thing called the paperclip problem, right? And if you like tell the thing to go build paperclips forever, you might find yourself in a world that has been completely converted into paperclip factories. And it's basically taken out all the humans in the world, but it's not doing it because it's malicious. It's like your instruction was not precise enough, right? So anyway, that I would say is AI related, a little more of like critical thinking on where this could go. KK Anderson (19:30) wow. Mark Petruzzi (19:31) that was a great book and it was at the perfect time. It was late enough in the history of our world for him to have a really strong point of view and have some data behind it, but still so speculative versus what we're seeing just 10 years ago or 10 years later from there. So what's the best piece of advice you've received? when you were transitioning from a corporate executive to a startup founder. Sunil Rao (20:00) best piece of advice is... Mark Petruzzi (20:02) And that could even be from yourself, like something you just came up with and said, you know what, I gotta do this now. Sunil Rao (20:08) I would say it's actually the realization that a lot of people have advice and opinions. I think, especially when you're out and you're doing this for the first time, know, I, my personality is to seek advice and like really learn from the experience of so many others that have done tremendous things. but also keeping in mind that you need to carve in path, like your own path in your own way. so that's been, it's been, it's been good to keep in mind because You realize very quickly that no one has all the answers and no one's really figured it out. There are people that have done amazing things, but you have to kind of take all of that and make your own path out of it. So that was a good realization for me. KK Anderson (20:43) so interesting. And even as an entrepreneur myself, sometimes the people that love you the most or they're closest to you are the ones giving you the worst advice. Like, are you crazy? Why are you doing this? You're quitting your job? You're doing what? ⁓ Okay, on the advice line here, what's some advice that you would give your 21 year old self? Sunil Rao (21:02) there's many things that I won't say here, but I think from ⁓ what was interesting to me is, the... I've always wanted to build something and I've pursued endeavors in the past as well. So this is not the first time that I kind of thought about startups and building something. think taking the jump earlier and believing in yourself a lot sooner is something that, you know, it's just like, you can go make a dent in the world. doesn't like, you don't need permission. Go do it now. Mark Petruzzi (21:29) beautiful. All right, well, Sunil, thank you so much for taking the time with us. And this has been a great discussion. And I always like to thank our audience who we are so appreciative of, and we so enjoy connecting with you all every week. So thanks again and then I always have to do a special thank you to KK, my partner and all this and yeah, it's ⁓ just too much fun for us to even have to say that we're doing work here. ⁓ And people like you make it really fun. So thanks so much, Sunil. Sunil Rao (22:06) Thank you for having me. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 118 – Running Uphill at Full Speed When AI Keeps Raising the GTM Bar with Sunil Rao – Part 1 | 18 mars 2026 | 00:19:45 | |
In this episode of Selling Intelligence Podcast, Mark Petruzzi and KK Anderson sit down with Sunil Rao, founder and CEO of Tribble, to explore how AI is reshaping enterprise sales, go-to-market execution, and the future of software itself. Sunil shares why AI-driven productivity alone is no longer enough to create advantage, how the rise of agents is changing what software should do, and why trust, personalization, and institutional knowledge are becoming even more important in a world flooded with AI-generated noise. The conversation dives into the productivity paradox, the coming consolidation of fragmented SaaS tools, and the shift from software that assists humans to systems that can actually take action on their behalf. What You’ll Learn:
Key Topics:
Guest Spotlight: Sunil Rao Sunil Rao is the founder and CEO of Tribble, an AI-native platform built to help enterprise sales teams scale knowledge and automate critical go-to-market workflows. Before founding Tribble, Sunil began his career as a software engineer at SAP and later held leadership roles at Salesforce, including GM of Consumer Goods. Tribble was founded in 2023 and has quickly gained traction for helping companies automate RFP responses and improve GTM efficiency with AI-native workflows. Resources & Mentions:
🎧 Listen now and follow Selling Intelligence Podcast for more conversations on AI, modern go-to-market strategy, and the future of enterprise sales. Mark Petruzzi (00:31) Welcome to today's episode of Selling Intelligence Podcast. I'm thrilled to welcome Sunil Rao, founder and CEO of Tribble, an AI native platform that's fundamentally changing how enterprise sales teams scale knowledge and automate critical go-to-market workflows. Sunil's journey has been fascinating. He started as a software engineer at SAP. moved into leadership roles at Salesforce, including and general manager of consumer goods, and then founded Tribble in 2023. Tribble was quickly added to Salesforce's ventures, $500 million generative AI fund, and has since revolutionized RFP automation, helping companies like Clary, Sword Health, and others slash response times by up to 80%. Today we're exploring a critical challenge facing every sales leader. AI is making us more productive, but the bar keeps rising. It's like running on a treadmill at full speed and just when you your stride, the incline keeps going up. How do you stay ahead when everyone else has access to the same productivity gains? We're gonna focus on four critical themes. The productivity paradox, why AI-driven efficient isn't enough to win anymore. From software to agents, building AI that actually does the work, not just assists, scaling institutional knowledge, the hidden competitive mode in enterprise go-to-market, and the human element, where AI should take over and where it must step back. Sunil. First off, we're really happy to have you here. Thank you for taking the time with us and welcome. Sunil Rao (02:10) Thanks for having me. It's nice to be with you all. Mark Petruzzi (02:12) Excellent. So topic one, the productivity paradox. Let's start with what you have called the treadmill problem. Every sales team now has access to AI tools, chat GPT, co-pilot, all these niche engagement and enablement platforms. And all sales teams are getting more productive, or at least the ones that are investing in this. But here's the thing, if everyone's running faster, you're not actually getting ahead. You're keeping up with the pack. And worse, buyers' expectations are rising because they know that you have these tools. So how do you think about this productivity paradox? Sunil Rao (02:47) Productivity paradox, it's interesting because I think there's a couple of ways that I like to think about it. You obviously have this tremendous technology. It's almost magical. It's been distributed to everyone almost simultaneously. And they're all able to see how much productivity it brings into all aspects of their job. But I back to beginning of when we started Tribble, and this is when Chat GPT has just come out, November of 2022. And everyone had that aha moment of, whoa, this thing can write coherently for such a long time. It can actually write code. It can write snippets of code. And it just started to become a way for you to use in your workflow versus going to Google, searching for information. This thing can synthesize knowledge. So when you look at that and that impact, It already was a tremendous time saver for a lot of smaller jobs. But I think what's been going on and what's been happening over the last few years with these foundation models getting better and better, it gets to the point now where these systems can run for hours on end and complete much more complex tasks. And that's where it's more interesting where, you know, what was not possible to solve with software three years ago. is possible today. And that's where agents come in and everything comes in. it's interesting because like you have that happening in one side and it's really magical technology. But then at the same time, you kind of create new work. when you have access to this technology, because now everyone's a creator. And I see this a lot in the engineering side. Everyone's writing more code, and then it's the question of who's reviewing it. If everyone's writing more content to go in documents, who is doing the human check? So you have this trade-off of, yes, there is efficiency in one part of the process, but you end up creating some work elsewhere. So I think it's the paradox, because it actually changes the distribution of where work is being done. KK Anderson (04:30) Really, really interesting. So when we think about it from, you know, a sales or revenue perspective, right? It's, you know, for, for so many years, it was, do you have this Salesforce CRM? Do you have this outreach, you know, program set up? Do you have this automation set up? And it was, you were always running to keep ahead and to keep up to pace with all of the different technologies that were available. And that was just sort of table stakes. Right? And now with AI, as you just said, like everybody has it. And so now it's how you use AI is, is, and how you become a, differentiator using AI is the new game. Because otherwise it's this, we, you know, ⁓ as Doug Landis, one of our good friends and colleagues says is we're in a culture of sameness right now. Sunil Rao (05:15) Mm-hmm. KK Anderson (05:16) an era of sameness, I think is what he says. So talk to us a little bit about that. So now here we are, we all overnight got Chappie, GBT and these amazing programs. How do we differentiate ourselves in this world of AI? Sunil Rao (05:30) it's an interesting way to think about it, right? It's almost like everyone got upgraded, but exactly to the same level. So then how do you differentiate is the It's how do you stand out from the pack? And, you know, and I take the example of outbound and emails. Like I think what's happened, it's both a gift and curse. KK Anderson (05:37) Yes. Sunil Rao (05:45) I mean, I'd it's more of a curse because now there's so much garbage when it comes to outbound, right? In terms of mass generation of emails that are not personalized, that are not targeted. And I still think that the age old, you know, what makes you really good about that style of top of the funnel engagement is when you are very personalized and targeted. think that just actually gets even more amplified as an important way to stand out, right? Don't, don't try to sell something to the masses. Really think about what signals. indicate that this may be a buyer that's interested and engage with them on the journey at the right time becomes way more important. Because otherwise, you're just feeding into the sea of noise that's being generated because we have these tools that can mass create this content. So I think there's that aspect of it. How can we be much more tailored on the engagement side? And I think about it at different parts of the funnel. For us at Tribble, we think deeply about this problem. when we talk about our customers using our products and how they engage with their customers. So we look at it from two sides of that coin. Mark, you'd shared our respond product, which is all about responding to RFPs, responding to customers. You have to be very particular about what it is you do as a business, how you differentiate. And that's informed by your conversations, your knowledge basis and all this stuff internally allows you to differentiate against your competition. But then on the engaged side, where we have software that helps BDRs, SDRs and others engage with their customers. Like we think really about what is the information that we have captured in all the digital exhaust with all the touch points we've had with this customer that indicate that this is in fact something that they're interested in. And how can we in real time kind of guide that conversation and coach it? So we get to the. And I think customers really want that level of detail and personalization because otherwise you're kind of feeding the sea of noise like you've said. KK Anderson (07:29) All of a sudden to be human is to be cool. Mark Petruzzi (07:30) Yeah. Sunil Rao (07:32) I mean, I think people are purposefully putting spelling mistakes in LinkedIn posts because it's like now become a sea of, and you see it, right? When you look at the posts and you see the dashes, the end dashes or the dead giveaway of ChatGP, everyone's using them now. KK Anderson (07:43) yeah. The dashes, Mark Petruzzi (07:44) 100 KK Anderson (07:45) I can't, emojis make my blood curl now. I'm like, ⁓ you know? Sunil Rao (07:50) KK, like, here's a funny question. I actually thought about this the other day. I actually don't know how to type the dash on the keyboard. So it's like, where is it coming from? KK Anderson (07:55) I don't know. Mark Petruzzi (07:56) That is great. You know what, Sunil, when you mentioned the top of funnel and what's happening there, that's an area that KK and I spend a lot of time with our clients to make sure that they don't fall into this AI paradox where five years ago, before we were in the, KK Anderson (07:57) really don't? That's awesome! Mark Petruzzi (08:18) Gen. AI era before it even had a name. You saw that there was so much outbound going to prospects and customers. And what we found is there's been more damage in that than benefit in a lot of companies, meaning they are pushing more potential clients away than in some cases they're ever bringing through the door. So taking you back to your time at Salesforce and when you were running your go-to-market operations initiatives there and seeing all the inefficiencies that were happening with customers of Salesforce but also right in with Salesforce as well, what was the breaking point for you that made you realize traditional approaches to sales productivity were just fundamentally broken? Sunil Rao (09:07) You know, I think it's. Once again, this comes back to the point earlier of what is now solvable by software simply wasn't solvable five years ago, right? So what did you do? The problem was solved by hiring humans and kind of building processes, building checks, building scaling functions, building these expert groups within the company that house knowledge that would scale the rest of the organization. You invest heavily in resources like that and all the supporting functions and resources to keep them going. And I think, you know, that that goes far and frankly if you don't have the technology you have today, that's the only way to do it at the time. For me, the inflection point clearly was the rate of change of the technology outside that was indicative that, hey, if I had to build a company from scratch today, I would probably not staff it the same way, given where tech is at this moment in time. That was 2022, right? And then you go forward in time one year, the number of people factors down even further because the technology is now improving at an exponential rate. And you fast forward another two years and it's crazy how fast things are moving. So I think, like I would say the tools and capabilities and what it is that you are building from a scaling standpoint, as more is becoming available outside, really how quickly can you factor that into the organization and how quickly can you grow? Like this has to be top of mind for every executive at every company right now, right? And I think that that is changing at such a fast pace that folks are just open to having those conversations now and like really thinking, how do we build this differently? KK Anderson (10:32) And it, does it become less fragmented? Right. Or more fragmented. You're adding in, there's a big one million AI products and solutions out there. And there's one, you know, go to market inside this, this, this company. Right. Like, how do you even begin to look at and think about. you know, how you're gonna weave in and out all of these products and how they're gonna talk to each other and I don't know, talk to me a little bit about that. Sunil Rao (10:55) Our thesis on this is there's a mass consolidation coming. And I don't think that that is a very unique point of view. I think most people realize it. The general purpose nature of the underlying technology serves itself very well to addressing many use cases. And what I mean by that is when we started the company, thought about a category and we were, the vision was always to do something much broader and go to market, but then you kind of say, hey, what's the thing I'm going to do tomorrow really, really well? And we picked RFP. And the reason for that was it's a known problem. People knew how to buy software in that domain. And there's a lot of pain there. But that being carved out as a product category, and this is true for any other category of software, these are artificial boundaries created as, this is a category of software. There's a level of functional kind of capability locked in it, technical difficulty to enter it and build it. But there's no reason sometimes these adjacent categories shouldn't be talking to each other. So think, KK, to your question, I think people will expect tools to do a lot more. Hey, I want you to be a tool that does x, y, and z, not I need a tool for each of these. I think the last decade with all this fragmentation of SaaS and so many point solutions, there's just fatigue in buying. And AI is now going to be a consolidation on top of that. Because the beauty of this technology is it can connect to the downstream systems and become the new interface on top of several so it can orchestrate across them right and I think a lot of the companies that are building like us have that as an advantage. KK Anderson (12:18) Makes a lot of sense. let's take us into the second topic here from software to agents, just as you're talking about, and building AI that actually does the work and not just assists in the work. And you've made a very deliberate choice with Tribble, and you didn't build another SaaS app, right? You built an agent. ⁓ So talk to us about the fundamental difference between AI assisted software and truly agentic AI. I think a lot of our audience and sales leaders would like to really understand that. And why does that distinction matter for go-to-market teams? Sunil Rao (12:54) I think there are a couple of implications of thinking about it. just to orient how I think about this and what we think about it at Tribble. Software up until the point where this new stack of technology, specifically LLMs, vector databases, and everything that goes into the new kind of architecture has historically been, you know, You have a database and then you have a UX on top of that database and you have a whole bunch of workflow capability automation and even AI as it was, I it has been around forever, right? It just changes what it actually is. And that's been the way things have been built, but it really is predicated on this transactional data store on which a user interface exists for teams of humans to go operate. And You know, lot of companies have done really well. And even my previous employer working at Salesforce, one of the things they did really well is they did the cloud first really fast. And I still remember when we were talking to customers 10 years ago, comforting them that the cloud was a safe place to put their data, right? Now that's, that's not a problem anymore because folks have like taken that modality as a good, it's a good way to scale subscription model makes sense. Software makes sense when you deploy it in the cloud. ⁓ and all of that stuff. So now what happens in the last three years is we've got technology that allows you to kind of short circuit some of those layers. So when we think about what is an agent-first product, well, what is the layer between where the data is stored and how it's served up to the user? And in which cases do you even need to serve it up to the user anymore? The entire idea of user interface for us, for us to go in there, see the knobs and dials, and change things. Mark Petruzzi (14:20) Thanks. Sunil Rao (14:25) I think that doesn't go away because obviously humans are in every company and they will continue to be for the foreseeable future. Then the question is, okay, what parts of that process maybe can we automate away where they don't need to see it, right? It doesn't get served up to the UX. So I think it changes the way you think about how you build these products because when you have this broker in between you and where the data is stored, and you can rely on that broker to do some of the work for you, it's kind of like having a really, really capable employee that's going to do stuff and you trust them to do it. So like, if you had that as part of it, do you need to see a screen that's as busy? Maybe not. Do you maybe need to see as many screens? Maybe not. Maybe you just have approval buttons instead of actually seeing the detail every time. So there's these architectural implications in how you build the products. And I think, you But the thing that also changes when you build it this way is when these foundation models, like these companies like Anthropic and OpenAI, they're moving at blistering speed. If your two model releases behind... you're not harnessing like 60 IQ points of new capability. So how do you build a product that can seat itself on top of that innovation and harness it as it comes out? That's the way you have to build software in the future. Now, if you built it the old way and you sprinkle the new stuff on top, you still have to bring along the old stuff for the ride, right? And, you know, lot of big companies have very, very smart people. I've worked with many of them. And when you have a large customer base using the old stuff, it's really hard to just go to the new stuff. Mark Petruzzi (15:25) Hmm. Sunil Rao (15:48) have to think about how you bring the old stuff along for the ride, right? So I think that's the way I like to think about it. When you're AI native, you've been given the privilege to make some choices that allow you to move a lot faster. And this could also just be true of startups, right? think it's like we're seeing it at an accelerated rate. KK Anderson (16:02) It's a master class. Mark Petruzzi (16:03) and Sunil, of the things KK will tell you about working with me is that, and I know it myself, I'm always focused on productivity. I use that word too many times in a day. And I've learned, having worked with many CEOs, having been a CEO myself, that you learn how these CEOs, some of them get caught up into the process and the control access or the control aspect rather is the right word of being a CEO versus an enablement aspect and just a value add role. And it's going to happen, it is happening the same way with agents just as you described. So I love how you describe this, the agents, have to be autonomous. This is not another form of automation. We're moving through much more productivity and ability to learn, get better, get smarter, do a particular job better. Now what I'm seeing now is a lot of customers and clients are looking at it and saying, okay, well, they're monitoring the agents. They want to see it just like a CEO that wants to be copied on every email from every VP and up within a company. tell us a little bit about how you, like how do you feel that, how do you make that change? How do you get a client to look at this and say, I'm gonna be bringing these agents into your business with I know you're gonna have to do your due diligence and you're gonna have to really get confident in it. But when you get confident in it, let them roll. Look at them just like human employees, just unfortunately for us humans, they're a lot more productive. They don't take a vacation. They work 24-7, we don't. Sunil Rao (17:54) You know, I think Mark, it's a very timely question and KK, I think you said something along these lines at the very beginning. Trust. Right? Like it's never been more important and it's relevant to the fact that we have the sea of sameness, right? How do you trust that this is a real message meant for me? How do I trust that, you know, how do I trust this relationship from the very beginning? Are you just treating me as one of the many masses? I think that theme comes into even product strategy and how we think about where we show up with our customers. So if you are going to use a product, especially if you're going to use a product that you give a level of autonomy to, and it's going to go in right against your master and your systems of records, you better trust it. So then it's like, okay, how do you build that trust? What kind of transparency do you put into the product? do you make it very clear? The log of decisions that were made, right? Sunil Rao (18:40) Makes sense. Mark Petruzzi (18:41) let's talk about the SaaS fatigue problem. Companies are drowning in tools, licenses, and many unused platforms. Yeah, you built the company in the enterprise software space to go right at that. How did you design Tribble to avoid becoming part of the problem and rather being part of the solution? Sunil Rao (19:01) I think one of the things we deliberately did in the early days was really think about like, where are things going, right? Just in the next three to five years, what do we think happens? If you go back to ⁓ the way back machine, which allows you to see kind of websites from. can take look at Tribble's website in like December, 2023. had the headline, Kiss Your Apps Goodbye, Say Hello to Agents. And that was, founded the company in 2023, but it was very clear to us that, hey, this idea of having all these applications. KK Anderson (19:23) I love it. Mark Petruzzi (19:30) Cool, okay, so we'll jump in so let me go read that one again and we'll go and we'll do that question one more time. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 117 – Escaping the Crisis of Sameness in Modern Sales with Doug Landis – Part 2 | 11 mars 2026 | 00:20:40 | |
In this episode, Mark Petruzzi and KK Anderson sit down with Doug Landis to explore why storytelling has become one of the most powerful skills in modern sales. From lessons learned in the film industry to practical strategies for enterprise selling, the conversation highlights how narratives help sellers build trust, create alignment, and close deals faster. Doug explains that buyers don’t actually buy products; they buy the story attached to the outcome those products create. When sellers focus on telling clear, meaningful stories rather than listing features, they make it easier for buyers to understand the value and communicate it internally. The discussion also dives into the shift from traditional inside-out selling (focused on CRM data and internal information) to an outside-in approach, where sellers study the buyer’s business, strategy, and external signals to craft a more relevant narrative. What You’ll Learn
Key topics covered include:
Doug also shares a powerful reminder: people don’t buy features; they buy the outcome the story promises, whether that’s solving a problem, improving their business, or simply getting their Sundays back. Mark Petruzzi (00:31) Now that is some, that's really, really great stuff, Doug. And I'm gonna share a little bit about how I use, how I've learned to use stories into my selling process. And not only my selling process, running companies, working with private equity firms, communicating with people in all kinds of ways. And it really came down to about 15 years ago, Doug Landis (00:45) Mmm, yes. Mark Petruzzi (00:56) I was involved with a couple of ⁓ and brought in by friends of mine in a couple of films and TV series. I invested in a couple of them for a little bit of a while. was like, forget about enterprise software and selling. And I'm going to be running around with Steven Spielberg soon. That didn't happen. But we did pretty well with these movies. And I'll give you an example. Somebody I've done work with is a filmmaker by the name of Michael Corente. And he's just one example of about a half a dozen that I got to work with. But he's a producer. That's what he focuses on. And in the entertainment industry, I learned there are no, well, there are, I found in my career, there are no better storytellers, not even than the writers. Of course they know how to tell stories. Doug Landis (01:20) So cool. Mark Petruzzi (01:44) but the producers that are out there getting investments and everything else. And man man, Michael was one of them. He's done some amazing things. He's created some really just incredible films that he made happen and he does a lot of stuff with Netflix now and Hulu and incredible stuff. So my point in this is for everyone in business, Doug Landis (01:48) Yep. Mark Petruzzi (02:09) Find your way of getting exposed to individuals like that. Now we all can't typically just call up and get to know a producer. I just happen to have some friends in the industry that I grew up with and got in that track. But maybe it's about writers. It's about different people who run businesses that you just look at. And just learn that side of the equation because It's as specific as you define it, in my opinion, and it's also as generic as just like if you learn how to be a good storyteller, you're going to be successful in business and life. Like I use these same skills with my two children. they love to hear stories. It's just incredible. good. Doug Landis (02:48) Amen. KK Anderson (02:49) People will like you, Yeah. Doug Landis (02:53) Well, I got a caveat to that. I have a caveat to that. Everybody loves somebody who is a good storyteller. Everybody despises somebody who not despise that's pretty aggressive, but it's not a big fan of the people who ramble. They think they're telling a story and they're just it's just one ginormous run on sentence that you never know where going to end. Because reality is it right like it's like no one wants to be the person stuck at the party with I ⁓ I got to sit next to them. ⁓ they never shut up. They always say KK Anderson (03:09) Yes. 1,000. Mark Petruzzi (03:17) Excel. you KK Anderson (03:23) Is there any time? Doug Landis (03:26) All they do is talk your ear off or they just talk about themselves, right? They don't ask, they don't treat it as a conversation, right? So like, this is what happens. I mean, this is why I always think selling is just a series of conversations. We're having a conversation to see if it makes sense for us to have another conversation. And if so, who else should be involved? What's interesting is in conversations in everyday life, we tell stories, right? So like, just get better at being really clear and succinct about the story that you're trying to tell. And I think it's hard. Mark Petruzzi (03:28) Yeah. ⁓ KK Anderson (03:45) Thank Mark Petruzzi (03:45) Yep. Yep. Doug Landis (03:52) Like I think it's hard to be able to do on the fly because you have to be really thoughtful. It's a muscle, like practicing your discovery muscle, just like practicing your negotiation muscle. These are muscles that you have to practice. ⁓ I love it. KK Anderson (04:06) And you gotta get good at telling stories on the Doug Landis (04:08) And so you need to know what stories you need to know what stories are the best stories to go tell for this particular audience in this particular moment. Right. And so that's why I say like, if it's a first conversation with a with a prospect or a buyer, I need to be really thoughtful about what stories do I want to tell? What stories do I want to bring in the conversation? I'm thoughtful enough about what questions I'm going to ask. I'm thoughtful about what about what products I might talk about or, or, or maybe infuse into the conversation. KK Anderson (04:26) Right. Doug Landis (04:34) Why don't I just spend the extra minutes to be thoughtful about the story or stories I might want to tell in the conversation. KK Anderson (04:39) and practice it. So I wanna also talk about what happens when we're not in the room as sellers with our buyers. We know that they have to turn around and very often, I mean, the last number I saw was like on average, anything over $25,000 would go to a CFO of all things. Like even people who've had buying authority and budget for... Doug Landis (05:01) Yeah. KK Anderson (05:04) most of their careers no longer do because of what's happening right now. And so who you're talking to, they have to turn around and sell it internally, they have to be your champion. And I will tell you, the stories are what they remember. So if they're gonna turn around and go talk to their coworker about it or get buy-in, they're probably going to be telling that story. Like, you told me the story, they'll be able to recite it. Whereas like you said, the multiple choice question, like they're gonna be like, can't remember. I don't really remember what it does, but it sounded cool. Doug Landis (05:32) I can't remember which vendor actually says they can integrate with Salesforce or with, with all of that. I can't remember. Like honestly, even if I'm looking at two solutions, I'm like, shoot, I don't remember which one actually is like, yeah. ASC 2019 integrated like, well, I don't remember. Right. Cause they're all saying the same thing. By the way, here's the, here's a little, here's a little tagline. You can share with everybody. Well, if everybody listening, people don't. KK Anderson (05:35) Yeah. Mark Petruzzi (05:44) Jesus. KK Anderson (05:47) Yeah. Doug Landis (05:58) buy products. They buy the story attached to it. Right. It's connected to an outcome. It's like, Oh, this, if I, this is one of my favorites. we, we do a lot of work with Salesforce and MuleSoft and it's like, do know how many people are in the API integration world are working on Sundays because all of a sudden integration went down on Friday. And if it's not up and working on a Monday, then guess what? They're not actually doing transactions. Oh no. So Imagine if you buy a solution like MuleSoft, you never have to work a Sunday again, now you can hang out with your kids. That's the story I'm telling you in my head as I'm trying to solve for this integration problem that I have. It's like, I want my Sundays back. Not like I want a faster integration solution. I mean, that's nice, but like, no, I want my Sundays back. KK Anderson (06:33) Right. Mark Petruzzi (06:41) And Doug, the way you just said that is great because some people would answer your question is, well, people want solutions. But no, I mean, that's a solution. You're giving them a solution, but it's the net effect of that solution on you and to your life and your response. Excellent. Let's, and your organization. Doug Landis (06:58) Yep. your organization and like your team and like the things that yeah, the things that you care about. Like this is how, this is how they're making decisions. It's the story that they're crafting in their head. And it's, what, by the way, like we've all done this, right? We've had to buy solutions. I was a box and I'm like spending a million dollars on the solution. And I'm like, I gotta go sell this internally. I tell you what, I'm to go create a story and I'm going to, I'm going to paint this picture and I'm going to create that story. Mark Petruzzi (07:04) Yeah. Yeah. Doug Landis (07:24) that can connect everybody so that we can all be aligned. Because it's way easier than be like, here's everything it does. People will be like, okay, great, why does that matter to me? It doesn't matter to me. The one thing on list matters to me. But guess what? I build a story to tell, and it's a lot easier for me to tell. I can get way more alignment and buy-in. Mark Petruzzi (07:43) Yeah, you just defined it there. Okay, let us move to topic three, outside-in strategy and one-shot selling, the world we live in today. So most AI sales tools organize internal CRM data, right? You've worked in the Salesforce space for many years, I have as well. We look at some of the challenges there. We look at even bigger challenges in dynamics and other products. And we all know that these CRM systems are just, they don't have a great deal of just accurate data and things to be able to lever as we go forward. So you built something outside in here and what's, if you built in that process, what's broken about an inside out preparation versus an outside in? Doug Landis (08:30) I don't think there's anything broken. think it's just short-sighted. here, I'll give a little context to this. So, you know, my co-founder, ⁓ he was brought in to go do these ginormous product stories, build these product stories for Mark at Salesforce. Giant, like, you know, we're going to change the way Marriott interacts with their customers in the next 20 years. okay. How are we going to do that? How Salesforce going to power that? We've to build a narrative from a product perspective. Well, you what he did and what great sellers do is like, well, okay, what do I need to know and understand about Marriott's customers? What do I need to know and understand about how Marriott does business, how they think about themselves, how they brand themselves, how their competitors think about them. That's all external information that we need to synthesize to get a deep, deep understanding. What does the CEO think about strategically over the next five years, 10 years about the business? The reality is is most people are using AI technology to build internal sales AI solutions based on Salesforce data, gone calls or zoom info, chorus information, calendars and emails, right? And notes. Cool. To me, that's all kind of lagging indicator data. It's important. I'm not saying it's not important. It is important, but it's only half the picture because that's all usually a lot of stuff about information that's already happened. Right? We've had these meetings, we've had these conversations. They said, no, They said, yes, like these are the people that we know. That's cool. But then when I'm getting ready to go have a conversation with somebody, I need all that outside in perspective. I need to understand the nuances of an article or a webinar, a podcast that my buyer was on and they said something specifically about what they're really thinking about. You know, it's like, if I just heard that the CIO of an organization said, we are literally on a spending freeze for the next six months, until we re until we integrate. Let's just take Salesforce as an example. They just bought Informatica, right? We they are a customer of ours. We're working with them. And you know what? Do know how often I get the hold on? We can't actually talk to you right now because we're so deeply ingrained in this Informatica integration from a people from a process from a product perspective that like we're a little distracted. Like, okay, cool. Guess what? I'm not going to bother any of the MuleSoft folks. I'm actually going to go work with Salesforce core. If I didn't know that I keep bugging them and they're gonna be like, dude, leave me alone. So the outside in perspective gives you information and insights that most of us miss. And partially because it took us, used to take a tremendous amount of time to aggregate all that information, to contextualize it and synthesize it around the opportunity that you have. But now you can do it in four minutes. KK Anderson (11:03) you know, it's something, it's interesting because you're getting on the phone with your buyers and everything in the CRM is basically about the company, about yourself, your company as a seller, who you're representing. It's all very self-centered, obviously. And as you said, lagging, lagging. And you want to be able to see and use a tool like a StoryPath, which is incredible at doing this, at kind of getting in that outside-in approach. so that it actually helps you when you're in that customer conversation to approach it from their perspective. I mean, if I had a dollar for every time I've said this, I would be a billionaire. It's like, when you're in a customer conversation, you wanna be sitting on the same side of the table as them. You wanna pretend like your email is kk at you'llsoft.com or whoever it is that you're trying to sell to. Like you're not even, you're not there to educate. You're there to Doug Landis (11:42) Amen. Yeah. KK Anderson (11:54) you know, solve a problem, right? And so, you know, thinking, kind of thinking about this, this kind of different paradigm. If I'm a seller and I'm spending so much time reading through the Salesforce history and all of a sudden getting really scared because I know there was a closed last deal in 2024 with a different rep and I had no notes and they didn't log anything and I don't know anything and I'm about to call this person and I'm like, you interested yet? Right. That's just like what a salesperson's like, you know, all of a sudden all of their self-limiting beliefs are creeping up and their confidence is shattered because they're seeing what's in CRM, right? What is your world like? How is that different when you use a tool that is outside looking in versus inside looking out? Doug Landis (12:19) Hahaha I think there's a couple of different ways to think about it. Like when I'm thinking about an opportunity, I need, what is my strategy to win? Like org chart, who's who, like we know we got a multi-thread, we know there's all these things, what's my strategy to win? What are the thread lines, what are the through lines that I can pull on that are connected to us that actually can help us orient around our differentiation? So. I need to think strategically. So I need a strategist. I need an analyst to help me analyze all this information and show me the things that matter the most. Show me the things that matter the most. And I need it quickly. Because if I'm jumping from meeting to meeting, I got to get booted rather quickly, right? Oftentimes, it's like, you know, it's six or seven o'clock at night, I look at my calendar tomorrow, my ⁓ I have a call at 8am. I am so not ready for that. Right? And so like, cool, what how do I what's most important for me to get out of this conversation? I want them to say, great, this sounds interesting. I want to learn more. I want them to say, I want to have another conversation. Great. Well, then how do I prepare for that? Think strategically about the plan for the account. I think analytically about where are the opportunities, where are the threads that I want to connect. And then I start to of craft my narrative for the conversation. All that information is external insights, external signaling. that I want to, that I want to tap into so that I can pull into the conversation and sound credible. Sound like I understand what they're trying to put myself on the other side of the table sitting next to them is ultimately what I'm trying to do. Right. And that's what outside in information really does. My perspective. KK Anderson (14:01) And so instead of spending 80 % of your time researching what's in CRM, what would you say? Do your 20 % to know what's there, what the history is, and then 80 % to swap it? Yep. Doug Landis (14:10) Yeah, totally. Great. Yeah. mean, the 20, the, the stuff in CRM, you know, it's, know, it's, just even think about this because we ingest all this information and we look at a gong call. It's like 90 % of it's trash. There's 10 % of that conversation. It's really valuable. It's like, they said these things. Cool. That's what I want. Right. I learned these little thing nuggets. That's what I want. Everything else, the commerce, all those other orientation of the conversation, this question. It's like, all right, that's interesting. That's why CRM data is helpful. It's like, what have we already tried? Who have we already talked to? But to be honest, a real true enterprise seller is gonna go, cool, I'm not even gonna look at what's already happened. I'm gonna put myself in their shoes and try and think about what are they trying to accomplish? What's getting in their way? What is that gonna do for them if they accomplish this? who else is involved in this, I'm gonna put myself in their business first. And then I'll go back into CRM and be like, hey, have we done some of this? Or do we have a way in, right? KK Anderson (15:06) Doug, I have met my soulmate in selling. Doug Landis (15:08) You Mark Petruzzi (15:08) Hahaha KK Anderson (15:09) I like I have met my soulmate in selling. just so thrilled to know you. Okay. I'm going to take us to the last topic, because this is the fastest hour that has gone by. know our listeners will do it in two parts, but before we get to the rapid fire, which is everybody's favorite, I do want to at least cover a little bit of this leadership in the AI era, sales leadership in the AI era, because know, boards... Doug Landis (15:13) Mmm. Ha KK Anderson (15:32) are gonna fund what they can measure. so we know that story sell, that trust sells, that we have to go through this process of why change, why you, why now. What are two or three ways or indicators, I guess, leaders can do to go to their boards and say, trust-driven selling is working. We need to try this. Like how, what's the proof? What's the proof story? Doug Landis (15:58) Yeah. I mean, so this investor that I was talking to this morning, we were talking about this, you know, like if sellers really truly develop that level of trust with their buyers, that they truly understand how to become a trusted advisor, which is ultimately what kind of what we're talking about here. And the simple fact that buyers are already 80 % through the buying process or 90 % through the buying process. Guess what that means? We can close deals faster. We can close deals. KK Anderson (16:19) Hmm, there's a good leading indicator. Doug Landis (16:22) We can close deals faster. And he literally said, he's like, I have our portfolio companies are there, especially smaller deals, man. They're getting done in 24 hours. Like, boom, not two weeks, 24 hours. I closed a deal a week ago in 24 hours. It's like, that was easy. Great. Let's do more of those. ⁓ big deals. I think we can accelerate the conversion rates, the conversion rates across whatever stages you have, because again, If the buyer's already done this invisible evaluation and it didn't take them nine weeks to do it, they did it in two days. So like, cool. We now can move a lot faster. So I think speed of closing, speed of conversions important. I also think to be honest, if you are truly showing up and speaking your buyer's language and understand their ontology, guess what? Deals are going to be bigger. KK Anderson (16:56) Mm-hmm. Doug Landis (17:05) It doesn't come down to feature function. We're not like, I'm not just comparing two features and it just becomes a price war. It's like, no, we have a real strategic relationship here because I get you and I know what you're trying to do over the next five to 10 years. And we're in this together. I mean, I was talking to a president to a week ago and he's like, Hey, talk to me about your pricing. This is a true conversation. Talk to me about your pricing. I don't, I'm not negotiating, but I'm just going to get a sense. Cause I'm going to meet with the CEO next week. And I was like, cool. Here's the deal. I don't negotiate. price is the price. mean, unless you want to do a three year deal cash upfront, then we can talk about it. But guess what? I set the price to where it's a non issue. And he's like, we'll explain that. And I did and he's like, Okay, that makes sense. So this is KK Anderson (17:43) I remember the reaction I heard when you first told me your price. I was like, what? That's it? Doug Landis (17:47) And it's just like, here's the deal. don't want this to be, I want a long-term relationship. want, like, I understand the value that we're delivering and are we leaving money on the table? Probably. there potential upgrades in the future? Absolutely. But I don't, it's not about price. It's about delivering value. KK Anderson (17:53) Mm-hmm. Love it. You're so good, Doug. Mark Petruzzi (18:03) let's to our last here that both KK and I love, and that's our rapid fire segment. First question for you, first thing you ever sold. Doug Landis (18:04) What? You newspapers. I think I was like 10 years old, selling door to door. I'm like, Hey, I'm selling the Palo Alto Times and they and you already get the San Francisco Chronicle, but you want the Palo Alto Times because it's local. KK Anderson (18:22) ⁓ so good. Mark Petruzzi (18:23) And see now that's beautiful. You had differentiation even then in your product. Doug Landis (18:24) Hahaha Yeah. KK Anderson (18:29) Okay, a storyteller that you admire. Doug Landis (18:31) ⁓ Simon Sinek starts, starts with why, like I just, stories live in the why, right? KK Anderson (18:33) Yes. Mark Petruzzi (18:37) For sure. Okay, one practice every sales leader should adopt this quarter. Doug Landis (18:43) start asking your sellers for the story of the deal. What's the story of the deal? Start practicing storytelling more frequently, like have create story time in your team meetings where somebody steps up and they tell a story. And then you go through the exercise of, that really a story? Was that just a sequence of events? Because the more you, you infuse story into your culture, the more it becomes easier to actually communicate and share stories with your customers. KK Anderson (19:08) Boom. Okay, my favorite advice that you would give to your 21 year old self. Doug Landis (19:13) This is a doozy, because on the one hand, I'm kind of like, just keep doing what you're doing. Life is great. On the other hand, it's like, you can work on the people pleasing a little earlier in life, because that doesn't necessarily get you what you think it's going to get you. Mark Petruzzi (19:29) Interesting. Okay, last one, your favorite non-business book. Doug Landis (19:32) Michael Singer's The Surrender Experiment. It's incredible story. Have you read it? Mark Petruzzi (19:35) read that one. Wow. I have not, no, but I will. Doug Landis (19:38) It's so good. It's actually so it's really cool. It's what anybody that's in business should read it because it's really all about like, look, there's only so much we can control in our life. Right. So you have like a hippie living in his van in Florida, ⁓ who's a total yogi becomes the CEO of a multi-billion dollar publicly traded software company. And he talks about his entire journey and how he continued to surrender to kind of the flow of life, even in some of the most challenging times. It's a great book. KK Anderson (20:05) Okay, well, we'll definitely put the link to that in the show notes. I'm gonna get that one for sure. Okay, Doug, this has been so much fun. So much fun. Thank you. I can just say thank you on behalf of our audience. You just did a great job. I appreciate it. Mark, you're awesome as always. Doug Landis (20:15) Thank you. It's been great. Thank you. Mark Petruzzi (20:23) Thank you. Thank you. What a great show. So thank you all. Appreciate it again, Doug, and all the best. Doug Landis (20:25) Cool. KK Anderson (20:30) All right. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 116 – Escaping the Crisis of Sameness in Modern Sales with Doug Landis – Part 1 | 03 mars 2026 | 00:26:43 | |
In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Doug Landis, Co-Founder of StoryPath.ai and host of Sales Stories, to unpack how AI is reshaping the buyer seller relationship and why most sales teams are still playing by outdated rules. Doug shares why AI has enhanced the buyer’s world more than the seller’s, what he calls the invisible evaluation, and how today’s buyers are 80 to 90 percent through their decision process before ever speaking to a rep. The conversation dives deep into the crisis of sameness in modern sales, why traditional discovery no longer works, and how trust and story have become the last true differentiators in a crowded market. If you are leading a sales team, building a pipeline, or navigating complex enterprise deals, this episode will challenge how you think about first meetings, process, and positioning in an AI driven world. What You’ll Learn:
Key Topics:
Guest Spotlight: Doug Landis Doug Landis is Co-Founder of StoryPath.ai, an AI native guided selling and storytelling platform designed to help sellers show up with differentiated perspectives, not just better automation. He previously led global sales productivity at Salesforce, served as Chief Storyteller at Box, and was a growth partner at Emergence Capital. Doug is also the host of Sales Stories and a long time advocate for trust based, story driven enterprise selling. 🎧 Listen now and follow Selling the Cloud for more insights on modern go to market strategy, enterprise sales, and how to win in a one shot world. Mark Petruzzi (00:34) Welcome to Selling the Cloud. Our guest today is Doug Landis. We're very fortunate to have Doug, who is the co-founder of StoryPath.ai, host of the Sales Stories podcast. He's a storyteller and he's just successfully built early stage companies time and time again. Doug has led global sales productivity at Salesforce. He served as the chief storyteller at Box and spent seven years as a growth partner at Emergence Capital, helping SaaS companies scale smarter. He has sold everything from newspapers and ice cream to enterprise databases and cloud software. Today, he's really focused on and really enjoying building up StoryPath.ai. StoryPath is an AI native guided selling and storytelling platform that helps sellers show up with differentiated perspective, not just better automation. Three topics we'll cover today. How AI has changed buying behavior more than selling behavior. Why trust and story are the only real differentiators left. And how sellers can compare differently and win in a one shot world. Doug, we're so fortunate, as I said, to have you here, and welcome to Selling the Cloud. Doug Landis (01:50) Thank you. So great to be back. That was all I think I was on a long time ago. I don't even remember what we were talking about back then. And you know, it's interesting as you were doing the, you're going through the intro, I was thinking, I was like, well, given the fact that it feels like everything's shifting to be AI native AI first, everything's all AI. Just does the podcast shift to like selling AI instead of selling the cloud? Mark Petruzzi (01:53) Be back. Doug Landis (02:14) By the way, not yet. Just for a little side note, was on a webinar with about 250 operational leaders, sales and rev ops leaders. And I asked the question, Mike, what percentage on average of your entire go-to-market tech stack is still pure SaaS versus AI? And the answer was at least 85 % of their stack was still pure SaaS. So while we say everything is moving AI and it's moving fast, really fast. There's still so much that's already like fully baked in. so now everyone's been trying to figure out like, how do we actually, make it additive instead of completely rip and replace. But anyway, so the pod selling the cloud is still relevant for awhile. Mark Petruzzi (02:52) Yes and no, we're actually working on exactly that now, Doug. So you're hitting us right at the... KK Anderson (02:56) Your ears must have been burning, Dad, because we've been talking about a Doug Landis (02:57) really? sit in a space all the time like, hmm. Mark Petruzzi (03:01) No, no, you do, you actually put out these ideas without even saying it. Because I actually came up with this idea last night and shared it with KK. So I was waiting. you know, we'll talk more about that, Doug. And so maybe you influenced me without even knowing it. But there are things that are changing. There are things that we want to make sure our audience is changing with it. Doug Landis (03:10) No way, that's amazing. Mark Petruzzi (03:25) And it's just really, it's incredible to have you here and you keep getting smarter than even the last time we had you here. So we love it. a couple times you've said something that really stuck with us through your writing, through your podcast. It's all blurred to me because I've listened to all of it over time now. but that AI has enhanced the buyer's world more than the seller's. What do most sales teams misunderstand about what's happening right now? And how can they change their approaches and their processes to be able to really make sure that we are clicking and fitting with the new buyer's world that is out there? Doug Landis (04:06) Hmm. Such a great conversation to have. I love this. You know, when AI first hit the scene, I think everybody asked like, okay, what does this mean to me? What is this? How can I use this? And I think what the reality is for buyers and sellers, AI has dramatically changed how they engage with each other. The relationship between buyers and sellers is changing pretty dramatically. If you think about it for buyers, know, AI has actually become a real superpower for them. You know, they can aggregate data, they can run analysis, they can do things so much faster than ever before. They're just leveling up overnight. And so I'll share some statistics with you. think that are really, really important to understand how what's changing and shifting in this relationship. If you think about this, LLM traffic is projected to overtake traditional search by the end of 2026. So what that means is more than 50 % of your buyers are going straight to a chat bot to begin their buying journey. So think about that and why is that? And the reality is this as agents have gotten better, you know, it's really interesting is what they can do in minutes or hours is what it used to take buyers weeks and months. So the buying process used to be months long and now they can actually go through it in hours because what an agent is doing is an agent will actually look at their, they will form preferences. And they're going to do it in a way that like humans do. But what's crazy is the amount of information they can, they can analyze is stuff that buyers would normally think about over time. Things like, I don't know, think about the data points of like user reviews, right? Or community sentiment or tech, technical documentation or support quality or integration pricing, all of that. And agent can analyze all that in seconds. And a buyer would normally take, you know, weeks or months to go through that. So if you think about it, Statistically speaking, what is it? 89 % of B2B buyers are using gen AI in their purchasing process. The crazy thing is 83 % of the buyer's journey happens without a seller. So that means if a seller is only involved in 17 % of the buyer's activities, then sellers need to show up a little differently. They need to understand and almost anticipate the fact that the buyers are going through a buying process without them. We call this the invisible evaluation. They're evaluating solutions and they're evaluating ways to think about solving problems without any of us knowing. So if you think about like, we've all bought software, right? And so we normally would think about buying software, like maybe we'll go to a webinar, we'll go to a website, we'll talk to some people, we'll reach out to an SDR, we'll download a white paper. That is leaving signal. That's leaving breadcrumbs all over the internet. And solutions out there could pick up on that and be like, ⁓ hey, Doug is out exploring something to solve for forecasting. Awesome. I can reach out to him. can do some, you I can do some outbound now all that's happening in a chat bot and there are no more breadcrumbs. And so like how do sellers know how to marketers know how to brands know that their buyers are actually out there in market. It's really, really difficult. The problem is sellers show up. And I fundamentally think this is going to change the entire sales process. When you think about sales process, what do we think about the traditional sales process? We're going to take a buyer through like, you know, all these stages, discovery demo, you know, negotiation, more discovery, multi-threading, all of that buyer. like, no, I have two questions. I've whittled this down to three vendors. And when sellers try and go backwards, it's like, as a buyer, I'm, losing my mind. Mark Petruzzi (07:20) Doug, you, wow, would. And I'll tell you, I'd love to share a couple thoughts on that, that maybe can even, you know, maybe escalate us even a little more in some of this analysis. So I have been personally on a journey for about seven years where I have been telling all my clients, anyone who reads anything I put out that, you know, It's a different process. was a different process seven years ago even. At least that's when I figured out. Probably was five years before that. But with all the tools that were out there, buyers wanted to buy differently. And I was amazed that some of the best sales reps that I've ever worked with were not responding to that. Some of them were, and I've been able to turn teams of sales reps into into really understanding the buyer journey and understanding that the seller journey means nothing in all And I'm so proud of what I've done with some clients, but I've seen some clients just not wanna go there. They just won't. That was seven years ago. Now you compound all this with AI and what you just described so articulately, there is like, it's all. whole new game. Like we almost have to get these sales leaders like bats that they can run around sort of hitting sales reps a little bit on the head and saying like, you have to believe now. It's so different. It's not even there's no resemblance. So it's incredible. But I love how you set that up. And I'd love to go deeper into what do we do with with that? And how do we get Doug Landis (08:44) Hahaha. KK Anderson (08:50) So. Mark Petruzzi (08:58) the most stubborn sales reps to understand that we're in a new paradigm. KK Anderson (09:03) Well, and Doug, before you answer that, let me just add on. let me add onto that. So the buyer motion has changed, but we still have to go, we still have to take them through the process of what I call running the bases, like in baseball, right? And you still have to go through this whole idea of what we call the two-cell. Doug Landis (09:05) Great question. Mark Petruzzi (09:05) It's okay. KK Anderson (09:23) process, is like our sale is getting that buyer to articulate why they need to change. What is the problem they need to fix? And the second sale is why you and why now? And so if they're, when they're coming to you, and this I know is where something like Story Path is so incredibly powerful. We've seen it firsthand with our clients, but if you're getting to that first conversation and that buyer is like, dude, I already know this. I don't want to hear this, right? Like what are, what's your advice to the sales leaders out there who are working on this with their sales team? They still have to close that first sale. They still have to like make that psychological invisible sale happen. Talk me through like, what does all this mean? Doug Landis (10:00) Well, look, I mean, why change? Why now? Why us or why change? Why us? Why now? The whatever flow you use is still relevant, 100 % relevant. The difference is sellers need to show up anticipating the fact that buyers have already been thinking about this. And so instead of going through the traditional discovery questions, which is, you know, kind of a Spanish inquisition of stupid questions, it's like, I need to like, let's just call a timeout. My hunch is you've already analyzed You've already deeply understand the problem you're trying to solve. You've already analyzed all the different options out there. You've done all the analysis if you're a modern buyer like most of the buyers that I'm speaking to. So the first question is, since you've already done that, you probably have a pretty good idea why changing right now, why changing from what you're currently doing might make sense. I have a hypothesis about it. I'd love to share that with you, but I'm curious as to as if you've actually gotten to that point already. KK Anderson (10:51) So the upfront contract, the way you set it up. Doug Landis (10:52) Interesting, right? It's like Right. It's all, it's all how you set it up. It's like, if I anticipate the fact that they've already done this and they've got a pretty good understanding as to why change might make sense. Awesome. Let's have that discussion. I've got a perspective about it because I talked to other people just like you all the time. And I'd be happy to share that. ⁓ but I also want to know if you're, if you've already done the analysis and you're already there because most of the buyers I talked to you already have. Right. So It's almost like, it's almost like kind of making an assumption. I'm not going to tell them that they've already done this, but I'm going to kind of, it's a little bit of assumption that's like, you know, if this is a big enough problem here and a hair on hair on problem that we continue to see, then my hunch is you've already done some around it. KK Anderson (11:32) Talk us through, I've heard you say this multiple times now, what you call the crisis of sameness. Doug Landis (11:37) Well, so unfortunately, the crisis is so on the seller side, we all thought like, AI is going to make us so much more productive, we're going to become superhuman sellers, right. And the reality is, sellers are all using the same, you know, custom GPT that they built, they're all using chat, GPT or gems, they're all using kind of their own internal data. And they're showing up with the same messaging, the same pitch, the same everything because they don't under because they haven't stopped and said, wait a minute, if my buyer's 80 % of the way through the buying process, if they already have a pretty good idea of why change, why changing might make sense and why it might make sense now versus waiting and what are kind of my best options. And if I take them through a standard pitch or use the same email kind of framing that everybody else is using, then I sound like just like everybody else. There's no differentiation. And I think that's one of the challenges. I literally was talking to an investor right before this call. And I was sharing this with him because this is kind of a part of our core thesis is as an organization is we've to get people away sellers away from sounding just like everybody else. And he was like, I literally have gotten 11 of the same emails in the last 24 hours. It's they look in, they look and feel the same. And so it's like, okay, if we're, if we're all kind of following the same playbook and we're using the same tooling, then how do we really start to differentiate? And I think the first thing is you got to first understand where your buyers are now. That's the very first step. The second for a seller to get out of this crisis of sameness is you got to start thinking about being different, you know, and we have a whole thesis on that. That's through trust and story. Mark Petruzzi (13:04) and you know what Doug and KK, I'm gonna ⁓ kind of bust this out, I think, to a whole level here with some of these thoughts. So, and this is why KK and I are so good together and why we're so impactful for our clients because we have these debates all the time. So I'm gonna bring one of our debates to this podcast. KK just described the four bases, like you've gotta go around the four bases and she's incredible. from a process standpoint, sales competency perspective, and I totally get the perspective. I kind of think it's gone to a different point here. And when I show up to a sales process, I kind of think of like I'm showing up to play baseball with the Savannah Bananas, that group that does all that goofy, crazy stuff, right? Doug Landis (13:51) Love that. Mark Petruzzi (13:51) So what I have to do is I first have to understand what are the rules today, like real quickly, not deep, but what are the rules that we're gonna go to to play this game? Let me do my research, let me learn how they played every other game they've ever had. Let me come in with that. And then I wanna see, are we even using bases? Or are we just hitting home runs and catching balls behind their back, whatever they do. Doug Landis (14:15) Ha Mark Petruzzi (14:16) So I think that's where we are here as well. And that's why I also feel like the concept of the sales rep being a CEO of their territory is real again. And we all watched over 10 years, 12 years, the last 10 years, 12 years, all the technology that sales leaders were putting in place. Doug Landis (14:30) Yeah. Mark Petruzzi (14:39) They then started to say, well, we don't really need people that could be the CEO of their territory. We're going to give them great process and great technology. And hey, it works. Worked. They were growing, especially in SaaS companies, super fast during this time. So I don't argue with the success. But before that, and I think now again, you need at least a subset of your sales team to have that level of intellect and curiosity. and really figure those things out. So I'll weave that together if you don't mind with a question, a more specific question. So if we think buyers are now 80, 90 % through their decision process before they even talk to a seller, how should it change how the rep shows up in a first meeting? And my hypothesis here is that a good one, right? Like you almost have to go in and figure out what game not to call this a game, but what are the rules of this process before you even jump in? And you gotta be smart enough to be able to figure that out, which also comes down to the talent management, making sure you have the right people and the right roles. Doug Landis (15:35) Yeah. Yep. it's interesting, you know, it's, would, I would argue what a seller needs to do in the first meeting and first conversation today is arguably the same that I've been touting for years, which is show up with a point of view, show up with a hypothesis, anticipate, try and anticipate where you think they might be might by the way, is a very important word because I'm a linguist at heart because you can't tell somebody where they are. If you come in and tell the buyer where they are, to be like, GFY, you don't know me. ⁓ think, wait, here's, I wanna actually address that, by the way, I love the of the metaphor of the Savannah banana baseball team versus traditional baseball in terms of the shift that's happening. I believe there's two parts actually going on. There's the operational piece of selling which still exists. We still need to understand where does procurement fit in this process. KK Anderson (16:19) Yeah. Doug Landis (16:31) What about security? What about legal review? We'd like, those are operational things that we need to do to get the deal done. Correct, right? We still need to do that. Also, people likely still need to see some sort of demo. They need to understand how this might look and feel and fit in their environment, right? They may conceptually understand the problem they're trying to solve and the options, but you know, they can do all that through these chatbots, but they also then need to look and feel and think more deeply about the integration and how the data flow and then... What kind of risks is this gonna create? So like there's, me, that's kind of the operational stuff of the process. And that's where I agree with KK and that like, there are still bases that we still have to, you know, touch, right, to get a deal done. However, I'm gonna put on my Savannah banana outfit and go like, the way I get to those bases might be a little different, I might, by the way, run to second and then go to third and then to first and then to home. I might go like high five the pitcher, right? Right? So, but here's the key. The key is in order for me to leave home, the home base in order to go to any base that makes the most sense. I have to show up with a perspective and a point of view and an understanding of where my buyer is. And I have to speak their language. I have to understand their ontology. I have to understand Mark Petruzzi (17:20) There you go. Yep. Doug Landis (17:42) you know, who they sell to and what they're trying to accomplish with their customers. And that's the language that I need to speak. And if I just show up and I'm speaking my language and I'm asking my discovery questions and I'm putting all the pressure on the buyer to go answer my questions as a buyer, I don't want that interaction anymore. And guess what? I shouldn't have to have it. I shouldn't have to have it. Right. So, and so like, KK Anderson (18:03) Totally appreciate that Doug Landis (18:06) I'm going to go into the conversation and say, like, let's just say, Mark, I'm trying to sell to you. I'd say, like, Mark, I have a hunch. My hunch is you're so sophisticated that you've already done an insane amount of analysis about the problems that you're currently trying to solve. Just a hunch. And that you've already kind of whittled this down, your selection down to maybe one, two, three different potential partners to work with. My hunch is you also have very specific questions that you haven't really wrapped your arms around yet. And the reality is those questions, that's kind of where I want to spend our time. Mark Petruzzi (18:35) And right after I gave you a big giant hug and said, wow, you get me, Doug, would then be like, yes, and Doug, here's what I need. I need to get X, Y, and Z done. And if we get those things done in a positive way, you got my business. And we're gonna do it really fast because you get me already, Doug. that. Doug Landis (18:35) How does that sound? Yeah. That's, mean, and, and, and, so this is, this is the new reality, right? And I think the challenge is both at a leadership level is we got to quit forcing reps to follow this process. And we also at the leadership level, we need to coach our reps to be able to show up with a really, really strong point of view and an understanding of how to speak our, our buyer's language and understand their ontology. The challenge is if I'm a rep and I have a territory and like, I'm the CEO of my territory, but my territory has like, 50 different verticals, different kind of companies and different industries, I got a context switch and that's really hard. Instantly, I've got a series of meetings, I've got calls back to back because my BDR is crushing it and setting up meetings, which we know is really hard. But now I'm going from talking to somebody on oil and gas to manufacturing to retail. I'm like, ⁓ how do I do that? And so what's easier for me is to let me just go through my playbook, follow, ask my questions. KK Anderson (19:28) Mm-hmm. Doug Landis (19:47) do some validation, talk a little bit about us. ⁓ Unfortunately, it happens way too early. And then the buyer's like, all right, well, you sound just like everybody else. Cool. KK Anderson (19:58) Yep. So true. You, I you are articulating this so well. Really. It's incredible. the value hypothesis is critical and you know, well, I don't want, we, don't want to go too far into Story Path, but the very first time I logged into Story Path, the first question it asked me was, what is your value hypothesis? Who are you? What percent are you selling to? What challenge are they trying to solve? And why are they trying to solve it? Doug Landis (20:00) It's hard Thank you. KK Anderson (20:20) right, so that you can know exactly kind of what your POV is. So let's move on to the second topic here about trust and story and how they help us win the deal. And so in this kind of world of sameness where we're flipping between industries and on back-to-back calls and we all sound the same, right, a lot of times we're reciting the same case studies, the same stories, and sometimes Like sometimes a salesperson will literally feel like a broken record because they say the same thing 100 times, right? And so, you you and I both know that that story is not just case studies. ⁓ Most case studies aren't even real stories. Like, let's be, let's be real, right? They've taken on a life of their own over time. And so, you know, talk to me about, about what it is. Tell me about why story is so important and how that helps build trust. in the first Doug Landis (21:10) Well, I mean, look, here's the thing. think, well, there's two parts to this, right? So again, our core thesis is to really truly differentiate as a seller today. It's all about trust and story. Trust is understanding your buyer in a really, really deep way. I was about to use intimate, but that's weird. But like truly understanding your buyer, Mark Petruzzi (21:27) You Doug Landis (21:29) having, putting yourself in their shoes, having the assumption that like, you know, Mark's already 80 % through the process. He's done the analysis. I understand your language and ontology. That's all going to build trust, right? And I can take that from the company level all the way down to the individual level. And we'll talk a little bit more about that. When I'm sharing back, when I'm communicating back with Mark as my buyer, I want to communicate back in a way that is easy for him to understand, a way that demonstrates some level of empathy, connection, right? And easy for him to internalize and turn around and go share with others. Because Mark is one of 17 people. If the deal is over $250,000, thanks to my friend Jen Allen, she just posted a whole bunch of stats. If a deal is over $250,000, there's like 17 buyers now involved in the process, or on the buying team. That's crazy. So guess what? Mark has to go talk to 16 other people and try and build alignment. Like is this a problem that is worth solving? Can we get everybody on the same page? If I just go, here's all the facts and stats about our product, here's what we do, here's how we do it, here's our case studies, Mark has to internalize all that and be like, all right, I'm gonna do the best I can to try and share this. However, what if you were to flip this? What if you were to reframe the way in which you orient the conversation and share a level of, here's what I think I understand and then. and weave that into a narrative, into a story that is a very short, very crisp, easy to digest for Mark, then guess what? I'm earning the next conversation. I'm earning a deeper relationship. I'm building that connection with empathy because story is how we naturally communicate. We can use facts and stats and data to back up the story. But when we just lead with all these statements, it's really difficult for us as listeners, as human beings to remember that. I mean, just think about school, multiple choice questions. At the end of a test, if you were to ask me like, do you remember that question? I'd be like, nope, blacked out. All right, the essays I remember. KK Anderson (23:23) So, love what you're saying, Doug, and I couldn't agree more. And where my head is going is are things like you're telling a day in the life story or a future state story or here's where you are now. Tell me a little bit more about when you're Doug Landis (23:35) Totally. Bunch of different types. There's a bunch of different story types that you can actually tell. Yeah. Current state to future state. Look, at the end of the day, a story is really about from two. You're taking, you're trying to help somebody imagine going on a journey from somewhere to somewhere else. Right. It's either I'm taking from first base to second base or from first to third. I don't know. Right. So like, and so you can tell that from, from the experience of another customer that was similar and the journey that they went on. KK Anderson (23:50) first face to say and juggling balls behind your back. Doug Landis (24:03) You can tell that from the standpoint of like, hey, by the way, it could just also be like a, hey, Mark, we're just starting to get to know each other and starting to unpack like the connective tissue of this problem that we think might actually be bigger. So let's, let's, let's talk about the next conversation and talk about the story, about the flow of our, of our ongoing conversations. Cause I know there are 16 other people involved in this and how that might look and feel. There are a number of different stories that we can tell. Oftentimes telling a customer story is a really great way to demonstrate some level of credibility. The problem is, sorry marketers, I love you. Stop following the old school frameworks. Problem, solution, ROI. No characters, companies aren't characters. I don't know how to go tell that story, so what do I do? I say, well, yeah, know, Mark, this reminds me of conversation I was having with Cisco. They're like, okay, how is that even relevant? They're not even like, it's like apples and tree bark. Mark Petruzzi (24:36) Mm-hmm. Doug Landis (24:56) doesn't even connect. You know, it's like, oh, okay. And then I'm trying to draw some connected tissue, because that's the only story I remember. And again, take that territory where I've got 100 different industries. How do I remember stories, customer stories for every single industry? And so it's like, so there's a bunch of different stories you can tell, right? So how about tell your own personal story? Right? Your own personal aha story, because you understand if I understand Mark's world really well, I'd like, you know what, here was my experience. KK Anderson (25:00) Right. for the opportunity to ask questions. Doug Landis (25:21) You know, I've, I understand your problem that you're experiencing because I've actually had something similar. So maybe it's a personal story. Maybe it's a, you know, maybe there's a, you know, a why so, many stories live in the why not the what or the how. Right. So like, why did we decide to go? So, so for example, why did we, why as an organization, did we decide to tackle this particular problem? Why have we made it our mission to help people solve for this particular problem? KK Anderson (25:35) What do you mean by? Doug Landis (25:46) Why, why did I decide to come work for this company? I decided to come work for this company. started, decided to start Story Path because I fundamentally want to change the world of enterprise sales, period. Right? So like, guess what? I know Mark loves enterprise sales. He and I are aligned because this is what we both want to do. So like, I just told my own personal why story or I could tell my personal why story. And it's like, all of a sudden now we're building connection. Right? So there's, it's just a lot of different stories that we can tell in every conversation. I think there's a couple of things. One, we're not thoughtful enough to just take a minute and be like, what stories do I actually want to tell in this upcoming conversation? Just take a minute. Just think about that. How do I want to incorporate those stories in the conversation? Which one should I be ready, ready for? The problem is, is a lot of people just don't understand actually how to tell stories. and we haven't really helped them. Well, we are now as a company. I mean, at the end of the day, Story Path is the story company. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 115 - Building Repeatable Sales Success in Enterprise B2B with Glenn Poulos - Part 2 | 24 févr. 2026 | 00:21:35 | |
In Part 2 of this conversation on Selling the Cloud, Glenn Poulos dives deep into what it really takes to scale a distribution business from startup to successful exit. From growing Gap Wireless from 1 million dollars in revenue to 84 million over 15 years, Glenn shares the strategic decisions, mindset shifts, and leadership disciplines that enabled sustainable growth in the telecom technology sector. Glenn unpacks the importance of franchise vendor relationships, why brand positioning determines sales velocity, and how to structure an organization with the right people in the right seats. He also tackles one of the most critical dynamics in distribution: building trust with manufacturers while managing the real risk of going direct. The episode closes with a practical and grounded perspective on AI in sales. Glenn explains how to use AI as a powerful assistant across departments without sacrificing the human connection that ultimately closes enterprise deals. Plus, stay for the rapid fire segment where he shares hard lessons from selling his first company, advice for his 21 year old self, and the sales habits he still practices today. What You’ll Learn:
Key Topics:
Guest Spotlight: Glenn Poulos Glenn Poulos is a sales expert, author, and serial entrepreneur with over 40 years of experience in complex B2B selling. He co-founded Gap Wireless and scaled it into a multi million dollar distribution company before its acquisition. Today, Glenn leads ProgUSA and is widely recognized for his thought leadership on sales growth, leadership, and the practical application of AI in business. 🎧 Listen now and follow Selling the Cloud for more conversations with leaders shaping the future of enterprise sales. Mark (00:31) So let's move to topic three, scaling a distribution business from startup to exit in the telecom technology sectors, as a whole. So let's talk a little bit about your journey building Gap Wireless. You co-founded it in 2007, hit a million dollars in revenue that first year. Glenn Poulos (00:33) Okay. Sure. Mark (00:51) and I believe it was 15 years later, sold to 10 WS. What were the major inflection points or really what were the decisions that enabled you to scale in the way that you scaled? Glenn Poulos (01:02) So numerous things. at the end, we were 1 million in the first year when we sold it to NWS and we did 84 million in revenue. So over the 15 year period, we grew from 1 to 84 million. And again, we were a small company, right? So I mean, was, you know, and at the, when we exited, there were 44 people. Right. So it was pretty good, pretty good growth. Right. So, in a distribution company or in many, I've been into the distribution my whole life. So really can't comment much on any other kind of company because I've never really experienced them. Right. But, it's the first thing is always focusing on the relationships before the transactions. Right. So that no need to really beat that to death. the people piece is very important. The relationships with the, the customers, the employees and the suppliers is critical, right? when you're a distributor, the key is having the key, the killer brands under your moniker, right? Like you need access, franchise to access. to the key brands, right? And the kind of world that we were in ⁓ and I've been in is one where it's kind of a, we'll call it monogamy based franchise relationship. Meaning I wasn't, I'm not the Rexel or Ingram Micro that has every brand and I'm a trillion dollar corporation, right? That's not what we are, right? We're a multimillion dollar company. And so, the screws, we would only represent this screw company. Right. There were other competitors, but our goal and our job was to get a franchise relationship with ABC screw and sell their screws and their screws only no competitive. Right. And so we would build the market for them. We were approached that company. They were maybe in Italy. They make the best screws in Italy. And we'd say we want an exclusive franchise relationship. with you guys in Canada, the US, North America, Central America, wherever it was we were selling, wherever the territory was available. And so you get that, you wanna build that relationship with the vendor early and that's the most important thing really because you wanna be having the best brands to present to the customers. Then it shifts and the customer becomes the most important, right? But if you, let's say you have the customers but you have the D, E and F brand. it's game over, right? Like I won't even, I challenge people, sales guys and gals that when they get a job, spend a few months and figure out where you are in the pecking order of the world of your market, right? Are you guys the number three, the number four, the number five, the number two, the number one? If you're below number two, I say quit and get a better job at a better company because you can't, you can't replace today, right? Once today's gone, it's gone. And so if you're trying to promote brands that are well down the stack of what people want to buy and what have you, you waste too much time selling the company and not enough time selling the solution and the product, right? So you want to have those vendor relationships. and so ⁓ some of the other things about about building the business, you know, is learning how to step back and put the right people in the right seats, right? So ⁓ structure first, people second. And everything has a process, right? So what do I need in order to be successful? And then do I have the right people in my organization to occupy those seats? And if not, I find the right person and put them in the right seat. I don't say, hey, our finance things are growing. We got more challenges in finance and we've got, Jack and Sally and you know Sally's been here longer and she's doing a good job and whatever let's give it to Sally. No it's like I need a director of finance now or I need a CFO what are the rules for the CFO? Does Sally or Jack have possessed that? Anyone else in the company? No I have to recruit out of the company. And I'm sorry, don't, it's nothing personal, right? You got to the right person in the right seat. And so, and that allows the founder to step back a bit and focus on the higher level visionary type functions of the running the company, right? And guiding the direction, knowing that the different, the different roles are well covered, right? so I'll just take a quick breath and see if there are any specific questions about that or KK Anderson (04:48) It's so, it's fascinating and so interesting. we do a lot of, and I do a lot of work with distribution companies and with manufacturers alike. And so one of the things that comes up a lot is trust, right? Distributors worry about manufacturers going direct. Manufacturers worry about losing control of the customer experience and conversation and getting to talk about their product. So from your perspective as the distributor. what actually builds that trust with the manufacturers? And is that, from your perspective as well, difficult to be able to trust the manufacturers with your pipeline, with your customer base, going, know, co-selling, if you will? Glenn Poulos (05:28) so yeah, that is like the key of it all. Like, I mean, that's really like, that's like a like a masterclass what you're just asking there, right? Like, you can go in so many different directions. But but ⁓ and I hear you so well what you're what you're asking me the the you have to be a little bit paranoid. You have to be pragmatic, and, sometimes you just have to, you you just have to let it be what it's going to be and accept it and, sometimes move on. Right. In the sense that, the company I'm in now, it's not a huge company. we have 11 franchise relationships. And so I have to balance the needs, wants and concerns of those companies, but some are bigger than others. Yeah. My main brand and what have you. And yeah, I I if I get them to a certain point, they might go direct, right? So it's a bit of a balanced mediocrity, right? If you grow them to a certain value, it's cheaper for them to open an office in that country and put in direct salespeople. But the thing is, it'll happen, right? And so you always want to be using that brand to leverage new brands coming on board. in the possibility that you might lose it. Because you can't defend against an inevitability, right? And so I sort of like trust. KK Anderson (06:36) to you before where lost like a manufacturer's gun direct Glenn Poulos (06:40) Yeah, so essentially we sort of, unless they're a company that's pure distribution focused, ⁓ where they only sell through distribution, it's just about doing a good job and stuff. But if when it's a difference between going direct and distribution, if they might go direct, then if they hit 5 million, you can, you can basically count your days until they go direct. because mathematically it's cheaper to go to rec at 5 million. So if you can get them from one to 5 million, you're kind of in the sweet spot making lots of money. They got a lot of ifs and buts about whether they will or won't go to rec, but above that, it starts to get risky, right? In terms of... like sharing the information and what have you, I believe in, like I call it humble bragging early and, and always. Right. And so I like, for instance, with my guys, they'll, they'll call me and they'll say, Hey, I'm just on the way home from, you know, XYZ. And they're looking at a new, discombobulator 50 grand, like blah, blah, blah. I go, that's amazing. Did you tell the vendor? Right. And they're like, no, I said, you should have called the vendor and told them. And I said, you got a humble brag, right? and, what I mean by humble bragging is like, you don't want to do it in a, in a way that's like negative in, in any kind of capacity. You want to say, you know, Jack, my God, I just had an amazing call. I just had to share it with you. We're in an XYZ. They're looking at a discombobulator. They might need two of them. It's 50, a hundred K. my God. I might need your help with the demo, And so what's the vendor doing? He's thinking, ⁓ Mark (07:37) Thank Glenn Poulos (08:03) Bob's in at XYZ, Bob's got two discombobulators on the go. That's a hundred grand. I could really use that towards my quota. What can I do to help Bob get the deal? And also what's happens is, that Sally from the competitor who maybe there's two distributors, right, calls and says, I got wind that there's like a week later calls. got wind that XYZ might be looking for some discombobulators. Nope. That's covered by, by Glenn's company or whatever, right? Stay away. And they, because that's what just manufacturers often do. They divide up the landscape, right? It's like, nope, we've already, we're already working with someone there back off, right? And, and so I believe in being very liberal in my new company here, small as we are, my ERP system, I had custom programming done so all my vendors can log in and look at the funnel and see only their funnel items, obviously they can't see my other vendors, but, and, they can see most of it, but not all of the records, right? Like the internal chatter box notes they can't see, but there's a more generic note section. can, they can see probabilities, dates, products, who's involved in center, et cetera. Right. and so I'm not sure I directly answered your question, but I mean, Oh, okay. KK Anderson (09:08) For good, you absolutely did. You did, thank you. Mark (09:11) Beautiful. All right, well, let's move to our final topic. you know, this is a popular one or maybe popular is not the right word. It's it's just out there everywhere we look. AI and technology and sales. how do you use tools without losing that human connection that you've shared within your book and within a lot of the work you do online? What's what's great about what you've achieved in the social media world and the media world. you're a LinkedIn top voice. your focus and a lot of what you do today, you describe yourself as an AI and sales growth expert. But after spending 40 years building relationships, mostly face to face and mostly over the phone, how are you thinking about AI's role in sales with all this new capability we all have? Glenn Poulos (09:58) Okay, so my, and of course this is my opinion, right? Obviously. And, and so some people might argue or they touted it for different, there's so many things on social media now about using AI and I'm like, yeah, no, no, I don't think so. But, so I, I think of AI and I want to use AI to remove friction and, not replace the connection. Right. And so I treat it like a strong assistant in every department. Right? Finance, marketing, operations, sales, legal. And so it can help you with research, with prep, with summaries, with drafts, with ideas. Right. And but not to replace it. Like, for instance, I know I didn't try this, but I mean, we have. you know, we, in my organization, have like BDRs and they're actually in the Philippines and they phone customers and they try to get new names onto our list. And do you use the stuff that prod sells? Right? Yes or no, blah, blah, whatever. Then they pass our insight guys who try to massage it any opportunities that it goes to the outside people. Right? There's literally no way that could be done by AI because maybe in a few years it might be able to, but, But not right now because I mean the stuff we're selling is to like super geeky guys that drive pickup trucks and climb towers with 500 kilovolts on it and it's just too There's no way you can have a meaningful conversation. It's very very specific, right? So It can assist you but it can't replace right? We like we don't get appointment setting or anything like that. So It's like building a deck, right? You can screw the screws into the deck with your, with a hand by a screwdriver, you can get a power drill, right? I mean, you're still building the deck. It's still your design and whatever the other area, for instance, you want to do some social media posts, right? And it's like, okay, well, you know, this, this week's topic is on this or this month's topic is on that. I mean, if I say to myself, Glenn, give me 30 ideas that I can talk about this month on sales growth, right? Or on funnel management. I mean, I could come up with two. If I need to come up with 30, I would take a month, right? But AI can give me the 30 in a few seconds, right? And you could even say, write all 30 posts for me. And I mean, people would all unfollow me if I just posted those. You have to then humanize it, right? And you have to socialize it. And so the research and prep part is amazing. But also the other areas like any new contracts we drop into a legal element and it looks at all the points, insurance and terms and termination and liability and it says, look at this point, look at this point, this point's one way, it's not a two way clause, et cetera. And I mean, I don't really wanna read 80 page documents ⁓ and so it helps with that. And so, and also I'm not a strong financial accounting guy, right? Like, mean, I'm generic knowledge, but I'm not a CFO. And so you can put your financials for this year and last year and your cashflow state and everything. And you can say, can you give me some advice on, and it comes up with amazing insights into that, that you'd have to hire a $250,000 CFO. To give you right and nor do you need them full-time? But you can still get the value right and so so it's an amazing assistant and And that's the way we're using it and that's and we've gotten incredible ⁓ Incredible value out of it, right and so Yeah KK Anderson (13:12) love that analogy. it's Mark and I talk often about how it's almost like sales is in a giant pendulum swing, right? It's, you know, we've always heard people buy from people they trust, right? Over the last, 10, 15 years, the AI sales tech world has exploded. have every kind of engagement platform, CRM, MarCom. Glenn Poulos (13:24) Yeah. KK Anderson (13:34) every kind of tech you could possibly want to support sales and marketing. And it almost got to a point where everything was so automated and so robotic that, you know, we lost the humanness, right? And now here we are on the other, we've swung all the way back thanks to AI. And, you know, it's like AI can speed things up, but trust still closes deals. And so, you know, Glenn Poulos (13:46) Yeah. Yeah. KK Anderson (13:56) I love this analogy, this idea that AI should be your assistant because what must always stay human is the connection. I've quoted him before, but Rory Baden who runs Brand Builders Group, he always says that your humanness is now your greatest uniqueness. That's awesome. Yeah. Glenn Poulos (14:00) Yeah. That's awesome. awesome. Yeah. The, saw an interesting spec this morning where. And it really resonated with me is that YouTube now is spending the most of its time filtering out all the AI clips because, and, and I'm like, really? And then it went on to say like, you're probably still seeing a ton of them, but you have no idea how many they're filtering out of the babies in danger. You know what I mean? And all the baby dancing and, and the, there is obviously the AI stuff, right? Or like people lying with tigers and bears and things, and it's all AI generated and it's just polluting YouTube. to the point where they're seeing some of their core user base like log off because there's no longer, there's no longer a value. It's just like, this is all AI. I'm not getting anything from it. It's not even real. Like I don't want to be a part of it. Right. So YouTube's like, uh, addressing that as much as they can, but you, individual can use AI to create an amazing content that isn't babies dancing on gorillas or whatever, you know, and get a lot of value out of it, right? But it has to be human. Yeah. Yeah. KK Anderson (15:12) and you make it human, you make it human and it's super powerful. I couldn't agree more. Glenn Poulos (15:18) Yeah. Mark (15:20) All right, well, we're coming towards the end here and we're moving to the area that KK and I love the most. And that's some of the rapid fire questions that we do with every guest. They're all almost always the same or very close to the others. So first one, what was the first product or service you have ever sold? Glenn Poulos (15:23) Okay. So the first product that I sold was probably when I was nine, I got a job at my parents' motel. We lived in a motel. Our house was attached to the motel. And I sold rooms to strangers coming in off the street that needed a place to sleep. my second job as a teenager was I worked in a jewelry store selling jewelry and stuff like that. KK Anderson (15:59) Natural born salesman, Glenn Poulos (16:00) so. Mark (16:00) and what Glenn, that brings me and makes me think of the show Schitt's Creek. So if you haven't seen that. Glenn Poulos (16:06) So yeah, exactly the motel was exactly like Schitt's Creek, except our motel, our house was at the end, not in the middle. ⁓ but that's, that's where we, that was my life growing up, was living at Schitt's Creek. Absolutely. Yeah. Yeah. Mark (16:17) That's fun. That's fun. KK Anderson (16:19) That is awesome. Okay, what is the biggest mistake you've made in your career and what did you learn from it? Glenn Poulos (16:25) So, well, the biggest mistake I made in my career was I sold my first company on an all stock deal. And before the stock, before I had a chance to sell the stock as an insider, the company went bankrupt and I lost millions of dollars and gave them my company for free. So I realized that when you sell your business, you need a mostly cash deal. So. KK Anderson (16:46) it's hard to hear that. Glenn Poulos (16:46) Yeah. So that was why I started Gap Wireless because I sold my first company for quite a bit of money and we had three partners, but we only took stock and the company ended up having a lot of problems that we didn't realize or investigate, I guess. And they went bankrupt before we had a chance to sell our shares and we ended up broke basically. yeah, horrible story. ⁓ Mark (17:05) Yeah, but I'm KK Anderson (17:06) like you redeemed Mark (17:06) sure it was the baseline of all your success afterwards. So cool. Best piece of advice you have ever received from a mentor or a business partner? KK Anderson (17:06) yourself. Glenn Poulos (17:17) I guess, you got to learn the skills you want to learn how to follow up, ⁓ you know, you want to do research and rapport and whatever ⁓ the tools evolve over time. ⁓ But the base skills stay the same. You need to be good at the basics, right? it's Mark (17:32) Yeah, you know that that really resonates with me. I kind of remind people of that and remind myself of that. Maybe too much, but it's I mean the basics really drive everything else from there. Okay, I can't take this one from KK because it's our favorite one. Yeah. KK Anderson (17:45) I know, it's my favorite question. You've tried to take it from me, Mark. I'm getting in there. Glenn, Glenn Poulos (17:50) Okay. KK Anderson (17:54) advice you would give your 21-year-old self. Glenn Poulos (17:56) so the advice I would give my 21 year old self is that my favorite saying is you only get forever to make another impression, right? And my 21 year old self would say, no, mom said, you got to make a good first impression. And I'm like, yeah, that's right. Me. But every impression in your career needs to be treated as a first impression because imagine you're sitting beside your adversary at work. Mark (18:15) Mm-hmm. Glenn Poulos (18:19) sales territory and a growing expanding company, that's growing rapidly and people are moving up the ladder, right? You're sitting amongst your, your cohort of peers and the boss walks in and he sees you on Facebook, alt tabbing over to the CRM when he walks by and Sally's beside you and she's on the phone cranking out deals, right? A week later, CEO walks by quietly again notices you're on Instagram you look over you see me all tab into the CRM, right Sally's bringing the bell book in another order. Who do you think is? He's moving to senior sales rep, right and so Next thing is they send you to the trade shows, your feet are sore. You're whining It's kind of slow, you sneak away from the booth for a few hours. Nobody'll notice there's enough people there blah blah blah what you need to be doing is going into the aisle, pulling people into your booth so the boss can see it. When the, when it's slow, you want to be talking to the executives that are at the show with you, figure out, Hey, what makes, what are the five things I need to know about your product? Why are you here? What's so great about your stuff? What, how do I, how do I dominate and kill it? Right. And always be, always be making a good, first impression because that every impression is an impression and it's there, And so, and, and that's how you go from being a tow motor driver in the warehouse to being the CEO 40 years later. And there's many examples that we see all the time in the news and whatever of people that started in the warehouse and ended as the CEO of a major fortune 500 company or huge company, right? Mark (19:44) Yeah, very cool. All right, let's final finalize with our last question here. And what's that one sales habit or practice that you do every day or week without fail? Glenn Poulos (19:50) Sure. well, one of the ones would be, yeah, never fax the facts and never ship the shit. Right. And so if somebody asks me for something, and of course I made this up in the eighties, right. And so now I have to argue with all the other people like, well, don't think it's a fax machine. Yeah. So I'm like, well, whatever email doesn't rhyme with facts. Right. And so, but when someone calls me up and looks for something, KK Anderson (20:11) What the fax with you? Mark (20:13) Yeah, yeah, yeah. Glenn Poulos (20:21) I try to turn that into an opportunity to go visit them. Now, of course, I'm the president, I'm in the head office and I, United States is a big place or whatever, but it's, but generally speaking, it's a philosophy, right? Like if, if they're within driving distance and the guy from Duke energy asked me for something, I'm saying, you know what, I'm actually going by Duke and in a couple of days, can I drop it off? And so I never fax the facts and they say, we need a demo. Can you ship it in? I go, no, no, we're not allowed company policy. We have to deliver all demos. You have to set them up, plug them in and make sure you can push the buttons. Then we'll leave it with you. Right. And so, because what ends up happening is, is that you ship those demos. And oftentimes when you go to pick them up or they ship them back, your, your packing tape wasn't even opened. Right. And so never fax the facts and never ship the shit. Yeah. Mark (21:09) Great. Well, Glenn, this was a pleasure and thanks so much for taking the time with us. Thank you again for joining. Thank you, KK, for being my co-host and thank you to our incredible audience for being here every week like you are. All the best. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 114 - Building Repeatable Sales Success in Enterprise B2B with Glenn Poulos - Part 1 | 17 févr. 2026 | 00:25:02 | |
In this episode of Selling the Cloud, Glenn Poulos joins Mark and KK Anderson to break down what truly drives success in complex enterprise B2B sales. With over 40 years of experience selling technical solutions across telecom, wireless infrastructure, and power utilities, Glenn shares the practical frameworks behind building trust, mapping decision processes, and creating repeatable sales performance. Drawing from his book Never Sit in the Lobby and decades of hands-on leadership, Glenn explains why buyers in complex sales are not simply purchasing products. They are buying safety, trust, and confidence that their decision will not backfire. The conversation explores how to slow down early, uncover real risk, build consensus across multiple stakeholders, and implement disciplined follow-up that keeps long-cycle deals moving forward. If you are leading an enterprise sales team or looking to scale predictable revenue in complex markets, this episode delivers actionable insight you can apply immediately. What You’ll Learn: • Why complex buyers prioritize safety and trust over price and specs • How to build trust early by slowing down and asking better questions • The importance of mapping decision makers and influencers in enterprise deals • How to prevent deals from stalling due to unseen stakeholders • The habits that create sales repeatability and predictable results • Why disciplined follow-up is a competitive advantage • How to coach sales teams before, during, and after every call • Glenn’s philosophy of greed-based learning and how it accelerates product mastery Key Topics: • Trust-driven selling in high-risk B2B environments • Mapping enterprise decision processes • Mutual action planning and consensus building • Sales discipline and behavioral consistency • Curiosity, preparation, and active listening • Scaling sales teams through repeatable behaviors • Coaching frameworks for enterprise sales leaders Guest Spotlight: Glenn Poulos Glenn Poulos is an award-winning author, sales expert, and serial entrepreneur with more than four decades of experience in complex B2B selling. He is the co-founder of Gap Wireless, which he scaled from startup to a multi-million dollar distribution business serving North America’s mobile broadband and wireless infrastructure markets. In 2022, Gap Wireless was acquired by the organization, where Glenn stayed on as Executive Vice President and General Manager to help integrate and grow the combined entity, now operating as NWS Canada. Today, Glenn serves as President of ProgUSA, supporting US power utilities and service firms with electrical test and measurement equipment. He is also the author of Never Sit in the Lobby, a practical guide to winning and sustaining success in complex sales environments. 🎧 Listen now and follow Selling the Cloud for more conversations with leaders shaping enterprise sales, go to market strategy, and revenue growth. Subscribe wherever you get your podcasts. Mark (00:31) Welcome to today's episode of Selling the Cloud podcast. I'm excited to welcome Glenn Poulis, an award-winning author, sales expert, and serial entrepreneur with over 40 years of experience in complex B2B selling. Glenn is the co-founder of Gap Wireless, which he built from startup to a multi-million dollar distribution business serving the mobile broadband and wireless infrastructure markets. KK Anderson (00:57) and the infrastructure market. Mark (00:59) of North America. In 2022, GAP Wireless was acquired by Network Wireless Solutions, NWS, a portfolio company of green management. stayed on as the executive vice president and general manager to help integrate and grow the combined entity, which is now NWS Canada. Today, Glenn is president of Prague USA, a company that supports US power utilities and service firms with electrical test and measurement equipment. Thanks so much for joining us here, Glenn, and welcome. Glenn Poulos (01:31) Thanks, Mark. Great to be here. Mark (01:32) Cool, so today we'll explore four critical themes. First one, the core of complex B2B selling. How deals really get done and when the product is technical and the risk is high, how do you make sure that you build very strong efficiency into your selling model? Building sales repeatability. The habits and systems that make results predictable. Scaling and distribution business. We're gonna go a little deeper in that than we normally do. But really from startup to exit in the telecom and technology sectors. And then AI and technology and sales. Using tools without using the human connection. Topic one, just start with the B2B selling model as a whole. Glenn, your book, Never Sit in the Lobby, is full of field-tested wisdom from 40 years in technical sales. When you're selling complex products, whether it's wireless infrastructure, equipment, or power utility testing solutions, what fundamentally determines whether a buyer says yes or ultimately walks away? Glenn Poulos (02:32) Great question. So, and we're talking about complex sales, right? So, right. Okay. Yeah. So, you know, complex sales is a little different than just, you know, box selling or when you're just selling commodities like printers and computers or something. And, you know, when, when someone's buying something that's complex, right, they're not really buying a product. Mark (02:36) We are. Yes. Glenn Poulos (02:52) I always like to tell our people they're buying safety and solutions, right? Like they've got a problem. It could probably be solved in many ways with a complex solution, right? And it, and they're buying the safety that it, the, that decision will work, won't blow up in their face. No one's going to get fired. That's where the old, nobody got fired for buying IBM or Hewlett Packard came from, right? And that someone will stand beside them when things get hard, right? The specs matter. but trust matters more, right? That's the most important thing is the trust. And if a buyer doesn't feel safe saying yes, price doesn't become an issue, product doesn't become an issue, you're kind of dead in the water. And that's just a little, Looking back, it's like that's why a lot of times people would say to them, so I can't believe I didn't get the order. Like I had the best product, I had the best price, I had the best delivery, but they didn't trust you. rather, and again, I love saying, nobody got fired for buying IBM, right? They knew IBM was going to be there even if they were twice the price. And it's like, you know what? I'm going to buy IBM. Then I don't have to worry about it. I can say, Hey, I bought IBM. What do you want from me? Right? So that's kind of my first part of it. so the question is like, how do you build safety and trust, right? That's the key, you know, and so one of the key things that I always say is, you build it by slowing down early, right? You got to ask better questions. Listening more than talking the old God gave you two ears and one mouth you do the math, right and ⁓ the so listening more than talking, know, and you want to you want to be open honest and upfront about the risks, right and Challenge them with the risks a little bit so that they're out there and you're discussing the real risks that are in play and when the buyer you were trying to establish report to the point where the buyer feels feels you're helping them and not pushing them to buy Right. And so that's, that's, that's one aspect of it. Right. And, you know, some of the biggest mistakes people make are, you know, pushing price too early, trying to dive into specs for bigger, faster, wider, deeper, 20 % cheaper, you know, all those kinds of, you know, salesmen kind of things. Right. And pitching before understanding. And yeah. So. KK Anderson (04:53) So in a complex sale where it could go on for six to nine months and there's lots of dollars at stake as we were just discussing, what are some tricks or ways that you teach or talk about building consensus as you go through the sales process, as new people are added on into the conversation, as complexities increase? you know, everyone's got a different opinion. Like what are some ways that you build, build consensus, if you will. ⁓ Glenn Poulos (05:20) Okay, so or get to the order or whatever, right? I guess is yeah. So first, you got to understand the risk, right? Like that's the you got to present it to the customer, you got to present what the risks are to them and getting the job done. And you have to understand what the risks are to you and presenting your product at like your solution. You know, as being the as being the solution, right, you have to always remember early on and throughout it that buyers are not afraid of the price. And that proves itself out by just looking on the road and there's people that are driving Toyota Corollas and people that are driving Mercedes Benz S-Class, right? And so clearly some people just want to spend more on a car, right? And so they're afraid of being wrong, making the wrong decision. So you got to ask questions that uncover ⁓ what failure would look like if they make the wrong decision and who gets the blame if it happens, right? You're trying to identify that kind of stuff, right? And then second, This is so important, right? You wanna map the decision process, who influences, and there's many models and sales strategies out there. I don't teach these, but like the challenger model and what have you, where you're identifying the technical buyer, the financial influencer, the key decision maker and what have you. But you need to know, ⁓ especially the way I explain it to people is you have to look at the dollar value of the solution that you're selling. Let me, it's 50 K 500 K 5 million, 50 million. Right. And you have to say in the company that I'm selling it to who's signing that check, who's signing the PO, the authorization, the final, where does the buck stop? Right. Because if you're selling something that might be, you know, let's say, you know, 250 K and it's a $5 million company, it's probably the owner that's signing it. Right. But if it's, if it's a 250 K deal, but it's a $5 billion corporation. with offices around the world, chances are some vice president, regional manager, finance guy, whatever you need to map out and know exactly where you got to go to, find out why and where it's stuck. Right? So you're mapping the decision making who's the influencers, who decides and who could stop the deal. And, you know, and most of the time the complex deals fail because you ignored. the person you didn't know about or you were surprised late in the game who that was and that you never talked to. And sorry. KK Anderson (07:32) I think the key word I'm hearing you say, Glenn, here is mapping. And we are huge fans of the idea of a mutual action plan or map, right? And so, and what's great about that is that not only are you mapping out the strategy of what's going to happen over the next six to nine months and who needs to be involved and who can say yes and who's going on vacation when, so you don't, you're not shocked at the end of the quarter when you're not getting a signature because you're Glenn Poulos (07:42) Nice. Yeah, good. Yeah. KK Anderson (07:58) You know, the signer is in Barbados, right? But the trick I would think is, and I believe, is making sure that it's mutual. And so to the extent that you can really build trust by saying, hey, here's our plan, you know, when you have a champion, I think that action of creating a mutual action plan helps to really build that trust and build that relationship. And then as you're bringing new people in, it becomes easier because you're all singing from the same song sheet. Glenn Poulos (08:23) yeah, for sure. The there's a funny story in my I always like to say shameless plug for the book, right? But in my book, right, there's a story about a guy that sells high value tow motors, right? Like our forklift, some people call them. And these things are massively expensive machines, right? And $120,000 or whatever. And so, in the stories about a guy who shows up, he and he's trying to sell a company tow motors, right? And he works for Toyota. And so he looks at the organization and he says to himself, so they need like four machines. That's like half a million dollars. It's probably the CEO that's gonna, that could be the CEO that signs off on that, right? So what does he do? He calls the CEO and he says, hey, it's Glenn from Acme tow motors, right? You know, we want to show you the, these tow motors, they, know you're using Kawasaki, but you know, we'd love to get these in for a trial or whatever. the guys, what are you talking about? Glenn? says, I don't get involved with tow motors. the vice president of warehousing is responsible for all that stuff. That's Jack. I'm like, all right. Okay. Yeah. Fine. No problem. Let me give Jack a call. So call Jack. Jack, it's Glenn. was just on the phone with the CEO. He told me I really needed to get your attention. We've got these tow motors, right? We know you're looking at a few, you know, know you're a coil stock user. We want to show you the Toyota. says, Glenn, stop wasting my time. says, I don't get involved in that stuff. Right? I've got a director of warehousing. That's Bob. Right? Why wasting my time? Bob, Bob, I've been on the phone all day with the CEO, the vice president. They told me if I don't get these machines in front of you, you know, lickety split. Mark (09:41) . Glenn Poulos (09:53) He's going to have my head. Right. And so, and he's like, glad, come on. I'm a director. I don't have time to look at tow motors. You got to talk to the warehouse manager. You know, that's Jack. Right. So Jack called Jack. Yeah. Of course, Jack refers you to the shop steward or whatever the floor manager or whatever. And before you know it, you're bringing in the tow motors. You say, look, I've been on the phone with the CEO, the vice president, the director, the manager, the, you know, the foreman. And now, you know, here they are. Right. So then you bring the machines to the, to the work. The whole idea behind that story is that at any point you can call anyone in the stack and figure out where the deal's stuck, right? And so, and one of the things I always like to do, and again, this is a metaphor, right? But it's very valuable and I've used it my whole life, right? Is he call the CEO and you say, look, I know you don't get involved in this stuff, but I got to, you know, I know you're putting half a million dollars of machines on the floor. got my machine down here and we're doing circles around Kawasaki right now. Like you need to come down here and have a look at this. And he's like, I need two minutes. That's it. And you know what the guy's saying? I'm tow motor ripping around my warehouse, brand new, whatever. I'm going to come have a look. And the CEO walks in and the, you know, all these people are like, what the heck's the CEO doing here or whatever. Right. And, but at any point you can call the CEO and say, why is my deal stuck? And then he says, well, Glenn, he says, I forgot to tell you, know, we have a deal with the national deal with Kawasaki and it doesn't expire until 2027 and And I mean, you want to figure that out from that guy as soon as possible. And hopefully before you delivered a demo or whatever. And, ⁓ but I like to try to give people real world examples of how it plays out and, what happens on the opposite side when people don't do it right is, you know, your sales guy says, ⁓ I, you know, I got an appointment to do the demos and it's now with the powers that be. Right. He, gave his report to the powers that be. He sent it upstairs, right? And all that stuff. I'm like, when salesmen tell me that makes me want to like blow my brains out, right? I'm like, who's the powers that be? You know, the people upstairs, right? And I'm like, no, those are the people that are buying your competitor. And you're going to come to me in a few weeks and tell me you lost, right? If you don't know that everyone in the chain and you can't call them, then you blew it. And the problem is you have to start at the top. and go down because you can't like start with the foreman and then he gives you the old powers that be and then start calling up the stack and alienating the guys below, right? You want to be pushed down, not up, right? And because, you know, it's like, how dare you call my boss, you know? And, and so that's like a real world ⁓ scenario of how it can play out in a way that people can relate to, right? So, and ⁓ yeah. And so I kind of got a little off topic. The other thing was, you you were asking me about, you know, how do you, how do you ramp it over time? Right. And, know, you, you always want to make sure all the trust is built before the brochures in the, and the pitching and the, know, you want to be sharing your insights and then you want to be playing to what you've learned. And you want to, you want to demonstrate and, and prove out only to that. Cause oftentimes mistakes I see guys make. is like a good example would be myself, but don't make the mistake of using yourself as marketing data because you'll probably be wrong. But when it comes to cars, I love Mercedes-Benz, but Mercedes-Benz is known for the speed and the AMG ⁓ motors in the car, and there's a lot of ⁓ very fast and very powerful cars, but that's not why I like Mercedes, right? I don't drive them fast. I mean, I do whatever the, whatever the proportional amount over the speed limit I'm able to drive is that's what I set the cruise at. And I, and I never, don't, you know, I'm not worried about dropping it down into third and going, you know, I'm what I like is the luxury and the comfort. I don't care about the speed. So, but most salesmen would start laying on 500 horsepower, dual torque, overhead cam, dual turbos, you know, new zero to 60. don't care. I'm already lost and I already know that you've not built rapport with me. Right? So how is it, he's not presenting to, you know, to sell $120,000 car to someone, you know, in the right way. Cause he didn't figure out what part of it's important to me. I don't even need to hear about the speed or the motor size. I don't actually care. You know, and it's the same with many, many things, you know, and, but people are they're scared and nervous. And so they kind of like want to drop back to like the training, the bullet points they learned in the training class. You know, we do this, we do this, we do this, we do this, right? Whereas you want to be stopping talking and start listening. What is it you need to do with these? Why am I here? What is your biggest problem you're trying to solve? You know, is it quality throughput, timing, speed, you know, power, you know, accuracy, know, resolution. Whatever, you know, so sorry, I rambled. I said it. KK Anderson (14:40) makes perfect sense. It really does. And like it, this kind of is the perfect bridge into our second topic, which is around building sales repeatability, right? And the habits, you talk a lot about habits. As a matter of fact, on LinkedIn, I reposted one of your posts this morning around the habits and the systems that make results predictable. And so in your book, you outline 57 winning sales factors and that's a lot of variables. And so when leaders hear that, their first reaction is probably something along the lines of how do I make 57 factors repeatable? So if you had to distill it down, are there three to five that are the most? Yeah. Glenn Poulos (15:07) Yeah. Sure. Yeah. I love him. Yeah. Yeah, sure. Yeah. yeah. And so, and just to touch on the 57 and the number, and I mean, obviously I'm not gonna run off 57 of anything on the show, but the... KK Anderson (15:31) Yeah. Glenn Poulos (15:34) But these are factors that cover the whole litany of things you have to do during the day and throughout your career in order to be successful running the business and in sales, right? And so it's selling and so it's how to get act and stay in front of your customers and be a pleasure to do business with always, right? And yet you have to be a pleasure to do business with because most big customers are repeat customers. And so it's not a one and done, right? It's not like, you can be cranky with them and get the deal and then you're good because you got the deal because All the customers I work with, they're 20 year investments of time, right? They buy with for me forever, right? And the company Gap Wireless, I started in 2007 and the first call I made, you know, was a lady named Arefa and I was still making calls to Arefa the day I left, 20 years later, 18 years later, right? and so the... And so then another insight into the 57 is these are rules that I always follow. I don't break my own rules. Right. And so, and the book never sit in the lobby. That's one of them never sit in the lobby. Right. And we can talk about that later. If there's time. Why, why I say that. but the habits to be repeatable, I guess would boil down to as first as you want to be prepared. Right. And so you've done your research, you know, you're selling this kind of a system to this kind of a company. What does this company do? How does this company make its money? Because they don't care about your system, right? They care about whatever goes out their back door and with the invoice and what they get paid for doing, right? And so again, a quick story. I always like to put this in the real world so people understand, well, what do you mean, right? Or it's not just hyperbole that I'm saying. It's like Xerox, right? You're calling on Xerox, right? Well, Xerox makes photocopiers. And so I need to figure out about, you know, how they can make better photocopiers. No, that's actually not what they do. They're a bank, right? They're a finance company. They make all their money, you know, on either one leasing you a machine or two, selling you costs per page, right? They don't come and tell you that that photocopier is 40 grand. They tell you it's four cents a page, eight cents a page, nine cents a page, minimum thousand pages per month, you know. And so You need to understand how the company makes money. So you want to be prepared, right? ⁓ You know, so, and you want to keep and always be prepared, right? Second thing in the repeatability stack is, you know, discipline follow up. And so this is where people get scared, lazy. They're just averse to it. Right. And so, so often you say to him, like, did you follow up? And he's like, yeah, I, I, I call them. And okay, did you call him? Okay. Did he answer? No. I left the voicemail. Okay. Did he, what'd you say on the voicemail? And you know, maybe he says it and again, there's rules on leaving voicemails in the book, but, then I'm like, okay, well then what'd do? He says, well, I sent him an email. Okay. Okay. Did he reply back? And no, no, he didn't reply back. And so I'm like, okay, so let me get this right. So you emailed the guy, didn't reply. So you call them, left a voicemail. He never phoned you back. And so, so basically you'd never talked to the guy. Right? Kind of thing. But you have to, you have to be able to figure out ways and means to be able to follow up and stay on top of it. And what ends up happening is, is, know, you call him, he doesn't answer. So you send him an email and then you say, follow up Monday, right? Monday comes at a fight with your spouse. You're not in a good mood. You didn't get enough coffee. You don't really feel like making the call. You snooze it to the next day. And then the next day you have meetings. You're like, I didn't do the call. Damn snooze it to the following Monday. Now you're two weeks away. Right? Like, I mean, that's not discipline, it's avoidance and it happens like a thousand times over every week with a thousand salespeople. Right? And so you want to be disciplined. and whatever that means. Right. And, you know, and the deals are always one after the meeting. Right. And so, third, you want to be taking good notes. You want to be, and then reflecting on what's happened, what's happening. you want to be reviewing sort of the conversations and then looking insights. And that's where I teach, sympathy, empathy and compassion, right. And trying, trying to put yourself in the customer's shoes, figuring out what they're dealing with, et cetera, right. And applying the right technique at the right time. and you want to be reflecting on those conversations, like I said, and taking the notes and following them up. Right. And then, and so those are sort of the keys, but some of the other elements, you know, was curiosity and ⁓ you never want to assume, you know, there's the horror story where I in the book about me assuming something about a guy and I just made him so mad by my assumption. And I was just very difficult to establish rapport after that. Right. And and you want to be consistent. Right. You want to always be a pleasure to do business with, even when they say you're not getting the order. because you'll get the next one or you had the one before or you want to be called back in a year from now because you don't want them to not call you because they know they upset you and they're scared of you, right? It's like, I'm not calling Glenn. Pardon my language. He snapped the last time we, you know, we couldn't buy from him because of a, you know, a minor issue and, you know, a technical anomaly or whatever, right? So that's how I beat repeat. That's how I build repeatability. Mark (20:22) Yeah. Perfect, good, well, yeah, those are some good thoughts and ideas. So Glenn, you've built multiple companies and have hired and managed dozens, maybe even hundreds of salespeople over the years. When you're trying to scale a sales organization, when you're trying to bring these principles into a team, how do you transfer what's in your head and in your book to the team? How do you make your process you know, more easily teachable. Glenn Poulos (20:50) So. Well, you know, how do I transfer? mean, you have to break it up into the behavior that you want and not just the talent, right? So repeatable behaviors create talent of itself, right? That's why when you look at sports people and all that, they're always doing the basics, right? You know, it's like, they're like NFL players. Why do they have to keep doing that same thing with the running with the legs and the tires? And because, you know, because they're building, they're building the talent through a set of behaviors, right? So, and you you wanna be teaching what you do before, during and after every call, right? So we're gonna go in there, we need to figure out what it is the problem is, know, da da da da. So then you're trying to coach them during the call. And then after the call, you're like, Jack, what went wrong on that call? Right. ⁓ I was talking too much. didn't, I saw there was an opening. didn't take it. You know, we could have got a referral to that. You know, he kind of deflected that it was another team was involved, but you didn't get any names, you know, so you want to be, you want to be, coaching before, during, and after. Right. and you know, I always like to say, you know, Like the methodologies are the frameworks, but the winning factors are the behaviors that you follow. And you can follow a methodology and still lose because you, I would say you ignore the basics like respect, timing, preparation, follow up, what have you, right? And they all build on each other and compound into being more of a disaster the more you fail at that, right? And so, you know, and then you're like, then the question is like, how do you pass, how do you teach people and how do you pass it on? Right. And so one of them, that's a highly personalized ones, it's from the book, right. It's my, my philosophy of greed based learning. Right. And so, and again, I hope, hope I'm not going on too far if I'm spending too much time on each one of these topics, but, greed based learning is the key to how I've sold technical products for 40 years. Right. And I, and I realized that. you know, a long time ago and, and I allow it to, I allow it to, to work in my day to day, you know, behaviors, right? So what greed based learning is, is that, and again, I use an analogy, I love to use buying car analogies because everyone has a car. And so Like I told you earlier, I don't care about the horsepowers and stuff on cars or whatever, right? And don't even actually care. I just want to be comfortable in a nice car and whatever with the gadgets and the cruise and all that. Right. But, you know, and so I don't really know a lot about cars where other guys know every spec off the top of their head. Right. But every four years, you know, I get a new car or something like that. Right. Well, you can bet for the, for that very small snippet of time. And for me, I'm probably going to be looking at, you know, Mercedes, BMW, Volvo, something like that, right? And you think I can't go home and talk to my spouse and spout off every speck of those cars that I'm looking at off the top of my head with little need for memory, right? And it's a thing that I call, that's why I call it greed-based learning because my greedy little nature knows I'm getting a car at the end of it, right? And I'm able to absorb those facts painlessly and effortlessly. Right. Because I'm getting something at the end of it. Whereas if someone just said, here's a 40 car manufacturers in the, or, car companies in the U S right. Learn all the, learn all the facts about all these 40 cars or whatever. be, it would be categorically impossible for me. There's no win in it for me. Right. And so, what you want to do is you want to sort of defer your learning until it's relevant to something where there's something in it for you. And then it becomes effortless. Right. You're selling a million dollar system to a company you can bet that you're going to be able to remember the facts because you know what your commission is on it. Right. And so I show these guys how to allow greed based learning and gals to in their, in their career. Right. And so it's just a little, a little gamification on the, on, on learning that I do. Right. and if I have an important call with an important piece of equipment on a company and I don't really know the box, And whatever I'll call the manufacturer, I'll call the product manager. I'll say, give me the five things they need to know in order to be a rock star with this product. And if I get stuck, I'll call you from the, from the customer site. And, and they're like, well, it's this, this, this, this, and this, right? And I'm like, look, I'm not the expert, but these are the things, you know, and then you're again, you're probing and learning and what have you. Right. So, that's the basics of it. Mark (24:52) No, think See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 113 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 2 | 10 févr. 2026 | 00:22:27 | |
In Part 2 of this Selling the Cloud conversation, Mark Petruzzi and KK Anderson continue their discussion with Jason Baumgarten, diving deeper into how boards think, govern, and evaluate senior sales leaders once they reach the highest levels of leadership. Jason unpacks why boards care less about confidence and more about clarity, learning, and diagnosis. He explains how CROs must evolve from operators into enterprise leaders who understand risk, governance, succession planning, and investor expectations. The conversation also explores what executive vetting really looks like at the senior level, how boards assess integrity and credibility over time, and why understanding context behind results matters more than headline numbers. This episode is essential listening for CROs, CEOs, and revenue leaders aspiring to board seats or the CEO role. What You’ll Learn:
Key Topics:
Guest Spotlight: Jason Baumgarten Jason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he advises boards, investors, and executive teams on leadership selection, succession planning, and governance. He has led more than 250 CEO and board transitions and brings deep expertise in evaluating executive readiness, integrity, and long-term leadership impact. Resources & Mentions:
🎧 Listen now and follow Selling the Cloud for deeper conversations on executive leadership, governance, and what it truly takes to move from CRO to CEO. KK Anderson (00:31) Let's talk about board governance for sales leaders. Jason, sales leaders are, as we've talked about, they're heads down. They're working on pipeline. They're working on deals. But investor expectations are ultimately what shape the pressure that's behind the number and behind the quarter. so talk to us about why. should sales leaders care about board governance? What changes when they start thinking like the investors instead of thinking just as operators? Jason Baumgarten (00:56) So it's hard. I don't have a perfect one size fits all question because obviously every situation is different and every sales leader and company is in a different position. But I would say going back to this concept of empathy of the individuals, if you're an investor that has to return to your LPs, you've got a job to do. You're showing up and trying to explain how this investment is going to drive LP returns. And I think the first and foremost thing is for people to understand that individual connection that somebody showing up in your boardroom has. Like why does it matter to them? what's driving their anxiety, their pressure, their sense of, combated and this at times or, or, skepticism that you're doing good job. So that's one. think the second thing is really bringing that mindset of what have we learned, not just what have we achieved. the problem is half, I would argue frequently sales leaders when they are successful, they have no idea why. And when they are unsuccessful, they have no idea why it's like I walk into a CEO's office and they say, look, the stock price is up. And I'm like, why? It's a good rumor going around. So I think the reality is it's really important to hit your numbers. It's even more important to know why you hit your numbers, because that allows you to do it again. And when you don't hit your numbers, your board and your investors are going to be disappointed. But the critical question is, can you understand why? and articulate what you're going to do about it, even if you don't have the perfect solution, you can bring them into the problem with you and say, here's what we believe happened. Here's now what we're trying. If you have other suggestions or people that can help us unpack this, we're all ears. I think the people who often lose their boards are the ones whose confidence overpowers curiosity or humility. And they come in just sort of claiming that they're going to hit their numbers next time. Because the problem is, if you succeed, great. But if you miss again, you've now lost the confidence of the group. And the problem is, you don't have perfect control over your outcome, right? You could walk into a market that's falling, and you haven't figured out that it's falling yet. So what are you going to do to sort of unpack that? Now, you know, listen, at the end of the day, nobody likes to be told that the numbers aren't good. But they want to they want to understand why too, because they don't want to be surprised. if it's a bigger problem or it's a structural problem that they don't understand. And salespeople are often the tip of the spear because that customer intimacy, they understand. But for example, are you seeking out that information? Are you trying to figure out what went wrong? if you were sure you were going to close a deal and you didn't, are you really honestly asking what went wrong so that you can diagnose it? Or are you trying to explain away the miss? And I think people get caught up in the game of ⁓ performative explanation of like, let me look good explaining the miss as opposed to being genuine and saying, I put the wrong person on the deal, or I was overly optimistic and I didn't realize we actually had five competitors well positioned and I thought we had won or our pricing was a total miss, right? Whatever it is, really being honest about trying to figure that out, I think goes a long way versus trying to, use bravado or confidence to convince them that it'll just be better next time. Because if you're right, great, but you don't really build your case as an executive. Whereas when you can really bring them into what happened and what you've learned from it, what you're going to try differently, what the team's trying differently, you build an enormous amount of trust and confidence that you're on. that you know what you're doing and you're ready to tackle it again. Mark Petruzzi (04:13) So Jason, what does thinking about governance actually mean for a working CRO? How does it change how you run your organization? Jason Baumgarten (04:22) So it's a really good question and it depends on the governance of company, but I would say there's probably three things that should circle in your mindset from time to time. One is risk. Most sales leaders don't think a whole lot about risk. They think about missing a number, but they don't think about what is the risk of that? What is the broader risk? What is the risk of serving a particular customer? What's the risk of a hire? So first and foremost, it's, part of the board's role is to think about what could go wrong and how do we mitigate that. So I think when you start thinking about it with a governance lens, you do temper some of the things you might do and say, that actually could be risky. We, something bad could happen to the company if we pursue that approach. So I think that's one is just this mindset that risk matters. By the way, there's another side of that, which is the risk of inaction, right? The risk of not doing can also come back. So I think that's one. I think the second thing is that it does get you in this stakeholder mindset of beyond the incentive plan, beyond the annual comp structure, beyond the value of your equity in the secondary market right now. What is the bigger picture of what's going on here? And what am I really solving for? There was a book years ago, probably 30 years ago called How to Become a CEO. And I always remember this line from it. said, Your job is to make your boss look good and your boss's boss look even better. And, one of the things sales leaders should think about is, you know, the board isn't ideally is not there to pass judgment and be critical. They're actually there to help you be successful. There's nothing they want more. So how do you think about, your role in all of that and how it ties into the broader trajectory of what the company is trying to do again, so that you can connect those dots and you can, you can be a more holistic leader. And then I would say the third thing that board spent a lot of time thinking about, and I think is helpful for sales leaders to think about is succession planning. And the reason it's important is if you've got a lot of aspiration, you're hopefully thinking about what you want to do next. But it also helps you think a little bit more about your team and how you're developing your team. And I think boards think about that because it's one of the things that, you know, probably stresses them out more than anything is not if it's going badly, but when it's going well, that somebody is going to walk out the door or something's going to happen. And so I think showing that maturity of planning ahead and planning for, Hey, what happens when I'm not around? You know, who's gonna, who's gonna run the play. KK Anderson (06:32) Well, speaking of that next, getting to that next level, a lot of sales leaders say that they themselves aspire to sit on a board one day, And few understand how boards actually select members when they're looking to add a director and specifically one with a revenue background, right? Talk to us about what boards are looking for when they're tapping a sales leader, someone with sales leadership experience to sit on that board. And then how can the sales leaders today, in succession planning, I suppose, right, but for themselves, like how can they begin to prepare and plan toward that ultimate goal of being able to sit on a board? Jason Baumgarten (07:10) Yeah. So I would say that there's a couple of things. One is there's, venture boards, there's private equity boards, there's distressed asset boards, there's public boards, a lot of different kinds of boards out there. So the first thing is, they're not all the same. And they're not all transferable skill sets. The more established the board, the more it's about governance, the more the board is, you know, maybe for a smaller company, then often the board is a little bit more about I would say it's the team you can't yet afford to hire, right? It's the folks that are just, you couldn't bring them on to your executive team, but you want their assistance, you want their help, and you want them rowing on your side. So the first thing is to really understand that those are all different boards or different selection processes or different approaches. Within that spectrum, I would say the smaller boards are looking at you as more the person who's a step ahead, right? Who's seen a movie they're about to go to and they want the advice and counsel. And in that case, it's really just about being a excellent near day job and be showing up knowing you don't have every answer and there's other people in the room are going to have good answers. And, you're there to be of service to the, to the management team and to the investors, typically investors, as you get more seen, you know, as you get more, to the established boards, either very large private equity, a pre IPO or a public board, it is a little bit more about governance. And then the question is, you know, The way that those boards operate is typically they've a very, very defined spec. They'll come in and say, we need a, CFO who has experience in Latin America, specifically Brazil, who has also worked in Japan and who has deep channel experience and Revrec, with Revrec and channel experience. They don't come to us and say, need a good person. Right. And so The first thing is recognizing that just because they're seeking a board member doesn't mean it's you. The second step is figuring out, when they do need a sales leader, what are the kinds of topics they're often dealing with? And how do you best position yourself as somebody who's thoughtful, who is advancing the state of the art in sales leadership, in revenue leadership more broadly, in the industry you're in more broadly, so that people see you as an expert. a little bit beyond your current, domain or your professional experience. And then also recognize that part of the role on the board is not just to bring your expertise, but especially as you get to the bigger boards to be thoughtful about risk, ⁓ &A, succession planning, all of these other topics that boards are responsible for. Even understanding that those are the topics boards talk about. I mean, I always say to somebody says, I want to be on a board, I'm like, do you know what's on a board agenda? And they're like, no. And I'm like, well, that's a good first step, right? Like, KK Anderson (09:32) You Jason Baumgarten (09:34) And not in a bad way, but like, go to your own board and figure out, go to your board members and ask them if what they would advise, right? Do they see you as somebody who can contribute to a board, get to know your own board as a first step. I think then really thinking about the then really thinking about how do you bring that perspective because they don't, they're not interviewing you for how excellent you are at meeting a quarter or Mark Petruzzi (09:34) Thank you. Jason Baumgarten (09:57) breaking into a new account because that's not your job as a board member. They're probably going to interview you about, if they're if they're contemplating in organic growth, they're going to say, great, how have you thought about the big picture integrating sales teams at scale? How have you thought about that? Or how have you thought about advising a team that's that's, you know, going through a business model transformation or a pricing transformation? They want to see that you can think at a more strategic and advisory level versus being a great operator. you know, and I would say, I get asked a lot about executive classes and about trainings, they will not help you get on a board. But they may help you sound like you know what a board does. And they may make you more capable if you are lucky enough to get on a board. At a minimum, find a book about boards and read it. They're usually not the most scintillating reading to warn you ahead of time, there's no blockbuster movie about governance. said to anyone ever. But there is, you know, there's some wonderful books that take you through the legal responsibilities of a board. And if you're serious about it, you should you should do that again, not because it helps you get on a board, not because anyone's going to select your resume, because you added your LinkedIn that you read the ABA manual on boards. But because when you're talking to a head of non gov or an investor, they're going to go, this person actually sounds seems to understand what we do. Mark Petruzzi (11:11) Excellent. Well, Jason, I can't finish up here without having you go a little more general on all this around, landing your next role, topic four. what really matters at the senior executive level. So, you've also said out there in some of your publications that salespeople think they can BS their way to better gigs. But at senior levels, reference in referencing gets really intense. for those who haven't been through a significant vetting process, what changes at that next level? Jason Baumgarten (11:44) And by the way, I wish that was only sales leaders. think many, many leaders think they can talk their way through the next role. The reality is, I mean, just to give you a perspective, for a senior executive, typically a company, you know, working with us, for example, may take 20 to 25 references. They may do a four to eight hour assessment. They may do a psychological assessment on top of that. Mark Petruzzi (11:50) Ha Jason Baumgarten (12:07) They are typically going to do a background investigative check that doesn't just say that you had a job, but they will be sending representatives to call on every courthouse in every city you've lived in to make sure there weren't cases that were dismissed that didn't make it to the digital databases. They will screen your social media posts for inappropriate comments. They will look for any shred of evidence that you have done things that are unethical. or that will cause risk or challenge to the organization. All of that, and then there's the bevy of actual interviews. And then typically a case study or a working session, typically a few dinners or lunches or breakfast. So by the time you're done with that process, most likely they're going to find out what they're going to find out. So that's a couple things. One is how do you get a great gig be excellent at your current gig? Second, really try to build bridges along your career. And even if you don't like somebody, don't make a big deal of it because it'll come back to get you. Third, be really upfront with anyone trying to hire you about what didn't go well and why, because they're going to find out. And so it's much better to say, hey, you know what, that job that was two years, it actually was not a success. I learned a ton. Here's what I learned. I had a boss that just was oil and water. Here's what happened. Because if you try to position it as No, no, was really successful. And I do 15 references and everyone says you were an ogre. It's not explainable because then it's an ethical lapse. It's an integrity lapse. So that would be, kind of what the process looks like. Now, there are plenty of roles where it's, I called a buddy and the buddy vouched for me and I got the job. And, you that's awesome. That still happens. But at the more senior levels, I would say, generally speaking, expect that level of scrutiny and process. Certainly for a CO role, if not a CRO KK Anderson (13:47) Wow. Yeah, that sounds exhausting. Jason Baumgarten (13:51) Yeah. And by the way, even customers, I have had numerous examples in the last decade plus where somebody says, I built the so-and-so account. Well, guess what? If that CEO is a good friend, which chances are we know them or our clients know them, we're going to call on them. If you're not working right now, we're going to just ask them flat out what the story was. But if you're working, One of the most powerful reference questions is, hey, Mark, you get called on by a lot of salespeople, a lot of software companies. Who do you make time for? Boy, don't make, I now know you didn't mention Johnny, but Johnny's told me he's your best friend. So now I'm saying, well, Mark, you sounds like you've done a lot with these four or five companies. Is that true? No, you don't mention Johnny's company again, strike two, strike three. Well, I know you're not mentioning, XYZ company, but what about Johnny, Chris and Mary? You seem to know them all on LinkedIn. they people you really, I don't even know who that person is. Well, now you've lost me at the company knows me. I'm important to the company and I actually have personal relationship and don't underestimate those calls that will happen, particularly investors. They will do forensic referencing where they'll take that. They'll go through your resume and look for every connection you've ever every client you've listed, every connection, everything you've done. And then the other is probably goes without saying, but the other Holy Grail is just never, ever, ever mistake. published document, I mean, in any format, but particularly anything that is, you where you're really putting your name to that, that you did that, whether it's a degree, a job title, we've, found this recently, where people are being a little loose and fast with job titles, just stick to the facts. You don't need to elaborate. Don't put a, don't put a, P and L leader, if you weren't one, don't put a general manager, if you're really not one, don't elaborate because You may not be thinking about it now, but in 10, 15 years, that'll catch up to you. We had an executive years ago who overstated something probably 20 years at a company, but in his official biography with the company, he had overstated something and he didn't even remember doing it. It was when he was like, you know, in his twenties and years and years later, he went to switch roles in a very, very senior role and this became a real issue for him and his entire career almost unraveled because of this thing he did 30 years earlier. And he didn't even remember, I mean, it wasn't like he got anything from it. He wasn't trying to obfuscate down the road. He just did it unthinkingly as a 23 year old, you know, guy filling out a corporate form and it caught up with him. KK Anderson (16:14) Wow. So speaking of the resume, you know, and sales leaders, you know, lot of, a lot of sales executives are going to lead with the numbers on their resume. So when what firm like yours is starting to dig deeper, like what are you really wanting to understand about those, like how those results were achieved? Right? Like what, what do you want? What do you want? How do you want the sales leaders to show up and talk about those results and those outcomes? Jason Baumgarten (16:37) Yeah, there's a few things. First of all, what was going, what was the context, right? What was going on around that industry? Are you actually showing me the best numbers you have, but they're the worst numbers of any of your competitors? So the more you understand the competitive landscape and your peer group, the better. The second is what was the momentum when you caught it, right? If it was going up 30%, now it's going up 20, you can tell me how amazing you are that you hit 20, but actually you decelerated the rate of growth. So I want to understand what happened because that's actually a story of negative, you know, negative impact, even though it's a positive number. The third thing is do you seem to understand what you did to achieve those numbers? Right? And that's a recurring theme that you'll hear from me. But, you know, do you have clarity as to what you did? One of the most common things is people who are in jobs for very short amounts of time, but the numbers were good. They're like, Oh, yeah, I was there 18 months, but wow, we crushed it. crushed it so amazingly, I could go on to the next role. And I'm like, let's unpack how you crushed it in 18 months, because it took you six months to find out what the name of the people what, where the bathroom was, and what the names of everyone on the team was, and what the products were all called, and blah, blah, blah. Any human being, takes months just to normalize. And then it probably took you three to six months to find your next gig. So in that short time, you were actually working enough to speed, what did you do? And if the answer is kind of fuzzy, it's not that I worry that they didn't have a great 18 month tenure, I worry that they're so busy trying to tell me that they did something they didn't, that that demonstrates how they show up as a leader, and how they show how they show up as a as a colleague on a team. And that's way more concerning than that they didn't have an amazing 18. Anyone who's at somewhere 18 months, and probably it wasn't an amazing run. I mean, the odds are good that if you're there less than two years, Something went wrong, whether it was up to you or not. Something probably went a little off. That's fine. Just own it. Just be like, hey, that wasn't so good. Or it was so good that it led to this next thing coming out of the blue. But also have the humility to be like, I inherited a great situation, didn't screw it up, as opposed to saying I did everything and I'm amazing, because things just take time. I mean, in 12 months, you can't turn around that much. Mark Petruzzi (18:41) Jason, and thank goodness that companies are doing this and focusing and figuring out how they can get senior executives that are ethical and honest and trustworthy. Because if not, who knows what our general economy would look like. ⁓ Because it's one thing if you hire a sales rep who maybe is a little unethical, you figure it out, you you... you move on that individual. But if you hire your CEO, CRO, and Chief Operating Officer with those kind of backgrounds, it's going to come out. It's going to show up at some point. so I'm really glad to hear the, I've experienced it myself in the vetting process, but to hear you articulate it takes my understanding to an even greater level. Okay, we just have a couple minutes left. We love doing these rapid fire questions that we do with our guests and I'm really interested in hearing your responses on these. So what was the first product or service you ever sold? Jason Baumgarten (19:43) I sold jewelry. I bought jewelry wholesale and sold it at street fairs. Mark Petruzzi (19:48) I like that. KK Anderson (19:49) That is so cool. How old were you when you did that? Jason Baumgarten (19:49) And you learn a lot selling jewelry. I was like 14. KK Anderson (19:52) Really cool, wow. You knew you would be going to Stanford at that point. The entrepreneur at 14. ⁓ Jason Baumgarten (19:57) ⁓ I knew I loved business. I knew I loved business. KK Anderson (20:00) Jason, who's your favorite CEO or business leader that you've worked with over your career? Jason Baumgarten (20:05) You know, I have so many, this one's really hard. I actually find that I learned so much from so many of the CEOs I work with and they're all amazing at certain things and they all have ⁓ foibles. I think that rather than share the person, I'll share the story. A CEO that has had an unbelievable career. He always takes the time to learn and get better. And He's got coaches, he's got advisors, he's got, but he's just a learner. you know, he's one of these guys, it's a household name, but you reach out to him and he says, I'm busy. sitting down with a 24 year old to learn about how to do better prompting. I'm like, you're retired. What are you doing? He's, I got to get good at this. It's really important. And I just, I think there's a amazing, the CEOs who keep wanting to get better are just really inspiring. Mark Petruzzi (20:51) Yeah. So a resource every aspiring board member should use. Jason Baumgarten (20:55) their network. Mark Petruzzi (20:56) Excellent. KK Anderson (20:57) That's a good one. Okay, my favorite question is not listed here, so I'm gonna go out on the limb and say it anyway. Jason, what advice would you give your 21 year old self? Jason Baumgarten (21:07) Take more risk. I think that's the thing that we underestimate when we're young is that you can recover, can do, you can get a do over. People are very tolerant of youthful, ⁓ you know, behavior. don't mean behaviors in a social sense, but you know, just try to start your own company, try to join a startup that's a high flyer, try to, do something that's risky, because when you get older, it's much harder to take risk for all kinds of reasons. So do it when you're young and within whatever is relevant to you. You might be the most risk-seeking person out there But you know, would say I think most people when they're young They squander good risk They take a lot of risk in their personal lives and not a lot of risk in their professional lives And I'd say take some professional risk Mark Petruzzi (21:47) Excellent. Well, Jason, thank you so much for your time, your great analysis and answers. We will add for our audience here, we'll add a bunch of show notes and make sure you get to read some of the good stuff that Jason has put out there and learn some more about him as well. yeah, so thank you, Jason. Thank you to our amazing audience. We so appreciate you and thank you to my co-host, KK, as well. Jason Baumgarten (22:16) You guys were fabulous. Thank you. KK Anderson (22:17) Thanks, team. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 112 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 1 | 03 févr. 2026 | 00:24:38 | |
In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson are joined by Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stuart, to unpack what truly separates sales leaders who advance into CEO and board roles from those who remain stuck at the functional level. Drawing from more than 250 CEO and board transitions, Jason shares a rare behind-the-scenes perspective on how boards evaluate CROs, why ambition alone is not enough, and what sales leaders must change as they move from execution to enterprise leadership. The conversation explores founder-led transitions, boardroom presence, customer lifecycle thinking, and why sales excellence alone does not guarantee executive readiness. This episode is essential listening for CROs, founders, and revenue leaders who want to move beyond quota and operate at the highest levels of leadership. What You’ll Learn:
Key Topics:
Guest Spotlight: Jason Baumgarten Jason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he leads executive search and board advisory engagements for companies ranging from early-stage ventures to multi-billion-dollar enterprises. He has advised on more than 250 CEO and board transitions, with deep expertise in founder-led technology companies, succession planning, and board effectiveness. Before joining Spencer Stuart, Jason was an Associate Principal at McKinsey and a Program Manager at Microsoft. He holds an MBA from Stanford Graduate School of Business, serves as Chairman of the Board for IslandWood, and is a frequent contributor to Harvard Business Review, including his article How CEOs Build Confidence in Their Leadership. Resources & Mentions: • Spencer Stuart • Harvard Business Review: How CEOs Build Confidence in Their Leadership • Mark Roberge: The Science of Scaling 🎧 Listen now and follow Selling the Cloud for conversations with leaders shaping the future of go-to-market, executive leadership, and board-level decision making. Mark Petruzzi (00:37) Welcome to today's episode of Selling the Cloud Podcast. I'm thrilled to welcome Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stewart. Jason leads Executive Search and Board Advisory for one of the world's premier leadership consulting firms. He's completed over 250 CEO and Board Transitions. across companies ranging from early stage ventures to multi-billion dollar enterprises. His expertise spans CEO succession planning, board effectiveness, and leadership transitions, particularly for founder led technology companies. Before Spencer Stewart, Jason was an associate principal at McKinsey and a program manager at Microsoft. He holds an MBA from Stanford's Graduate School of Business and serves as chairman of the board for Island Wood. His thought leadership appears regularly in the Harvard Business Review, including a recent article, How CEOs Build Confidence in Their Leadership. What makes Jason's perspective uniquely valuable is his vantage point. He's interviewed thousands of sales leaders and observes what separates those who successfully transitioned to CEO and board roles from those who just can't get there. Today we'll explore four critical themes. The sales leaders evolution from operator to strategic executive. Founder transitions building a leadership capacity beyond the go-to-market motion. Board governance for sales leaders. Why thinking like an investor makes you better at your job. and landing your next role, what really matters at the senior executive level. So I guess a couple of things there. You really don't work hard enough or really haven't accomplished most in your life Mano man, Jason, what an amazing career you've had already. And I'm sure you're not going to be slowing down anytime soon. So thank you. Thank you for joining us and joining us here on Selling the Cloud podcast. Jason Baumgarten (02:40) Well, thanks for having me. And I felt a little tired listening to it, but it was all fun in the moment and delighted to try and share some learnings from the many, many, interviews and board discussions and CEO discussions with your listeners. Mark Petruzzi (02:53) Yeah, and Jason, we have an audience of mainly CROs, some of the best in the business. And, you know, there's a number of them that I've already prepped to make sure that they've watched this because they're looking at the things that you do. ⁓ And I have many CRO friends who join us as well that have made this transition. So I love the, I love where we're going here and excited. to dive in. Topic one, the sales leaders evolution. How do you evolve from somebody who's great at sales to configure out management and understand leadership, and then they really have to move to the next level as a strategic executive, often without the background, not to say an MBA or a more prominent type of... ⁓ educational background gives you all the recipe to do it as well, but many of them, you know, just they feel like they don't have that. So in your interviewing of thousands of sales leaders, what fundamentally distinguishes those who you feel can successfully transition to the CEO role or to board roles from those who just you feel maybe we'll struggle with that? Jason Baumgarten (04:04) Yeah, it's a great question, Mark. I mean, first of all, it sounds perhaps silly, but I start with do they really want it right? And the reality is not everyone really wants to be a CEO once they learn what that role is all about. ⁓ And so you have to start with not wanting it for ego reasons or control reason, but really do I want to do that job more than the job I'm doing today? So that's sort of step one. It's important. A of people breeze right through it, but I'm like, no, actually, do you really want it? And why do you have thought out reason why. The second thing is, you know, sales, ultimately, I think have a sales leaders have a couple of critical advantages. One great sales leaders have real industry and customer intimacy, and great organizations are built around solving customer needs. And so if you can really lean into that proximity, that superpower, that's super helpful. The second is most sales leaders are great people leaders. And so if you're really thoughtful about how do you lead a team? How do you lead people? That's another thing to lean in. What are the areas they tend to be less good at? Well, the first is genuine curiosity, right? One of the challenges with sales is one can become quite transactional. How do I hit my number? How do I move the sale along? How do I move the conversation along? How do I get what I want done, done? And the reality is great leaders are deeply curious. They're deeply interested in learning about other functions, other aspects of the company. So the first thing I'd say is tap into your innate curiosity to learn about what's going on in finance, what's going on in legal, what's going on in product, what's going on in marketing, what's going on in customer success. So that as you evolve your thinking, you understand more about what's happening in other functions. The third thing is actually rising up. and doing two things. First, think as a systems thinker about how do all the pieces of the puzzle fit together to make revenue and profit happen and get knowledgeable about that system. And then two, ensure that you are not coming across as somebody who believes sales is the answer or the cause of all problems or solutions. So those are a few of the things that I'd share. We can go into more depth on any of them. But there's some of the high-level things if I had to add a final one, I'd say humility I always laughed that if I interview all the top sales leaders at a company that revenue will beat will go up at least a thousand percent from the interviews alone when you just add up all the numbers and of it is there's an amazing quality of confidence and You know that a lot of sales leaders have but recognize that when you're interviewing for a CEO role or for something else you've you've got to temper that a little bit with Mark Petruzzi (06:24) Yeah. Jason Baumgarten (06:40) that empathy, that curiosity, that humility. Mark Petruzzi (06:42) KK, I think you're on mute. KK Anderson (06:43) Well, that's a first for a podcast to land. Jason, really interesting what you're saying. And you've said that board members can sometimes be like Christmas lights. Like, you know, they turn on once a year, right? And so for a CRO walking into, you know, a board meeting, like, and thinking about how, how... Mark Petruzzi (06:46) Yeah. Jason Baumgarten (06:46) Yeah. KK Anderson (07:05) What advice do you give? Maybe they're not aiming to be CEO, but what advice do you give them around not just being seen as a salesperson? Talk to me about that. Talk to me about a CRO walking into Jason Baumgarten (07:15) Sure. You know, first and foremost, it's think about your stakeholders and most salespeople do this really well. So think about who's around the board and what matters to them. What are they thinking about? What's their what did they show up worried about or excited about in that board meeting? And I don't mean conceptually and for all time Memorial, but like in that meeting, what's on their mind? What's going on in their companies? What's going on in their investment groups? If it's a public company, what's going on in their day jobs or their other boards? What is the context? know, are you, are they walking into a new product launch being announced at your company? Are they walking into a bad quarter? So the more you start with who am I presenting to, who are these people on the other side, not just in the singular dimension of them as your board member or investor, but also the rest of their lives. So that's sort of step one. Step two is to your question of how do you appear as more, you know, how do you present a more holistic perspective? You know, I think It really comes from that ability to connect the dots between what's going on with your customers and the market, you know, competitive point of view, you know, customers need shifting product evolution, technology evolution. So that's one. And then the other is being able to connect the dots inside the company. You know, we did this thing on, ⁓ our customer support initiative. It had this impact on renewals. This then led us to be able to change the way we're going after new logo. The more you can stitch together narratives that are multidisciplinary, the more they start to see you as not a one-trick ⁓ answer. And the other thing I'd say is know when the answer is not sales. One of the most powerful things any functional leader can do is to say, that's a great question. I actually think the answer is in marketing or is in HR or is in finance or is in customer support. You could give us more resources and sales, but that would be the worst place to put the capital to solve that problem. Because showing that shows that you are stepping out of your functional role to really think about what's best for the company and how you as a systems thinker would apply that capital or that resource. Mark Petruzzi (09:15) Jason, so in general, when should a CRO start thinking about building the capabilities beyond the pure sales, execution, sales leadership side? What's the signal? Jason Baumgarten (09:27) So I think there's two things that are working in tandem. One is their ambition, right? Do they have ambition to do more bigger, more complex, even sales roles or CRO roles that are broader than sales? And then have they mastered where they are? So at a very simplistic level, do they feel like they've kind of got the, you know, the training wheels off in their current role? You know, do they have sales ops team leadership, you know, forecasting KK Anderson (09:37) it in that Jason Baumgarten (09:49) all those key skills down, if they do, it's a perfect time to now start to think about how do I broaden? If you haven't got those mastered, you know, probably need to spend time there. But if you feel like you've got your quote unquote day job in good order, it's only going to make you better in your day job. And that's I think one of the things people often forget is they think, I'm doing this to become a CEO or to become a board member, or to take on more, it will actually make you much better in your day job. because you'll start to think about ⁓ other levers you can pull with your colleagues to help move revenue beyond what's in your control. And that influence in your leadership team, you will be more effective because you won't be seen as somebody lobbying for your team's resources, but for solving, know, every function wants more revenue, more profit. So when you start solving for that, you become an enlightened sales leader who, everybody wants to pull into their opportunities, their, you know, their initiatives, et cetera. KK Anderson (10:46) Isn't that the truth? Yeah. Jason, let's move on to the second topic and talk a little bit about founder transitions and building, as you've been discussing, that leadership capacity beyond just the go-to-market motion. And you have worked with many famous founders, ⁓ and you've had the ability to see a lot of these founder-led companies up close. And so I would love to hear you know, maybe a story or two about some of your, your favorite famous founders that you've led. and then specifically like when, when they stopped becoming the primary salesperson, right. And the company starts to scale. I'm curious, like what usually breaks first, right. And just talk, talk us a little bit about some of your, favorite famous founders. Jason Baumgarten (11:30) So I think I've worked with almost all of them in some form or fashion. ⁓ You know, I would say that what tends to break is sleep. If I'm realistic, it's, it's the thing is you just only, no matter how amazing somebody is, they only have so many hours in the day. And so that's one. I think the other thing is that, you know, and you know, this as well as everybody ⁓ who really is an expert in sales, the one-on-one connection of an individual can only scale to so many people. KK Anderson (11:36) Okay, there we go. Jason Baumgarten (11:54) And so I think what starts to happen is that while they typically are doing more of a business development motion, more than a real scaled sales motion, they start to realize, I need some channel sales. need some indirect sales. need some marketing driven conversion. I need more tools in the basket. And then they start to build a sales team beyond them. Now, I think the early sales leaders of many companies are individual contributors themselves. And so there's almost two evolutions. There is the first, you know, it's the founder being the salesperson, and then there's the first salesperson being the only salesperson. And then it's you as a sales leader kind of going to the next level as a ⁓ building a team, building a, you know, a model of sales. So I think that's often the trajectory these companies go through. I would say the other watch out is Mark Petruzzi (12:28) Thank Jason Baumgarten (12:42) founders who have a couple of really good early deals and think, boy, this sales thing is easy. And then they start to scale it. And they realize that that was just friends and family. And people thought it was great. Or they got some early pilots and it's not easily replicable. And so I think when you really ⁓ move from founder stage to a growth stage is when you can replicate that journey, when you know that you can hand this to someone else and Mark can go sell. just as well as I can. Founders are always going to have a special edge, right? The reality is if a founder calls a company, they're always going to have a little extra time. It's a little easier to get through to an executive, but until you can replicate it, you really don't have a repeatable sales process. ⁓ You know, I would also say that what we're seeing now is a real evolution in how people are thinking about it, because you are also seeing ⁓ much more complex sales motions. And in some cases that's complex because we're seeing them look more like consumer sales motions. And in some cases, much more like consulting or professional services. So we're seeing more bifurcation than for a while we were into the fairly low complexity SaaS sale, you know, and that is on the edges starting to fray a little bit in terms of just the complexity of, the heterogeneity of all the different types of products and services we're seeing in technology. So maybe avoiding a particular person, but, you know, I think everybody goes through that wave and, you know, I worked with one leader who his startup was in the sales technology space. And that was perhaps the most incredible cause he was one of the best salespeople period. And he was one of the best salespeople for that company, even when they were at, you know, several hundred million dollars in revenue. But he realized he had other things he had to do. And if he spent all his time selling, So what he started doing was spending more time teaching and making sure the right process was in place to scale as opposed to saying, I could do that better. Because of course, but he also couldn't do everything. had to, he had to pick what he was spending his time on. KK Anderson (14:38) Especially if he wanted to sleep, right? Mark Petruzzi (14:40) Now that Jason, that is spot on. So in some of your publications, articles that I've read, you mentioned two critical dimensions. Building the right go-to-market engine as one aspect of it. And then at the same time, readying the organization for when it's not founder led sales anymore. And they're not spending 50, 70 % of their time on sales. How should boards in particular approach these transitions? What responsibilities do they have in all of this? Jason Baumgarten (15:13) Yeah, it's a great question. It does depend on this on the type of board and this, even for startups, what's the type of startup and the ambition of the startup? You know, I think the thing that boards should spend the most time on is what is the theory of the sale? Like what is the theory of the sales system that the company is starting to move towards when it goes from an individual to a system? Second, based on the data, you know, the early returns early data, is that hypothesis or theory holding true, right? So for example, if we say, we're going to sell into this ⁓ type of executive, we believe it's get a demo, show the demo, do a pilot, you know, whatever the the march you're taking people through, is that actually proving out in the early data? And then the third thing is, is the company continuing to appropriately experiment and test whether they have the right model? Because I think it's probably the most dangerous thing is to very early and we see this when an executive comes in and says well I've heard it I know the way to sell is XYZ and I'm gonna bring that into this startup and it isn't the right model right something is off either the ideal customer profile is off or the literal ⁓ you know Approach is off or the pricing is a little bit off Something in there is a little off and instead of catching it early. They catch it really late That's really bad for that sales leader, but it's also really bad for this for the company. so board members can really try to make sure there's a crisp hypothesis as to here is how we're going to sell. Here is the data that's going to show us that we've got the right model. And then three, are we seeing reinforcement that we picked well, or lessons learned that maybe we've got something off and what are we doing to adjust. ⁓ And then you can start to diagnose what's going on if you're not hitting or beating your expectations, you can say, we had something wrong. And that's okay. I think The worst thing is to double down and say, we just aren't trying hard enough. It usually is a strategy or a process problem, ⁓ not a try harder problem. You know, unless people are just flat out lying about what they're doing, but I don't find in, especially in startups, people are usually pretty excited to grow the company. And so they're showing up, you know, trying to kill it. The other thing is not recognizing that whatever works early is probably not the forever model. And For example, there was years ago, an enormous number of SAS companies that had very low cost direct models. And they realized that that wasn't going to scale that they needed to get a more enterprise motion. And yet they built teams that were so well oiled for a particular model that when the when the growth rates started to slow down, they didn't they weren't as quick to transition or try new things. And that's a failure. The know, it's a failure of the leadership team. But even a failure of the board because the board should have been asking those questions earlier than the executive team because the board's role is to try and look ahead of where the executive team is is reacting to right now because the executive team might be You know 70 % reactive 30 % planning the board should be the other way around and should be able to say hey I think this is going to come and hit you in a year or two years. How are you prepping for it? Now? What are you doing now? How are you learning now? So that's how I think about that board interaction early on KK Anderson (18:14) You know, we were just interviewing Mark Roberge this morning on the release of his upcoming book, The Science of Scaling. And he was talking a lot about, you know, an early, you know, indicator of retention around, you know, customer success. And so for a sales leader, you know, they are a CEO might be thinking like, hey, just get us more leads, you know. get it, we just need more pipeline. Pipeline will fix everything, especially in these early stage companies. And Mark's argument was actually, what you really should be focusing on is your retention. Like, are you hitting those benchmarks that show that people, your customers are staying and you have, you know, product market fit, you have go-to-market fit, your customers are there and they're coming back and they're renewing. So, you know, talk to me a little bit about kind of your perspective on on that idea and what are some, like when you see founders, you know, start to show maybe a lack of leadership or like you're like, I want to coach them to increase their acumen as their companies grow and scale. And you need to take into consideration things like, you know, the retention metrics, you know, more so than the sales metrics. And you said earlier, recognizing that sales isn't always the problem. Like what does all of that make you think of? what's your perspective there? Jason Baumgarten (19:24) Yeah. I mean, first of all, I think he's spot on and I'd go so far say, you know, you want your metrics across the whole consumer lifecycle, you know, the whole client customer lifecycle, because it may be showing up in retention, it may be showing up in a lack of cross sell, it may be showing up in different areas. And the point is not to say we did a good or bad job, let's understand what's going on. It may be that you're got great conversion, but with all the wrong clients. And the real issue is you're going after the wrong clients, the wrong customers. not ⁓ that you are incapable of turning those leads into opportunities. So I think the first thing is I'm a big believer in capture the data across the whole life cycle so that you can understand what's going on with the sales approach, you know, depending on the type of product we're talking about, the, you know, the onboarding, the services side, the customer support side, et cetera. So I think that whole life cycle is critical. I think that when, ⁓ You know, when founders are finding themselves stuck, usually the answer is go talk to people who have done who are a little further along in the journey than you are and ask them for advice and counsel about what worked for them. And don't take one person's advice. Don't say, well, you know, one investor told me the answer is this metric. So I'm going to go chase that metric, triangulate different people, get a good kitchen cabinet together. and ask different people and don't just ask peers, don't ask other founders alone, don't ask other CEOs, ask people who are in CRO roles, ask people who are individual salespeople, ask people who are in other parts of the ecosystem so that you're hearing perspectives from, you know, the person who might be junior entitled to you, but much higher than you in scale. You know, I always laugh, you can be CEO of your own business, just pop a magnetic sign on your truck and drive around and Mark's got Mark and Co. He's a CEO done. You don't, you don't need to actually have a company to be CEO. Same thing with the sales person, right? If you're selling lemonade, you're a sales person. But if you're, you know, you could be a very junior person selling millions of dollars in a very complex way for an enterprise SaaS company, or you could be a founder who's got a big title and a lot of sense of importance, but you're selling half a million dollars. And that doesn't make you more sophisticated as a sales strategist and the person who's a Mark Petruzzi (21:09) Mm-hmm. Jason Baumgarten (21:36) senior manager at a big SaaS company. So don't just think about your peers. Think about, you talking to people in different roles and different scope and scale? And to me, that helps you understand what's going on. It also gives you empathy because when you start thinking about things like incentive plans or how to inspire the team, you also are thinking about, wow, how does that work when you've got 40,000 people? I've got five, how does it work at 40,000? So I think the more they can get out of their own atmosphere, it helps a lot. Mark Petruzzi (22:08) So Jason, I'd like to take you back to the board perspective for one more question here. So what mistakes do boards typically make in the timing and structure of hiring professional sales leadership as they move from a founder led selling motion? Jason Baumgarten (22:26) Well, I think that I think the two biggest mistakes I've seen is they don't do it early enough. Right. There's a sweet spot. If you do it too early, you don't, you don't have product market fit. There's no point in bring on your professional sales leader. If you wait too long, things get pretty calcified before somebody has a chance to think about your incentive design, your partner design, your channel design, all those things. I would say the other piece of the puzzle is hiring somebody who is going to bring the And if you don't, you know, you can either start with a very open mind, you know, classic beginner's mind and say, I don't know what model, but I'm going to use this recruitment to help figure that out. Or you can do the work to say, we've actually figured it out. I figured it out or your team has figured out. And we now know what kind of sales leader you need, because if you believe your PLG and you're really not, you can hire the absolute wrong person. And that's not good for anybody. And I'm a big believer that there's, there's there's not good and bad sales leaders. There's not good and bad leaders is actually people who are the right fit for the right time. And so you need to make sure that the fit of that sales leader is what you need. ⁓ The third thing I'd say is sometimes they just over, ⁓ you know, there's a desire to sometimes signal a Rolodex and get somebody who's got a big Rolodex. And maybe because I'm in the Rolodex business, I always laugh. like, listen, if you've got a product that's solving real problems, getting access and the Rolodex will be the least complicated thing. And people want problems solved. And so if you really have a good solution, you will find a way to those people. That is probably the least value in most industries. That's probably the thing I would not get hung up on early. And yet I think a lot of founders think that's the magic unlock. The reality is most human beings at best, best have 100 to 150 relationships. And that's actually overstating the real quality of most of those relationships are ⁓ not preferential. Meaning if you and I have the same product and we both go, I'm not going to win it just because I have that relationship. It's really going to come down to who is the better product. And so I would say don't over bias to that concept of access. 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| Ep. 111 – Building AI Fluency, Trust, and Modern Sales Leadership with Cherilynn Castleman - Part 2 | 27 janv. 2026 | 00:13:27 | |
In Part 2 of this Selling the Cloud conversation, Cherilynn Castleman joins Mark and KK Anderson to unpack what strong CRO leadership looks like in a time of rapid AI adoption and constant go-to-market change. As every team claims to be AI-first and tech stacks continue to converge, Cherilynn explains what truly differentiates leaders who drive real results. This episode dives into how curiosity with AI, disciplined daily usage, and protecting selling time translate into cleaner pipelines, shorter sales cycles, and fewer end-of-quarter surprises. Cherilynn also shares practical guidance on modern operating rhythms, how to run meetings that actually matter, and which metrics prove that change is working now, not quarters from now. What You’ll Learn:
Key Topics:
Guest Spotlight: Cherilynn Castleman Cherilynn Castleman is a sales and leadership advisor who helps revenue teams adapt to modern buying behavior and post-pandemic selling realities. She is the author of Post-Pandemic Selling, a top Amazon bestseller that has been recognized by Salesforce as one of the top sales books for modern leaders. Cherilynn is also an active LinkedIn voice, hosting frequent LinkedIn Lives where she shares practical insights on sales leadership, AI fluency, and authentic connection. Resources & Mentions:
🎧 Listen now and follow Selling the Cloud for more insights on AI-driven leadership, modern sales execution, and building trust across today’s go-to-market teams. Mark (00:30) All right. Let's move to topic three. Leading as a CRO in a time of intense change. So every team nowadays says they are AI enabled, they're AI first, and everyone's sales and marketing stack just looks very similar. So from the seat of the CRO, what actually differentiates leadership right now in your opinion? Could you give us two or three weekly behaviors you expect to see in the numbers of a CRO that is leading well. Cherilynn Castleman (01:04) Yeah, so a couple things. I think that if a CRO is demonstrating curiosity with AI, they are using AI, they are sharing with their team, this is what I did. I was working with the CFO for a huge company recently and they do a pricing exercise. And they normally would sit down for a couple weeks and work on this pricing exercise. And I challenged them to open AI and pull their data into their proprietary system. And in 30 minutes, they had done the entire exercise. And so it was like, wow, everybody's going to be impressed. I said, no, it's transparency. Tell them you used AI to do it. Demonstrate, model that you're curious. If you fail, talk about that. So number one, they're modeling curiosity. Two, it's a discipline. They're using it on a daily basis. They're talking about it on a daily basis. There are somewhere between 50 and 200 new AI tools every day. There are, when you look at go-to-market tools, there are somewhere between seven and 10 new tools every day. There's no way you can master the tools. Stop chasing the tools. It's a mindset. It's about confidence and clarity. The next thing that I would say is that ⁓ protect the selling time. Look at your meetings and make them very efficient. Get them down to 30 minutes. The goals is most sellers sell about 10 hours a week. You want to get your sellers to 15 to 20 hours a week. And so where you're going to see this, are you going to see a cleaner pipeline, you're going to see higher exact meetings. And so those are things you want to measure is not just meetings, but exact meetings, decision-maker meters. It will shorten the sales cycles and you'll have fewer surprises at the end of the quarter. KK Anderson (02:43) So good. was just on a coaching call just before this podcast episode actually, and was coaching a new seller that was joining the team and was asking about the hustle and the grind and around hunting. And so we popped open Chachi BT and we put in the overall team's average deal size, average win rates, know, sales cycles. And he... figured out that he needs to make 6,700 calls in the first six months to be able to get the number of opportunities in his pipeline to be successful. And he was like, what? 6,700 calls. But you break it down into a daily rhythm. And you break it down into who you're targeting. And you can use AI for those things to get smarter and hone in on offers based on personas and POVs. It's interesting. Cherilynn Castleman (03:24) Absolutely. It is. And the other thing is that the goal, and so I think Mark mentioned this, we're opening emails and we're like, yep, AI wrote that, yep, AI made it. And so what I challenge people to do is, yes, you have to do your volume, but what if you spent 15 to 30 minutes every day sending a couple better emails? Where you actually, you know, and so, then, yes, if you sent a humanized email, I love it when every once in a while I get an email and I'm like, yes. KK Anderson (03:50) human Cherilynn Castleman (03:56) this lands. We all know what those feel like. We'll learn to send those kind of emails. And if you're not sure, I tell people, email them to yourself and then open it on your phone. If you won't open it on your phone with the subject line and the first sentence, why would anybody else? So send it to yourself, look at it, and yes, get your numbers in, but spend time figuring out how to craft. better emails and micro segment because once you've done your micro segmenting, you can do emails to Gen Z, Gen Y, Gen Alpha. You can do it by title, can do it by industry, West Coast, East Coast. AI will do all that. Do all your micro segmenting and then you're now doing a more humanized outbound and I promise you, you'll hit your numbers and make fewer and send less noise. KK Anderson (04:43) meaningful, more meaningful outreach, yeah. Okay, so you said something a second ago. You said when Mark was asking about the CRO and leading well, you said less meetings and the meetings that are, having the meetings that are meaningful. And nobody likes a meeting, everybody hates a pipeline call, we know that, right? So like what in today's day and age, like what is like, Cherilynn Castleman (04:46) Yeah. KK Anderson (05:05) What are the non-negotiables, but what gets cut and what changes and what, talk to me about that operating rhythm, is it changing? Cherilynn Castleman (05:11) So I think it is. I think that, so what I encourage people to do is do 30 minute meetings because of AI and technology and Facebook and Instagram and everything. The 10-minute spans are very short. So do a rapid 30 minute meeting. Revenue review, focus on what are blockers, what is getting in the way. Focus on owners, deadlines, next steps. No slides, no noise, no operational. I used to call them my quick stand up. I taught my team the rule of three. They had to come in and in one minute or less give me three things about this deal that I needed to know and then end with, so it's a bottom line up front. Bluff is a military phrase, bottom line up front. Three things, one, two, three, and then conclude with here's what I know, here's what the so what is, or here's a call to action. People come in without slides. and give you those updates, you're gonna see your pipeline tighten up. And you're not gonna have surprises, you're gonna have that transparency. And then every meeting must either build a skill or make a decision. How many times you sit in meetings and it's just updates and it's updates and there's nothing. Either we're going in to make a decision or we're gonna build a skill. And like I said, I would do a 30 minute meeting, that, teach me something in five minutes at the end. KK Anderson (06:18) Excuse. Excuse. Excuse. Yeah. Cherilynn Castleman (06:27) So everybody is learning something every week and I have teach me something AI. And again, if it rotates, know, KK is going to teach us her best AI tip this week. Mark's going to teach us next week and next week I'm going to teach them. Everybody's best practices and people are going to learn things so they can teach them. Mark (06:39) and KK Anderson (06:42) it. Mark (06:43) Great. So we all know boards and CFOs fund what they can measure. funding is a big part of ensuring that you really are able to build the type of capabilities you're looking for and keep those skill sets building. So what three numbers belong on a page one to prove that change is working? And what targets would you make to ensure that you can be confident that the program, the leadership you're bringing to the table is gonna create the lift now, this quarter, not quarters from now. Cherilynn Castleman (07:20) So the three numbers that I would look at, one is cycle time with a warm sponsor versus one without. So if you're doing this right and you're leveraging AI, it's very simple. You just want to say, here's what our cycle time is with a warm sponsor. We're seeing a lift in this. Number two, executive meetings by stage. So when do the executives join and what stage are you at? And being able to track that. and the win rate on multi-threaded deals. those are the three things. And what I think you're looking for is somewhere between a 10 and 20 percent quarter over quarter. That is proof that you are driving change. KK Anderson (07:56) Amen. That is proof. Okay, Sherlyn, we are gonna go to our favorite section of the podcast. We call it rapid fire. And Mark, I want you to kick us off so that we land on my favorite question on me. You go first. Cherilynn Castleman (07:58) at Mark (08:07) You got it. I'll start the first one. What is the first product or service you have ever sold? Cherilynn Castleman (08:15) Mark, I've been in sales since before Girl Scout Cookies were 50 cents a box. Mark (08:18) my goodness. Excellent. KK Anderson (08:19) did you do, Roscoe cookies? Cherilynn Castleman (08:20) Every girl's got cookies. And I mean, I was probably in the first grade. Okay? And yeah, I was in the first grade and my brother would pull the wagon and then there were no order forms. They just gave you cookies and you went and sold them. And I would stand there and I just would say, you know, they freeze well. What's your favorite ones? And oh, and if you tried this, this is, know, and I'm telling you, you put them away, you freeze them, you'll have them at Christmas. And I just up-sold and I was... I a top salesperson and I just loved it. I was probably six years old. KK Anderson (08:51) That's amazing. Okay, who is one of your favorite sales or leadership voices that you like to follow? Cherilynn Castleman (08:56) So I have always followed who he was known as the client success guy and that was Bill Green, the former CEO of Accenture. He's just made such a change in the way I sold and Bill always said two things that stuck with me. One, if you criticize people, you raise their defensiveness. If you challenge people, you raise their game. And so that's why I coach and I challenge people. And the other thing he said, Sherrilyn, three C's. Competence, be damn good at your job. Be great at what you do. Confidence, just have confidence, have courage. And the last one, which I repeated here, is give a damn. Care about your clients, care about your industry, care about your product. He said the three C's, well, that is what makes you a great leader. And so I've read and listened to everything that Bill has done. Mark (09:48) right on. So one practice you believe every sales manager should adopt this quarter or maybe even this week. Cherilynn Castleman (09:56) I say curiosity. AI lets you be curious. ⁓ I was read in a couple of places that they say curiosity is the KPI for 2026 for sales leaders. So I think if you're going to leverage AI and build your AI fluency, curiosity, curiosity, just keep asking questions. What can I do better? And also one of my favorite prompts is what did I miss? What could I have done better? So even though you've done the prompt, you've done the analysis, stop and say, okay, what did I miss? What am I not thinking about? How can I do this better? So curiosity. Mark (10:28) So this may be one way that humanity is evolving a little bit, because they used to say curiosity killed the cat. And now it's not going that way anymore. And think about it, with AI, there's so much power in curiosity. So I really love that one. Thank you. Cherilynn Castleman (10:39) You know Yes. KK Anderson (10:46) So good, okay, and my favorite question. Okay, Sherrilyn, what advice would you give to your 21-year-old self? Cherilynn Castleman (10:52) So I would tell myself to trust my voice, trust myself earlier. I would tell myself, if given a choice, Sherrilyn, always choose kindness over being right. And the final one is always, always have the courage, regardless of what anybody else says, just have the courage, have the kindness, and trust yourself. Mark (11:13) All right, well, I'm gonna close this up with, and I'm really interested in this one with all the great stuff we learned about you during this call, Sheryl Lynn. What is your favorite non-business book? Cherilynn Castleman (11:24) The Untethered Soul. I read it every year. It makes me pause. It makes me spend a little more time on my rug. It is about self-reflection and choosing love over fear. And I've been reading it every year. I don't know, probably since it came out. I'm a voracious reader, but that is one book that I read every year. I love The Untethered Soul. Mark (11:28) Wow. And I love that idea of like reading something every year. I've never really, it's not like I haven't read books again, but the idea of having something that's so impactful and rereading it every year is really cool. Well, so. KK Anderson (12:02) Wait, when are you going to release your book, Sherrilyn? Surely there's one coming. Cherilynn Castleman (12:05) Well, so I have a book. It was actually top of Amazon's best sellers for women. It's been recognized by Salesforce, actually one of the top 10 best sales books and link. You can go to post pandemic selling.com. And that's, you'll find out it's also on Amazon. It talks about a lot of things we've talked about coming out of the pandemic, why we had to connect with people, why people need us to be authentic and us to be curious and how to connect with people. It's called Post-Pandemic. It's what's in the cards. Post-Pandemic Selling is the name of it. Again, you can get it at postpandemicselling.com. You can also find it on my LinkedIn page or SherrilynCalfsman.com or just connect with me on LinkedIn. KK Anderson (12:48) You're right. Mark (12:48) Very cool. Cherilynn Castleman (12:49) Thank you. Mark (12:49) Well, Cherylin, thank you so much for taking the time with us. This was really a pleasure. And thank you to our amazing audience. I hope I remember that every single time. I don't know if I do, but we want to thank them as well, especially as we're moving in and through the holiday season. So again, Cherylin, thank you. KK, thanks to you as well. Cherilynn Castleman (13:12) Thank you, KK. Thank you, Mark. And thank you to your listeners and your audience. KK Anderson (13:15) Make sure to check the show notes and to catch Sherilyn's LinkedIn Lives. They're awesome. Almost every week. Okay. Thanks everybody. Cherilynn Castleman (13:20) Thank you, Kate. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 110 – Building AI Fluency, Trust, and Modern Sales Leadership with Cherilynn Castleman – Part 1 | 20 janv. 2026 | 00:25:36 | |
In this episode of Selling the Cloud, Cherilynn Castleman, enterprise sales leader turned strategic coach and Harvard instructor, joins Mark Petruzzi and KK Anderson to break down what AI fluency really means for modern sales teams. Rather than treating AI as a shortcut or replacement, Cherilynn reframes it as an amplifier of human strengths like perspective, empathy, and trust. She shares practical, Monday-ready routines that help sellers show up with stronger points of view, deeper buyer relevance, and clearer deal strategy. This conversation also dives into the science of trust in a noisy, AI-saturated world. Cherilynn explains how the questions we ask and how we listen directly influence buyer confidence, especially inside complex buying committees. From discovery to prospecting to executive conversations, this episode focuses on how sellers and leaders can create credibility without adding more noise. What You’ll Learn:
Key Topics:
Guest Spotlight: Cherilynn Castleman Cherilynn Castleman is an enterprise sales leader, strategic coach, and Harvard instructor focused on helping sellers become trusted advisors through AI fluency and relationship-driven selling. She is the creator of highly rated AI and sales programs available on Udemy Business and leads large learning communities through weekly live sessions and workshops. Cherilynn is on a mission to equip one million women in sales and leadership with the confidence, fluency, and playbooks needed to thrive in modern go-to-market roles. Resources & Mentions:
🎧 Listen now and follow Selling the Cloud for more insights on modern sales leadership, AI-driven GTM strategy, and building trust at scale. Mark (00:31) to Selling the Cloud. Our guest today is Cheryl Lynn Castleman, an enterprise sales leader turned strategic coach and Harvard instructor as well. She helps teams become trusted advisors with practical AI fluency and relationship skills. She also builds accessible learning at scale as a new to me creator. Her course, Smart Tips, Sales, Master Relationships Driven Selling Via AI is super highly rated and available versus a via Udemy business. Her programs focus on outcomes you can see on Monday morning. Better discovery, cleaner deal strategy, clear next steps. She has coached thousands of sellers and leaders, lifted promotion rates through hands-on coaching. and built a large learning community through weekly live sessions and workshops. She teaches simple operating rhythms that free time for customer conversations rather than adding more dashboards. And she's on a mission to equip 1 million women in sales and leadership with the fluency, confidence and playbooks to thrive. Here are three topics we'll cover today. AI fluency as a daily mindset. How to use AI to amplify strengths and turn prep into a repeatable routine that shows up every day in results. Relationship selling and the science of trust, the questions and behaviors that build credibility fast with modern buying groups, and leading as a CRO in a time of extremely rapid change. How to focus to team, communicate change, improve impact without adding any additional noise. Sherlyn, we're so happy and proud to have you here. Welcome to Selling the Cloud. Cherilynn Castleman (02:13) Thank you, Mark. Thanks, KK. I'm thrilled to be here today. Mark (02:16) All right, we're gonna take you right into our first topic. And our first question is, you frame AI as an amplifier for what sellers already do well. If a CRO asks you to install AI fluency in 30 days, what would reps and managers need to do each day and each week? And what early results would you expect by say week four? Cherilynn Castleman (02:38) So first of all, I would start with a 15-minute AI prep session for every rep. I would have them spend 15 minutes asking AI, first of all, one, to develop a POV, a point of view, which I know we're going to talk about a little bit later, for each of their clients. It's something they can do very quickly to triangulate and develop their opinion, because as you know, state of sales reports from LinkedIn and Salesforce told us that 87 percent of B2B buyers expect us to show up as trusted advisors, meaning we have to have a POV. So use AI to develop your POV. Second of all, spend five minutes using it to look around the corner. Where is my industry going? Where is my product going? Where is my company going? If you ask those questions every morning, you're going to get insights. And the final thing is, what can I do better? What can I, what am I missing? How can I, so for example, I'll say, How can I be a better coach? How can I connect better with my audience? What is a new training insight I can try? What's a new engagement I can use on Zoom? I am every day getting better. They spend 15 minutes every day amplifying what they already do. They're going to accelerate deals. Number two, I would encourage managers to add to their weekly minutes, teach me something in five minutes. Have every rep teach something to the rest of the team. once a week. That means by the end of four weeks your team has learned five AI insights. Over the course of a year they will learn 50 AI insights. And I had a client who was in the middle of the pack as a manager for a Fortune 100 fintech company and she became the number one sales manager of the year within six months just by doing that one exercise. That will free up And what you will see is you will see about 30 minutes a day freed up from your reps. That 30 minutes, if you have 50 reps and they're doing about $100,000 per deal and they're doing one deal a month, if you take that math out, that will give you an additional $4.5 million in new revenue that and no additional headcount. KK Anderson (04:44) Wow, it's really fascinating when you put it that way and you break it into numbers. Cherilynn Castleman (04:47) Yeah, and that is one of the biggest takeaways, I think, that sales leaders and chief revenue officers can look at is when we first started using AI, people were talking about how to use it for email and how to ⁓ sound better. And what the most recent research is coming out is you have to ⁓ apply what I call ICB, insights, context, business impact. How is it driving revenue? How is it saving you money? How is it increasing operational efficiency? How is it increasing your ROI? Those are the questions that leaders want to start asking every single week. This is what my reps are doing. How is that making me money, making me more money, or saving me KK Anderson (05:28) And it's interesting because you need the leaders, the L1s and the L2s asking AI those questions and using the data to get smarter. But the sellers as well, like you said, use it to look around the corner, research your competition, your customers. And we know and have known for a long time that our customers are much smarter when they get to us. They know more about our product than we probably do. Cherilynn Castleman (05:48) It used to be there were a ⁓ couple of months ago we had about 79 % usage today. B2B sellers are 98 % using AI. Customers are 100 % using AI. So your customers are using AI and 100 % they know your company, they know your competitors, they know your product. They probably have done more research than you have. So that's why you have to show up. Mark (06:02) Thank Cherilynn Castleman (06:12) with a POV, you have to connect with them, you have to build trust with them. People want to do business with people they know, like, and respect. Period. And we can leverage AI to do that. KK Anderson (06:24) And so where I was gonna go next was, I actually, I kind of thought people were getting over this idea that AI is cheating until I was in the car with my kids of all people. And one of my daughter's friends was like, AI is cheating, I can't believe AI, it's just not fair. And it's interesting, do you hear that still in your trainings and your classes that people feel like it's a cheat? Cherilynn Castleman (06:47) And with a lot of women, Harvard did it. There was an article that was recently said how AI is impacting women's career. And they discovered that women use AI in business 10 to 40 % less than men. And when they asked them what was the real reason, women said, because it's cheating. And so I tell people, just reframe it. I said, take what you already do well. What is your superpower? What is the one thing that you're better at that AI will never replace? AI will never replace your authenticity, your ability to care, ⁓ your ability to connect with people and ask AI to help you elevate that, to amplify that. Take 15 minutes in the morning and say, I'm a great listener. How can I be better? I ask great discovery questions. How can I do better? I'm meeting with this client. We don't seem to connect. How can I connect better with this type of client? My client's very analytical, very amiable, very expressive. A trick that I tell people is write a simple email and then ask AI, rewrite this for an analytic, rewrite this for an expressive, rewrite this for a driver, and rewrite this for an amiable. They're different as night and day. That alone will help you connect. with your clients, just reframing that. Another example is if you go to LinkedIn, go to the three dots, and it says PDF this profile. PDF the profile, attach it to the AI tool that you're using, and say reframe this email specifically for this person. And it will say, they're very innovative. They're very amiable. They're very analytical. And it will reframe it. You will connect with them. That's the power of AI and connecting with people. Mark (08:24) All right, well, that's very cool. So please help us to make this a little more Monday ready. Let's say a rep has a discovery call this afternoon with a new account. Walk through the 15-minute AI assisted prep that produces in your mind the most useful point of view for the call and how you coach them. How do you coach them to bring that into the conversation? We've discussed a little bit this here, but take us a little deeper if you would. Cherilynn Castleman (08:51) Absolutely. So what I always coach my clients to do is to triangulate your POV. It's something that AI, generative AI tool does so well. So first of all, research your client. Pull down their LinkedIn profile. If they're an executive, pull their bio and that's number one. So you want to triangulate. want three things, industry, company, person or persona. So if you can't find the person, do a persona. Pull down several CFOs in that industry. Pull down, if they're a Gen Z, pull down Gen Zs in that industry in that job role. So the better you can micro-segment, if you can't do the person, do the persona. That's number one. Number two is company. My favorite company document for publicly traded companies is a 10K. The Form 10K, as your listeners know, I'm sure, comes from the Security Exchange Commission. You can get it on the investors page of any publicly traded company, and the third one is an industry analysis. My favorite place to get it is Value Line. Value Line is free on every public library. If you work for a large enterprise company, they have this information for you. They have an industry analysis. They have company analysis. Pull it in and ask AI to triangulate this for you. and it will pull the three together and develop a POV. And then you just say to somebody, Mark, if I said to you, I have an idea I want to run by you, what would you say? People say, yeah, nobody's going say no to an idea. And that's all it is is an idea. Even if you're wrong, you get credibility because you showed up with an idea. So show up with an idea. This takes 15 minutes. This used to be an eight-hour workshop that I did on how Mark (10:15) Yeah. Cherilynn Castleman (10:31) to research and how to read a 10K. Value Line has the ratios in there, so it can pull it and it has the ratios in there for three years. It will do a financial analysis POV, it will do an expressive one, any way that you want it. Fifteen minutes. KK Anderson (10:46) And then you take that information and you turn it into a value hypothesis for what outcomes your customer wants to achieve and what's going to get in the way and how you can help. Cherilynn Castleman (10:54) Yes. Right. So if it's a first interview, those are the three things. If it's a second interview, I include the discovery document with it. And whether you are going into a meeting and saying, have an idea to run by you, and you're starting your meeting that way, or you're sending a follow-up email, or you're going into your solutioning, or you're doing a demo, it doesn't matter. You always want to show up with your opinion. I'm the trusted advisor. I have an opinion. And that's what it is. And you could say, how does this land with you? Or this is what I'm discovering in the industry. How does this resonate with you? You're asking their opinion, but you're showing up with somewhere to start other than just with open-ended questions. KK Anderson (11:35) So let's, we could stay on this topic forever. Let's move on to the second topic though, relationship selling and the science of trust. And what's interesting is I was listening to a podcast just this morning about how, thanks to AI, right? And if you, I mean, you see it every day, you scroll LinkedIn and it's like emojis and dashes and it's just a bunch of chatty-bitty trash, noise. Let's call it noise. I wouldn't say all of it is trash, right? And so, and people are used to seeing that now. And so it's like the trust continuum is getting longer than it used to be. Like it used to be, like if you had a really slick website, you know somebody dropped 10 grand to build a really slick website or way more than that, right? You you used to be, and now an AI tool can turn that on and you know, 30 seconds flat. And so it's harder for people out there to know who they can trust and what's real and what's not real. And so, you teach that trust shows up in what we ask and in how we listen. you know, AI is making that harder. Like how, like, how do you balance that? Like how have you added that whole dynamic and that change into your teachings and your coaching? Cherilynn Castleman (12:41) So the first thing that I do is I ask my clients to pause for a second and tell me what is it about their client that they really care about. You have to give a damn about your client. There's no AI tool out there that's ever going to do that. And that's where you start. So if you really care about your client and you pause and say, what is it you care about? What is it that's important to them? And if you don't know, that's the first place you start, because that's what you have to start from. is you have to care about your client and what's important to them. Once you care about them, you can craft discovery questions that are high connection questions. And for example, and AI can help you do this. again, it's a tool to amplify and elevate you. So Dr. Jane Dutton at the University of Michigan has done a lot of research on high quality connections, HCQ. If you go in and ask AI, to reframe your discovery questions as high quality connection questions, what you're gonna do is you're gonna trigger what I like to call the love hormones. It is the oxytocin. It triggers the hormones that makes clients trust you, like you, want to do business with you. For example, I had a client who was in the financial services industry. And she used to ask her clients, tell me about your insurance policies or your insurance that you have. you how you feel when somebody asks you that. Her second appointment rate was around 17%. When she asked AI to refrain that, the question was, what is it about insurance that scares you? Can you see that just that little switch there makes somebody connect with you? I have another client, she's a career coach, and she used to say, tell me where you want to be in three to five years. And she was coaching women and AI suggested that she ask, when was the last time you cried at work? Because if you're a woman and you're going to look for a coach, it's probably because something is upsetting you to tears. And so you can ask little questions that just connect with people. have a client that she sells ⁓ data to, she sells data and All of her clients are data scientists. And she said, Sherrilyn, data scientists don't have feelings. I can't ask you questions. And I said, hear me. Just for one week, let's just try it. She came back, and her clients now know her as a data therapist. Because she started asking them, what does it feel like when your company asks you to change the algorithm real quickly to come up with something? And this frustrates and angers, and they don't have the right data. And so her solution helps. resolve this and she's like now all my clients want to start with how they feel every time we meet. So she connects with them. She was able to renew more accounts than she ever has just by starting asking those types of questions. ask better discovery questions. Two of my favorite ones are either first or finance. What was it like for your first podcast, KK? Can you remember your very first podcast? KK Anderson (15:38) Yeah, the instant emotions, instant Cherilynn Castleman (15:39) Okay, you see the emotion, you see what happens? Versus telling me about what's it like to have a podcast as a first question. Or if I asked you, Mark, what was your finest podcast? So first and finest questions are great connections to connect with people. You can make these very technical, very financial, very industry specific, but an AI can help you do that. KK Anderson (16:01) And I know Mark's gonna jump in here, but I gotta ask one more question. That's brilliant, by the way. I absolutely love that, first and finest. What about in prospecting, when you're trying to get the meeting? How are you breaking through the AI noise and building trust? Cherilynn Castleman (16:15) So just bottom line, offer value, offer value. Offer case studies, offer assessments, offer checklists. People are doing research. People want knowledge. And so I say leverage social proof. AI, anybody can go out in AI and say, I am a great coach, or I am a great podcaster, or I'm a great ⁓ strategist. Use. LinkedIn or whatever platform you use or emails or whatever, however you're doing your outbound to demonstrate that you can prove you do this. So offer social proof. Here's a case study where I helped a client like you do this. Here's a checklist that I use with my clients. Here's an assessment that you and your team might want to take. I have an AI assessment tool that I give out and I'm constantly saying, do you want to see where your team is for AI fluency? Take this AI fluency assessment. It is just a free tool. Here's a handout on how to prompt like a pro. Give value. Once you give the value, then I always say, if you have more questions about this, jump on my calendar. People know how to book meetings today. You don't have to book them. You can wake up every day with new clients on your calendar by offering value and insights. I ended up with ⁓ a huge client from a major retailer who said, KK Anderson (17:19) Yeah. Cherilynn Castleman (17:27) She just, she used all my free resources for six months and finally she's like, okay, now we gotta bring Sherrilyn in. And she just got on my calendar, so we want to hire you. It's just that quickly. so what it is. The trust is there. Here, give value, give value. Stop saying, hi, I read your post and let's have a meeting. never, don't ask for meetings. Just give value. And again, if you can't think of what to give away, AI can help you come up with tools, resources. You have case studies. I've got clients who've gotten job offers. and ended up earning six figures more than they ever had just by posting case studies on LinkedIn. Here's what I did with a client anonymously. Here's what I did with the top 10 airline. Here's how I helped them and the percentage I helped them did the case study. And I had a woman, the chief revenue officer called her and said, I want you to come in and be my head of sales ⁓ and went around HR and didn't even look at a resume. It's like, whatever you did with that client, I want you to do that for us. Because it's proof, it's a social proof, a lot helps you do that. Mark (18:29) Right on. Sherilyn, that's so you've taken us through some of the things that you want to say and things that add value to the full discussion early on. Let's talk a little bit about things that that you want to make sure you don't say or things that could actually trigger things like buyer defensiveness. And in general, like what two behaviors that do you see that you know, that you can then do the lower that threat and increase that openness right away. Cherilynn Castleman (19:01) So one of things that I call is don't be cringy, okay? There's so much information out there. It is so easy to take someone's information and abuse it. Don't do that. Just treat people the way you want to be treated. So number one is don't be cringy. Don't take the data, don't share somebody's information. Be respectful, be kind if given a choice between You know, right and kind, choose kindness, just always be kind. I always say a fool with a tool is still a fool. There are fools out there with AI. Just because you have AI doesn't mean that you have to abuse it. Be ethical, stop and think about does this make sense? Is this ethical? The other thing is you will know if you're not triggering the trust and the love hormones, you're triggering their amygdala. And what happens when you trigger their amygdala is you see fight, flight, fawn, or freeze. If you're seeing any of those with your clients, they're fighting with you, they're arguing with you, they are freezing, they are not showing up, they are stalled, they are fawning. You ever ask a client a question and they sit there and they look at you? Well, they are fawning. just, you know, that's where they are. Or they just ghost you. Any of those say, okay, I've done this, it's time to stop, and AI is a great tool. I tell people, open a Word document, dictate just in your own voice what happened and ask AI to help you analyze it and say, what did I do wrong? What could I have done better? What made my client freeze? And learn from it. Another thing I see is that you mentioned it. So people try to sound ⁓ more intelligent or more technical. And how do you feel when you're around people with pretense? How do you feel when you go to that Thanksgiving or holiday meal and your in-laws or somebody has a girlfriend or boyfriend with them and they're just putting on airs. Everybody knows it. They can't stand it. Well, we don't want to do business with people like that. So the best way to be authentic and have your authentic voice come through is to just dictate. I use Word because it's not intimidating. I tell people just go into Word, hit the dictate and just dictate the email. Dictate the script. Dictate what you want to do and then drop it in. AI will use your words. they will use your intonations and you will sound like who you are. So those are a couple ways to avoid triggering the amygdala and have somebody go into fight flight freezer form for you. KK Anderson (21:27) I'm a big follower of Rory Vadin. I don't know if you know him. He runs Brand Builders Group and he wrote the book, Take the Stairs. And he says, my gosh, I feel like I've been quoting this every day. He says that in today's age, your humanness is now your uniqueness because everything else is, Cherilynn Castleman (21:34) Okay? KK Anderson (21:46) AI generated, like you have to leverage your humanness as your uniqueness. That's, that authenticity is still, is now even more than ever, you know, paramount. So buying groups are larger, they're complex. Very often, in these times, leaders who used to have decision-making authority now have to get the CFO involved and, and, and they're. Cherilynn Castleman (21:51) Yeah. It is. KK Anderson (22:09) more constrained than they've ever been. And so how are like, on this theme of building trust and authenticity and triggering the love hormones, I love that by the way, how do you do that when you've got like a buying group that's constantly changing? Like you're halfway through your sales process, you're on a, you have a meeting to negotiate or talk about terms of something and then next thing you know, boom, the CFO is there and you've never met him before. Like what are your kind of tips on that? Cherilynn Castleman (22:36) So a couple things. So first of all, I always ask at the beginning of any meeting, whoever's there, because like you said, buying committees are much larger. They used to be three to five people. Today they can be 12 to 18 people on a buying committee. Regardless of how large the buying committee is, at the very beginning, always go into the meeting asking each and every one, if you could get one thing out of this meeting, what do you want out of this meeting? Because... That may change the direction of the meeting. So you don't want to guess where the CFO, the CFO could be there because they're looking for operational efficiency, cost savings. They could be there because they're looking to drive revenue. They could be looking to improve the pipeline. You don't know why they're there. And so ask, and so I always ask, even if there are 15 people in the room, I'll take 15 minutes and say, real quickly, what's one thing you want at this meeting? And I note those down. Now I have the direction of the meeting. That's number one. Number two. Do your homework and do like I said, so do a POV for the chief marketing officer, do a POV for the CFO, do a POV so that you have those. So you're not changing the agenda, you're just changing the lens. And number three, executives want to talk about numbers. Develop your financial fluency. Understand what the key numbers are. Are they interested in what's driving revenue? and be able to tell stories. And the stories, again, is the insight, what is the number, what does this number mean, and where is this number going? How will it impact us in the future? So is it the cost of acquisition? Is it the cost, is it the life, the cost, the client life cost of, you know, of maintaining the lifetime value of that client? So. Know those numbers and be able to speak to them. And one other tip I always tell people when a CFO is in the room, take your numbers out three digits. Never say 50 million. Say 47.2 million. Know your numbers by three digits. CFOs will dismiss you if you round your numbers as a salesperson. So know your numbers. I'm sorry, what? Yeah, if you talk to CFOs, they'll tell you, I hate it when somebody says 15%. KK Anderson (24:33) That's a good tip. So that's a good tip. Cherilynn Castleman (24:42) Because nothing is exactly 15%. It's 14.7 or 15.2. So know your numbers, know them out three digits, know your numbers and tell financial stories with them where you can talk about the insight from the numbers, the context, and what it means to the business. And be able and have a financial point of view in your back pocket so that you're just changing the lens, you're not changing your agenda. Mark (25:07) Well, you know, Cheryl Lynn, that is also it's like speaking with someone who's bilingual and, you know, speaking in the language that they may be struggle with the whole time and maybe touching it for a second. You know, CFOs, are they are bilingual. And one of the items is numbers. It has to be. So that makes a lot of sense. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 109 - Scaling the Right Way: Product Market Fit, Retention, and Go to Market Readiness with Mark Roberge - Part 2 | 13 janv. 2026 | 00:17:30 | |
In Part 2 of this Selling the Cloud conversation, Mark Roberge joins KK Anderson and Mark Petruzzi to go deeper into what happens after product market fit is achieved and why going too fast too early can quietly break a business. Mark breaks down the transition from product market fit to go to market fit, explaining why these stages must be earned in sequence, not pursued in parallel. He outlines what real go to market readiness looks like, how to design a buyer centric sales system, and why retention and unit economics are the true signals of readiness to scale. The discussion also tackles sales process design, hiring profiles by stage, and the common mistakes founders make when front loading headcount after a fundraise. Mark closes by sharing a disciplined pacing model for growth and why predictable scaling beats vanity growth every time. What You’ll Learn: • Why product market fit must be proven before optimizing go to market execution • How retention serves as the strongest signal of long term product market fit • What defines go to market fit beyond revenue growth alone • The core components of a buyer centric go to market system • How to build a sales process that mirrors the buyer journey • The difference between discovery driven selling and pitch driven selling • How sales hiring profiles should change across product market fit, go to market fit, and growth stages • Why aggressive headcount expansion often leads to future layoffs • How pacing hiring and spend creates predictable and durable growth Key Topics: • Product market fit versus go to market fit • Retention as a leading indicator of success • Founder selling and unscalable early motions • Go to market system design • Ideal customer profile and buyer journey alignment • Discovery, qualification, and modern selling principles • Sales hiring by company stage • Scaling headcount responsibly • Unit economics and growth pacing models Guest Spotlight: Mark Roberge Mark Roberge is the founding CRO of HubSpot, where he helped scale the company from zero to IPO. He is a Senior Lecturer at Harvard Business School, co-founder and managing partner at Stage 2 Capital, and author of the bestselling book The Sales Acceleration Formula. His latest book, The Science of Scaling, distills decades of research into a practical, stage specific roadmap for sustainable growth. Resources & Mentions: • Book: The Science of Scaling by Mark Roberge • Book: The Sales Acceleration Formula • Organization supported: McLean Hospital • Opportunity to download the first chapter via Mark’s website • Pre order The Science of Scaling with proceeds supporting mental health research 🎧 Listen now and follow Selling the Cloud for more insights on building durable go to market engines and scaling the right way. Mark (00:31) I do wanna go deeper into the topic three here, go to market fit. Before I do that, Mark, is there anything you definitely just wanna cover? in addition to what we did already on product market fit. If not, I've got another question for you. Mark Roberge (00:44) Not at all. Like so far we have is like, you need to try product market fit first. We're quantifying that as retention in the long term and defining a lead indicator retention in the short term. And we created a framework for that. And the famous Paul Graham says, the founder of Y Combinator says, do unscalable things early. We're not worried about a scalable demand gen channel, a scalable sales process. We're doing founder selling. I don't even need to optimize price at this point. And I prefer to pay my salespeople with equity and not industry commission. Let's just get to success. KK Anderson (01:06) I mean, stop it. Mark Roberge (01:12) Once we have that, we move to go to market fit. We can't do them at the same time because you risk optimizing the go to market on the run market. If you don't prove product market fit first, but we moved to go to market fit and that just tells us that we can create this value profitably as measured by unit economics. And this is the stage where optimal quota price, demand, gen channel and sales process come into play. That's where we're at right now. Mark (01:32) Yeah, right on. Okay, topic three. So go to MarketFit. We want to go deeper into the process, the hiring, the demand, the pricing side, the compensation side. This is where I think a company gets to run and increase their productivity the fastest of any other stage. So you define go to MarketFit as generating customer success and revenue consistently and profitably. Starting with process, so starting with process, what should a codified repeatable sales process include at this stage? And where is the line between useful structure and a little bit of bureaucracy that slows deals at the end of the day? Mark Roberge (02:12) yeah, sure. Okay. Framing out one step. talk for a decade now around the go-to-market system design. This is what we teach at Harvard Business School. And so trying to move away from sales is just an art form. Let's give our salespeople a bunch of leads and let them do what they do best and go close business. Now, like we have a system for our finances. We have a system for our product development. We need a system for our go-to-market. So we call this go-to-market system design. The go-to-market system sits on top of obviously your first target market, your ICP, ideal customer profile. On top of that is a definition of how those buyers buy, the buyer journey. And on top of that is your sales process, which just helps them buy. There's two inputs to the system, the salespeople you hire and the demand that you create. And then the system runs by how you coach and pay them. And it spits out in sequence, sales activities like meetings and demos that lead to a forecast that lead to revenue. That's the system. And so within that system, Mark is a process. So it depends where you're like, at the very bottom is the ideal customer profile, which we can talk about. It's just really who we've proven to be able to sell successfully and make them successful. And so I mentioned like on top of that is a buyer journey. This is a part that's often skipped in sales process development. I think founders think that their sales process is a pitch deck. think like a good meeting is like, I went to the meeting and I got through all 27 of my slides about the problem I'm solving and how my product works and the awesome case studies we have. It went great. And there's a million studies that we know that shows that that is suboptimal selling. I can't find a study that says it's good. We know that in the first meeting, the less that the seller the better. And so what's happening in there is You're qualifying and discovering. You're discovering what the buyer perceives as their biggest problems and how they're thinking about it before you tell them about your product. And you're qualifying to see if you can make them successful, if they're in a position to buy your product and be successful with it. That's our objective. And we can't do that unless we understand a buyer journey. So the buyer journey is really just like sequentially how the buyer comes to terms with purchasing your product. They don't wake up one day and be like, where's that contract? need to buy that product. They wake up one day saying, I have a major problem. And that's their first stage is it's just like the awareness stage is like, is this a problem? Is it a big problem? Yeah, it is a big problem. Why is it a big problem? How do I think about this problem? How do I frame this problem? Then they start considering solutions. how do I fix this problem? Do I delegate it to someone on my team? Do I hire a consulting company? Do I buy a software product? And then once they've decided how they're going to solve it, they choose a solution. I'm going to delegate it to Mary. I'm going to hire a seller in the cloud. I'm going to like, you know, I'm going to buy this software product. Right? So like, no matter what you do as a seller, that's what they're going to do. So if we understand that and frame it in that way, and we look at our sales process, not as going out and Mark (04:45) Thank Mark Roberge (05:01) pitching the world on everything we've built. But instead going out and discovering how people are perceiving this problem and qualifying whether we can help them and help them make a good purchase, that's modern selling. That's buyer-centric selling. with that in mind, the components of your sales process is your ICP definition, it's your buyer journey, and then it's how you take that, how do you run that first meeting, which is often called the discovery guide. And then once you've done your discovery and qualification, whether that's in five minutes or five meetings, you usually move on to some sort of a presentation process on how you explain how we're a fit. ⁓ then once we're, you know, hopefully the outcome of that is a purchase and we get to a onboarding and customer realization process. like, you know, obviously within there is negotiating contracts. It's like, there's a lot of different steps, but those are generally the components of the sales methodology. KK Anderson (05:52) You are preaching from the AGS playbook the framework that we talk about a lot at AGS, we call it the two sale mentality, which is taking, I feel like I say this every single day actually, whether you're selling Girl Scout cookies or you're selling multimillion dollar software. Mark Roberge (05:56) Yes, exactly. KK. I figured. Mark (05:57) ⁓ KK Anderson (06:12) every sale is really like two distinct sales. And the first one is getting the customer to articulate why they need to change. And it has nothing to do with what you're trying to sell. It is why, this is a problem, why is it expensive? why getting that and getting them to say it right. And the second sale is why you and why now. And, and one of the things that we do a lot of our competency assessments where we'll, we'll take a sales team and we'll give them, the assessment we use objective management group, and we'll be able to see that they're really low on that discovery, those competencies on the discovery end. And then the second sale, they're like aces. They're selling value is like 80%. They're really good at presentation approach. Like they're really good at selling the second sale. And that is like the immediate recognition of, my goodness, you know, our sales process is not matching our buyers journey. Mark Roberge (06:48) Yeah. Yes. KK Anderson (07:02) And that's, that's, love everything you just said there. So go ahead. Mark Roberge (07:05) KK. I mean, to your point, it's like you have to meet the seller where you are and that's what you all preach. It's just like, okay, we're selling Girl Scout cookies. Like, where are they at right now? Like, thing is like, are they even hungry or not? Like, if they're hungry, I'm gonna pitch them in a different way. I'm like, did you already have... KK Anderson (07:18) you Mark Roberge (07:24) Lunch? Yes, I did. Would you like a treat then? Yes. Now I just have convince them that my Girl Scout cookie is better than the candy corn or the dark chocolate. It's a very different pitch versus if they're not even hungry, I can still sell them a box, but my pitch is different because it's like, are you going to be hungry later? And would you like to support a co- like, you know, it's just, it's a very different perception I'm leaning into. So, but like, you know, many founders come out of the gate. I've never sold before. and they just think this is about getting through the 27 slides. Mark (07:52) Yeah. And Mark, though, the one problem with that is that being hungry has nothing to do with when I eat a Girl Scout cookie. It just pretty much is when it's accessible and then I just start eating them. So complicating fact for our sellers. Mark Roberge (08:00) Yes. Right. Just looks really good. KK Anderson (08:06) So I have a quick question though before we keep going. This has just been so fascinating. So let's say you're in go-to-market fit, you've got your go-to-market system down. What are you looking for in those first five A's that you're hiring? How do you know you're gonna get someone that can sell to their sales process? Mark Roberge (08:28) And you're raising up another, I think important abstract point that we take away here, KK, which is at this point, we've got a clear definition of how we move through the readiness to scale from product market fit to go to market fit. eventually we get into the growth stage. What we haven't covered yet, and we have also discussed the go-to-market system, that this isn't an art form, just like we have a finance system and a product development system, we have a go-to-market system. And we've talked about the components of those, you know, our ideal customer profile, sales methodology, our sales hiring, our demand gen strategy, and KK is asking about the sales hiring component. Now what we haven't talked about this important point, which is the optimal design of those components is contextual. have discussed that a little bit. Like don't... Don't be bringing like an AI cyber product to market in 2025 and copy what HubSpot did in 2010, bringing a marketing product to small businesses. Like these optimal designs are contextual to the product you're selling, the buyer who's buying, and nuances of your own business in terms of stage and culture and all that kind of stuff. But another contextual driver is what stage we're in. Product, market, fit, go to market, fit, growth and moat. For each thing. including KK's question of the odd deal sales hire. I will tell you, if you are bringing a new product to market and you're in the product market fit phase, the absolute worst hire you can make is the number one salesperson at workday right now. The number one salesperson at workday is a genius. They are like the Michael Jordan of sales. They make millions of dollars a year. and they will destroy your company if you hire them during the product market fit phase. Because like when they joined Workday, they went through a month of training with all the objections, the entire playbook. Their manager was there coaching them through. You don't have any of that. You don't even know if you have the right product. Right, so like. The optimal hire at the product market fit phase is kind of like half account executive, meaning they can talk about commercials and do a little discovery and all that kind of stuff, but half product manager who can like reflect on the 10 conversations they had with the market this week, summarize the patterns and talk to engineers about them. That's what we need. When we move to go to market fit, which is specifically where KK is asking is, okay, we feel like we've got product market fit now. Now we need to build the process. So we need a couple salespeople probably, and one of them has to be really good at sales methodology development, which the number one rep at Workday has no clue how to do. Okay, so we need a process builder. And then finally, when we get on the growth phase, that's when we got the number one rep from Workday come in. If they're the right hire, again, like the optimal hire for Workday is probably different than the optimal hire for us. But at this point, it's more of as if I can quote the sales learning curve, a coin operated salesperson. that's going to take the pitch deck, it's going to take the comp plan and it's going to sign up a bunch of healthy customers for our business. Mark (11:16) Excellent. Okay, so let's move into our final topic here, growth and mode. So when teams set the growth and mode stage, you warn against front loading, hiring and pushing vanity growth. What pacing model do you like for headcount and program spend and which board level guardrails keep an honest quarter to quarter? And I'd like to really take this deep, just kind of... Mark Roberge (11:24) Mmm. Mark (11:39) reminding myself even how brilliant our audience is and how this is an area that they don't often get guidance on because most of these, whether it's podcasts or things that are written for sales leaders, doesn't go into the level of just execution and structure that I'd love for you to go into in the few minutes we have left here. Mark Roberge (12:03) and yeah, just to frame it, I every quarter I run into this story. You know, whether the company is at like a million trying to go to 10 or if they're at 10 trying to go to 100 or whatever. it's like, just had this one happen. Some founder was pitching me and they're like, yeah, we'd love to raise around and we're gonna go from 1 million to 6 million this year. And that's possible without headcount with like a PLG type distribution, but this wasn't a PLG distribution. I was like, how are you gonna do that? And they're like, well, we hired 15 salespeople last month. And I was like, How many salespeople did you have three months ago? And they said one. And I was like. They're like, what's wrong? I'm like, you're going to lay off 12 salespeople in like eight months. And that's just what I know why it happens. I know exactly why. Well, first off, why does this break? Okay, this breaks because you're just not ready to hire, ramp and enable that many salespeople that fast. Mark (12:47) without question. Mark Roberge (13:00) And there's no appreciation of what that takes. Let's just start with the recruiting muscle. Like I, let's, I don't have like raw data on this, but I know that if you are, generating for each hire sales hire, if you generate 40 candidates and screen 20 and interview 10 and hire one, that hire is going to be better than if you generated one candidate screened one person. interviewed one person and hired one person. It just is. And you just don't have the recruiting muscle to even attract that high of a quality talent bar and interview them. Nevermind you don't have the demand gen formula on how they're going to get meetings. And you also don't have a proven process and you don't have a management layer. Cause the average manager ratio right now For outside is six to one and for inside it's like eight to one that will probably change with AI, but we're not there yet. So there's just all these like very obvious reasons why this is going to fail. and so I know why they do it. It's just that they promised their VCs this massive valuation and the VCs bought it. So now they promised this massive growth rate and they just opened up Excel or a Google sheet and divided by the expected revenue divided by. the quotas and that's the number of reps they have to hire next month. And that's what they think of scale pattern is. And so let's go get more leads. So we triple the burn now. So anyway, the easy fix in our final two minutes here is don't think about scale at that point as a one-time event at the beginning of the year or after a fundraise and then absorption over the year of those reps. Think about it as a pace. KK Anderson (14:14) And that's why the CROs are saying, get us more leads. Mark Roberge (14:34) So don't think of it as like we're gonna hire 15 reps in January of 2026 and cross our fingers and try to hit our number. Think about it as we're gonna hire three reps a quarter. And so like, let me just, to finish it real quick is there's gonna be signals every month and every quarter that will tell us if we're going too fast or too slow. It's really the leading indicators of retention and the leading indicators of unit economics. And so if we make those three reps and we go through the ramp and like, we look at this two quarters later and it's like, wow, things are good. Then we go to six reps a quarter. And then it's like, if it breaks, we'll fix it. We'll know a way ahead of everyone else and we'll fix it. It might take a week. It may take a month. It may take a quarter, but we'll fix it. And then we'll go to 12 reps a quarter. And then we'll go to 20 reps a quarter. And then we're a unicorn. And we did it in a very predictable way. KK Anderson (15:18) That sounds amazing and like a strong game plan. If only it were that easy, right Mark? Real quick before we wrap up, I love that you're donating 100 % of the proceeds from this book to McLean Hospital. Why is that important to you? Tell us a little bit about. Mark Roberge (15:24) Exactly. Yeah, I just think like I don't know the last proceeds to an awesome for sales acceleration form at bill.org. That's another really big motivator for me writing a book. You know, you never want to do badness with tech. We always want to make the society better. never want to see that's that's the cause right there. That was awesome. So you never want to. Nice. I love it. I'm feeling the joy. Mark (15:49) got to ⁓ KK Anderson (15:51) Yeah, that's my senior finishing his final. Mark Roberge (15:58) You never want to do badness with tech. I think like mental health has been a little bit of a negative ramification as we've gone through various variations and I've suffered dramatically myself. I've had severe anxiety and there's a stigma out there in the world around mental health. If you find out that a candidate is a cancer survivor, a job candidate, I think that elevates your perception of them. If you felt like they had severe depression and we're hospitalized for it, you have concerns and that's not right. They're both diseases. I've had that and I've been fortunate to be blessed with things that people perceive as successful so I can speak openly about this without massive concern. We're getting better with each generation ⁓ but we need to do even more and I think McLean is the global leader around that. In addition to helping with your skill pattern, just know that you're also helping with the great societal cause as well. KK Anderson (16:50) Well, that is incredible. And so the Science of Scaling is available for pre-order now. It releases on February 2nd. And Mark, if it's okay with you, we will leave a link in our show notes to where they can go to your website and they can download the first chapter. will get you there. Mark Roberge (17:01) Great. I'd love Mark (17:04) Yeah, and we should also include a link to just the donations at McLean. So we will add that as well. Mark Roberge (17:11) Yeah, and you can pre-order the book now if you want to do it that way. That'd be helpful. But thank you, Mark. Thank you, KK. It's an amazing platform to be a part of. KK Anderson (17:19) Thank you so much. Mark (17:19) Pleasure, thank you as well, Mark. Mark Roberge (17:21) All right. 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| Ep. 108 - Scaling the Right Way: Product Market Fit, Retention, and Go to Market Readiness with Mark Roberge - Part 1 | 06 janv. 2026 | 00:19:30 | |
In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Mark Roberge, founding CRO at HubSpot and author of The Sales Acceleration Formula, to unpack why most companies scale at the wrong time and with the wrong signals. Mark introduces a stage-specific, data-driven framework for moving from product market fit to go to market fit, and explains why managing to readiness and retention beats chasing top-line revenue alone. Mark breaks down how founders and boards get trapped copying outdated playbooks, why product market fit is often misunderstood, and how to define it through value realization, not just revenue. He also shares a practical approach for finding a leading indicator of retention, then translating unit economics into clear operating KPIs that make scaling repeatable, profitable, and measurable. What You’ll Learn:
Key Topics:
Guest Spotlight: Mark Roberge Mark Roberge is the founding CRO at HubSpot, where he helped scale the company from zero to IPO. He is co-founder and managing partner at Stage 2 Capital, a Harvard Business School senior lecturer focused on sales and go-to-market strategy, and the best-selling author of The Sales Acceleration Formula. His newest book, The Science of Scaling, distills decades of research into a stage-specific roadmap for scaling with measurable readiness. Resources & Mentions:
🎧 Follow Selling the Cloud for more episodes on building durable GTM systems, improving sales execution, and scaling revenue with confidence. Mark (00:00) Welcome to Selling the Cloud. Our guest today is Mark Roberge, founding CRO at HubSpot, who has helped lead the team from zero to IPO, a beautiful IPO. He's now the co-founder and managing partner at States2 Capital. He's a long time Harvard Business School professor of sales and entrepreneurship and go-to-market. And he's the best-selling author of the Sales Acceleration Formula. Mark's new book, the science of scaling distills 25 years of research into a stage specific data driven roadmap for moving from product market fit to go to market fit and ultimately to growth and mode. Personal note, Mark and I have known each other for a few years here and he is a great person to know as a friend and certainly as a business colleague with all the incredible success he's had throughout his career. So let's jump into the four topics we will cover today. also just to remind us all to make sure we cover a little bit of the amazing things that Mark does for McLean Hospital and for mental health and in general throughout our country and the world. Four topics, why scale scientifically? The failure patterns leaders repeat and how to replace borrowed playbooks. with a measurable readiness model. We're go deeper into product market fit, defining ICP, instrumenting a leading indicator of retention that proves value creation and learning how to run fast learning loops within your organization. And then what does it mean to go to market fit and deeper there, how process hiring, demand gen, pricing and compensation. evolve to make revenue consistent and profitable. And then the dream, the growth and most, when you're pacing head count, choosing scalable channels, raising price with confidence and appropriateness, and running a metrics cadence board, an approach that drives trust throughout the entire organization. Mark, thanks so much for joining us. Welcome to Selling the Cloud. Mark Roberge (02:14) Hey, thank you, Mark. Thanks, KK. Appreciate all the preparation in that wonderful intro. Mark (02:20) Beautiful, thank you, Mark. So yeah, topic one, why scale scientifically? We see teams copy a hot playbook, know, ramp up spend, and then they learn six months later in many cases that renewals are soft. So they kind of work on the first side of the equation, but they really don't do the right planning and approach in making sure that they're really able to build long-term client relationships. The science says, manage to readiness and retention, not just the top line. We all know that companies are feeling that for the first time in a number of years as we move from the pandemic to a little more of a specific focus on making sure the growth is there and also that we get to profitability with many of these early stage SaaS companies. So what changes when a founder manages to the readiness and retention? instead of just revenue only. And what is one decision you would stop immediately when the data is noisy and contains more clutter than signals? Mark Roberge (03:25) Yeah, there's a lot to unpack there. So really a lot of the origination of that question comes back to my time after HubSpot before starting stage two. I had this interesting five year period where a lot of this work was originated. ⁓ I honestly did not intend to write another book, but sometimes you do a speech or write an article that ⁓ becomes something bigger, I suppose, and people want more. And then you can start to see the timeliness and also the abstraction by which some of the framing could be applied. And so at the time I was teaching full-time at HBS, but also had a lot of time to participate in the startup ecosystem. As a board member, angel investor, advisor, I basically chose one company every quarter. to spend a day a week with and help them build out their opening sales org. ⁓ At the same time, I was a senior advisor at BCG and I was working with these massive global conglomerates on launching new products to drive revenue, top line growth and EBITDA. And I just found in both situations that there was an unnecessarily high failure rate because this concept of like, when you were ready to scale, like you got your product, you got your beta, you got your whatever. And like the time that you were ready to scale and the pacing was not analyzed strategically well enough. And that's what made me kind of start to reflect on these things on like ⁓ how can you use your own data to figure that out? In the startup arena, Pretty much it was aligned with like when they raised capital. They just happened to convince ⁓ VC to give them some capital and then that was the time that they were ready to scale supposedly because they had capital. And the pacing was essentially like copy whatever some other unicorn that just went public. What did they do 10 years ago the year after they raised their seed round? Mark (05:47) Thanks Mark Roberge (05:47) Which like is, it doesn't make any sense. The contextual differences are so, so off. And then on the, on the big company size, it was like, Hey, we're going to launch this new product and engineering, you build it. We're going to launch it at our customer event in nine months and marketing, change the website and get the collateral going and sales, train all the salespeople and customer support, get all your scripts ready. And then they launched and wasted tons of sales motions on a product that didn't have product market fit. So it's like two different diagnoses with the same issue. And that's what led to the research and understanding why some of these went, some of the companies that I'd worked with did an IPO, a billion dollar outcome, some went bankrupt. And what was the difference in their plan? And it was this three sequence framework of product market fit, then go to market fit and growth and moat is what Over last decade, we've been coaching people to at State Shoe Capital and my work at Harvard Business School with my founders to have a more scientific approach to that. Now, to your point, Mark, you're asking about a focus on customer value creation. And I said the first step is product market fit, which isn't like profound. Normally when you go into like a classroom and ask like a bunch of 30 year old founders, how do know when you're ready to scale? they'll say product market fit, which is a great answer and a term that didn't exist in the year 2000. I think it was popularized by Eric Reese at Lean Startup or Steve Blank. it's like, the term caused us to progress as entrepreneurs. It's fantastic. But what's weird right now is when you turn around and ask those hundred entrepreneurs, what is product market fit, you get a hundred different answers. And half of them are like correlated to revenue and customer count. we have product market fit when we hit a million in revenue. We have product market fit when we have a ton of inbound leads. We have product market fit when we have 15 customers. Mark KK, we all know that like great sellers can sell ice to Eskimos. They can. ⁓ But Eskimos don't need ice. You know, when you can sell, you have market message fit. It just means you're going out there, people get interested and they buy. Mark (08:02) Yeah. Yeah. Mark Roberge (08:12) But the essence of product market fit means that whatever you promised them came true. It means they realized the value. It means they succeed with your product. And in a lot of the businesses that we work in, ⁓ that's best quantified by customer retention. Right? So that's really the backstory mark on your question of like, you know, why do we have to root the opening stages here in customer value creation and retention as opposed to top line revenue growth? And it's just because like acquiring a customer, generating revenue is just a step in the end process ultimately to get to the value realization. Mark (08:51) Mark, you've given us so many things to unpack here and we're gonna dive into all of those. Before I do though, I wanna make sure I cover one item you mentioned there that really, so many things hit me, but this one hit me directly. This concept of like taking the last similar company that went public or had a great exit and trying to replicate the plan there. That would be like Harvard Neuroscience researchers. saying we're going to start a new study, but we're only going to use information of 10 years old or longer. We're not going to look at anything in the last 10 years or five years. We're going to start from there. And we all know where that would bring us, and really not bring us in. Mark Roberge (09:33) And even worse than that, Mark, it's not just like someone doing a neuro study today and copy what was done in 2015, but also that they were in the potiatry department in 2015. That's really the fair analogy is like the context is so different. It's like, oh, we are bringing, you know, a cyber security AI agent to finance departments today. Mark (09:46) Yeah, that's a better one. KK Anderson (09:47) you Mark (10:02) Right. Yeah. Mark Roberge (10:03) So let's copy what HubSpot did in 2010 as they brought marketing software to landscapers. Mark (10:11) Perfect, that is perfect. That is much better, love it. All right, KK, let's take us on. We're going upward. Mark Roberge (10:12) Ha ha ha ha ha. KK Anderson (10:19) First of all, Mark, thank you so much for giving us a pre-read of your book. I can already tell that it's going to 100 % become a Bible in our industry. I was just reading the other day that I think just this year alone, there were something like 2000 AI businesses that started up. So it's very timely. A lot of founders. Mark Roberge (10:22) You bet, KK. KK Anderson (10:39) starting up and they're going to be going, as I was reading this, was thinking of our clients and thinking, I wonder if Mark will let me forward this onto our clients because it's just, it's on the mark every step of the way. ⁓ retention, you talk about retention, I couldn't agree more. But that's lagging, you that's a lagging indicator. And so we need an early signal that Mark Roberge (11:01) Yes. KK Anderson (11:05) that actually helps us kind of figure that out. And so you talk about in the you know, that the framework and figuring out that that leading indicator of retention. So what is like Talk to me about how you figure that out. It's a chicken or an egg. You need revenue, but you need retention. How do you, in those early stages, how do you do that? Mark Roberge (11:19) Mm-hmm. Yeah, that's a great tee up on where we left off here, KK. So, you know, what we've got so far is like, okay, that makes sense. I have my product and I need to figure out my first North Star. And we're arguing so far that like, don't get in front of your company and say, we got the product. Let's get to a million in revenue. We're saying we got the product. Let's get to dozens of customers using this and being successful. Let's have our percent conversion from sign customer to successful customer would be really high. And we're measuring that with retention. To your point, KK, like we can't, like a lot of times we don't really have a sense of the retention on the customers we signed up this month for like a year. You know, like, or at least like many, many months. And that's just too much time in startup world. So we need to pull that measurement back to right now. And that's where we come up with the term leading indicator of retention. this is a term that's been talked about for 20 years. I think we probably framed it at State Shoe Capital in this way. I think in sort of the B2C to B PLG ecosystems, they talk about it. was like the aha moment, even in like some consumer environments. ⁓ and what this is essentially, what can we observe of our customers experience with our product in the first month? That if we observe it. In the long term, they'll be with us forever. And if we don't, they're a significant risk of churn. That's essentially the leading indicator of retention. And I go so far to, I haven't found that there's a universal right answer, like wow, Dow ratio, weekly active user to daily active user ratio, or like time and product, like lead, you know, there's all these different ways of measuring. We can speak about how to come up with it for you. And this is one of those cool, like creative. elements of entrepreneurship is like you get to find this unique thing about your business that's magical. But let's talk about a framework around it. We talk about as P percent of customers do event every T time. So P percent of customers do event every T time. So now we just have to work on three variables. All right. So Slack has a famously documented example. Eighty percent of their customers send 2000 team messages every month. Wonderful. Right, like just imagine like the early days of Slack, there's like 10 people in the room, mostly engineers and designers, and the CEO says, we did it, we're launching. The first goal is to get to a million in revenue. You can imagine like what actions occur. Higher salespeople generate tons of leads, but versus the first goal is to get 80 % of our customers to send 2000 team messages every month. It's just such a healthier foundation of the business. And hopefully through that narrative, we understand that like how we can pull this back to measure this on a week by week, month by month basis. So we can go at startup pace. Now to your point, KK, there's this tension between maximizing revenue and maximizing customer success. This is not necessarily the same. We certainly like, I bet if the CEO of Slack stood up and said, let's get to a million in revenue versus let's get 80 % of our customers to send 2000 T messages every month, they probably would have gotten a million dollars in revenue faster, but it's highly likely that that customer base and revenue base would not have been as healthy. And that in the former situation, they probably would have ended up with a churn rate somewhere between 20 and 40 percent. But by rooting it in the leading indicator of attention, they end up with a churn rate of five to 10 percent. So if I had to choose between getting to a million in revenue in two quarters, but ending up with a 30 percent churn rate versus getting to a million in revenue in three quarters with five percent churn rate, that's a no brainer. the latter's better. And so it just helps us like find that trade off is like revenue growth is critical in the success measure of a business, but it has to be healthy. And we have to have the right guard rails in there to check it. Mark (16:00) Yeah, very, ⁓ very cool. So, okay, so when a CEO says we're missing our number and the first thing they do, CEOs, even boards, we need more leads, we need more pipeline. And you've said in the past that that's rarely the right fix. And it's often this issue is that the system isn't ready to convert the leads it already has. How do you quickly test if that's true? Mark Roberge (16:14) Haha. Yeah. Mark (16:30) And if you can give us a few examples, stories of some fast checks that you use or any founder can use that they can run this week to decide if the problem is readiness versus volume. Mark Roberge (16:37) Yeah. Yeah, okay. So that progresses our discussion to the next phase of go to market fit. Okay, so what we have is like, we have a clear understanding, duh, the first thing we need to do is to get product market fit. But we have a much clearer definition of what product market fit is. I think if you go into Wikipedia and Google, know, or JackGBT, you know, product market fit, you get like a lot of like, it's just a feeling you know. So hopefully now we've like really quantified it and we know what we need to achieve. However, when we're sitting here and it's like the third month in a row and we've closed 10 customers and nine out of 10 customers have hit their leading indicator of attention, we are calling success on product money fit. Are we ready to scale? No, because of what Mark just asked. All we've proven is that we're gonna sign up 10 customers and 90 % of them are gonna be super successful in our product. We're not ready to add 10 salespeople because we still have a lot of questions. Like what's the process? How do we feed them? ⁓ What's the quota? What's the price of the product? I actually don't care that much about these things during the product market fit phase. I just care that these people are taking it seriously and they see success. But like now we have to figure out all these things out, like what Mark is saying around like, is it the lead flow of the process? So we call that go to market fit. Right? like product market fit is I'm, I'm confident that when I sign up a customer, they're going to be successful. Go to market fit as I can do that profitably. Now, when we talk about profitability here, we're not talking like gap accounting profitability out of your income statement, because that accounts for like your entire business, your, your, your office, your, your C-suite. These are some of these things don't necessarily scale with revenue. We want to isolate profitability here. to what scales with revenue and we often in our world talk about that as unit economics. So we need good unit economics. There's a lot of ways to measure unit economics. People that are listening here, you might say LTV to CAC. Lifetime value divided by customer acquisition cost greater than three. That's been a popular one for the last 20 years in SaaS. You might say payback period. How much does it cost to acquire a customer divided by how much do they pay us every month? There's burn ratio. There's a bunch of different like you and economics. And so like, let's just talk about LTV to CAC greater than three. Technically when a salesperson joins your company, picture a 27 year old account executive joins your company. And like, what's my job? The perfect answer is to generate an LTV to CAC greater than three. That would cause a 27 year old account executives had to explode. Like what, is that? How do I do that? So that's where we have to do the work. And we've kind of implicitly done this is we have to algebraically extract that target back to more understandable KPIs. Like how much is the contract? What's the close rate on leads? ⁓ how many, how many leads, how many meetings per month do I need to generate? Right. So that's, that's, you know, we can do that algebraically, you know, to extract it back to like, okay. Cost per lead, number of leads, close rate on leads, et cetera, et And so that's what our go-to-market formula becomes. And now all these things become important of like, how much are we charging for this thing? ⁓ What is our sales process? Do we have a scalable demand gen channel? I don't need one during the product market phase. I do need one now. And that's really what Mark's asking about is trying to get that like math and formula down. KK Anderson (20:29) really what we're asking about terms of. Mark Roberge (20:34) ⁓ So now we're like through that process, we've got three or four salespeople. We have a quota. You know, we're generating, each of them is like either each salesperson is either generating or marketing is helping or SDRs are helping, but they're ending up with like 10 new meetings a month to start off. But the close rate isn't high enough to get to their number. How do we know if it deletes or the sales? That's what Mark's asking. That's really tricky. ⁓ when you're at greater scale, it's a much easier answer. And this is an area that very few boards look at, which is individual rep performance and conversion rate. Cause if I have a team of 10 and four salespeople are constantly achieving a conversion rate of 30 % on their qualified meetings and other salespeople are converting 10%, then I know this is a sales process issue. Now, put aside like to changes in territory and all that kind of stuff, you got to make it fair for everybody. But like that helps me understand that it's, it's some sort of lead, you know, it's a sales process issue versus if I have 10 salespeople and they all have relatively the same conversion, despite probable variances in their skill sets, then, ⁓ you know, we probably have a lead volume or quality issue. And that's where I'd look, but the bottom line is like, You kind of attack both. know, our friend, Jaco at Winning by Design, like famously talks about like, you can do a 10 % improvement in every stage of the funnel. Like it's like, it's not like we're either going to double lead flow or double lead conversion. We, let's attack both and we're probably not going to be able to double both, but we probably can increase one by 10 % and one by the 20 % and the cumulative impact is massive. Mark (22:31) Incredible, incredible. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 107 - Building Revenue Teams That Thrive in the Age of AI with Amy Weber - Part 2 | 28 déc. 2025 | 00:13:45 | |
In Part 2 of this Selling the Cloud conversation, Amy Weber joins KK Anderson and Mark Petruzzi to go deeper into how modern revenue leaders should think about AI, outreach, hiring, and coaching. Amy challenges traditional sales motions like cold outreach and rigid playbooks, and explains how AI should be used to personalize engagement, free up seller time, and enable more meaningful one on one conversations. The discussion also dives into assessment driven hiring and coaching, unpacking why resumes are a poor predictor of success, how to identify true talent signals, and how leaders can reduce friction by understanding identity, motivation, and communication styles across their teams. This episode is a practical guide for CROs who want to build revenue teams that perform, scale, and adapt in a more human centered, AI enabled world. What You’ll Learn:
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Guest Spotlight: Amy Weber Amy Weber is a strategic advisor to growth stage and enterprise revenue teams and the founder of VEDA Sales Consulting. She specializes in aligning people, process, and purpose to drive measurable revenue outcomes. Amy works closely with CROs and executive teams to improve hiring, coaching, and leadership effectiveness using assessment driven insights and practical operating frameworks. 🎧 Listen now and follow Selling the Cloud for more conversations on building modern, revenue focused GTM teams in the age of AI. KK Anderson (00:31) if I could kind of double click on that a little bit, what's one of your favorite starting points? Like if you're gonna recommend to a CRO, I know it's obviously where they wanna focus, but what are just some examples of where you would have them start first? Amy Weber (00:46) Yeah. So I think that of the first pieces of it is that, look, I don't think cold emails work anymore. I don't think cold outreach works anymore. think it's figure out your ICP who is already engaged and then how do you automate some outreach to them in a way that makes is impactful to them. So using AI tools to be able to take that outreach and instead of a ⁓ rep, doing what you're saying, making a thousand emails a week or a hundred calls, kind of automating that outreach, whether it's through, and maybe it's a multifaceted approach, right? Getting more information out on LinkedIn. One of the things that I hated when I worked for big companies was that they wanted, like they wanted to silence your individual voice and they wanted it all to be very static and documented. Well, then you're getting the same message over and over again. Mark Petruzzi (01:28) Hmm. Amy Weber (01:34) Using AI to take that static message, but to personalize it based upon who you're going after is a real tool and trick today. And so you're getting out in front of more people and you're getting your message out in more ways. The second part is, like I said, figuring out what your ICP is and what's impactful for them. And then leveraging those AI tools to kind of create a outreach that is not generic. and is not just cold, it's taking the people that you know today that you want to talk to and making it more important to them, you know, in that capacity. ⁓ an understanding really kind of that the goal is to free up more time for them to meet with these individuals one-on-one. So automating the things that are getting your message out in a content personalized manner so that the AEs and leadership is getting freed up time so that they can actually engage one-on-one because look, The other thing I think is ridiculous, again, I may get in trouble for saying it, a playbook should just be a framework. If you think there's one answer to how to be successful in sales, you're going to fail. Because you have to understand the client and their business need, and not every need is the same. It doesn't matter if you're selling the same product. or the same service, it's how that product or service is going to impact that end user in a new way. And you can only do that if you actually get in front of them and understand what their business or challenge or issue is, how that solution is going to play. Mark Petruzzi (03:12) Great, well let's move to topic three, which is assessment-driven hiring and coaching. And again, something that's near and dear to AGS's heart and what we do, and we're learning a lot as we've gotten to know Amy ⁓ over the past couple months. So how should a CRO use assessment insights wisely and the most productively? Who do they need to assess? Amy Weber (03:35) Yes. Mark Petruzzi (03:36) what two to three signals matter for this role and how do those signals translate into the right interview questions and then most importantly, the coaching plan for that new hire. Amy Weber (03:48) Yeah, like I said, I'm a huge proponent of this because I do think we hire people or we have historically hired people based upon their resumes. That might be the worst possible thing you could ever do. Now, the resume might get you into the door to talk to the recruiter, to the team or get into the interview process, but it shouldn't be indicative of how successful you're going to be in this role. 85 % of millennials will tell you that they are in the wrong role, but they're afraid to change. And so they're just going to keep taking jobs because that's what they did in the past. It doesn't mean that they're in the right role. And scientifically, 1 % of your past success will dictate your future success. So when we do this, we assess people in three different ways. We assess them during the interview process. So you get through the initial screening to say, ⁓ I think they might be a good fit. What are their really, their talent signals? And you're not gonna figure that out just by interviewing them. Because so many people will interview someone and say, I think there'll be a good culture fit. I like them. I'd like to have a drink with them. Great. That means they're a good person. But are they, do they have the right skills to do the role? Right? I'm glad you like them, but are they going to fit the role? like, you know, talking about the hunter, a hunter needs to have a really high drive and desire to go out and be with people and meet people and drive impact and outcomes. Whereas a CSM needs to have a really high precision to say that I can execute on a vision and I can track and make sure that all of the steps are going, that need to be in place for this person to, their rollout to happen in the right timeframe or their, you know, we're engaging the right individuals from their team on a weekly or bi-weekly basis to ensure that everything is going as planned. Those are different people. so understanding those key characteristics, even your emotional resonance, how you deal ⁓ with emotions. And if somebody has, and we can test for that, if somebody has a really high ER and you put them in a hunting role, it might take them a long time if they lose a deal to deal with the fact that they lost that deal. If they have a lower ER, they're going to be like, okay, I lost it. I can move forward to the next piece. And then we customize through the tools that we work with the interview questions to really pull out those key characteristics and those key identity markers because they're different based upon what you're looking for. From there, Once you've hired the people and you've got your team, then you need to determine who your leader is and kind of what their core identity is and how they individually need to understand managing people. That's going to reduce the conflict. And we build out custom management plans for each of those individuals. So we say either here's your team, here's all your benefits. Here's how you should look at your team overarchingly. And then if they have specific issues with a certain individual, whether they're like, I don't feel like I'm getting the most out of them, or we've got some sort of conflict for the use of a better word. How do I address this? Because I really want this person to stay and be successful. We build out specific plans for them in that regard. KK Anderson (06:58) Yeah. Well, and kind of where my head is going is around that conflict, like what you just said. Like there is, and even kind of pivoting more toward that coaching aspect of making sure that the new hire is successful. There's very often just natural friction, especially in the sales world, right? When you have sellers who are entrepreneurial, you get a lot of friction between sales managers and individual contributors. And like some things that come to mind are, a sales manager may, be insisting that you're multi-threading and talking to different stakeholders in a prospect where the individual contributor is like, no, I have a champion. I've got this under control. I don't want to go around them. So deal strategy, right. Or, or there might be, like communication style issues, right. Where. Amy Weber (07:38) Correct. KK Anderson (07:43) A manager is wanting to review the pipeline and have those laborious, sounds like a broken record meetings every single week. And the individual contributors like would rather just, you know, eat nails. And so like when you have, when you have this kind of friction, like what are, are some ways that you can, you know, that you help alleviate it? Like what's it, walk me through like what you would do. you know, trying to. Amy Weber (08:05) Yeah. So, like I said, number one, when I work with clients, I figure out, I do these assessments and I figure out kind of who the people are that we're working with and what their, what their identities are and then how those are impactful to each other. Right. Because you're right. Look, when you are a driver and you're going out and you've got maybe a manager that was really successful and they want you to do it the way they did it, you're going to have conflict because they have to understand that. that ⁓ they can give an outline or framework, but that if they are trying to say, mandating that you have to do it in a certain way, you're gonna probably lose some of your top performers because those top performers are going to, they thrive in chaos. They're going to figure out the best way to work. And they do maybe have that champion and understand the relationship better. It again is going back and looking at opportunities as individuals, not as ⁓ just repeating the same process over and over again. So I figure that out and then I go in and figure out where the tension lies. Is the tension a communications issue? Is the tension a conflict of you've got two really strong opinions and so they're just butting heads? And then it's not so much about changing either one of them, but it's changing how they communicate with each other. It's changing the language. Honestly, what we talk about in business works in parenting, right? You can have two different children that are very different people and maybe how you communicate to one is going to be different than how you communicate to the other. The same is true in the workplace. And you have to think about it from that perspective. If you've got someone who does have a really high empathy level, and so that means they're going to take everything in more personally, then you have to address that problem or that conflict with them in a different way than somebody who has a really low one and you can say, hey, I don't like how you did that change, right? Because they're not gonna take it personal. So we go in and we try to figure out really each of those core components. and then create frameworks for those leaders and those executive leaders accordingly so that they know based upon their core how they should address the different people on their team. And like, I don't think that you should have a team of people who are just clones of yourself. I think that diversity is important, but it's understanding how to manage that diverse environment and where based upon that diversity. you may sometimes falter. We learn as much from our failures or maybe more than we do from our successes. And so if we fall down with somebody, we need to figure out how to pick it back up. And that's just educating ourselves on who we are and who those people are as well. I'm a huge proponent of positive intelligence. I don't know if you know anything about that. Positive intelligence, it's a book, it's been a course. And it says that all of us have ⁓ our saboteurs and, you know, high achiever. Everybody's got the judge and it's trying to figure out how you get to your sage. And that's what we try to coach people on is that it is okay to be hard charging, but understand that you need to take that pause before you just treat everybody the same way. understand who you're talking to before you make that comment. That works, by the way, with your clients as well. So it's just a framework and figuring out where to go and what it's signaling. And then like I said, you also may determine that you just have the wrong people in the wrong roles, be that the individual contributor or the leader. Mark Petruzzi (11:27) Yeah, very good stuff. Cool, all right, well let's move into our final segment here and that is our rapid fire. So real quickly, first product or service you ever sold. Amy Weber (11:38) long distance and you can put an asterisk there for anyone under a certain age to tell them what that means. Mark Petruzzi (11:42) Exactly. KK Anderson (11:43) Like long distance phones, like services. Amy Weber (11:44) Yep, door to door to evaluate people's ⁓ long distance bill and sell them on a lower cost solution. It was hilarious and it was really good at it and it was probably I had no. Yes, long distance for businesses. It did. KK Anderson (12:03) It started you on your career in sales, that's for sure. Yeah. Okay. So who is a, like a chief revenue officer or a CEO that you love to follow? Amy Weber (12:11) I follow several, lots of them, and some people I've worked for in the past and other people. When I sit down and think about it, there's a few that come to mind. Like, think Mark Cuban is phenomenally interesting to listen to, just the way that he drives companies forward and as a CEO and his mindset and the fact that he is very open to giving his opinion. I'm going to mess up his name, but Satya Nadella at Microsoft, I think is really fascinating today because he He has taken a very different approach. worked for Microsoft and trust me, he is a very different leader than the leaders I had when I was there, because I think he looks at it from a people perspective. Alicia Tillman at Delta, she's more of a CMO, but she's taken a real people approach as well. So I think her conversation is interesting. And then there's a guy now that's the CEO of a water company that is very active on social media. name is Jay Williams. And he kills me because a lot of what he puts out there is not related to business at all, but he is increasing his following and his brand in such a creative way. I mean, it's water and people are engaging with him at huge rates. you know, I was in Nashville recently and it's kind of like what the guys at Liquid Death did. KK Anderson (13:26) Yeah. Mark Petruzzi (13:26) Excellent. All right, one leadership habit more sales leaders should practice. KK Anderson (13:30) What a great conversation. Mark Petruzzi (13:32) Excellent, thank you again, Amy. KK Anderson (13:34) All right, and thanks to our amazing audience. Mark Petruzzi (13:36) Of course. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 106 - Building Revenue Teams That Thrive in the Age of AI with Amy Weber - Part 1 | 16 déc. 2025 | 00:22:01 | |
In this episode of Selling the Cloud, Mark and KK sit down with Amy Weber, founder of Vetta Sales Consulting and strategic advisor to GrowthStage and Enterprise revenue teams. Amy specializes in aligning people, process, and purpose so strategy translates into real performance. She shares why many revenue organizations stall not because of tools or plans, but because of role confusion, misaligned talent, and leadership gaps. Amy breaks down how to design roles that reflect reality, how to hire and coach based on true behavioral identity, and why companies must stop promoting top reps into leadership without assessing desire and capability. She also explains how AI can power a stronger customer experience by removing low value tasks and freeing sellers to focus on discovery, executive access, and relationship building. This conversation hits the core of modern revenue growth: the right people in the right roles, operating in a healthy, human selling system. What You’ll Learn:
Key Topics:
Guest Spotlight: Amy Weber Amy Weber is the founder of Vetta Sales Consulting and an advisor to high growth revenue organizations. She helps CROs and CEOs fix the people's side of revenue through role clarity, talent fit, and leadership development. Her work replaces outdated activity goals with clear rhythms and systems that actually change behavior, increase productivity, and create healthier teams. Amy also advises organizations building AI for talent decisions. Resources and Mentions:
🎧 Listen now and follow Selling the Cloud for more GTM insights from leaders driving the future of revenue. Subscribe wherever you get your podcasts. Mark Petruzzi (00:31) Welcome to Selling the Cloud podcast. Today we're joined by Amy Weber, a strategic advisor to GrowthState, Stage and Enterprise Revenue teams and the founder of VEDA Sales Consulting. Amy's work centers on aligning people, process and purpose. So strategy turns into the most powerful performance. She's known for helping CROs fix the people side of revenue, writing roles that match reality, hiring for fit. not just overall pedigree, and coaching managers to run simple weekly systems that actually change behavior and drive the highest level of productivity. Amy Kevin Lee serves as a strategic advisor to organizations building useful AI for people decisions. And she's led transformations that replaced the old fashioned ad hoc activity goals with clear operating rhythms. This allows there to be a freeing up of more human time for discovery, executive access, and relationship building. Her lens is tool agnostic and outcomes first. What should change on Monday morning and how do we start measuring it? We'll cover three topics today. People and with the focus on them being greater than tools, roles, fit, and real leadership. Why growth stalls when the wrong people sit in the wrong roles, and how leaders create clarity and accountability. AI plus a strong experience culture, freeing time for human selling, using AI to take low value work off the team's plate so sellers could spend more time with customers, and assessment-driven hiring and coaching, really tool agnostic but practical ways to use talent data to hire coach and fix manager IC friction without turning it into a tech commercial. So most people who know us and are on this ⁓ podcast with us every week know that's all things that are near and dear to KK and my heart and to what we do at AGS as well. So in another way, we're bringing an opportunity to get a... a different perspective or another perspective, but I think we're going to agree on a lot of things here based on the stuff we know about Amy already. So Amy, thank you so much for joining us and welcome to Selling the Cloud. Amy Weber (02:43) Thank you both. really appreciate it and I'm looking forward to the conversation today. Mark Petruzzi (02:46) Excellent. Cool. So first question, lots of teams have the right strategy and plenty of software, but the people role fit isn't right and results off install. As a CRO, what are the three fastest tells that role design or fit is the real problem and that it's not the plan or the overall tech as well? Amy Weber (03:04) Yeah, it's great because everybody steps back and they're like, what tool can I put in place? What new playbook can I roll out? What's our strategy? But they forget about the fact that the number one thing that they need to determine is do we have the right people in place and are we managing them correctly? So number one is, are your top performers miserable? Are they out there driving sales, but they are updating their LinkedIn? They're telling you that they're unhappy. They show up and they are on Monday mornings. you can just see that the energy is drained out of them. Because they're driven individuals, they're going to go out and they're high achievers, they're going to go focus on success, but you can just see that they're deflated. So number one, top performers are just absolutely miserable. You the second thing I see is that you see the same mistakes over and over again. You're providing individual or team coaching. You're giving a... guidance, you're rolling the playbook out, but you're seeing that the mistakes are just compounding. That's just repeating themselves. And then really the third one is we're promoting people incorrectly. So promotions are causing problems. I tell people that leadership is not a reward, it's a responsibility. So we're taking top sales performers. We're like, oh my God, they killed it. They were 300 % of their number again, and they've made club every year. So we're going to make them the manager. a director. And they may be a phenomenal sales individual, but they have both not the desire nor the actual skills to lead a team. And that desire component is really important. You could be the best sales rep in the world, but really not have the desire to want to manage, train, create empathy, you know, in other situations. So for me, those are the three glaring ones that I see that when I go into organizations, I'm like, They say we can't grow or we're stagnant or we've got a lot of they say culture problems. It's it's not culture. It's people you people problems KK Anderson (04:56) That's so interesting. what we see with our clients and sales organizations is that the quote unquote job description for the sales roles, I mean, they're conflicting. You've got this mandate to go out and hunt and prospect and build new business, must hunt. And yet they need to be also an account manager and running projects and programs and keeping the relationship of the... keeping everybody happy, right? And then, you know, some of them are also part-time analysts. And so it's just like a lot of conflicting roles. And I think that probably leads to what you described with that burnout almost, right? Amy Weber (05:37) Exactly. I call those Frankenstein job descriptions because they're like, I want a self-starter who's a good collaborator. And I'm like, what? You know, I need somebody who's going to really go out and drive revenue and has the executive relationship that's good at doing the research. OK, well. KK Anderson (05:41) Yes. Mark Petruzzi (05:46) Ha! Amy Weber (05:54) They're just, they're putting together these, what they think the requirements are and they really need to hire for the key components of what they're looking for. A hunter role is different than a farmer role. A customer success manager, and sadly we see that get cut from companies all the time. It is cheaper to maintain a good client than it is to find a new one. And I could repeat that over and over again, but people don't understand it. And they're like, well, they, Accounting executives as Hunter can be the CSM as well. You know what? They probably don't have the right skills because a good CSM is going to be somebody who really wants to be a collaborator, can hide behind the scenes, is very detail oriented, likes to follow a process, right? A good salesperson thrives in chaos. There's somebody who goes out and can just drive opportunities because they're listening to the business needs. and they can kind of pivot and determine how to pitch the right solution, but they're not following a step one, step two, step three mentality that a good CSM really needs to do. That's why I don't think, and I get in trouble all the time, and I'm going to say it and just throw it out there. Most SDRs are not salespeople and should not report to sales. SDRs are operations people. They are good at following a script and setting an appointment, but they're not doing the key core KK Anderson (06:53) Right. Amy Weber (07:10) attributes of sales, is listening to the business problem and creating a solution. KK Anderson (07:14) Right. So I follow up on that real quick though. So once we get those kind of roles rewritten and we figure out like what are the real core behaviors as you said, that that job demands, do you have any tricks on how to like test for those behaviors in interviews and specifically, know, a hunter, right? It's a very hard role to hire for. And they may think, for example, that Mark Petruzzi (07:15) Great. KK Anderson (07:38) because this person is an extrovert that they're gonna be really good at picking up the phone and making connections and calling people, not necessarily true. So talk to our audience, if you will, a little bit about how do you like kind test for behaviors. Amy Weber (07:50) so I actually do test and I leverage psychometric analysis tools in that regard to really determine people's core identities. So the irony is this, look, I've been in these roles 30 plus years now, which I like to tell people that means I was 12 when I started because I sadly do not want to acknowledge how much older I've gotten. But ⁓ we took this personality test from the time I was in college. KK Anderson (08:07) That's right. You were. Amy Weber (08:16) and your personality changes as you grow and as you meet new people and things, but your core identity doesn't. So somebody who is a self-starter should really have a high drive of influence. And there are specific questions that you can ask during an interview and or a promotion stage and or as a sales leader to determine if they have that true drive, right? If somebody is saying, talking about the influence that they have or that they that they've had in a deal or with a specific executive, you know that they're a high influence type individual ⁓ versus someone who says, work really well and I like when people bring ideas and I like to brainstorm those and I like to work in a group to determine that. That is not somebody who's going to go out and be impactful from an influence perspective. They're going to be good at working behind the scenes. Someone who's a good influence person is going to kind of be a strategic thinker and then you need those people with the lower influence to implement that strategic vision. The same is true on like, I don't care if they're an introvert or an extrovert. Some of my favorite people I know are incredible introverts that can turn on that extroversion because they're passionate about the solution or the product or the service that they're providing. But once they've done that, then they... they'd master that Irish goodbye, they can just leave. They don't like that small talk or that networking where, it doesn't matter. You don't have to be that extrovert, but there are, there are solutions, there are tests that you can take that really get to the core of who you are. And then there are interview questions that we coach people on asking to really understand kind of where they are from a influence, sociability, consistency and precision perspective. Mark Petruzzi (09:35) Ha ha. Amy Weber (09:56) to model out who makes sense in these different roles. Like I said, I had a young lady who worked for me. She was fabulous. And her previous leader was like, I would fire her. And I'm like, okay. So I interviewed her and when I was bringing her onto the team and I laughed because they had her a ⁓ hunting role. She was a farmer. She was very precise. She was very good at maintaining clients and getting them to buy new products. She did not like the aspect of going out and building new relationships every day. She wanted to take a relationship and grow it. That is a farmer versus a hunter. And you have to understand as a company, what are you really looking for and where are you putting those people? And then coaching them and managing them per their identities versus everybody's the same. Mark Petruzzi (10:40) Amy, those are all great insights and I'm going to bring us back to a point you made earlier where you were saying how, there's all these companies that are cutting customer success and the value and the cost of driving a new deal, finding a new one, hunting a new one versus the concept of just, you know, keeping clients, keeping them happy, keeping them expanding. I've always, I am always saying that to my clients as well. And there's a couple thoughts I have behind that. And in the first book that I wrote, Selling the Cloud, I have a whole chapter around how in general, I believe women are better sales reps and sales leaders than men on average. That's just the nurturing. Amy Weber (11:07) Mm-hmm. Mark Petruzzi (11:25) perspective, the empathy connection, all those things are so valuable. Even grit, I think women have more grit on average than most men I know, including myself. So with that in mind, this concept of like hunting being more valuable than farming or customer success is something I fight about every day. And I think it's a bit of a machismo type of mindset that we all know. most CROs or sales leaders over the last 20, 30 years are men, not women. And luckily and thankfully, that's changing. But when we look at that concept, it all kind of comes down, guess, this. Nobody celebrates the person who comes back with a, a bucket of fruit or nuts and something they just cultivated and brought back into a village. but the person who has a deer or some other animal on their shoulders and they're carrying it back, they get a big celebration when that happens. So how do you think you change that mindset when it really comes down to it? How do you make companies just understand that it doesn't matter. A dollar of revenue is a dollar of revenue. Amy Weber (12:34) Yeah, you know, I've got a specific story I'll tell you. Back when I was a young sales rep, I walked into an account, literally walked into it. The receptionist wasn't there and I just wanted to figure out what the company was doing. I'd never heard of them. And I met the CEO. Luckily, he didn't just pitch me out of the office, which he could have because I was well. I had inappropriately entered their building. And I ended up having this great conversation with him. He's still a friend of mine to this day, so I think it's hilarious because I just walked in and knocked on his door and I said, hey, what do you do here? And when he got done laughing at me, he's like, how did you get here? And I said, well, no one was at the front desk. But the long and the short of the story is that they were a growing company and they were a small business when I first met them and they are now a massive provider of technology. Mark Petruzzi (12:54) Yeah. KK Anderson (12:54) That's my thing. Mark Petruzzi (13:05) you Amy Weber (13:16) and he's no longer the CEO there, but across the country, across North America. And they said, I was working for Cisco at the time and they're like, you're too big, you're too expensive, we won't need you. And I said, okay, that's your opinion, but really I just wanna hear what you do. And they appreciated kind of the fact that I just wanted to learn. So they invited me into a technical meeting. Long story short, they had zero Cisco when I took them on. When I left Cisco all those years later, they went from zero to 95 % of their footprint was in our product. they, whereas they were never going to spend any money on us, 95%. And it was because we listened to them and we helped them determine ways in which they could leverage the technology. They became a reference of look out. They were a multimillion dollar customer for us. Right. When I left Cisco and I was no longer the rep at that time, I had moved into leadership and other aspects. But I had stayed engaged with them. People did not keep that relationship going. And they moved off of all of that platform. So they went from zero to 95 to back to almost nothing again, because I had built the relationship, I had listened to them, but I had supported them not just when we needed a PO. I had supported them when they were growing or they had ideas and we went and talked. It wasn't about just celebrating their success when they were spending money with us, it was helping them figure out what their plan was for the future. And that's why I say the number one skill in sales is listening. And then it's that customer engagement. I'm kind of, you know, I talk to people about, getting back to that point where that client experience is going to be the key. And whether you are a retailer or a technology company or a restaurant. I was down in Miami for a holiday weekend recently and we went to this fabulous restaurant and it was a Michelin star place and they could only seat 16 people at one time. And you're having this curated prefix menu experience. And I whisper basically to my significant other, I'm a little chilly. And within seconds, cashmere pashmina was draped over my shoulders. That is a client experience. I never said a word. And that is what we need to take to our companies, that idea that when we're talking to them, that we understand their needs, even if it's just that they're cold. Right? And so it's really just taking that step back and figuring out kind of what we need. And what we need is client customer experience to go out and ensure the client is continually taking care of. We need the account type reps that aren't out for the big kill, that they're not looking for the next elephant, but that they understand that they can take their current client and continuously grow them. And then you still need the hunters that are gonna go out and find new business. KK Anderson (16:00) So I love that story. And it's actually the perfect segue into our next topic, talking about AI and really kind of this customer experience culture that you're talking about. And what you described, is just so human. And that is the human part of selling that will never be replaced by AI. Right? It will never, it will never be replaced. Now that said, that's, that's what's critical. And you're right. and we talk about this a lot on our podcast. The pendulum has swung from everything being process heavy tool, heavy, you know, send 5,000 emails a day, make 100 calls a day, being able to use technology to just, increased productivity, even if it's not productive, right? Or effective, all the way back to, wait a second, people buy from people they trust and relationships are what matter. And Mark, maybe that's why women tend to be so effective in sales roles because that's paramount, you know, in our hearts and in our minds is that relationship like you described. Amy Weber (16:53) Correct. KK Anderson (17:06) Knowing and appreciating and 1000 % agreeing that the relationship and the human activities and the experience are paramount. How can a salesperson use AI for the other things? Like what are some things, specific tasks that they can do that you've seen your customer or clients doing to give them the time to have that human experience? Amy Weber (17:23) Yeah. ⁓ Yeah, it's great questions and all of that I agree with as well, right? I think that one of it is ⁓ that research and account prep. I don't want a rep to ever go into a meeting that they don't know the answer to the questions that they're asking, right? They should have done, there's so much information out there, but instead of them spending time, I mean, I remember being a young rep reading when it was a publicly traded company, I was reading the financial reports. And thankfully I have a degree that taught me how to do that, but a lot of people don't, right? And so using AI to do that research and that account prep to really build out kind of a portfolio and the tools are so good at that and kind of reaching out across all the different platforms, know, is the person you're meeting with, are they active on LinkedIn or socials or are there blog posts? What's interesting? So that you build that connection. So that's one. And then being able to take that information and personalize the content that you're sending back to them. Whether it's the communication from you speaking to them, whether it's the emails that you're sending, whether it's you you see an interesting article that you think would be good for them, that content personalization. And then post meeting intelligence work. So being able to automate all of that. So that you're not spending time doing the mundane tasks of the follow-up. and those repetitive outreach type solutions, automating that through AI and having that process put into place. One of my clients is actually, they've ⁓ got an individual that has been writing on Medium for like the last 11 years. And so his voice is really interesting. And he is, instead of him continually having to write and post because he's really busy, they're now using, they built in their, LLM to be able to go out and kind of pull segments from what he said in the past so that they can then automate it to repost it on the social channels in different ways. And that's fascinating because you're taking his intellectual property and AI and you're putting it together. So his voice is still being heard, but in smaller bite-sized pieces. So there's a lot of really different. cool ways to leverage AI that what it's then going to do is free up time for me to be out in front of the customer more. I think we spent a number of years back in front of the video camera like we are now. I think that now we are pivoting back to, we want to be out in front of the customers and clients and talking to them one-on-one and listening and understanding and engaging in group discussions and all of that. And AI will free up our time to be able to do that. because it's going to just take away those repetitive tasks that we don't need to be handling or doing. The tools will do that for us so that we can get back to the real interaction of the human engagement. Mark Petruzzi (20:14) Good stuff, Amy. ⁓ Teams say that we use AI, but at the end of the day, nothing really changes in our calendar. What weekly operating changes, cadences, coaching, or metrics ensure AI actually creates more customer time, more selling time, and not just a lot more dashboards or new processes? Amy Weber (20:35) Yeah, analysis paralysis is kind of the mindset that comes to me, right? That they just keep linking on additional tools and instead of thinking, how is this providing benefit to the teams or to the organization? So I like to think of it as stop trying to boil the ocean, pick one tool that's going to make a difference, implement that, and then move on from there. So have a plan. If there's multiple tools that you want to engage or that you think might be good and you're testing them, pick the one that you think is the most impactful first, deploy it, and then execute based upon that tool, right? Automate one task out of the gate instead of all the tasks. And then measure the time savings that you're getting from that tool, not just how many people in the organization are using it. we tend to, organizations are like, I've got a 50 or 75 % adoption rate into this tool. But is the tool really giving the people back more time or is it just another tool that they're using, right? Then layer in the next piece of automation and analyze that behavior and just follow that routine. Because that's how you're going to determine, am I really getting any results from this versus just investing in multiple tools and multiple components. So it's stop trying to boil the ocean, pick one thing, focus on it, do that well, and then move to the next step. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 105 - Turning Personal Networks Into Pipeline: Inside the Relationship Intelligence Era with Drew Sechrist - Part 2 | 07 déc. 2025 | 00:19:14 | |
In this episode of Selling the Cloud, Drew Sechrist, CEO and co-founder of Connect the Dots and longtime Salesforce veteran, joins Mark Petruzzi and KK Anderson to unpack what it really means to build a relationship intelligence layer that changes how your team goes to market. Drew shares why his own career win stories at Salesforce led him to build Connect the Dots, and how mapping real relationship strength can turn stalled enterprise deals into closed revenue. He breaks down the nuance of activating networks at scale, aligning incentives around introductions, and embedding relationship data directly into the existing workflow so new processes do not die on the vine. From Monday pipeline reviews to executive access and stuck late stage opportunities, Drew explains how the best revenue teams treat relationship intelligence like the air they breathe. What You’ll Learn:
Key Topics:
Guest Spotlight: Drew Sechrist Drew Sechrist is the CEO and co founder of Connect the Dots and a former Salesforce executive who rose through the ranks during the company’s hyper growth era. His experience closing large, relationship driven enterprise deals at Salesforce inspired him to build a platform that operationalizes the power of real networks for modern revenue teams. Today, Drew helps companies turn hidden relationship capital into measurable improvements in win rates, cycle times, and deal size. Resources and Mentions:
🎧 Listen now and follow Selling the Cloud for more GTM, sales leadership, and AI driven revenue insights from leading voices in enterprise growth. Subscribe wherever you get your podcasts. KK Anderson (00:31) And this really feeds into our second topic, which is around building that kind of relationship intelligence layer. What you've been describing, right? That is, it really is a different approach to like, to go into market. And so like, and if you think about like, let's say we do, you do this 90 day plan, it's working, like your team is, show this team that you're piloting this with is showing success. You build kind of the playbook and the process for how you could repeat it or scale it. Does this become something then that your managers start coaching? Does your pipeline meeting sound differently? What happens then? Drew Sechrist (01:08) Absolutely. So do anything except use our network to go to market. That's it. That's all we do. I can't actually say it's entirely true. It's like we do some events. We'll go out. I was at Dreamforce last week. We hosted the Salesforce alumni reunion. So we do things like that. But that's also kind of relationship based as well. But we don't do anything else. So we're kind of like this purist in this new motion. So the answer is absolutely yes. But I will say we don't have it all figured out yet. We have some of it figured out. The challenge, think, is really like. The challenge is a lot about protocol. Protocol and aligning incentives for everybody. Just because you can see everybody that knows everybody in the world and how well. Just imagine there's some magic way for you to see everybody that we collectively as a company know and all the people that they know and how well they know them so that we could say, great, Mark's got this really strong, looks like he's got a strong relationship with the CEO of this. Fortune 500 companies, let's leverage Mark to get to that person. How do you do that? Like it depends on, there's a lot of nuance. Who is Mark? Is Mark one of our senior executives? Is Mark an investor? Is he an advisor? Is he just a friend from the gym? Is he my neighbor? What are his incentives aligned with us? Is he a customer of ours? You know, like all of this. those things play into the, how do we activate Mark's relationship with this person? Just because we can see that it exists. That's, that's like, call it 50 % of game. But then the other 50 % of game is how do we actually activate this in a way that Mark feels good about that's going to be effective. That's going to, know, he's going to facilitate the introduction. one of the big challenges I think on this is like, the incentive alignment thing, like, let's just talk about compensation here. Let's talk about compensation for a moment, if I can take it that direction. If you really want to unlock the network, then everybody's got to be compensated somehow. Now, I don't want to be too capitalistic about this. I don't want to be too capitalistic because many moons ago when I was starting my career at Salesforce, it was around that time. I read Malcolm Gladwell's The Tipping Point. you've read it, KK. Mark, have you read that? Yeah. So deep in our brains, right? And I definitely identify it as a connector, even at that young age. And I was like, I'm a connector, and I love this. And so no surprise that years later, I started Connect the Dots. And I do make connections for, Mark Petruzzi (03:09) I certainly have, Drew Sechrist (03:25) Many like Matt, vast majority of the connections that I facilitate in my life are not, I'm not expecting any kind of, know, compensation for that. let's say certainly not any monetary compensation. might like, would, I might like, Hey, thanks a lot, Drew. That was really nice. You helped me out a lot here by introducing me to this person. I like that. makes me feel good. So. But if you want to do this at scale, you got to figure out like, what is the compensation that everybody's in the network is going to have? and it could be straight up, just, you feel good doing it. Like I'm a connector and I do feel good doing it. KK, if you wanted to get to get to somebody, let's say, totally random idea. Like you're, you're going to go to Dublin and that came up and you're like, I really wish I knew great. whatever pubs in this little town outside of Dublin, cause that's where I'm going to be. like, you know what? know somebody from that town. Let me introduce you to, I'd feel good. You go to some cool pub and have a great time. And that person that I connected you to probably would be like, yeah, that's kind of neat. Somebody's going to my town. And so my compensation on that one is, you know, it's, basically, it's a dopamine hit. I feel good that I've connected to people and their lives are going to be a little bit better because of that connection. But KK, if you hit me up like. 40 times a day, every day for introductions to various people, for various reasons. At some point I'll break and I'll be like, KK, I got a day job, I'm sorry. You know, like I can't help you with, you know, 40 introductions a day. Now, if you hit me up with 40 at and say, Drew, I'd like you to make 40 introductions a day for me. And these are the introductions I'd like you to make. And it's good for the person that you introduced me to. And by the way, Drew, for every introduction that you make, I'm going to give you $10,000. I'd be like, hmm, all right, KK, you only want 40 a day? you like 50 a day? Would like 60 a day? I'll see what I can do. Right? So incentive alignment and compensation are important here, it's so nuanced. mean, think about it. Like, you're getting paid to make an introduction to somebody, you're a friend. That doesn't feel... KK Anderson (04:58) Yeah, or 400. Yeah. Mark Petruzzi (04:59) Yeah Drew Sechrist (05:14) Right? Does it? You know, it feels, that feels wrong. Like if, he's, if KK you say, Hey, Drew, could you introduce me to one of your friends who is a good prospect for us? And if they buy, or even if they don't buy, I'm going to give you a thousand dollars or something like that. then I don't know. just, it feels weird. that feels weird. Now, if I were an advisor for your company, KK, you're CEO of company and You say, Drew, it looks like you've got a great network into the companies that we want to sell to. would you be an advisor for us? We're going give you some equity and we'd like some advice from you. We'd like you to open some doors for us so that we can get in and sell our product and get feedback and grow and become a successful customer. That doesn't feel bad in the same way as getting paid with cash, right? so there's a ton of nuance here. Candidly, we don't have it all figured out yet. I think this is like this whole space is taking shape right now. It's like there are tools that are making it possible to leverage networks at scale like never before, but you got to figure out how to, how to activate those relationships and make everybody feel good about it and also incentivize. KK Anderson (06:05) Yeah. What's old is new. Relationships are old as time and here we are, right? Drew Sechrist (06:14) Mm. Mark Petruzzi (06:17) Yeah, so that makes perfect sense. this is, I love where this discussion is going. So let's just analyze a little bit. So everything we're talking about for most companies is a new process. And the adoption of new processes, they typically die if you can't get it into the core workflow. So how do you build this in? Like where should relationship intelligence live in the overall stack and the overall rev-up and what you're doing there so that you don't need to drive any heavy change management in this process. So what's the latest weight setup that still moves the needle that you work with your clients on? Drew Sechrist (06:54) Yeah. Yeah, that's a great question. I think it should be kind of like the air you breathe. It's everywhere. So whenever you're in any place that you would need this information, it should just be there and you shouldn't have to go look for it. So for example, our customers have access to us inside of Salesforce. Not everybody wants to use Salesforce, if you're using Salesforce, then you're looking at an account or contact. We have our relationship, your relationship data visible to you inside of Salesforce. So as you're doing your account planning, now sales managers are saying, okay, did we connect the dots? Literally, they'll say that and they'll look and be like, well, why didn't we use this contact here? So we have our board member knows the CMO has a strong relationship with the CMO at this company. Have we connected the dots there yet? And if the answer is no, then you just click the button and you initiate that request. And it gets routed through, however, it should get routed, it might get routed through your CEO to, the CMO of that company or whatever. so that's, that's one, other places that people work or Slack, either email, getting notified via email that you've got a relationship that you should be leveraging for a deal that you're working on. We do that. we also, we're launching an API shortly where your rev ops team will be able to put the data anywhere that you want. whatever that is, if you have a list in sales law for outreach or you've got some other single pane of glass that is the thing that you look at to figure out what's your next action with your target accounts, ConnectedOuts can just be one of the pieces of data that's on there that says, hey, don't be stupid here. Don't try to go cold into this account. You can get a direct introduction from You know your VP of finance who knows their CFO. And so just do that initiate that. So I think that the best way is not to have any new UI. We do have a UI that's no are tool as a UI, but I think the best way to do this is just not have any UI at all and just be where be wherever the users are already working. KK Anderson (08:48) makes a lot of sense and that sounds, that would be amazing, right? Gosh, this time has flown by so fast. I'm gonna move us along to the third topic and I'm afraid we're gonna run out of time. But let's talk about stories and playbooks and how we can turn some of these connections into outcomes. so I love a little story time. So like what jumps right out at you when you think about kind of a, a story where a relationship, changed the game and because of a relationship, because of a connection, then boom, an intro was made, like some magic happened and like what changed because of that? Cycle time, win rate, deal size, like give me a story. Drew Sechrist (09:27) Yeah. one story, one story was, from, early days at Salesforce we hired in, there's a really important relationship I made in my life was with my new boss who came in then was named Jim Steele. So that was probably 2004, if I recall correctly. And I just saw Jim at Dreamforce this week, caught up a little bit. Mark made Jim interview with a lot of people before Mark Benioff hired Jim Steele. And I was one of those people. so I love Jim at that point. I love Jim today. it was such a great decision to hire him. So I gave him, thumbs up, to Mark and then Jim, saw later in the hallways, like drew, I you gave me the thumbs up. Thanks so much. What can I do to repay you? And I was like, Jim, I'm so glad you asked that. And then I pulled up a, like, here's my list of accounts. These are my, this is my territory. Who do you know at these accounts? Mark Petruzzi (09:55) Mm. Thank Drew Sechrist (10:11) That's how you can repay me. And, we found, I won't name the names, but we found there's a large semiconductor company there that he had a friend at who was a very senior executive C level exec. and he's like, I know this guy right here. and I said, great, let's see if we can get in. So Jim picked up the phone, called him and we were in that senior executive's office the next week. Now I had been trying to crack into that account. I don't know, for the years, I don't know, for some long period of time, completely unsuccessfully. And then here we are sitting in the C-level executive's office, you down in the peninsula in San Francisco. And, and then, they had a conversation and I was kind of flying the wall and, know, I, basically was the errand boy on that. And I took all the follow-up notes and knew what we we had agreed to do next. And, but those two kind of, discussed everything And there was a high level of trust between them because they'd both worked together for long time in the past. and next thing you know, a couple of months later, we closed a very large transaction. I think it was a seven figure transaction. And, that was amazing. It was totally transformative and like blew out my number for that year. And it was a deal that would not have happened just zero percent chance that that would have happened. And that, and I wouldn't say it happened a lot for me. But it happened enough where I definitely, at some point I'm like, am I any good or am I just lucky that I'm surrounded by these people that have these relationships? And then I was like, what? I really want to be good, I want to be master of my craft, but I could also just continue to be unlucky and this is okay too. And the commission checks still cash. so that is, Mark Petruzzi (11:27) you Drew Sechrist (11:40) a big part of the reason why I decided to go start this company, Connect the Dots, because that magic is out there. It's just waiting there. It's just hidden. You can't see it, right? And if you can just see that that relationship exists, then you can manifest. KK Anderson (11:47) my goodness. You are best equipped to help the person you once were and those experiences that provided you that unlock is what you're helping others to achieve. Drew Sechrist (11:58) Yeah. Yeah, by the way, thanks if you're listening, Jim Steele, thank you so much. Mark Petruzzi (12:06) Well, that's interesting. So next time I speak with Jim, I'm going to have to see if you have given him his 5 % of the equity of Connect4Dots because that sounds like exactly when you came up with the initial idea here one way or another. Drew Sechrist (12:20) Yeah. Jim made plenty of money from all the deals that we closed together. He's fine. That guy's totally fine. Mark Petruzzi (12:28) That's true. Yeah, and Jim wouldn't want it. So no, that's really cool. Okay, so let's make this even more real. Let's go even deeper. So, let's say it's our Monday pipeline review in an enterprise SaaS company. And we've got all these late stage deals stuck with finance, lots of middle stage activity, and we need more executive access. what should we do? right after that, how do we make that happen? And what are the top three actions you'd put in motion right away when you're at that point? I'm sure you do every quarter with your own company. Drew Sechrist (13:04) Yeah, I'm sorry that you're just like giving me these layups about connect the dots, connect the dots. That's this company. I mean, the thing we do all day, every day is, is at every stage of our sales process, we are looking to connect the dots. that was, know, David, David Nitsky from, from Salesforce came up with that phrase back in the day, connect the dots meant, okay, who do we know at this company? How do we get into this company? Mark Petruzzi (13:08) No, and that's exactly where this one's gonna go, I know that. Drew Sechrist (13:29) How do we get hired in this company? And we basically built the tools like our dream tool for solving this problem. The problem is, we can't get in everywhere. doesn't, it doesn't work in every situation. You cannot assume that you always have an in at every company and, to be able to get to every executive, through your relationships. But it's definitely the first thing you should check. Cause if it exists, then that's it. That's your, that's your Trump card. Good play. Right now, play it immediately. Boom. ⁓ So, you know, first thing we do is we check to see if we know anybody and our heat map of the relationships is connect the dots. So we can, and we'll go into, we can go into Salesforce and see, do we have any relationships via our network and our network to sort of clear is it's all of our employees. You can see all of them are bored, our investors, our advisors, all of our customers happen to be on connected. That says you may. Be aware because they're using connect the dots. So we can see through all of those networks, anybody that knows anybody and all of those scored relationships. So if a deal stuck and you're at two weeks out from the end of the quarter and you've got a champion, but you've never gotten to that C level executive that is ultimately going to sign off on it. And by the way, we do this all the time. It's like happening today in the background right now. we're seeing, okay, Hey, we actually. have this former colleague who is now on the board of this company. And they're on the board. So they know the CEO who's going to be the ultimate decision maker on this this deal. Send them a text message. And just ask them, this is in, it's with your chief. It's with the chief legal officer of your company. It's almost done with red lines. It's going to be on the desk of your CEO for decision. Could we get your voice of support on this? Or could you introduce us to the CEO so we can have that conversation? And if you don't have those relationships, all you're doing is twiddling your thumbs and hoping that like, I don't know, when it gets on the desk of the CEO, they're going to say yes and sign it versus no for some reason. So that is what I recommend you do. You need to have that relationship map. We're not the only thing in the world that does this. We're the thing that does it the best. So, and if you're not using Austin, at the very least use LinkedIn. You Mark Petruzzi (15:28) you can see that, I've signed up about a month ago. I've been in the system. I was in it again last night and today. And yeah, it's a lot from LinkedIn, but it just makes the whole process move even more productively. Drew Sechrist (15:43) we didn't really talk about exactly what it is connected. That's does. So I should maybe I should say just real briefly what we do when a when a company turns on connect the dots, they plug connected out into their email server. Then we analyze all of the historical email across every email account that they've got. And we look at the metadata and we score the relationships of all the people that they have. So if they've emailed with anybody, ever, and it doesn't matter what job they were, we analyze that and we build a score for each person. And anybody who's outside the company that's already using Connected Outs, which is a lot of people now, so like, a lot of VCs are on it, a lot of PE firms are on it, your investors, your advisors, you see who they know. They've done the same thing. They've analyzed all their networks. So all you're sharing with each other is who I know and how well I know that person. But that's it. That's it. And it's super powerful. So what you get is now instead of with like LinkedIn, you just get this binary result. Like Mark and Drew are connected on LinkedIn or they're not. And in that world, you can't really navigate and figure out like, can I leverage Mark to get to this person or not? Cause the failure rate is so high on LinkedIn. There's such a high noise to signal ratio. And that's the complete difference on connect the dots and connect the dots. You can laser target and I can see just the people that Mark has a strong relationship with and never bug him about the other 95%, right? Just the 5 % that he really knows well. And what that does is you scale it across a large organization. That means that you really now have a heat map that gets you directly to the people you want to get to. So that's why you can do it the old fashioned way. You can use LinkedIn. can also, the really old fashioned way at Salesforce was just asking your colleagues around, like, hey, did KK Anderson (17:19) Who do you know at this company? Drew Sechrist (17:20) Yeah, holding up the list. That's I've been in a super old fashioned way. So there's like, you know, V zero, there's V one, you know, and now we're on, CTD is like V eight or whatever. don't know. but whatever you do figure, figure it out. Like you do need to connect the dots somehow. and you can do it manually or you can deploy technology to do it, but that is definitely the hack right now. And that is in a, in a very noisy world where there are too many messages from too many people that you don't know. KK Anderson (17:46) Mmm. Drew Sechrist (17:47) Basically, the answer is to all that stuff. You just delete everything right? The things you don't delete are if it's Mark sending me an email. I know Mark. I'm going read it. That's it. KK Anderson (17:56) It's so true. Mark Petruzzi (17:56) Yeah, and you know what, we're running towards the end of our time here and we don't wanna ask for any more of your precious time, Drew, than we already started with. But here's an idea. Would you be open to doing a LinkedIn live session with us where we go just a very deep dive into topic four and really talk about with all your great sales and sales leadership experience. how you're leveraging AI into everything, your product, your processes, your company. Drew Sechrist (18:26) Yeah, I'd love to do it. Count me in. Mark Petruzzi (18:28) Yeah, KK Anderson (18:28) And that will be. Mark Petruzzi (18:28) I think that would be great as well. And then we'll do our rapid fire then as well. So we're not gonna share that rapid fire with you and give you all this time to prepare, because we wanna really see your reactions to it. Drew Sechrist (18:38) Beginner's mind. All right, beginner's mind, I'm cultivating it right now. I will go into a deep meditative state until we have our LinkedIn live session. Mark Petruzzi (18:48) no better way to prepare. So Drew, thank you again. Thank you for taking the time with us. I think this was great. And we're really looking forward to diving into this next topic with you as well. And I'm sure our audience will be as well. Drew Sechrist (19:01) Likewise, Mark. Thank you so much, Mark. KK, a lot of fun. KK Anderson (19:01) All right, thank you, Drew. Mark Petruzzi (19:04) Awesome. All the best. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 104 - Turning Personal Networks Into Pipeline: Inside the Relationship Intelligence Era with Drew Sechrist - Part 1 | 30 nov. 2025 | 00:23:23 | |
In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Drew Sechrist, CEO and co founder of Connect The Dots and longtime Salesforce veteran, to unpack why traditional ABM motions and high volume outbound are running out of gas and what comes next. Drew shares how relationship intelligence, warm introductions, and network aware playbooks are giving revenue teams a durable performance edge over cold, volume driven tactics. Drawing from his experience leading enterprise teams at Salesforce and now building Connect The Dots, Drew explains how to operationalize real relationships at scale, how to reimagine the role of the account executive as CEO of the territory, and why senior sellers should lead the shift from spray and pray to relationship driven go to market. What You’ll Learn: • Why ABM has reached peak utility and where it still fits in a modern go to market motion • How relationship intelligence and warm paths consistently outperform cold outbound and one to many ABM • Why the best enterprise sellers behave like CEOs of their territories and how that model broke during the growth at all costs era • How to design KPIs that expose when your current motion is tapped out and ready for a relationship first rethink • A practical 90 day approach to shifting from volume based SDR motions to relationship driven plays led by senior sellers Key Topics: • The limits of high volume ABM and cold outbound as primary growth levers • Mapping networks, scoring relationship strength, and surfacing warm paths into target accounts • Dreamforce era relationship building and how those habits still drive enterprise deals • The return of the account executive as CEO of the territory, not just a cog in the sales tech machine • Using AI and systems like Connect The Dots to make relationship based selling scalable and measurable • Reweighting your go to market mix across ABM, intent, and relationships instead of relying on mass spray and pray • How SDRs evolve into behind the scenes orchestrators of introductions, routing requests through executives and board members without breaking trust Guest Spotlight: Drew Sechrist Drew Sechrist is the CEO and co founder of Connect The Dots, a relationship intelligence platform that helps go to market teams tap into the power of real relationships at scale. Before founding Connect The Dots, Drew spent more than a decade at Salesforce during its hyper growth era, rising from one of the first account executives to leading enterprise sales teams. His career has been built on leveraging networks, warm introductions, and trusted relationships to win complex, high value deals. Resources and Mentions: • Company: Connect The Dots • Event: Dreamforce • Topics discussed: account executives as CEOs of their territories, relationship driven GTM, shifting off pure volume motions 🎧 Listen now and follow Selling the Cloud for more conversations on modern go to market, revenue leadership, and the future of relationship driven selling in an AI enabled world. Subscribe wherever you get your podcasts. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 103 - Operationalizing Process and AI for Real Sales Impact with Paul Fuller - Part 2 | 25 nov. 2025 | 00:21:03 | |
In this episode of Selling the Cloud, Paul Fuller, Chief Revenue Officer at Membrain, joins KK Anderson and Mark Petruzzi for a compelling conversation on how modern sales leaders can use AI to coach more effectively, eliminate wasteful pipeline rituals, and build real self-leadership within their teams. Paul outlines how high-performing sales managers are shifting from performative metrics to meaningful enablement; using AI to flag risk, generate insights, and equip reps to close complex deals. He also shares how sales leaders can establish operating rhythms, drive accountability, and lead with trust; all while reporting to the board with metrics that prove the business value of relationships. What You’ll Learn:
Key Topics:
Guest Spotlight: Paul Fuller Paul Fuller is Chief Revenue Officer at Membrain, where he brings structure, strategy, and coaching to complex B2B sales organizations. A strong advocate for elevating leadership and execution within sales teams, Paul focuses on embedding process, insights, and AI into daily workflows to help reps and managers improve continuously. Resources & Mentions: • Company: Membrain • Book Recommendations: – The Greatest Sales Question Ever Asked by Brent Long – A Mind for Sales by Mark Hunter – The Speed of Trust by Stephen M.R. Covey – Mere Christianity by C.S. Lewis • Sales leader to follow: Matt Green (Sales Assembly) 🎧 Listen now and follow Selling the Cloud for more real conversations with revenue leaders building tomorrow’s go-to-market playbooks. KK Anderson (00:31) So building on that, Paul, from a sales manager's perspective, let's say they're in a coaching call with the rep and there's deal after deal that's stalled. And we know that stalled deals kill quarters, right? And so what are some ways you see top sales leaders leveraging AI? or AI signals, to help coach through some of those common challenges that sellers have. Paul Fuller (00:55) we personally, do it by, coaches that managers that use our system and, are doing, but we have a really robust flagging system and a really robust ability to, look at a pipeline by a variety of factors. then you can start to layer the AI in top of it. So we've built a flagging system for years. So something has been in stage more than 15 days. Let's check this out. Let's understand it. Let's, let's figure out and based on the profile of the customer and the actions that we've taken, red, yellow, red, yellow, let's categorize those flags. where you start to get into the AI stuff is that AI can then start to deliver based on that framework, very specific things based on to other reps that have been successful and move things based on situations that have happened across the organization and based on that rep behavior itself. If you do things like tie in, tie in recordings and fathom and gong and those types of things. So you can do some really cool work there. What I found is it's best for the flags and the AI to bring up suggestions to a manager saying, Hey, here is three three or four deals ⁓ that are specifically, let's talk these through, right? Bring up those flags. I do believe a hundred percent that it is on the manager then to dive in into those deals, understand them and human to human get that coaching on what are the barriers that are, are specifically in the way and how we're then improving. the skills, the who and the who of what we want to be and how we want to act. How are we improving that on ongoing basis? So we have a platform called Elevate within our tool set that is a, it's a cadence to coaching and cadence rhythm platform. So it ensures that we're doing the right work. we can set goals in that platform. It can bring insights from our pipeline. It can flag deals that we need to discuss. But if we don't actually have the meeting, I'm still a huge fan of that. Like we have to have those one-on-ones and dive in, discover and understand. And so for the sales manager, the most important thing data is about half of it. The other half of it as a sales manager is how am I improving as a leader in my ability to coach these deals? And they need to have a cadence on those. need to understand how Cause information is not the, we need the information and we need to have it highlighted. But if there's not a rhythm by which you're continuing to improve your coaching skills and ability and dive into deals and those types of things, the sales manager, doesn't matter how much information I give them. because the sales manager in that, that is coaching a lot of times, we'll just do the same things over and over again. It's a man. why aren't you closing this? I would have closed it. that's a lot of the coaching that happened that happens today. Well, I would have done this. And that doesn't that doesn't cut it. So I think that that layer of those sales managers and those coaches really need to work on that skill. Mark Petruzzi (03:44) Right on. So Paul, let's kind of anchor this maybe around like a mini cadence. So if we're reviewing pipeline for 12 weeks at a client, you if you're doing it within your CRO role for your own company, what are the three weekly review items and the three actions that you'd mandate and who owns each and when do they need to be done? which are the ones that really drive behavior to become sticky? Paul Fuller (04:14) That's a great question. Do I have to limit it to three? Mark Petruzzi (04:16) You do not. Paul Fuller (04:18) All right. Well, again, I can only go from my experience. And, this is weird because we've been talking so much about, the who and the, core of the people that we need to become and those types of things. and then the processes, and I am going to give you an answer that I think is completely outside of that. and it's a very simple answer that I think doesn't happen, across just about everyone. I've seen there needs to be and I don't care what system you're using. don't care if you're using Excel. I don't care if you're using a membrane. I don't care if you're using a pad and paper, but on a weekly basis, every rep and every manager of that rep needs to have a full understanding and picture of an updated pipeline and the deals in those pipeline in that pipeline. And, again, our system makes this easy. makes it much more, much easier and gives the ability to do it, and flags and pulls information out of it and all that stuff. But that habit in and of itself on a weekly basis for a sales manager, is something that is skipped so often and it changes everything. second. is the cadence of, if you have that, then you can effectively coach and have a cadence and rhythm to that. And I call it a cadence of accountability. The cadence of accountability is just as important to the sales manager as it is to the sales person, as it is to the VP of sales, as it is to the CEO, right? It is. What are we committing to this week that we're going to get done for each other? And that goes back. It does go back to that who like self leadership and the ability to be a self leader, but that cadence of accountability is critical and it needs to be written down. It just, it just has to, Hey rep one, I'm a sales manager. I am going to dive in and review through your accounts and I'm going to do this for you. Okay, and I'll do it by Friday or I'll do it by next Tuesday. Do you know how you're in sales? So you know this and you're in leadership and coaching and you know this is that how frequently that gets missed and pushed to the side and in favor of busyness is, is crushing. It's crushing to a sales team. It's crushing to a sales leader and it's crushing to a forecast ultimately. All right. And the third thing that a sales, I would say that's incredibly, incredibly important. And again, we, going back to the basis, you could do this on a pad and paper is, what are the things that I am accountable to my prospects and customers for this week? My top five, right? And in, and I might, I'm going to complete those. I think just those three things, absolutely. It's why I harp so much on, the self leadership and I, what I call the real intelligence, the leadership, the service, the way if I have accepted and we've defined that together, those three things don't become necessarily easier, but they become something that I will commit to, as, a person and as a manager and as a sales team member. and they become so, so important. And so again, Our systems, everything is a glorified system around that, quite frankly, but those things are so incredibly important to make an impact and to move forward together, lead well, serve well, and to really ⁓ drive performance. Mark Petruzzi (07:28) Yeah, and you know what's really cool, Paul, about what you just walked us through is you really define what the items that are really important in the selling process as compared to things that we have done for so long. For example, we've relied on a CRM and we all know a CRM doesn't do anything to make a sales rep more effective or even more productive. And so, okay, so we spent a lot of time with a CRM process and we all know that most of the data is just really not good within CRM systems. That's a whole nother discussion for another time. But if you look at the, even things like a pipeline, what amazes me is some of the clients that I work with, when I first get in there, they love that weekly pipeline meeting and it can be an hour, many of them are an hour and a half. A few of them I've seen are two hours by the time they're done every week, just sharing all this mumbo jumbo jumbo and also just manipulation that sales reps end up doing because it's a good way to do it. So when you could put a process together in the ways that you're describing it, that takes a lot of that out of the equation. And by the way, the business KK and I run, AGS, We're moving with some products that will allow you not even to have a pipeline call each week because the information is shared so closely and who knows, maybe some of those products we work with are good fits to coordinate and integrate with some of the great things you're doing with membrane. But you really hit me on some key items there. Paul Fuller (09:02) Yeah. Yeah, we don't have a pipeline call every week. which is fascinating. If I think about it, I do have a sales team meeting every week, but it's not a pipeline call. mean, pipeline is an individual that the reason people have pipeline calls generally is, I hate to say it. it's performative at this point and Mark Petruzzi (09:10) Mm-hmm. Paul Fuller (09:21) that really is it like performing, but it's more for the manager than it is for the salespeople. It's like, and, so I have a call. I took a format from one of our partners. it's a, we call it unpack, but it's updates and I do ask for short numbers, but I can look at the number because our CRM is actually clean. And actually we have a process that's built into it that understand and the sales reps agree helps them close deals. They use that process. Sometimes they get outside of the process, which is fine. They can call audibles. It's, fine, but they use that process to actually work their deals towards success. And so I don't need to have a long call where everybody's talking about their, their pipeline and individual deals and doing it in front of each other. Instead, we can start to have discussions about, what are some things that you're doing that is helping you improve your win rate? What are some things? How can I help you? And, we have discussions like that and in our number eight and then I, could say, Hey, this is what I'm really seeing in membrane. This is what the numbers are showing me. Is that true? Like, are you guys feeling that as a true, is it, how can I help you get those up? So the two hour performative pipeline call where you're forced to come in and a rep is forced to, to essentially embellish. Cause that's what they do. They want to look good in front of their, their team members. I don't, I don't need that. What I can have is a, is we can start to have just a mature discussion. Cause we've agreed that we're going to be self leaders and leaders in the organization. And we have a process by which to do that. And we can, we can talk about what's actually going on. Mark Petruzzi (10:38) Yeah. Paul Fuller (10:52) but I do trust, they have to have, there is no question like it has to be updated. That is just a habit. Like if we're going to provide this and we're going to provide this system that helps you close deals more effectively, it does have to be. And there are some things that I do need as a manager to update, but most of this is for you, Mr. Mastrip. So, you're dead on with that, right? Mark Petruzzi (10:58) Yeah. Paul Fuller (11:13) How do we drive effectiveness, not performative nonsense? KK Anderson (11:18) So Paul, I'm to take us into our final topic around focus, trust, and proof, right? Specifically from the lens of a CRO having to report up to a board of directors. And let's just start with, there are so many CROs right now that are beginning to invest in AI. Some organizations are further ahead than others, but I would say nobody wants to be left behind, right? And so if you're like, what advice would you give to your fellow CROs that are out there? Let's say they are just starting to kind of dip their toe in the AI water and they're gonna have to go to their board and ask for funding. And we know they're gonna fund what they can, boards are gonna fund what they can measure. So like in this era, what would your advice be to them on where to start? And later on, you would, some of these concepts of real intelligence, because that's really what AI, as we've talked about in this episode, allows us to do is to focus on the real which is the relationships and the trust and whatnot. So where would you tell a CRO to start in their journey? Paul Fuller (12:20) The greatest help that I've found so far, and let's talk about this in the concept and I won't talk about it necessarily from a concept of a CRO. If I can narrow that concept to almost a VP of sales in B2B sales. because I don't want to jump to the marketing side right now. I, cause there's a lot of stuff that I would, I think is really important. AI does extremely well there. So if you don't mind, I'll narrow the focus and on what we've been really talking about, which is it's the best thing that I've seen it do. And where we're heavily investing and investing on behalf of our clients as well. is summarization of data and taking things out of a manual taking things that can be taken out of a manual workflow and more effectively done by AI and so very specific examples of that. mean, call recording came in early, the fathoms came in early. I think what a wonderful tool, right? So how do you But how do you take that data and then systemize it in a way that you can say, ⁓ man, I am going to be able to give my reps back three hours after a really good call to systemize this and to improve followup and improve communication. Right. Amazing. It helps them be more accountable. It helps them drive better, better outcomes with, with reps. I love it. It's so good. where I would, I have struggled with this one as a, as a CRO is things like the prospecting, things like AI prospecting and those types of things. Cause I get so inundated with things that I guarantee that I know. and I've not seen anybody do it well. so KK Anderson (13:48) is based on the prospect. you Paul Fuller (14:00) I struggle with that piece and I'm still figuring that out. But I know the piece, emails, LinkedIn, everything. It's just the prospecting side of AI. People have sprinted towards that. Like they have really sprinted towards that side and how are we going to make that happen? And I have not I sprinted towards how I can make my full cycle reps more effective. KK Anderson (14:03) You mean inundated Paul Fuller (14:23) in what they're doing now to drive impact for the customer and the prospect. Like if I can have AI helped me make a conversation more effective and give me a better chance of winning that deal, I'm going to do it. And that's where I've been really heavily investing and looking. I don't think, and this is just a me thing. AI has a big place in the prospecting and that type of stuff. just, the operationalization of it has not worked well yet. in, a lot of when it's completely responsible for creating the message, getting it out, trying to get a meeting, doing all those things. I have not put, and it's partially also cause of how we operate as a business. like I have a partner network. That's how I get most of our leads in. I love our partners. I love how they operate. So they connect and they drive leads to us. So I haven't had to look as closely. but that, that would be where I would highlight, just there's been massive enhancements in empowering a good full cycle rep that understands how to sell. it's just so helpful. to drive improved output, help with notes, help with proposals, help with all those. It's so good. Mark Petruzzi (15:28) So Paul, so boards typically fund what they can measure. And we touched on that before, know, just when you were driving how these, how do you prove these items that we just were discussing to a board, to a CFO, to a CEO. So they typically fund what they can measure. How do we go about and prove that relationships matter in this? Like what three numbers should be on page one of a board book that defines like example cycle time with or versus worth without a warm sponsor or executive meeting rate by stage when we lift on strong familiar paths and how do you can define that versus you know other processes and paths that get developed along the way as well. And what targets do you focus on to make sure that you can convince the board and the executive team that this overall program that we're discussing here today works and is more productive and effective? Paul Fuller (16:27) Wonderful question. I wish I had them all laid out for you in a specific presentation and could give you the one, two, three, four. That's a magic formula. Unfortunately, I can't. Fortunately, I can't. I tend to... I tend to look at history and our historical metrics so I can look at what our future metrics could be. So if I'm looking at ARR and I'm looking at customer lifetime value and I can then see, you know, what is it, what is the number of touches and strategic touches that we need to have with a customer to increase our, lifetime value of a customer and how we're doing that and what is the level of, operation we need to have with them. So you can measure that in number of different ways, meetings per customer, conversations per customer, strategy sessions per customer, customer engagement with support, those type of things. If I can start to look at those and then I can say, what is, what is our average rate for a really good growth? And then I can say, what can AI actually help me cut down on the human element, but increase the actual strategic impact? That's really helpful. I'm sure there's a VC term for that or VC stat on that, that I don't know. but that is really, really, and I think they call it replacement to those types of things, but, that is a measure incredibly impactful. And so it's really, do we, we have the same level of service or increased level of service that will help us increase the lifetime value. and What do we need to invest to make that happen? Cause I already, we have proven models for this. We have proven models for this and what our people have done on an ongoing basis and what other people, know, and the type of things that we need to create that work well. I'll give you an example. I just had a meeting yesterday with a guy that I thought was ridiculously good. and it, he was selling to me and he, he created a marketing strategy document for me in 15 minutes. after we had, a structured, a structured call that he recorded on Fathom, after he used AI to research our, our market and, and the things that were out there, he had set up a couple of, agents to do that. And then he delivered me a document. He said, and how he said it, he's like, this is not going to be perfect. This is our starting point, but, and, here you go. Right. But it was, it was customized. It was me. It used my language and it was incredible. Right. Like in terms of the sales process, like I really loved that. So that to me is an enablement piece that I could help my reps be more effective in market by delivering more effective materials that are customized to a person. And I know I need to do those types of strategic documents regardless. Right. They just, in our type of complex sale, need to do that type of work. hopefully that's helpful. Mark Petruzzi (18:56) Now that very much was and let's finish up We only have a minute or two here more and we want to make sure we don't keep with you past our committed time So we're gonna do an extremely rapid fire segment here. We're gonna try to do this in about 40 seconds So we love the rapid fire segment That's why we really want to make sure we still do this with you Paul So first question first product service you ever sold KK Anderson (18:57) it's you Paul Fuller (19:22) Printing door to door in Arizona in the Tucson summer heat. Mark Petruzzi (19:27) ⁓ I was hoping you were going to say maybe Flagstaff in the summer, not Tucson in the summer. But that's a tough one. KK Anderson (19:35) Paul, who is a CRO or a CEO that you love to follow? Paul Fuller (19:39) Matt Green from Sales Assembly. KK Anderson (19:41) So look them up. Mark Petruzzi (19:41) So what, yeah, we definitely will. One leadership habit that more sales leaders should practice. Paul Fuller (19:48) self-accountability. Mark Petruzzi (19:48) be KK Anderson (19:51) My favorite question, advice that you would give to your 21 year old self. Paul Fuller (19:54) motions lie. KK Anderson (19:55) There's a story there, huh? Paul Fuller (19:57) and cut back on the drink. Partying is not the way. Mark Petruzzi (20:01) Alcohol is not the way, right? Yeah, it's kind of hard to avoid in college, isn't it? Okay, favorite sales marketing book. Paul Fuller (20:03) Yeah. there's a new one out. It's called the greatest sales question ever asked by Brent Long. Amazing. I need to throw out two other shout outs here cause I do love a mind for sales by Mark Hunter and then, the speed of trust by Steven and Mara, Covey is, just, I, it's life changing book for me. Mark Petruzzi (20:23) Yeah, I'm two for three with those books, but I've got a new one here with the Brent Long one. That's great. Paul Fuller (20:28) All right, yeah, great book, great book. KK Anderson (20:31) Okay, and what about your favorite non-business book? Paul Fuller (20:33) Mere Christianity by C.S. Lewis. ⁓ C.S. Lewis is my favorite author in everything he's written. It just blows me away. KK Anderson (20:43) That's awesome. Okay, well Paul, thank you so much. We had so much fun chatting with you today and we've all learned a lot. Paul Fuller (20:48) Thank you for having me on. Hopefully I wasn't too long-winded and if I was, cut it out. Mark Petruzzi (20:53) No, KK Anderson (20:54) You are awesome. Mark Petruzzi (20:55) you were great. Beautiful. Thank you to our wonderful audience and everyone out there listening. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 102 - Operationalizing Process and AI for Real Sales Impact with Paul Fuller – Part 1 | 18 nov. 2025 | 00:22:52 | |
In this episode of Selling the Cloud, Paul Fuller, Chief Revenue Officer at Membrane, joins KK Anderson and Mark Petruzzi to reframe how revenue teams win in complex, multi-stakeholder deals. Paul explains why many orgs over index on apps and one-off skills while under investing in operating rhythms, leadership habits, and relationship-driven execution. He introduces the idea of real intelligence as the who and why that guide the how, and shows how process plus AI inside the workflow can coach managers, focus reps, and change what happens every Monday morning. What You’ll Learn:
Key Topics:
Guest Spotlight: Paul Fuller Paul is the Chief Revenue Officer at Membrane. He helps complex sales organizations operationalize process, coaching, and buyer-centric execution so managers can coach and reps can execute without bouncing across tools. Resources & Mentions:
🎧 Listen now and follow Selling the Cloud for more GTM insights from enterprise operators and CROs. Subscribe wherever you get your podcasts. Mark Petruzzi (00:31) Today on Selling the Cloud, we're joined by Paul Fuller, Chief Revenue Officer at Membrane. Paul spent years helping complex sales organization operationalize process and coaching, bringing structure to multi-stakeholder deals while keeping sellers focused on what moves outcomes. At Membrane, he's championed approach that layers insights and prescriptive guidance inside the workflow so managers can coach and reps can execute. KK Anderson (00:40) you Mark Petruzzi (01:00) without bouncing across tabs. We'll dig into Paul's thesis on real intelligence, the durable leadership practices that operate, rhythm sales teams need to thrive amid AI tool bloat and rising partner competition. We have three topics we'd like to cover with you today. From skills to real intelligence, why systems, leadership habits and operating rhythms be one-off training. Process plus AI, kind of day-to-day actions, putting insights inside the workflow so reps and managers change what they do on Monday morning and every single day of the week. Focus, trust, and proof. Leading in the AI era, keeping teams competent, and proving to the board, CFO, CEO, that relationships and systems move the numbers. Welcome, Paul. We're so happy to have you with us here today. Paul Fuller (01:50) Thanks so much for having me. really appreciate being here. I'm pumped. I'm excited. Mark Petruzzi (01:55) Beautiful. We love it, All right. Let me open with a question here in topic one. So Paul, you've argued that revenue orgs over index on apps and one-off skills while under investing in the systems and leadership habits that drive outcomes. In your words, what is real intelligence for a sales org? And how is it different from adding another tool or another skill module? Paul Fuller (02:17) Yeah, great question. And I think you've, everybody's been there. in terms of we love in the sales world to focus on the how, And how do we get things done more efficiently and quicker and better and put more numbers on a rep and make sure that they get, things done more appropriately. Like The whole revolution of the past 25 years has focused on that. Let's, make sales and manufacturing line. Let's get an SDR. Let's get to an AE to an AE that does, another thing at a sales engineer to the next, to the next, to the next, right? How do we make this more efficient? there's, there's an interesting concept though, that I I'm really finding that more and more as we, today's world and what we're dealing with. is we have skipped some certain things. We have skipped some of the fundamentals that it takes us to operate as sales professionals as a human and really make a continual impact in the market. We have skipped things and pushed them to the side. Things like relationships, things like how we work on those relationships together, things like a long-term a relationship that is going to drive impact for your business for years to come instead of, and instead in much of what we focused on, have you gotten a conversation and is there an opportunity? So when I talk about real intelligence and building that into a company, I'm focusing more on the who we want to choose to be. And then the why that we choose to be this instead of, and then move into the how. And I think that focuses on three things that we choose to be in sales. how we choose to lead, how we choose to serve. And I have a word that it's wayfinding, but how we choose to problem solve and find a way to work with companies and, do that core to who we are and define the, make those choices about who we want to be in those actions. We can always figure out the how another app, another thing. and So many of us just focus on that. How let's just, my gosh, I got this, I got this for data. got this for this scraping. got this for this. And you focus on that so much that you've seen tech bloat. You've seen confused reps. You've seen reps promoted to AEs that just cause they know how to book a meeting, but they couldn't, they couldn't discover and ask a question for the life of them. Or they don't even know who they are and what a sales motion is. So that's what I. Mean when I'm talking about real intelligence. KK Anderson (04:27) So the real intelligence as my daughter would call it is like the invisible thread, right? That connects everything. It is the common denominator that must be there to be able to make a sale. And that's a true relation. It's a human-based relationship. that what I'm hearing? Paul Fuller (04:45) Yeah. Amen. and let's make it real with like one word that you hear a lot in sales today and you hear people throwing up their hands about accountability, right? I can't get my reps to be accountable to leadership or customers. And so how did most people solve that? Well, I'm going to throw, I'm going to throw test management at this. Right. I'm going to throw check boxes that they have to do in their CRM. I'm going to throw. And they think that's solving the problem. Well, the problem lies much deeper than that. Yeah, the problem is much deeper than that, right? The problem is that you haven't invested in your team and built leaders on your team that know how to lead themselves and lead others. So why don't you start? Why don't we start with core components of self leadership as a team and say, that's how we want to sell and what that means to us before we then create this in the line thing wall and KK Anderson (05:10) another box to click. Paul Fuller (05:33) of accountability, because you have so many see I was on a CRO forum the other day and they're like, I just can't get these Gen Z errs or whatever to be accountable. Well, quite frankly, look at the system they've grown up in look at a lot of things that has happened. I think you need to go back to the real intelligence part of this. Let's talk about what it means we want to hire leaders, have leaders in our culture and what that looks like for us here. Let's start there and how that can impact your life. Therefore, you know, so you start a little earlier in the cycle, get rid of that. You do the how, but start with the who. KK Anderson (05:57) Yeah. Mark Petruzzi (06:03) So Paul, where do teams get stuck in this? What's kind of a common anti-pattern? Something that looks smart, feels good, shiny AI, but doesn't translate into consistent behavioral change. Paul Fuller (06:17) well, I'll use, we, are heavily, we love sales process. I love sales process. I actually really appreciate, our, platform is built around sales process, and how we're able to do that. sales process is a wonderful thing. and, let's say it's created in the mind of, the sales process is created in the mind of the medic expert that knows everything and has been. been in there for 30 years and knows exactly the questions to ask and all of those things, right? And then I put that out there and I put it into an organization. I find out, why isn't this working? It should be. I mean, we had an expert design it. it was perfect. It's in a system, right? There are gaps in the people I think don't see where they say, okay, let's fundamentally go back to this. And I put this concept of real intelligence, but let's go back to these fundamentals of leadership there that are embedded into it. Let's agree on those and gain agreement for our team that that's what we're to practice. And then let's look at that in the context of a sales process. What are the actions that we're going to do continually and how is that going to, how are we going to craft reminders of that initial who that initial agreement, who do we want to be? Right? How do we're going to craft those in the sales process that actually helps us execute? cause if we have our who and our why figured out our how, we can systemize that really well. Right. So I think people get stuck in the anti thing is, well, I'm just going to put it in a sales process. Okay. If, if you just do that, you're going to get a bump. You're not going to optimize unless you have a complete and total agreement and, and, and focus and help people drive their core and, their understanding of why they're doing this and helping them and coaching them to do that. then you can execute on the how really well. KK Anderson (07:50) Sorry, are you saying then that where people get stuck is that they are skipping stages of the sales process or accelerating faster or skipping critical pieces of it and that's why their deals are stalling or, you know. Paul Fuller (08:05) No, I'm saying they're skipping stages. I think we're skipping stages and expectations a lot of times in our sales team themselves. And so for example, I was just talking to somebody last week and they're like, well, I hire really good salespeople. Right? that's what I do. And so I don't, I hire good salespeople. I have this process here that's helpful forum and I asked them to follow the sales process, but I asked them to, I hire good salespeople and I just count on them. And, and it's like, great, that is a wonderful step. They can do that. But I, the, the core thing is then, how, but how are you empowering them to be the best salespeople out there? Well, I really don't. I hire the, I hire the best ones and I let them run. now I think there's a, there's a step there and that is missed, which is all your hiring. You're hiring really good salespeople, but the step is how are you, how are you working with them, coaching them and helping them develop things that we know are core to continually get better. their leadership and account, their self leadership and accountability, right? Back at the ability, how they serve people, how they how they help people find what it is they need, right? Those are not things that are necessarily natural to everybody. And even the best salespeople need that help. So how are you continually helping them do that? And then how are you helping put things into the how, into the process that remind them of that activity, of the things that they need to do to be at the top of their game? And so that's really what I'm talking about. I think a lot of times we skip the step we, and we skip it far too often. We expect too much of things like new hires or especially new college grads that are coming in young sales reps that they understand concepts that are inherent to sales leadership service and wayfinding. we don't even give them, we throw them into a ⁓ niche role and we never pay attention to that. And I think it's time that we shift that, especially with AI, cause AI can do a lot of the how now. I can do a lot of research for us. And so we need to develop the things and the skills and the leadership service, the way finding on that side, much more impactfully to scale a good relational organization. Mark Petruzzi (10:05) Right on Paul. So give us a quick before after story where shifting from train to skill to build the system plus leadership habit materially change win rate cycle time and or forecast accuracy Paul Fuller (10:20) Yeah. I have one, that's a very recent one that we've been working with it. We have a partner, that we work with and he dives in and he very specifically focuses on a servant leadership based, who, right? Who we are is, servant leaders. They define that's how they define sales. And then once you decide that and, and figure out, okay. And then each individual is figure out why they're coaching. or why they're selling, which is more of an individual goal. He was able to put in a process and framework. So he's got a framework that he calls wins. And it's an amazing framework. That's how we're going to have these conversations, how we're going to do this continually, how we're going to lead, serve and way find as a, as a team. And then that framework then led into the specific sales processes themselves. So this is the order of operations that we want to follow. Right. Just by doing that work, but doing the hard work first on defining, who we want to be, how we want to lead, how we want to sell, what sales is. Right. And getting that hard work done first that is often skipped. but by doing that in, then putting in the processes of the framework and the processes afterwards, he's able to see, I think the stats on the recent case study or something like a 20 % increase in pipeline development. Quality conversations has gone up with all the reps. So qualification is massive. So pipeline flow through is incredible because they're qualifying more effectively from a place of confidence in who they are and what they can do. and so I will pull up the specific stats for you, but it's been tremendous. And so we do this through our platform. Like he implements a part of this in our platform. but the core of it, it becomes way before that platform. Right? It's, really deciding on who we want to be and the core elements of the, call it again, the real intelligence assets that we want to dive in, how we want to up or who we want to be and why we want to operate as a team. Is that helpful? KK Anderson (12:10) I think this is going to take us into our second topic, right? Around process and AI and how it impacts day-to-day actions. And so I know you love process. I believe one of the reasons you love it is because you also believe that this real intelligence is insights. they have to live where the reps work. Like it has to be in the workflow. in the CRM in membrane. And so on a Monday morning, what does an AE actually see? how does this real intelligence show up? Paul Fuller (12:40) Yeah, great question. So membrane itself is we love process because again, process helps us do the job that we have, we can do to the best of our ability. That's, that's what it is. It's consistently it's a checkbox, right? now let's tie this in. Before I answer that question, I'm going to use an analogy, if you don't mind. I'm going to tie it to the medical profession, KK Anderson (12:50) consistently. Right. Paul Fuller (13:00) Medical profession has this defined pretty darn well and a lot of things that they do. They have that who we need to be and the critical components of that pretty well defined. They have a Hippocratic oath. They go through a ton of training to understand the type and form of doctor they need to be and really get that down and the person that they want to be operating in that system. skip forward to the checklist, the checklists are there for a medical for a doctor to go through and a process is like, so I don't make mistakes. So I can bring my best self every single time to the surgery that I have. And a lot of times I've seen some of those checklists, like my brother's doctor and, and he'll even make his own. And it's like, before I go into an appointment, I will X, Y, Z, right. I'll take a time, take a second to center myself. I will do do the appropriate research on the client, on the patient that we have, and I will be able to head in. And then during it, they have additional checklists, right? So again, my thesis is that we're, and what the, is that we are skipping a lot of that stuff in sales that helps us define that who we want to be. Now, in terms of how we activate in that process and checklist, like very simple. a process and checklist that can score a pipeline based on whether or not you have a sales rep has actually had a prep meeting with their manager and gone through coaching on a deal to bring their best self to that sales meeting that they have. That's massive help. If you can score a check, if you can score a pipeline based on whether a sales person has actually gone in and reviewed, all of the core people in that deal has gone into their backgrounds and understands it, let's look at a certain stage of our pipeline understands how the, the vision, so understands the current state they're in, the vision state and the gaps. And you can then have that be a part of your process, but then also score your pipeline on. right and understand based on the actions that the sales rep is taking to be the best person that they can be in this thing, it helps and it also helps the reps. Like so many times CRMs just give data, they're like, just go fill out these six fields that you need to learn and go ask these questions. But they do nothing to help coach or guide and actually help a rep be really good. And that's what I believe a good checklist and a good process should do. Cause I mean, a pipeline is nothing but a lot of different sales processes, a lot of different checklists amalgamated into one view. And so what they did when they log in is, I'm just meeting them. Have we gone through, have we done our pre-call prep? we know, do we want to? Yeah, sure I can skip that, but I know if I skip that I'm going to be much less successful. And I can actually measure that have here are some suggestions based on AI and what we've had on questions based on our framework that we have and who we choose to be as a sales team. So serving that up right there in the context of where they're doing their job is so helpful. Instead of forcing them to go to seven different things or go back to a learning management system or call a coach or it's just really helpful to have it in one spot. KK Anderson (16:06) Makes a lot of sense. we talked a lot about kind of checking the box. And so I'm going to ask this question just because I'm wondering if others are thinking it. So we have a box. Did you have a pre-meet with your manager? But don't we run the risk of just having more boxes to check? Paul Fuller (16:22) Yeah, and I think that's the critical nature of, starting with who moving to why and then moving to how, right? And so we do run that risk. If you, and membrane can be abused like any other system, right? You can give a rep for 400 things to do, and say, check all these boxes and make sure you do them and measure them. That's just like any other system. where the difference becomes how do you define? And this is where I think a lot of sales leaders and teams skip is how do you define a process that actually brings in best practices and helps people? So if you, so for example, don't, don't give them a box to check and say, Hey, we defined, the org chart. in the organization and we know who people are and that it's a great box. could literally give a checkbox. I've done that. Right. Instead in the process, give them a way to actually do it. Well, right. give them a way to understand the organization and how they're operating, visually and easily and in something that helps them do it. We just did a big research study on the number of stakeholders in complex B2B sales and like the optimal number for deal success. And we found it hovers around four and a half, right? So between four and five stakeholders actually increase the deal success and above that decreases it. so if we're learning that and we're understanding that KK Anderson (17:36) Hmm, interesting. Paul Fuller (17:40) And we've decided as an organization that we want to, be the best sales team out there. And that's the who, and we're going to put the work in and be accountable to each other. Then a tool like that within to map those four to five makes is incredibly helpful. just right there. And then we can have great discussions and coaching discussions on, who those people are and how they operate and how they're going to help us work a deal. we could say, Hey, are we talking with too many or too few? it's right there and we can see it and we can work it and it becomes a step, but it also becomes a critical part of it. It's a critical part of winning a deal, that, we know we needs focus. most people, like they'll set up a CRM with, know, here's your 17,000 fields that you need to fill out and do. What we argue for is what are the core things that are going to truly drive both enablement for the sales team and excellence in results. And so take that time and really work on that. So I hope that answers your question, but that that's a philosophy thing that comes out of a lot of years of doing this. It's like, where is the impact and focus on that. Mark Petruzzi (18:43) Yeah, that is very easy to follow. So thank you, Paul. So teams don't need to be prompt engineers when it comes to generative AI. For example, at the same time, how do you enable and engage your team into what they can be doing, should be doing, how they should be leveraging the AI component of this? So can you share two or three prompted actions or snippets that do the things that really matter, like reliably improve their execution, discovery follow ups, multi-threading asks, building up the sponsor relationship and going deeper and wider at the same time. And where do you surface them so that they're used often by the sales teams you work with as well? Paul Fuller (19:29) Awesome question. I have one very specific example that I love and this actually came, it's an innovation. It's actually going into our product pretty soon, but it's an innovation that the team made. And it's actually ties onto that stakeholder discussion that we just had. So let's say we, deal with a lot of complex sales, right? So B2B complex sales. You have the four stakeholders, five stakeholders on a on a zoom meeting. And, one of the great innovations is that let's just say it allows us to be a more effective, salesperson, also ties into our processes. I now have the ability to, to follow up individually so much better. So I don't need to send that, I don't need to send that. to every person, here's my notes. Here's the action items for all of us. I can take a fathom fathom integrates with membrane. I can take that and I can take a snippet and say, Hey, for each of these people, pull out their core questions, their core actions, and some key insights that we have for them. and help me craft an, an email directly for that. Whereas that would have taken two, three hours, if you're really going to do a really well on a meeting follow-up, to do previously, you can now have that systematically built into a sales process. If you have a meeting with multiple stakeholders, four, five, six stakeholders, right? you now have this tool in here that AI and you can have a very specific, we do have what we call snippets in the system that takes that and says, help me craft these very specific email. And then, then it becomes an editing and execution point because we know that as if we decide on the who that we are, we are going to choose to be accountable and choose to be servants. know that the best way to do that is individually one-on-one with a core team. Let's make sure that they're getting the attention that we've given. The barrier to that has always been, why I can't spend three hours, four hours on a specific deal, especially for us, like it's if we're get a $3,000 MRR deal, right? that's great, but is that worth spending time, that level of time? And so there was always that trade off. You can start to remove those types of trade-offs systematically and it actually empower reps to be who you want them and who they want to be. And that's the type I think is stuff is awesome. And we're also process like we're processing methodology based. So being able to query a thing like having, we don't, you don't need to be a, context engineer to, if you have developed your sales process, right. And we're, walking through that and we're capturing all the data in that sales process, the system itself. engineers the context, right? Here's where we are in the process and here's maybe some of the differences that we can... And then you can start to query AI ⁓ directly and say, any recommendations based on our methodology, based on our process and based on what we've heard from them, that can help us be better and query that directly. Because you're right, one of the biggest challenges is that context engineering. And we kind of tend to throw... KK Anderson (22:16) Thank you. Paul Fuller (22:25) throw stuff at the wall in terms of that. we try to figure it out. if so, our, that's one of things I love about our system. If we've really defined who we want to be, the methodologies that we want to act, the process we can, then we can leverage that framework really well for AI to bring actual knowledge to us that we can translate to wisdom and how to act. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 101 – Unlocking AI’s Potential: Mastering the Art of Smarter Questions (Webinar Replay) | 11 nov. 2025 | 00:59:24 | |
In this replay of Mastering Sales with AI, AGS Co-Founder Mark Petruzzi is joined by KK Anderson and Scott Stollwerk, Chief Sales Officer at Pest Share, together with Gabriella Koenig of Collective[i], for a lively and practical discussion on how AI is reshaping the art of selling. The conversation dives deep into what separates average sales teams from AI-empowered ones—and it’s not the tech itself. It’s the thinking. The panel explores how smarter questions, better hypotheses, and trust-driven selling can transform AI from a productivity tool into a true strategic partner. They share real stories from the field: how AI predicted buyer shifts before humans saw them, how teams replaced pipeline calls with signal-driven insights, and how great sellers now act like the CEOs of their own territories—with AI as their superintelligence. Whether you’re a CRO, RevOps leader, or AE curious about where to start, this session shows how to go beyond surface-level prompting and turn AI into an amplifier for strategy, trust, and results. What You’ll Learn: • Why AI transformation in sales is not about technology—it’s about better thinking and sharper questioning • The “value hypothesis” framework for creating AI-assisted prep before every customer meeting • How leading teams like Pest Share use AI to forecast, coach, and prioritize deals in real time • What happens when sales leaders replace pipeline reviews with AI signal reviews • How to coach teams to trust and collaborate with AI rather than resist it • Why the best sellers now operate like CEOs of their own pipelines—and how AI makes that possible Featured Speakers: • Mark Petruzzi – CEO, Accelerant Growth Solutions (AGS) • KK Anderson – Co-Founder, Accelerant Growth Solutions (AGS) • Scott Stollwerk – Chief Sales Officer, Pest Share • Gabriella Koenig – Moderator, Collective[i] Key Topics: • Prompting for insight vs. prompting for confirmation • From search to strategy: moving beyond AI as a shortcut • Trust, empathy, and human connection in the AI era • Smarter forecasting and self-coaching with collective data • Building AI-driven sales cultures that embrace change #SellingTheCloud #GetAGS #ReimagineGrowth #AIforSales See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 100 – Leading and Scaling Revenue Organizations When the Old Playbook Is Obsolete - Part 2 | 04 nov. 2025 | 00:22:34 | |
In Part 2 of our conversation with Neil Graham, Chief Revenue Officer at Disqo, we dive deeper into how modern CROs must rethink their org design, marketing execution, and AI integration strategies to stay competitive in 2025 and beyond. Neil shares why curiosity, humility, and bias for action are now non-negotiables; and how his team is operationalizing those values inside a flat, fast-moving GTM system. From building AI-generated deal strategy sessions to deploying 24/7 agents on the website, Neil unpacks the real-world tools and team behaviors that are reshaping sales and marketing execution. This episode is packed with tactical insights for CROs leading through change. What You’ll Learn
Key Topics
Guest Spotlight: Neil Graham Neil Graham is the Chief Revenue Officer at Disqo. A proven growth operator and revenue architect, Neil has helped scale iconic brands like Salesforce, Siebel, and Jive. At Disqo, he’s building a flat, AI-accelerated GTM machine that prizes speed, ownership, and alignment over legacy hierarchy. Resources & Mentions
🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts. KK Anderson (00:32) to drill into this topic, topic three, talking a little bit more about the flat org and the expanding CRO role, we've had this conversation quite a bit on our podcast about how CROs are now... taking responsibility of the marketing org, of the customer success org, of the sales org, of the entire go-to-market revenue system. And one of the things we see every day in our customer conversations is how disjointed marketing can be from sales disjointed product and from product management as well. And so as marketing is kind of folded in under you and this kind of this new flatter org and you mentioned that the alignment that you're having with your SLT every week but tell me a little bit about how this is helping to kind of bridge that gap between marketing sales customer success like the whole go-to-market Neil (01:24) So I am a big fan of the CMO role in today's modern company and organization and, I know the SaaS and sort of technology world really well. So I'll speak from that perspective. I can't really make a comment on other industries, but I am a big fan of, the CMO's role, and, sort of ownership of a modern AI driven marketing strategy. that said, we're trying to innovate quite a bit and do some really cool disruptive stuff and shift the focus of our marketing strategy here. And my CEO is a big vision behind that as well. And, hoping that I'm actually a pretty good impact on that. and we've got some great leadership on our marketing team that's doing an awesome job thinking big and bold and in a differentiated way, but also really good at execution. And I think, this is a little bit of a side point, but I do believe in, making sure that on your management team, you've got a good, portfolio of leadership skills. from vision to execution oriented people. So you can do both. And we've been really careful to kind of put together our leadership team on the marketing team and the sales team. I don't own the success side of the business here, as you mentioned. We've got a whole, Chief Customer Officer owns all of our post-sale delivery and customer success functions, implementation consultants, all that kind of stuff. But doing a great job there. creating a leadership team that spans between visionary and execution oriented and has skills and that can kind of augment each other and kind of take both to market. That said, in marketing, I think what we've done a really good job at especially the last nine to 12 months, is shifting the focus to data-driven ROI creation activities and initiatives and making sure that everything that everybody's focused on has proven results when it comes to lead creation and continued pipeline development of those leads into high converting opportunities. Right. And so we look at the data constantly in terms of how many leads, how many stage one pipeline deals were created, what conversion rates are going on and how much closed business happened from the marketing activities we're doing and dropping the stuff that doesn't have higher ROI. And for us, some of the traditional things that most people in this industry think drive a ton of output are things that we've actually cut. And just from a perspective keeping our own sort of information and strategies a little bit behind the scenes, like I'll just leave it at that, but in a pretty severe direction from less inbound and more outbound pipeline creation strategies with our marketing team and our marketing skill. that's been a lot more focused on demand gen, content, sales-facing, market-facing content, and overall product marketing. And those are the skills that we've really built out on the team. because, you know, getting into like the final subject a little bit, but we can dive deeper into AI. But I mean, because of AI, it's like, it's allowed us to do this. there's mass personalization that we can do at scale, truly. And people have always said, you know, mass personalization at scale. like today with the tools that are available in the market for us to understand the ICP. that we're focused on, our ideal customer profile and the key personas at those companies that have challenges that we solve for in a unique way. That data is all now massively in our CRM and with other tools, it makes it easy to augment a message to those people at those companies based on specifically what they care about and specifically what the business issues and challenges are at that company at scale. so we can get out the best prospecting that the most senior BDR and or sales professional would do because they know this account and they know these people and they've worked with them the last 20 years, that's starting to happen at scale in an automated AI based way. So we can get a message out there to the market that's hyper contextualized for the person in the company that we're targeting. And create awareness and pipeline that way. So mass personalization. The other thing we're doing in marketing, like creative content factories, like we're getting with AI, we're getting five, 10 times the output and a consistent brand voice. through creative and through content creation than we did before. And it's all kind of wrapped around what I'd call before that curiosity culture, that experimentation culture, getting a lot of velocity there with, auto-generated hypotheses and variants and insights into how to create better content, have better creative, do better outbound at scale. And that's what the whole marketing team's focused on right now. Mark Petruzzi (05:58) Excellent. Neil, very cool. Mark Petruzzi (06:02) So Neil, what are the non-negotiables? Neil J (06:05) The non-negotiables. All right. Quick question back. Are you talking about what non-negotiables exist in terms of how I run my business, my team, the operation itself? Mark Petruzzi (06:14) Yeah, I mean, would say kind of yes, yes, yes, all three. Just what are the things you have to do for success in this business? Neil J (06:17) Okay, KK Anderson (06:18) as well. Neil J (06:21) Ah, that's a great question. I think they all, to me they all ladder back to, and maybe this is for other leaders too, they ladder back to the core values of the company that you're at. And hopefully as a business you've done a good job or as a business or a business leader flushing those core values out and making them applicable to the unique attributes of your culture and your company and the space you're in and all that kind of stuff. Because they shouldn't just be words that are up on a wall, right? here we've got four core values at Disco. I'm not going to go into each one of them. They're actually on our website. They are up on a wall, but at other companies they've been slightly different. And I think about, I go back them quite a bit in the way that I lead, in way that I help my leaders lead the organization. If we keep kind of connecting things back to, as we talked about before, the DSF, the overall objectives of the company, for us it's our Disco success framework. Or if it's... the core value of the employee experience and the culture itself, right? One of ours is together, win together as one team. Another is pursuing outsized impact. So delivering exceptional results, being relentlessly all in as a third. There's more, but I think those are really impactful for, especially for a customer facing organization that are driven by numbers and that have clear objectives in terms of what good performance is and what it isn't. Like having those three things be. kind of non-negotiable to me and the rest of our core values non-negotiable and we try and bring things back to that quite a bit, right? We do a lot as a business to really rally around that. There's some other things too. I just think that, you know, I think about attributes in terms of how we deliver results every day and how we behave and operate. I've mentioned the word quite a bit already in this discussion, curiosity. I want my team to be genuinely curious. I don't want people to like try to manufacture it. We're living in a world where AI is reshaping how we work. And when people lean into that and experiment and ask questions and figure things out, that's a real competitive advantage. And I think curiosity drives innovation and it's just non-negotiable for the skills of the people that are around my organization and how I lead. A couple others that come to mind, one is humility. I think we all make mistakes, but what matters most is owning them. And I tell my team, over communicate, fall on the sword for your teammate or your customer, do it naturally. Again, needs to be natural. It needs to be part of their core instincts and their core kind of makeup. You can't force humility. It's too obvious. I think when leaders model this kind of... behavior and they look for that in employees that they're bringing into the organization and they help reinforce it along the way. It really builds trust and unlocks a culture where people step up and support each other. And then I'd say the third kind of major attribute that is non-negotiable for people in and around the go-to-market operation that I want to be a part of is problem solving and sort of taking action. You can call it action orientation. You can say, you problem solving kind of mindset, but people that don't wait for permission, they take charge. we're in a flat company as we've talked about where it's small, it's nimble. We can't wait. We got to go make things happen. We may fail, but that's okay. Use data, evaluate the scenario, make a decision to move forward and then don't just bring problems. You know, what frustrates me as a leader is when we get into a meeting or I have a one-on-one and it's like, you know, data dump of all the problems that are going on. Okay. That's fair. There's always challenges, right? But what I try to coach and enable my leaders and the people that roll into my leaders are working with them and I am every day in terms of here's an issue I'm seeing that impacts our number one or number two priority. Here's the data that I'm looking at that calls this issue out. Do you agree with this data? Let's talk about this. Do we all agree it's an issue? Okay, cool. We agree it's an issue. Here's my idea is to solve for it. What else is there? help me out team, help me out Neil, whatever it is, Versus just bringing problems, right? So I think that kind of shift in people's approach to the market and how we're gonna move forward and communicating internally and also with customers and prospects is like something that's just non-negotiable. It's like, you either have that skill, sure, we're always tweaking it and developing it, but you either have that kind of mindset in how you operate. And if you don't, not a problem solver, if you're not action oriented, If you don't have humility, if you don't have a ton of curiosity, then we try and figure that out upfront and not bring those people in. Mark Petruzzi (10:26) Yeah, and those items are just far less coachable. So I totally get it and all great stuff. Neil J (10:31) That's a good one too. Yeah, people talk about EQ quite a bit, right? To me, there's that emotional, I think the Q was quotient, but it was like emotional intelligence, right? And that kind of sums up a lot of this self-awareness and self-management and just having a focus on relationship management and taking action. So I think that's a, it's a buzz term, but you got to like know what you want out of EQ and make sure that you're seeking that out. When we interview, we... Mark Petruzzi (10:40) intelligence, yeah. Neil J (10:57) we ask scenario-based questions to flush this kind of stuff. Like, how would you act in this situation? And if you're not doing that, it's just so powerful. And so I think you gotta sit with your leadership team based on the role in the JD that you're looking to bring someone in on and make sure that you agree on the types of questions that you ask and where you like to see the conversations go to flush out those things like humility and curiosity and action orientation. Because the stories, that people tell you will tell you if they are or not. And so I think that's a real way to be careful in terms of bringing people in that have the right skill set and the right approach to the culture and the DNA that you're looking at. KK Anderson (11:36) Let's dig into the AI conversation a little bit more. You've said that you've experimented with Gong, Clay, Chatubi-T, even building your own AI. Where are you seeing the most value? Neil (11:47) a lot of what you just said from a technology perspective. I think the disruption opportunities in marketing, I called some of them out already, like the, outbound personalization at scale, kind of creating these content factories. call them creative and content factories where you can. KK Anderson (11:50) Mm-hmm. Neil (12:04) really get higher output and get a consistent brand voice and create content and impactful creative at scale. I think there's a lot of automations just within marketing there and those disruptions, we have the always on personalization that we're, that we're able to have based on some of the tools that you mentioned and also through some of the tools that we're using on our website with chat bot and through the tools that we're using with our outbound strategy. But think about the AI agents and go to our website and you can now interface through an agent and they handle the questions and the objections better than a human and they're always there. And so we've been able to use agent technology to actually create more leads into the organization than we had before covering it 24 by seven when before we were kind of with higher propensity leads on our website, our chatbot interface would fall over to a human being. And we're able to cover that with an agent now. So we're able to kind of save a headcount or two just in one little process within business development. In sales, there's a lot of disruptions around mass prospecting, as I said. We're doing deal intelligence and deal strategy sessions with those tools that you mentioned ⁓ to surface multiple data sets of information into one document. and we're running deal strategy sessions for our top pipeline opportunities without the reps having to put anything together once a week. And we're typically getting through six or eight deals within about an hour and a half time. And the rep doesn't have to put anything into it. Like previously it would be, sales professional, let's do a deal strategy review with the team. Here's the PowerPoint template. You got to go fill all this stuff out. This data already exists. in Salesforce and in Gong and all these places. Today, the AI can just pull it all together into one place and use something like a traditional framework like MedPick or value selling as a methodology or whatever you have, whatever your flavor is as the basis for that strategy doc. let's say we use MedPic here. So walk me through this opportunity from a perspective of what's the pain points investigating the pain that the customer wants to try or the customer wants to solve for? what are the metrics that they have in terms of their business issues and challenges? And if they could solve for this pain, what's it going to drive their business? D, what's their decision criteria? Other D, what's their decision process? So AI can take all that stuff in and around a framework like MedPic and surface it all into a document that we can all come onto a call together and go through really quickly. but the information's all there and nobody has to put all the information together like you used to have to do. So things like that, deal intelligence, deal strategy sessions. If you think about customer success, QBR templates, customer success, health scoring, generation of QBR, support triage, support knowledge base, auto updates, all that can be kind of augmented and enhanced with the use of AI. So everything, marketing, sales, success, it's like we're seeing 510x improvements in efficiency through the use of AI, being able to kind of bring the base level of information up into one place and allow us to be more strategic and talk about how do we win, not what's happening, Mark Petruzzi (15:05) that makes perfect sense, Neil. So you've questioned whether the whole concept of SDR, BDR functions will survive in this world here of AI. In general, how do you see AI reshaping early stage prospecting? Neil (15:20) I think like any technology change, there's going be massive job creation, not job loss. anything in history. whether it goes back to, the industrial revolution to the creation of the wheel like, we don't, it's hard to envision. exactly what the jobs are going to be. But we all know that the information is there and it's up leveling the value that humans bring to the conversation. but we still need humans. we're gonna like the, roles of humans in the world of, which is technology, solving problems for businesses, communicating that, executing on understanding their needs so we can solve those problems and show them how we're going to do it and then implementing it and being there to support it. Humans are going to have to be involved in all that stuff. What they bring to the table is just quickly being up leveled and the job creation is going to be massive around the future. I think in the short term, There's efficiency gains. Like for example, we on our BDR team, because of some of the automation we put in place, we didn't have to fulfill on a head count that we had planned in this year. But that's just such a super in the moment tactical small point in time of what's going on. Ultimately, I think that, organizations are going to thrive with more and more job creation through the use of AI. than job elimination, like any technology ever in the history of mankind. KK Anderson (16:48) It's almost as if we don't know even what those drops might be. it's moving so fast that there could be a whole new role in sales that we haven't even identified yet, or that hasn't even become mainstream yet. Right? Neil (17:02) Yeah. It's smart because people smarter than me. And what I mean, one job that we did just create in the last six months is like on my rev ops team, just this, like we've got a really talented person who's super curious, super innovative, very good at collaborating cross departmentally that rolls into my VP of rev ops and has been more on sort of the system side of our revenue operation. Our rev ops team, like a lot, and maybe not everybody's as familiar with this, but our rev ops team is data and process and enablement, right? And so they're constantly looking at the data. They're, constantly using what we find in the data to drive new process. And as we roll out new process and tools and strategies, we have to enable everybody. So there's an enablement strategy and plan. There's resources in all those areas, our team of... people that are managing the tools, really talented individual there that we took and we promoted to be the head of our AI strategy from a tools and data model perspective. And I've practiced some other sales leaders that have this role on their team now. And that person has been in charge of understanding the potential use cases across. the entire go-to-market. pipeline generation, to execution, to ongoing customer success and adoption and renewal. And they're identifying the use cases across these constituents and narrowing down the platforms of which we will use to enable those use cases. And some of those tools that you mentioned are going to be, or are already our major platform for AI enablement going forward. So we've taken like 30 different technology potential ideas that we're kind of bubbling up either in the form of being used, being POCs, they're being evaluated across our go-to-market. And we've narrowed that down to about three platforms, maybe four. And we're excited about that because generally speaking, we can go tell our employees, go get creative with AI. You've got these platforms that will lead with AI in everything you do. Be creative, be curious, and lead with AI. And they're coming up with the use cases. We don't have to go solve for every use case. We just know that We've picked platforms that holistically help us enable use cases around a really solid data model. Mark Petruzzi (19:09) So Neil, unfortunately we are coming to the end or towards the end of our time with you. Can we do a quick rapid fire and a few questions here to finish this up? All right. All what was the first product or service you ever sold? Neil (19:19) Sure. man, you're catching me off guard. Product and service I ever sold. T-shirts. Junior high. Made a few thousand bucks and realized, wow, you I can be an entrepreneur and I can actually sell and win and pay for things. So at that time I bought my own motorcycle and then I ended up buying my own car, it was powerful. Mark Petruzzi (19:28) He searched I love it. KK Anderson (19:39) awesome. Okay, favorite CRO or CEO that you like to follow? Neil (19:43) My favorite CRO is a gentleman that's not a CRO anymore, people aren't going to know him. Just a great coach and career mentor of mine, guy named Carl Schachter. Maybe they'll know him. Some people will know him. Carl, you know him. Mark Petruzzi (19:54) Yeah, I think more will know than you think. Yeah, I know. Sure. Neil (19:58) In fact, funny, because I met with a client yesterday, a gentleman in New York who worked with Carl at their previous endeavor where Carl was CRO. And he and I hit it off. And I'm like, yeah, we both commented on the fact that he's been a great and this gentleman was a engineering leader. But he's like, Carl taught me how to sell anyways. Great leader with us in the early days. was even he headed up some of the alliances teams at Oracle back in the In the 90s, in the 2000s, I got to work under him at Salesforce as we scaled that company from 12 million in revenue to two and a half, three billion over about 10 years. This gentleman went and ran the Japan operation, went and ran part of Europe, but I got the fortunate experience to work for him and still call on him for coaching and assistance and all that kind of stuff. Couple other people, really, and this goes back a little bit to the Salesforce ecosystem, but people that I'm big fans of, and I think some of the people here will know these people. Eli Cohen, who's the CEO of a company called Saleshood, an amazing leader, an amazing innovator. John Barrows, the CEO of company called JB Sales. I've used John and his methodology as almost like an extension of our selling team. He has a methodology around just lightweight methodology on how to prospect really effectively for BDR organizations and how to go win for sales organizations. And it works. It's easy. It's logical. And the energy and the culture that he and his team bring to organizations when you partner with them are worth it. Outside of the methodology, it's just like an extension of your selling culture. And so really big fans of those people as CEOs of their companies. small business. Mark Petruzzi (21:33) Yeah, you you put out some great names there and I hope the audience does look and research some of them. Neil (21:40) no affiliation. Hopefully that helps. No, KK Anderson (21:42) Hahaha Mark Petruzzi (21:43) All right, well, Neil, thank you again. This has been fantastic. I guess real quick, where can people find you? What's the best way to connect if they'd like to? Neil (21:52) LinkedIn. I'm a big fan of being super real on LinkedIn reach out to me on LinkedIn, tell me what you need, and I'll be direct with you and let you know if I can help. Mark Petruzzi (22:01) Excellent. Beautiful. Neil, thank you again and to our incredible audience. Thanks for joining. All the best. Neil (22:07) Awesome. Thank you. 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| Ep. 99 – Leading and Scaling Revenue Organizations When the Old Playbook Is Obsolete - Part 1 | 28 oct. 2025 | 00:19:14 | |
In this episode of Selling the Cloud, we’re joined by Neil Graham, Chief Revenue Officer at Disqo and a seasoned revenue leader whose career spans Salesforce, Siebel, Jive, and Telem. Neil shares a ground-level view of what it takes to lead, scale, and modernize revenue organizations in an era where traditional sales playbooks are no longer enough. From breaking out of funnel-stage rigidity to building flat organizations that prioritize curiosity, Neil walks through the changes CROs must embrace to stay ahead. He also shares how Disqo is rethinking GTM structure and leveraging AI to drive personalization, speed, and operational clarity; without drowning in tools. What You’ll Learn
Key Topics
Guest Spotlight: Neil Graham Neil Graham is the Chief Revenue Officer at Disqo and a proven sales leader with decades of experience scaling GTM organizations from Series A to post-IPO. Known for his ability to bring structure without red tape, Neil has helped some of the most recognized B2B SaaS names balance scale with agility in high-growth phases. Resources & Mentions
🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts. Mark Petruzzi (00:33) Welcome to today's episode of Selling the Cloud Podcast. We're excited today to welcome Neil Graham, Chief Revenue Officer of Disco. Neil is a proven revenue leader who has helped scale organizations at Salesforce, Siebel, Jive, Telem, and now Disco, the best name of them all. At Disco, Neil leads a go-to-market organization of about 45 inside a nearly 300-person company. KK Anderson (00:33) Thank you. Mark Petruzzi (01:00) His career spans taking companies public, guiding series A to series F growth, and balancing early stage venture backed and private equity operating models. Today, Neil will share what it looks like to lead and scale revenue organizations when the old playbook is obsolete, which pretty much is all the time nowadays. Covering agility, operational discipline, and why CROs must embrace a new approach to building revenue in 25 and beyond. Here are the four themes we'll explore. First, when the old playbook is obsolete. So when these old legacy models no longer fit, no longer work, how do leaders adapt? Scaling from 10 to 100 million, that sweet spot, especially in the SaaS and ISV world. And then, the concept of lightweight operational rigor, like how to combine a sleeves rolled up selling model with really good process and tools, but not too many process and tools slow How flat orgs need to be structured and how they work and how that really puts more pressure and responsibility on the CRO. and also sprinkling AI into the go-to-market mix. How Neil is experimenting with AI to augment productivity and rethink traditional roles. Neil, thank you so much for joining us. Welcome to Selling the Cloud. Neil (02:26) Thank you, Mark. Appreciate it. Thanks for having me. Mark Petruzzi (02:30) Happy to have you here. All right, topic one, when the old playbook is obsolete. So, Neil, I've heard you say, don't even know what the playbook is right now. It's all getting disrupted. Tell us a little bit about what you meant by that. Neil (02:43) thanks for the introduction. That was great. look, privileged to be at a lot of great companies through the years and hopefully caught on to a little infrastructure and kind of prioritization through the years in terms of how I approach things. we're in a really unique age today. the traditional playbooks from the last, I'd say 20, 25 years in a way, are going out the window in a way they're still there. And I think if you think about what's happening with AI and with how that impacts operational structures, go to market strategies, people and process skills. And overall playbooks, it's like you really have to kind of reconsider the way you're operating at every step of the way yet continue to operate and make sure that you put one foot in front of the other and execute. And so what does that look like? we've spent a lot of time. I think about the back in the days at Oracle in the early days and then at Salesforce, where we really scaled some organizations from small to large. the playbooks that we created around, marketing and sales and customer success became kind of a standard. And it's like, if you think about the processes from lead development, MQLs to SQLs to, early stage pipeline and the sales process from stage one to being selected at stage four or five and getting into a negotiation, the process of value selling along the way where you identify. the customer's business issues and challenges, you map your solution to that. You think about trying to position how you're unique against the competition or the status quo and quantify that, that value and articulate that really well to the client. A lot of that was put on our people and we would train and enable around these processes and these plays, try to roll out frameworks like, every part of the sales process, dissecting it. providing people visibility and information into what it takes to be successful, whether it comes to discovery, whether it comes to running a great demo, whether it comes to positioning the differentiated value prop, whether it comes to building the business case of the impact that you're going to make at the organization in terms of driving business outputs, whether it comes to scoping and professionally delivering a plan to make the customer successful, whether it comes to the negotiation, the objection handling, the competitive intel. All that stuff's still there. And our customer facing people and processes need to execute flawlessly on that. At the end of the day, it's just that the information is so readily available and we'll talk more about it later with AI have to do everything that I just said, but it's so flat in terms of being able to access that information, position that information on the fly. and make it part of your cadence that some of the traditional models of the playbooks and the enablement plans and the objection handling frameworks and all that kind of stuff literally go out the window and they become kind of almost in the moment. So I don't like at the end of the day, I think the old playbook being obsolete, I don't know. I think from my point of view, customer value still wins, the modern model starts with the customer's business case, knowing their business issues and challenges, understanding the pressures and constraints they have, and your people being able to flush that out and have that information at their fingertips when they come into a conversation. Then being able to articulate how the solution that they bring to market is differentiated and tie that differentiation to the measurable outcomes. It's just doing it in a more productive and higher impact and flatter and faster way. But every interaction that you have should clarify, how you come back to the business issue and challenge the customer has. So I think second, the AI tech that's out there puts these answers within reach and, we're able to have this information quicker and faster than ever before. And then I think third, just creating a culture and sort of a overall. go-to-market system that is rooted in curiosity. So your people and your processes continue to evolve quicker and faster than the competition is really important for every company. KK Anderson (06:30) I echo everything you said, Neil. this morning, as a matter of fact, I pulled out my phone and I wrote it in my notes thought exactly what you just said. The activities, what's changed now is that the activities aren't the work. Going into CRM and working in CRM, that is what's obsolete. Right? You can't do the same things every day and expect to have a differentiated customer focused, customer obsessed approach, right? it's all about leveraging all of this super intelligence, leveraging AI, what's at our fingertips to do the hard. And so sales, in my view, is going back to what it was originally, the beginning of the sales profession, right? Where it was all about solving problems asking great questions and getting to know people and relationships. And then we had all of these years of playbooks here's what you do, here's what you say, here's how you handle this objection, here's how you position this, here's how you differentiate this. And it's almost now, like the second something gets turned into a PDF, it's no longer relevant, right? And so it is interesting. All of this is allowing sellers to do the hard things, which is if you go a day or a week, God forbid, and you don't feel that anxiety of what am I gonna say on this call or how am I gonna approach that person, then you're not doing the hard things. Ticking off tasks is old school. That's the old playbook, right? Anyhow, so as you think about this kind of seismic shift that's happening, what are the principles that are guiding you as you lead today? If you're going back to basics, back to you were just talking about, like what are those principles? Like how do you lead through this kind of a change? Neil (08:04) Yeah, look, first of all, think, it goes a little bit to the second kind of area of discussion. It's sort of how do you create this lightweight operational rigor, especially as you scale companies I've kind of been at a few companies now that are series A, series B. there's a disruptive technology that's solving for a problem uniquely in the market. Doing it, it's a better mouse trap than what was there before. And because of this unique model, the unique data set, the cloud, whatever it is, it's able to solve the problem in a more effective, more efficient, more holistic, better quality way. The company I'm at right now is disrupting the marketing media effectiveness measurement market, the old stodgy providers that are out there that weren't as innovative and disruptive. We're disrupting that. I'm entering into a company, I've been here about a year and a half, where had, a better mousetrap than the competition, that a company could build on their own. Companies want a partner, they don't want to kind of be in the core competency of doing what we do. so we've been taking share from the competition. in the early days as we built the product five, six years ago and started to take it to market, we hired some good people from the competitors and knew the space and they brought their book of business and their relationships and it was a lot of hard work. Don't get me wrong, but at the end of the day, we were able to take share where we had relationships and where we had knowledge and sort of the bottoms up, right? And now we're moving more towards what I'd say is understanding the total addressable market. aligning our skills and our people and our organization around that, picking our bets on where is the biggest total addressable market, what can we take on right now as we scale and grow and we get past 50 and 100 and 150 million, aligning our skills and resources, training and enabling, getting the right people, hiring the right people, all that kind of stuff to go take the market more from the top down. Having that bottoms up, but also that top down where... We know this is the right place for us to aim the arrow and shoot. And we're going to put a lot of emphasis behind where we shoot and make it really impactful, improve our win rates, execute more flawlessly from marketing to sales to success and do a great job serving that market. So as we look at doing that and things are at the same time getting disrupted by AI, I've kind of run this play before where you're taking a company from 10, 20, 30 million to hundreds. and have the playbook and kind of like know the motion, right? You build in some process, you bring in world-class tools, you align your people and your skills to the market opportunity, you help limit the distractions on stuff that's not within that market opportunity that's the biggest bang for the buck. However, you still have to be nimble, you still have to kind of pay attention and pivot at the same time. And so there's a lot of art and science to rolling out lightweight process and tools and enablement and skills, yet at the same time, not over engineering it so we can go execute and we don't get in our own way and we don't have a lot of bureaucracy and there's not a lot of layers. And I think we've done that really nicely here. It's like I kind of came into an organization where we had a marketing team and there was a bunch of different pockets of weird reporting structure. And we quickly fixed that where it's me to my heads of marketing versus like in demand gen versus product marketing versus PR and comm and then they have teams, right? And then on the sales side, we did the same thing. We kind of had a one size fit all motion for the salespeople and they were kind of going after the market based on what they all knew. We layered in where do we need to be and what skills and tools do we need to have in order to go attack that market? Let's bifurcate the sales team because we saw two plays going on in the market. And we did that. We aligned the right people with the right opportunity. We hired the right people coming in to grow into these two opportunities. And we've rolled out playbooks and processes and competitive packages and, objection handling frameworks and all that kind of stuff for all the people that are in these two swim lanes in terms of how we go to market. What's been really cool in the last 12 months is we've embraced AI to just do all that bigger, better and bolder. Right. And so, answering your question, I think first, leaders need to get out there and be in the market, especially at this size of a company. can't, more so than ever. It's, like, you have to be in the field. You have to be with your customers. You have to be with your teams. If you're not spending 50, 60, 70, 80 % of your time. even as the CRO is the operational leader, executive part of the executive committee, all that kind of stuff. If you're not out there in front of the market, then something's wrong, right? So that's number one. Number two, just building this culture of genuine curiosity, I think is critical. You have to hire then promote and exit people based on curiosity or a lack thereof. And that's in everything you do. It's if people aren't asking questions, if they're not genuinely curious in front of the customer, in front of their own internal teams, if they're not innovating and trying new things, and if they're continuing to be focused on delivering the results, right? Like we have OKRs here. We call it DSF, the Disco Success Framework. My marketing team knows exactly what's expected out of them when it comes to the specific overarching business goals, the key metrics to achieve those goals on a weekly, monthly, quarterly basis, and the initiatives that they have to go solve, to go generate those key metrics that they continue to evolve around. We're kind of continuing to tweak our initiatives every month, every quarter, to make sure that we're hitting the actual metrics in alignment with our objectives. And if you don't have people not only being curious and being innovative, but also keeping their eye on Hey, is this an alignment with the objective and the key result that I'm trying to drive? And if it's not, what the hell am I doing? Let me stop doing that, right? And allowing people to be informed around that, have the information be very clear so they can almost self-govern because as you create a flat organization, there's a lot of greatness with that, but there's a lot of challenges that come with that as well. And you have to allow people the power to kind of understand, does this map back to the key objective and... desired outcome that I'm working on. if it doesn't call an audible, let's get the hell out of here and let's stop doing this. Right. Mark Petruzzi (14:07) Well, Neil, you have me thinking and wishing this was an investor presentation rather than a podcast. And what I mean by that is we, get to a fair amount of opportunities to hear CROs like yourself when they're looking for funding and, get to get excited about that or not excited about that. And you actually made me put together a thought that has happened in the back of my mind many times, but not as clear as today. And that is when we're doing this podcast and a CRO or a CMO gets on and, or a CEO gets on, they start talking about their approach. And I start to just think exactly that of, this should be an investor presentation because I, want a piece. So that's very impressive. As you know, I hear these things and we have podcasts every week as well. So I love the way you, positioned all that and you went, radiant to this direction, but I'd like to have you tap a little bit and go a little deeper. Neil (15:03) it kind of a little bit of the, how do you build in this operational rigor, but also like, how do you do it in a flat world? So, I mean, feel free to drill in there because it was kind of two of those. Mark Petruzzi (15:14) Yeah, now that's great. And I also like, you described how these some CROs are clinging to these old cadences and funnel metrics and SDR handoffs and the whole process of lead generation. What do you feel are broken about these models and a little bit on how do you fix them? Neil (15:31) I don't know if it's broken. I mean, look, don't get me wrong. we still have operational metrics that we look to kind of the leading indicators on a weekly and bi weekly and monthly and quarterly cadence. And still one of the objectives is an objective around, MQL and lead creation, right, that my marketing team owns and SQL and down funnel lead, qualification that the BDR team owns and SAO generation, which is our stage one opportunity that the BDRs and the AEs and the CS team own in terms of creating net new pipeline. And we have a certain amount of pipeline that we got to create every week, every month, every quarter. And, we're trying to be in front of it with key initiatives that we're rolling out to improve our outbound motion. And we're looking at Salesforce dashboards and summarizing all this stuff up. just take the sales team, for example. We've got about 20 sellers and I've got three SVPs. And so our sellers are director and VP level, our SVPs are managerial level and they report to me. And so we flattened it those three layers. In marketing, it's three layers across the whole organization. on our success and delivery teams and our product teams and our engineering teams, we've gotten it down to three layers. I think that's really helped us as a business. Our CEO drove that and... made it a mandate and not everybody kind of understood the why. And we did a lot on our all hands calls and our internal communications to help people understand the why behind all this. And over a period of about a month, month and a half, we got the company that flat. And the goal was to get faster information flow and get quicker, better decisions and have more experimentation and fail faster and succeed faster, right? And just have. higher organizational ownership and impact, have impact be visible, versus lost in silos. And if you can really then build your, internal compensation and promotion and recognition system, which we do a lot there, we do stuff on a quarterly, biannual and annual basis around those subjects. If you can build it around impact. And make it impact based in alignment with your goals and objectives back to your OKRs and promote the people that are having high impact. Those are going to be the people that are the most curious. Those are going to be the people that are experimenting the most. And, if you do this the right way, you'll start to set those examples. And pretty quickly within about a year and year and a half, we've weeded out a lot of people that aren't curious. we've kind of weeded out people that aren't trying to make an impact. Now the challenges with that is when you have that flat of an organization, it can really blur decision kind of ownership and there can be competing initiatives and there can be some accountability gaps and it can overload some of your managers and your leaders. I'll give you an example. It's like my CEO and I are very tight at the hip on working with the marketing team and There can be times where my CEO will grab people that roll into me and send them in a particular direction. And it's like, he and I have to be really well aligned on what are we trying to accomplish here? What are the goals and objectives of the company? And let's make sure that we're pushing people towards the same outcome, because if there's any competing interests, it can get confusing for our employees. And so just the communication and the collaboration and the work that we do, have at this company, we've got about two hours set aside every week for SLT alignment. that for the executive team to meet, to go through all the key initiatives and strategies, everything from people to process, to tools that we're using, to the outcomes and the initiatives that we have, and making sure that we're all in alignment. in this flat culture, we get everybody kind of pointed in the right direction. So hopefully that helped a little bit, it can create an opportunity, but there also can be a lot of challenges with it as well. KK Anderson (18:57) You know. Really, really insightful, Neil. Thank you for that. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 98 – Driving Symbiotic Outcomes in High-Stakes Sales with Josh Hoffman – Part 2 | 21 oct. 2025 | 00:20:24 | |
In Part 2 of our conversation with Josh Hoffman, we explore the leadership mindset required to thrive in moments of high-pressure change, like mergers, long enterprise cycles, and AI-driven disruption. Josh shares how sales teams can stay grounded in customer value, build trust through co-created plans, and lead with consistency; regardless of who owns the company or what the logo says. We also talk about the real-world impact of AI on sales effectiveness, onboarding, and go-to-market readiness. What You’ll Learn:
Key Topics:
Guest Spotlight: Josh Hoffman Josh is Chief Revenue Officer at Totus Rx and a long-time leader in B2B revenue organizations. He’s built and led sales teams across tech, telecom, and compliance industries, with a focus on building high-trust teams and delivering real value to customers. Josh is known for his practical, human-centered leadership style, especially in complex, high-stakes environments. Resources & Mentions:
🎧 Listen now and subscribe to Selling the Cloud to hear more from enterprise GTM leaders shaping the future of sales. KK Anderson (00:31) our third topic is around leading teams in a time of change. And so where I wanna take us. All the pressure of a change. You know, it can be a pressure cooker. All the accountability, which we know sales is famous for. The behaviors and the mindsets and the relationship and the building trust. All the things, right, that go into being an exceptional salesperson. Like when you're... going through like some of these acquisitions or mergers or whatnot, people are under the microscope, like how do you get your reps to believe and act the right way on the same side of the table in these high pressure environments? Joshua Hoffman (01:07) It comes back to me to the word consistency. You have to maintain a consistent value based approach on what you're delivering to your partners and clients. That shouldn't change. Even in times of mergers, acquisitions, whatever they might be. I don't know that I've been through any of those situations where the value proposition of the company changed at all. There might have been something added to it. There might have been something taken away from it based on that. But the general value proposition, if you believe in the organization that you're a part of, who owns it doesn't really matter. If the value of what you're delivering to your client or partner has remained the same, the rest of it is noise. And you have to remain focused on the outcomes. I really can't think of a time that I've been forced to say, oh my gosh, the value of our organization or the value of what we're what we're providing to our clients has changed so dramatically that we've got to make a shift in who we are with them. Now, there may be other shifts that take place inside the organization. There's changes in leadership, there's changes in locations, there's changes in potentially having another strategy that has to come into the business because two things are coming together. But what doesn't have to change is that your approach with your clients and partners, it's still the same. you're still there to be a part of a team that's driving an outcome. And if you can remain consistent in that approach, you can help people remove the noise from the system and say, you know what? I don't have to worry about that. I don't have to worry about whether our company name changed. I don't have to worry about whether headquarters is in Dallas or Michigan. ⁓ It doesn't matter because I'm still doing the same thing every day. Now that's a lot easier, I think, for salespeople. than it may be for others in other parts of the organization. I don't want to paint it that it always works the same way, but for the pieces of the business that I've been the most part of over the years, sales, sales operations, marketing, very much consistency is an opportunity to make things a lot smoother and a lot better for people and to make sure that culture remains a consistent, strong, positive force in people's lives. Mark Petruzzi (03:11) Very cool. so let's talk a little more process here for a few minutes. What kind of role does a mutual account plan or an action plan that you may create with your team, what did they play in making sure both seller and customer are aligned and accountable? How much do you use them? What kind of value do you get out of them? And are there times that things like that are a distraction and not really productive. Joshua Hoffman (03:37) so first of all, I'm a little nervous answering this question with you because you've literally written the book on some of these things. I feel I might be a little bit on my heels, but let me try and answer the question as best I can. First of all, the idea that you're sitting on the same table with a client, with a partner, with both of them simultaneously, by default, that should mean that you have a mutual action plan. It should mean that you have a mutual calendar that you're working off of. It should mean that the outcome that you're trying to drive is identical because you've coordinated that you've co-created it. You've, but you know, back to my co words, right? You have co decided what those things should be. Now, whether you're a value selling person, a challenger salesperson, maybe even a spin selling person, there's all of these different models that are sitting out there. there are some attributes that those things have that are in common. And I always like to quote one of my favorite people. So I had this person in my life for a long time named Marcel Brunel. And Marcel was at this organization that did great work when it came to helping people work through the process of selling. And one of the focus areas that Marcel brought to me, it was a learning for me at the time, and that I've carried with me throughout these years, is about having that calendar in place. And for me, when I talk to a client or partner, it's about having a backwards-facing calendar. And so let's start at the end. Where is the end here? What is the date? What is the outcome? What is the goal that we share in? And let's work our way backwards and establish goals and milestones that are going to help us achieve that. And then let's hold ourselves accountable to that. And as soon as we have alignment on the end of the line, it becomes much easier to fill in everything that works backwards. And if you miss a date, you need to catch up and you need to come up with a co-created action plan to do that. And that kind of collaboration, it really solves not everything, but it solves an awful lot. And it's not that things don't go wrong, things do. But if you build the action plan the right way, if you build the outcome the right way, you also try and provide yourself with the opportunity. for things to potentially not go the way you expect. You build in a potential buffer. Maybe there's an extra day or two here. Maybe, depending on how complex it is, there's an extra week that's baked into that that allows you to still achieve the outcome. And so that kind of planning is something that I talk about consistently, whether it's with a person on our team, whether it's with somebody that's working inside of an organization that's actually delivering the product or service or with a partner or client. Let's start at the end and let's work our way backwards and make sure we're in alignment. KK Anderson (06:16) it occurs to me as well, especially if you're in any kind of a, you know, complex sale where, or a longer sales cycle, right? Where you may have different people coming in and out of the sales process. If you have a mutual action plan or mutual account plan, whatever you want to call it, you can always lead with that outcome, lead the conversation with that value that everyone is synthesized there together to accomplish. And whoever's new to the call just falls right in place. Right? Joshua Hoffman (06:42) That's right. You get onto a call of you. If you had that co-created action plan and you've decided on the outcomes and the dates and you're having, you know, let's pretend it's a longer sales cycle, so to speak for that. And maybe it's a two month sales cycle when you're having that series of meetings to get there. The first slide should be that calendar. What have we agreed to already? Are we on track or are we not on track? and let's make sure that we're in this together. And that way, when new people do enter the conversation, they walk right into a framework that allows you to be successful, that allows you to introduce other people into the process. KK Anderson (07:18) What allows them to have the confidence that the conversation has been effective and aligned so that when you're at the wire and procurement comes in and starts asking questions, you've built the value. So you don't need to worry about getting slashed in negotiations and whatnot. Joshua Hoffman (07:30) That's right. Well, and part of it is even is making procurement legal, whoever else needs to be engaged in that process. Part of it is making them part of the team. If they're part of the team that's creating the outcomes and the decisions, then you don't have those surprises. Now, candidly speaking, look, there's always a surprise. A lot of times there's still a surprise. But the more you engage in that model and the more you broaden the team that you're working with, the easier this becomes because everybody's in alignment. I know what the outcome is. I know what needs to happen to get to that. Mark Petruzzi (08:08) Perfect. Well, so I guess we're even now. You made me blush with your last comment and KK made you blush. So we gotta get KK to blush at some point here. You got anything? Joshua Hoffman (08:19) Well, the blushing trifecta. Look, I tried to do it at the beginning of the conversation because I have seen KK's work. I have seen the impact that that you have had on people's lives by helping to make them better. I've seen the modeling that you've done. I've seen the outcomes of the not only the analytics associated with it, but the coaching that comes along with it. And I've seen the relationships that you've built and and that kind. of thing goes a long way because you not only bring your shining personality to this conversation, you bring credibility to the conversation. And so if that doesn't make you blush, kick it. don't know what I'm So ⁓ KK Anderson (08:55) You got me. Mark Petruzzi (08:56) Now, let me tell you, that was beautiful. I have seen it all firsthand as well. So I echo everything you say. But yeah, that'll make you blush too. Okay, so last question within kind of topic three that I have at least is, so what leadership practices have you found? Do all these things that we're describing, like, KK Anderson (08:59) You made my day! Even it's Friday! Thank you. Mark Petruzzi (09:24) build that trust, that loyalty, that long-term performance inside a sales team, and again, with the clients that you work with and prospects that you work with as well. Joshua Hoffman (09:35) so the things that I've brought up already sort of round some of those things out. Look, you have to care. You have to have compassion. You have to want other people to succeed. You have to have humility inside of this. You have to own up when you make a mistake. And gosh knows I make enough of them. And so I do my best to own up to them every step of the way. You've got to make sure that hierarchy is not really a part of the culture, at least for me, it's not. I would rather be viewed as a teammate than be viewed as a CRO. We're, the same way that I portrayed the company-client-partner conversation of being on the same side of the table. I like to view myself as being on the same side of the table with all the people that are part of the internal organization, too. Look, it doesn't always feel that way. I know I'm not perfect at it, but I do my best. And If I don't make it happen again, I try and own up to it and say, look, there's a chance for me to be better. And I talk about behavioral change in the context of not just people on the team, but about myself and being humble about that and being sort of true to myself that I'm still learning after, you know, I hate to call it the number of years, but after this many years that I'm still learning every day, I want the same for everybody that's in the organization. I want the same for our customers. We learn together, we grow together. It's a constant force. KK Anderson (10:52) try to remind myself whenever I'm in any kind of a conflict or a difficult situation that it's okay because I'm going to be better on the other side of it. Right? It's gonna, we're gonna get stronger. Joshua Hoffman (11:01) Yeah. Yeah, it does. ⁓ I don't want it to, yeah, that old phrase, if it doesn't kill you, you know, makes you stronger. don't necessarily want anything that painful, but I've tried to make it work to my advantage. KK Anderson (11:15) So let's go to our last topic, which is the audience favorite always. And this is the future of go-to-market in the age of AI. so you have said that your mission is clearly helping others find careers that they love. You're very passionate about that, about caring for the individuals and helping them achieve things that they once thought were aspirational. Just like how you started out in the manufacturing floor at and look at you now. Right? So how do you see AI supporting that mission of yours for the next generation of sellers? What's going to happen in our world? Joshua Hoffman (11:47) look, AI is a game changer in so many ways. And look, I don't know that there's such a thing as an AI expert right now. And, Mark, you might be as close as the one that I know of. So again, you've written the book. And so I'm to be careful about how I how I answered these questions. Everybody's still learning right now. And I am part of an AI driven organization right now. We use AI. in how we deliver our services to our clients. AI reads evidence, AI scores evidence, and we still have to have people because we're an audit and compliance company and there's still people engaged. But we do use AI as part of what we do. And I get to see that every single day, the power of what it can do to save time, save money, save stress. I've also seen that you have to use caution because AI is not always right. The concept of hallucination is real. And you have to be careful and you have to make sure that you're using other sources to validate what you're getting out of AI. Now, I've also seen it in sales and marketing where you have the capability of not only getting information in a faster way than you did before, but having that information be more complete and having that information help guide you through a process. Using AI to learn about your clients, your partners, the industries that they're a part of, understanding the relevance of what's important to their outcomes is a very powerful thing. And it's not cheating. I think some people have viewed it almost like, oh man, if I use AI to give me the answer, I'm not being true to my own creative self. Well, the reality is that you should use it to make you better. You should use it to make you more complete. You should use it to validate the other work that you're doing. It does come down to one thing that's, well not one thing, there's many things, but a thing that's really important is your ability to write the prompt. And your ability to ask the right questions of AI is what will deliver an outcome that's going to help everybody be more successful in that. I watched my wife's business use it. She's actually far better at AI than I give her great credit. I don't think there's a night that goes by that she's not watching or learning something about AI. And we have had many conversations in our organization about how to use it effectively. But it does come back to prompt writing when I'm using AI, where I'm trying to teach myself is what's the right prompt? Not am I getting the right information all the time? And the better I get at that, the more useful it becomes. And it does help us solve problems. AI will come back with answers that I haven't thought of. I love to think of myself as being super brilliant, but the reality is I'm not as brilliant as what AI can go uncover in not only the universe of information, but the universe of context. And I find it to be incredibly valuable. Mark Petruzzi (14:31) and I kind of look at it like Josh is if you're going to go play some golf or play some tennis and do you want to go out there with the old tools, a tennis racket from 20 years ago or do you want to go out there and find something that is using all the state of the art technology? It's kind of what AI means to me at the end of the day. every we're kind of sick or at least I'll speak for myself. I get really touchy on acronyms and things like that, maybe because I've been in a number of the largest consulting firms and everything's an acronym and, everything's an acronym kind of built to get clients to spend more money. And so I look at those things and I say, OK, yeah, I'm not loving that side of the old eco AI ecosystem that we live in now. However, I need to shake that off and I do shake that off because at the end of the day, it's incredible. The things you can do and the productivity improvement you can bring in is just incredible. And we can't miss the opportunity to grab that and leverage it every step that you can. So with that being said, kind of share your perspective on that. how are you using AI today? Joshua Hoffman (15:37) That's right. Mark Petruzzi (15:43) How are your teams using it? I'd love to see what you're taking advantage of. Joshua Hoffman (15:47) Yeah, so let me use a couple of examples. You know, one of the examples is in trying to understand ⁓ value proposition and understanding what else is going on in the marketplace and getting context for the kinds of problems that people are trying to solve and how you go about solving that problem. And so from that, you can actually get great information about how you can best position something so that it's heard the way that you want it to be. You can get guidance along the way. If I'm in a situation where there's a new client that's coming in or a new partner, the ability to use AI to understand not only the data about those folks, but also about contextually how it fits into their vertical marketplace, what problems they're trying to solve, what problems are they most often faced with? What are the typical solutions that they use to do this? What are the pitfalls of those? These are things that you can work with AI to understand at a better level than you could before. And you can consistently figure out how to synthesize that information. so being able to bring that, boil that information down is another value of AI. doesn't have to be 20 pages long. You can figure out how to get that information into a much more concise manner, and you can help use it to teach you how to communicate it effectively. And I think that there's so much opportunity there. Now I do use AI for things like analytics and so I absolutely try and use it to help grade my work so to speak. Am I looking at this problem the right way? Am I using the information the right way? I certainly use AI every day on my writing. So I am not the best writer and giving it an opportunity to help hone in on the message that I'm trying to deliver is a constant force for me. As a matter of fact, I think that I use grimm really at times. And so every week I get my message that, no, no, I think I'm in the top 3 % of Grammarly users. Part of that is because I'm terrible. The other part of it is because I actually believe in the power that ⁓ there is this thing that knows more than I do. And I'm willing to listen and learn. It's changed the way that I write, being candid. It's literally changed how I go about things. And so there's other pieces of process that are important to me. Look, I happen to work in a very complex environment right now. The environment of compliance, audit and security, these are three things that require an enormous amount of technical capability. I'm in awe of our delivery team and what they're able to do. Sometimes the best way for me to understand it is to actually use AI to help explain it to me because I'm not an engineering level technical person. Even though I've been in tech for 30 plus years. There's so much that I don't know. And so it does give me the opportunity to learn more on the fly. Mark Petruzzi (18:28) Very, very cool. All right, let's do some real quick rapid fire questions and I'll just pop off. So what was the first product or service you ever sold? Joshua Hoffman (18:34) Sure. carpet cleaning a boiler room environment with a guy literally throwing phone book pages at me. Things that shape you, I romanticize it now, but it was awful at the time. And I know exactly how not to be. Mark Petruzzi (18:38) I love it. So were you the wolf of carpet instead of the wolf of Wall Street? Joshua Hoffman (18:57) I was terrible. By the way, I was a miserable failure with a miserable attitude. It was, it couldn't have been worse. And you know, my next two sales jobs were just as bad. I sold copiers and I, well, actually I should say I didn't sell And I sold, I tried to sell copiers. I don't even think I, I don't even think I'd ever sold one. And I sold insurance door to door. Mark Petruzzi (19:14) You tried to sell copiers, right? Joshua Hoffman (19:22) And you talk about three experiences in a row, it's no wonder I went into manufacturing. But it didn't help that I failed either. So I didn't make any money on top of being miserable. Mark Petruzzi (19:32) Hey, again, what doesn't kill you makes you stronger. So that's cool. Do you have a favorite CRO or CEO that you like to follow or read about? Joshua Hoffman (19:36) That's right. I do my best to stay up on what people are doing, learning and providing using things like LinkedIn, using things like Forbes, and reading as often as I find the time to do so. And so I don't necessarily have one favorite, but we talked about some of those leaders before that I've had the chance to be around, whether it's Mark Anderson or Russ Reader or Todd Abbott or Mike Jenner my current CEO Joe Burton who was the CEO at Polly for most of my time there I love reading what he writes Mark Petruzzi (20:13) Josh, again, thanks so much and we appreciated you taking the time with us today. Joshua Hoffman (20:18) I really enjoyed it. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 97 – Driving Symbiotic Outcomes in High-Stakes Sales with Josh Hoffman - Part 1 | 14 oct. 2025 | 00:22:21 | |
In this episode of Selling the Cloud, we sit down with Josh Hoffman, a seasoned go-to-market leader who has guided sales transformations at Dell, Avaya, Poly, Datto, and now ControlCase. Known for his “sell-with” philosophy, Josh shares what it really means to drive symbiotic outcomes, where sellers, partners, and customers win together. He unpacks lessons from decades of leading in high-stakes environments, including mergers, market pivots, and rapid scale, and makes the case for consistency, humility, and emotional intelligence in modern sales leadership. From shifting away from zero-sum thinking to building customer-aligned mutual action plans, this episode is a masterclass in outcome-based selling and team-driven success. What You’ll Learn
Key Topics
Guest Spotlight: Josh Hoffman Josh Hoffman is the Chief Revenue Officer at ControlCase and a proven sales leader with over two decades of experience building high-performance teams. With a track record of leading in moments of transformation, Josh is passionate about coaching sellers to exceed what they thought was possible, through shared success, customer obsession, and scalable systems of growth. Resources & Mentions
🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts. Mark Petruzzi (00:34) Welcome to today's episode of Selling the Cloud podcast. We're excited to welcome Josh Hoffman. Josh has built his career leading sales and go-to-market strategies at some of the most iconic companies in tech. He started in Dell's early inside sales organization and went on to senior leadership roles at Avaya, Poly and Datto, often stepping in during times of transformation. Along the way, Josh has become known for his self philosophy and his passion for helping people build careers and outcomes they once thought were completely out of reach. At the heart of that philosophy is symbiotic growth. The idea that sellers and customers succeed together. Instead of pushing a deal across the line, Josh frames selling as sitting on the same side of the table with a customer. tackling the problem on the other side and building shared wins that last. We'll cover four themes today. The sell with era that we feel like we're in today, lessons from a career across Dell, Avaya, Poly and Dotto, leading times in a time of change. We certainly have that world amongst us today. And the future of go-to-market in the age of AI and ecosystems. John, us again, welcome to Selling the Cloud. Joshua Hoffman (01:47) Thank you so much for having me here today, Mark. I'm so appreciative of you and the team and all that you've done to help us all grow. And so it's a pleasure to be here. Mark Petruzzi (01:56) Excellent, thanks again. All right, Josh, so you often talk about creating symbiosis in selling. What does a sell with model look like in practice? Joshua Hoffman (02:05) That's a great question. For me, it's about helping people understand that we're not here to pick up a PO. We're not here to get a credit card number. We're here to solve something together. We're here to deliver something that's gonna help all of the organizations be better off. And in a lot of those environments, I've worked in direct sales, I've worked in partner sales, and I've worked in hybrid sales. They all have a slightly different meaning. But when I think about it the most, you described it at the beginning. It's about making sure that all of us that are solving the problem together, we're all on one side of the table. Sales is not combat. Giving somebody a product or a service that they need is helping them be successful. And if we all focus on what that means, if we're all laser focused on the outcome that we're trying to deliver, then we're all in it together. We're all with each other in that. KK Anderson (02:56) could not agree with you more, Josh. And my question is, so how do you help your sellers make that shift from quota-driven, transactional, I need to educate, I want to talk about my product mindset to one where they are the problem solver sitting on the same side of the table. How do you do that? Joshua Hoffman (03:16) Yeah, Kristen, thanks for the question. I appreciate it. There's a couple of things. First of all, I do want sellers to be quota driven. I do want them to be successful. They have goals to meet also. And part of leading a team is making sure that everybody succeeds company, people, internal, external companies that you're working with. And so there is definitely a part of me as a leader of revenue that says that we need to make sure that they are quota driven. But the shift comes when you help people understand that the more that they listen and the more that they ask questions, the better they're going to understand why are they in the room today? ⁓ Why are they a part of this conversation? And if you can get them into that mode where they care in a way that allows them to open themselves up to different possibilities. And I know that's a very EQ set of statements. but you want them to be sitting there thinking that I'm here to help somebody else succeed today. And the way that I phrase it, for example, with partners is if I focus 100 % on your growth, then it's going to work out. If you grow, we grow. If you succeed, we succeed. And getting that mindset to take place. It's a big shift for people, especially people that have come out of a transactional sales environment or have come out of something that's maybe a little bit more cutthroat. I live and breathe this idea that consultative sell with strategies make a difference. they not only build a better business for the client, for us, for the partner, it does help us build a better world. And that might sound a little bit kind of hippie-ish. But the reality is that I do want the world to be better. And if we all work together, it's going to be. KK Anderson (04:56) It reminds me of, you said hippie-ish, I love that, my Austin, keep Austin weird roots, but one of the things, one of the tactics that I've used in my 20 years of sales training has been, as soon as you feel the compulsion to start talking about your product, ask another question. Joshua Hoffman (05:11) That's a really interesting way of phrasing it. know, Kristin, I've had the benefit of seeing the outcome of the good work that you provide and how you help enable other people to get better and grow. And that goes a long way. It's really well put. Mark Petruzzi (05:25) And with both of those examples, we're hitting on things that I hold near and dear to my heart. And we're living in a world that's not really built that way anymore. Everybody kind of looks at things. We look at it in politics, for one, that you have to win. And then you really have to make somebody else lose, too. And that's not the way I look at it. I've always been someone who's used the term win-win and that's something I always want to do. And then it's nothing in what I do, at least in sales. Maybe there are parts of sales that is closer to a zero-sum game. But when you're looking at the value you can bring for clients and the return on investments and the business cases you can build for your clients, that's not zero-sum. You really can look at it from a solution standpoint. and allow that to really hit home and work to your advantage, not against you. So we love stories here at Selling the Cloud. So can you give us an example, a story, where this approach has created an outcome that wouldn't have been possible in a traditional sell-to model or just a mindset of win-lose? Joshua Hoffman (06:36) I have a lot of stories and so I'm going to generalize just a little bit so I don't name names, but I'm going to use an example where there was a partner engaged as well, where we were the provider of the product or service, but there was a partner that had a client that was involved. And the way that things had traditionally operated at this organization is that the sellers were consistently focused on selling to the partners. You've got to buy this. You've got to buy this. And then you got to go sell it. You've got to go figure it out. You need to internalize and ingest all this information and data. And you got to figure out how to go make it happen. And we changed our approach dramatically. One of the first things we did is we actually brought partner salespeople and SEs into our new hire training. And we said, you're part of the team. we're not trying to sell to you. And sure, you might actually be the ones writing the PO for it, but we're in this together. And so we're going to enable you the same way that we enable our people. We're going to speak the same language. We're going to talk about the same benefits. We're going to learn together. We're going to grow together. And as that shift took place and people started to see ⁓ their cohorts that were on the other side of the table before, I'm trying to get a PO from you. Now they're saying, OK, we're on the same side of the table right now. We're in this together. And once we had crossed that chasm, we now had the opportunity to say, you know what? There's another chasm to go across. Now let's get the customer to be a part of this. Let's get the client to be a part of this. Let's put them on the same side of the table with us. And let's take the approach that we're here to deliver an outcome. And we're going to co-strategize. I'm going to use the word co- bunch right now. We're going to co-strategize, we're going to co-create, we're going to co-decide what the solution is. And when we get to the end of the line, we're actually sitting in that mode of getting a PO, getting a check, getting a credit card, whatever it might be, given the different organization. We're not closing a sale. We're solving a problem. And that became a constant driving force. in the approaches that, that candidly I was able to take, but really organizationally that we were able to take, because we're a team. It's not just me. ⁓ Whether it was at Palo Alto networks, whether it was at Avaya, whether it was at Datto, Poly, whether it's here at Control Case, where we view things the same way. We're here to solve a problem. We're here to create an opportunity. We're here to create an outcome together. and having a collaborative environment makes all the difference in the world. KK Anderson (09:08) win together, right? And I know exactly who you were talking about, Josh. And you're right, you get to a point where all of a sudden your customer is calling you and saying, hey, I've got this client call. Can you help me prepare for it? And then you're building pipelines. Joshua Hoffman (09:10) Yeah. That's right. multiple organizations. I've had the chance tell our team, look, go put on their shirt for the day. You don't have to wear a Control K shirt. You don't have to wear a Datto shirt or a Palo Alto Network shirt. Go put on their shirt for the day. You guys are part of a team. And that team mindset, it solves problems so much faster. And that's what we're really here to do. As long as you're working for a company where you believe in the product or the service that you're selling, KK Anderson (09:34) Put on their shirt. I love it. Joshua Hoffman (09:47) and you're not working for something that's trying to gouge people or trying to do something nefarious. I happen to have been fortunate, the companies that I've worked for for my entire career, maybe minus one or two at the early part of my career, we were really trying to solve something important. And it was something that I believed in. That's an important part of that as well. You've got to and I tell this to people all the time, you got to be happy. Part of being happy is making sure that when you go to work every day, it doesn't always feel like work because you believe in what you're doing. KK Anderson (10:14) Yeah, 100%. And it absolutely applies in the COCEL environment, but even in direct B2B, you at Control Case, are you more direct B2B, or are you more channel partner? Joshua Hoffman (10:26) we do business in 73 countries right now. Not every country has the same kind of partner model. so depending on where we are in the world, it could be direct sales. It could be consultancy partners. It could be referral partners. It could be technology partners. And in the case of one of the missions that we have, it's using MSPs and ITSPs. So I have a vision that MSBs and ITSBs should be a bigger part of the compliance journey. It's using partners that are actually part of the technical journey that the client's about to go on. so depending on where we are in the world, it could be any one of those things. KK Anderson (11:00) But you know it's one of the ways that we met previously Josh I've got a lot of experience in assessing sales organizations and going through this whole you know sales effectiveness and improvement process and almost always out of hundreds of organizations almost always the sellers come back as they're good at hunting getting the meeting and then the next best skill that they have is presentation approach or going into like sell value. And I think they get so comfortable in learning the value proposition, learning the talk track, learning about the features, advantages and benefits of the product that they're trying to sell. And they get that word sell so stuck in their mind that I'm a salesperson, just Mark, we were earlier talking about that very thing. There are so many people that don't even like the word sales. And so it's almost transitioning their mindset from I'm a salesperson to I'm a problem solver. So my question for you, Josh, would be like for the CROs that are listening, and that's probably most of our audience, what's one thing they can do now to help start to drive that culture of ask more questions, solve more problems? Joshua Hoffman (12:05) Well, part of coaching is spending time with people. And in any sales leadership role, you see people get their time pulled in multiple directions. Should I be working on this Excel spreadsheet? Should I be working on this report? Am I spending time in an operational meeting? Am I spending time doing X, Y, or Z? When one of the biggest opportunities that people have is to spend time with people in the environment where they're talking to customers or partners. and having the chance to talk about it afterwards, to talk about what went well, what didn't go well, what would you keep, what did you change, what did you learn? There's all kinds of cliche phrases around that. But that kind of coaching environment is what helps people get better. Now, of course, you have to be a sales leader that believes in this model, and not every sales leader does. And so you have to be a little careful about that. But assuming that you do, that time that you spend with people is one of the most valuable things you can do. The other thing that you can do is model behavior. And I'm the first one to say, look, I screw things up all the time. I'm not perfect. I don't always get it right. But what I do try and do is when I'm sitting inside of that environment, when I'm with the client, the partner, the salesperson, the account manager who's leading that account, is I do try and model that behavior and make sure that they're seeing what, at least what I hope good looks like. Again, said with a little bit of humility, it's not always great, but I try and be very consistent in my approach and it served me well. That's the advice that I give, spend time with your people. there's nothing more valuable than that. That's how you help people get better. And one of the ways that I've branded myself throughout my career is that helping people find a career they only thought aspirational. is a motivator for me, helping people learn and grow and develop into something that they never expected. And you can't do that if you don't get to know your people, if you don't get to spend time with them, if you don't get to coach them along the way. Mark Petruzzi (13:56) Very, impactful. Everything that you just said there. All right, let's switch over to the second topic. know, and this is a perfect build on where we've started, like lessons from a career in tech. So you have been through multiple transformations in your career and transformations within the companies that you've worked within. From being within Dell's Inside Sales team, to intern CRO at Poly, Dorn, what turned out to be a very turbulent year. What experiences has shaped your leadership style the most? Joshua Hoffman (14:29) good gosh. Let me start with, I feel so blessed because I have been shaped more times than I can count. I've been shaped by great leaders. I've been shaped by great situations of growth. I've been shaped by times of, as you said, turbulence where things are not always going well. And I've done my best to learn from each one of those situations. Picking one out of the group is a little bit challenging to consider, but I look back on my early career at Dell. My first job at Dell was putting screws in motherboards. Candidly, I had tried sales, I failed. It wasn't going well for me, and I said, I'm gonna go do something different. And getting the opportunity to walk into an environment at Dell is probably 1992. They said, the phone's ringing off the hook. We need more people in sales. came onto the manufacturing floor. Who wants to come to sales? me, so they chose about 25 of us raised our hands and me and Rick. So Rick knows who I'm talking about. We were the two that were selected and we end up, sitting on the phones for four hours a day and going back to our manufacturing job or vice versa, depending on what day it was. And I got to be part of an environment that was growing like a rocket ship that was also going through challenging times. This was the time of the exploding laptops. And so not exactly one of the best moments in that company's history. And I got to learn from some amazing leaders. Now that carried on. I had leaders at Dell consistently, actually throughout my career, I could probably call out 10 leaders easily that have made a difference in helping to shape who I am. Almost all of it leads back to a common theme, which is being given the opportunity to step into a situation and learn on the fly. I wasn't always put into places where I knew what to do. I wasn't put into places because I had the experience. I was put into situations where I had the opportunity to learn, to grow, to be creative, and to help come up with what are we going to do to solve this. And I give a lot of thanks to people that were willing to put trust into me at various points in my career. And that's what's shaped me the most. That's the consistent theme throughout all of those organizations is let's let Josh do it, which by the way, wasn't always perfect. It didn't always succeed, but I've been fortunate more times than not. It's been a successful. KK Anderson (16:53) You need to screw the tight, the screw is a little tighter on those laptops so they don't explode. Joshua Hoffman (16:57) Yeah, well, okay. It's a funny story when you look back on it now. It was unbelievably stressful at the time. Dell grew so much over so many years. when I started, it was a thousand people. When I left, I think it was 70,000. And, but they gave me opportunities to go learn on getting to move to China, getting to move to India, getting to lead the first services organization, doing things that KK Anderson (17:05) totally agree. Joshua Hoffman (17:21) that I hadn't done before, but also that the company hadn't done before. And so we got a chance to make things happen along the way. It was pretty spectacular. KK Anderson (17:29) Really cool, and I like what you were saying about trust. That's so important. So you worked under our mutual friend, Todd Abbott, and he's such a strong, awesome leader. I know that he had a strong style and impact on you. What would you take from that relationship specifically, just out of curiosity, that influences you today? Joshua Hoffman (17:37) did. ⁓ look, I love Todd. I had this amazing experience with him. I think it was three years or so that I had the opportunity to work for him. And ⁓ during that time, I got to experience a different type of rigidity and approach that I had experienced other times in my careers, but never with the clarity that Todd uses to set expectations. to create an environment for people to succeed, to approach things both analytically and with creativity at the same time. He was a champion of the people on his team and you always knew that Todd had your back. And by the way, I have actually been very focused in my career of finding people to go work with and for that are like that. that provide that kind of environment. It's not always easy, by the way. My CEO today, Mike Jenner, has many of those same qualities. And he has other great qualities too. So it's not like Todd and Mike are twins, they're not. But Mike provides that same kind of environment. And I feel fortunate to be in a place where accountability is sacred. And there's never a moment that you're confused about what needs to happen and what the outcome needs to be. I've worked for other leaders in my career where there was ambiguity all the time. And candidly, that's really hard to be a part of. And I do my best to make sure that I'm modeling that behavior that I get out of folks like out of Todd, out of Mike, out of other folks in my career. Mark Anderson at Palo Alto Networks is a great example. Earlier in my career, David Lockett at Dell. with somebody that had that same approach. And I've had other leaders too, so I could probably name 20 names and so forgive all the people that I didn't just mention. But these ones jumped to mind because of that approach and combining analytics and behaviors is a lot of what leading a successful revenue organization is about. You have to have both. And so thanks for asking that question. So I'll make sure and call Todd. Mark Petruzzi (19:44) Yeah, you described that really well. So Joss, through many of your companies you've worked with, you've lived through significant change and cultural shifts as well and acquisitions and putting companies together. What did you learn during those times about keeping teams motivated and effective during times of change? Joshua Hoffman (20:04) Well, there's a couple of things. Now I have been fortunate. Most of those times of change have been about rapid rocket ship kind of growth and how that impacts an organization. I know that one of the lessons that I've learned and one that I try and live, although again, not always perfectly, is my behavior doesn't change ⁓ almost no matter what the situation. The message may change. The requirements or the outcomes may change. but my behavior doesn't change. Nobody has to worry about schizophrenic Josh. There's an opportunity to know that there'll be a level of consistency there. The other thing is about making sure that people understand that change isn't necessarily bad. If you go back to the days of like corn fairy and FYI and the introduction of these competencies into the corporate world, I got to live through being one of the guinea pigs for that. One of the competencies was dealing with ambiguity. And getting the chance to teach that, to share with people the sort of the pieces that fit into dealing with ambiguity ⁓ is helpful. And giving people a future that makes sense to them, that change can lead to better things, you have to be consistent in that message. Now, by the way, there's times where change doesn't lead to that. I've been parts of organizations that did layoffs. I've been parts of organizations that were bought. And maybe that wasn't the best thing in people's eyes at the time. But it doesn't mean that the culture of the organization has to change. Candidly, everybody has to be a part of that. And that's one of the other key messages is that change doesn't have to happen to you. You can be part. of what makes things better and that you should feel empowered, you should feel emboldened, you should feel like you have a voice, you should feel listened to. And the other skill that I think comes with that is having compassion. You have to have empathy to be successful in any leadership role. If you don't have that, one, you gotta go find it. Two, you really do have to be able to put yourself in their shoes and say, What are they feeling based on this message? What are they thinking right now? How do I answer questions before they're even asked? And the more you can get ahead of things, the better off things will be. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||
| Ep. 96 – Scaling Sales with Value Intelligence with Max Elster - Part 2 | 07 oct. 2025 | 00:20:10 | |
In Part 2 of our conversation with Max Elster, Co-Founder and CEO of Minoa, we go deeper into how sales teams are actually operationalizing outcome-based selling; at scale. Max shares how revenue teams at companies like Vanta are moving beyond founder-led, feature-centric narratives, and building scalable, repeatable playbooks rooted in customer outcomes, business impact, and data-backed storytelling. Whether you’re leading a 10-person sales team or a 1,000-person GTM org, this conversation will help you reimagine enablement, coach for value, and build business cases that win over CFOs. What You’ll Learn
Key Topics
Guest Spotlight: Max Elster Max Elster is the Co-Founder and CEO of Minoa, a revenue platform helping companies scale value-based sales across the deal cycle. With a decade of experience in AI and B2B SaaS, Max works with companies like Vanta, Cognite, and others to operationalize value intelligence, from discovery to renewal. Resources & Mentions
🎧 Listen now and subscribe to Selling the Cloud wherever you get your podcasts. Stay tuned for next week’s episode! Mark Petruzzi (00:36) So let's move to topic three, stories from the field, moving from features to outcomes. So I have heard you say how you've worked with Vanta's CRO on shifting from feature led to value led sales. Walk us through that story. Max Elster (00:52) Yeah, I think it's a great example. Stevie, who is Vanta's chief revenue officer, she came from Twilio in the past and came to Vanta's organization, around probably somewhere between like the 20 and 40 million AR range. like basically Vanta is a good example, right? They initially were, basically kind of building this idea around a trust management platform and compliance and the importance of security and compliance with startups. And then they expanded over time. one important thing was that as they have more competition, they need to differentiate themselves. they basically, one way of differentiating is to focus on value, right? So Stevie came in and she talked about this publicly as well, many different times where she said that one of the most important things that she drove as an organization was evolving the company from a feature led organization, the initial founder led sales days to... basically focusing the company on value selling and moving away from feature to an outcome led and value led story across the board, pre-sales to post-sales. And then of course it starts with changing your narrative. It starts with changing the decks that you're creating. It starts with making sure that every single seller can talk about the business case and the value that in this case, Vanta provides different than their competitors are oftentimes against StatusCrow, So why should I do anything about the specific initiative here? And they have seen great success, And actually making that transition, but ultimately I would put it even into a larger scope. any successful company out there, whether you look at the old days, the SAP is the oracles, or whether you look into modern companies, Databricks, Snowflake, many of the other kind of modern go-to-market tech organization, like go-to-market teams, they all rely on the value principle and they all operationalize their thinking around how do we make sure that everybody can speak to. value across the board, not just pre-sales but also post-sales. And Vant has a good example where Steve done a great example at also articulating that a way. And yes, I think they're a great customer of ours. We're very happy to have them then kind of go take the ride with them. But I think they're just a great example of how they have transitioned. And the outcomes are incredible, rent rates go up, sales cycles go down. You can actually make sure that everybody is more proficient at articulating the value that you're driving. So even thinking about discounts, especially in very competitive markets where you want to avoid discounting every single deal, And if you can uniquely position value to a procurement team, that's going to help you actually have that conversation over your competition. KK Anderson (03:01) And all of that is stemmed from having outcome plans and business cases in that kind of value intelligence layer as you describe it. that the sellers are talking to outcomes and talking so that they can then derive the value to lead the sale. Max Elster (03:15) a good example of company, a couple thousand employees where have actually measured that they built mutually created over 500 business cases a quarter. And before it was almost basically 10 to 30, In a quarter where individual SEs were building business cases to support the sellers. In a future world, basically every seller will be able to build a business case, have that being automated and have it readily available to them for every single deal. So what happens was that actually we saw that VIN rates go up six to sometimes even 15 percentage points for specific segments, which was incredible. And it's less because you bring a business case late into the deal and you try to justify the value to a procurement person. It's more of there's a process and a guidance for an SDR or a seller or an SE to talk about value earlier. It's almost like teaching a kid kind of basically ride the bike. If you give them a little bit of a guidance of how to start with, they will do it themselves. And it's similar, in value where if you teach them that the end result will be you driving the bike or you actually closing more deals, they will kind of think backwards and think about, if I just need to get to a final business case that includes a few different questions I need to ask, but that will help me and the customer and the champion have an internal story they can tell to their buying committee. I can do that, I can make sure that every single discovery call has these like three to four questions that would help me then shape a better narrative as we go along the sales cycle. And then it's becoming a routine and a habit, right? And as soon as it's a habit, it can actually get scaled and be successful across the company. Mark Petruzzi (04:43) So Max, how did these stories resonate differently with executive buyers like CFOs who we all know scrutinize every purchase? Max Elster (04:52) looking at, have a few CFOs in our advisory board and I always say the CFOs will do it themselves if you don't do it for them. So they will run internal projections and internal business cases themselves. And if they don't believe in it, then they are the ultimate gatekeeper and they can just say, no, I don't believe in this. So as a seller, you're either destined to keep it up to them and you can't control it or you do it yourself. And you can control the outcome plan and the business case you're presenting to them. or equipping a champion ideally to do that. And we have a couple of interesting stories where sellers have actually reached back to us and said that the executive, whether it's a CFO, it's a CSOR, whether it's a CIO, they actually came into the application and they almost modeled the assumptions to the base minimum. So they came in and tried to understand if we almost have no success here, what is the minimum value? And they compared that internally to other initiatives and projects that they are currently exploring. And it resulted almost a CFO to have ownership and accountability on the business case, Because they actually control the assumptions and the narrative and they're doing it based on the framework that the vendor provides to them. And it just changes the dynamic. I also say, I don't think a CFO is kind of this alien on the other side that doesn't want to talk to you, But they want to see that you can relate to them. They want to see that you have experience dealing with similar businesses and the more you can do that proactively, the better. And yes, I think I had CFO conversations where I presented them a business case and they said, I don't believe in this number. And then I went back and said, okay, then tell me what you believe in. And then I think like you almost opened up the room and you have a conversation about a mutual goal that you're trying to go after and you find a good solution. It brings everybody closer together. think that's the ultimate desire of running a good sales process. KK Anderson (06:25) Really, really interesting. Okay, let's move to topic number four, which I know is a really hot topic with our audience. And that is the future of revenue leadership in an AI world. So I've heard you say in a previous conversation that many CROs, and I agree, fear their jobs because of AI and how quickly things are changing. And I just. I want to get your perspective, but do you think that is? Max Elster (06:50) Uncertainty is always a difficult thing for us humans, Some get excited by it, but the majority of people get afraid of uncertainty and not knowing what the future beholds. And I think that's the scenario right now where things are moving so quickly and it's hard to estimate where it's going and how you potentially react to it or how your competitors potentially are reacting that you're missing out on, right? That I think a lot of people either start almost freezing, And they start Not to move. that's a risk or they start to move too quickly. they make like, test a lot, but they don't make fundamental decisions about which AI solutions or strategies do I deploy and what's the underlying reason for that. think a lot of people are just trying to move and make a decision, but they actually forget about what I'm actually trying to solve in, my process and, kind of my day to day execution with my teams. And which solutions and vendors and strategies and data plays do I want to run in order to make sure that that can actually get accomplished? AI hasn't really changed that, ultimately it's going back to kind of yourself first and thinking about which problems do I want to solve for my revenue team? And then how do I apply the right AI solutions to that? I do think though that the quality of LLMs today give us an enormous opportunity to tap into unstructured data sources and data sources that have previously been so messy and so complex to analyze that it's going to open up a lot of more opportunities to improve your day-to-day work, whether it's one individual seller, or whether it's a CRO trying to almost run better analytics around the idea of, for example, why do we win? Why do we lose? Why do think there's so much data there that actually has never really been tapped into that now is possible with LLMs? But I would say It's going back to the fundamentals of thinking which strategies do you want to change? What are the underlying solutions and options that you have? then deploying and testing the ones that feel most suited for that particular purpose. And I think you will be successful, it's just probably give it a bit of time to, have everyone adjust it. But then it's a new reality that we all work with. I'm sure you too see it with your clients as well every single day, Where you help them have those conversations internally. KK Anderson (08:48) see AI reshaping all of these different roles of the direct level team members? So the sellers are obviously on chat, GPT all over the place. They're using AI inside a gong. They're using generative AI. The leaders are using predictive AI. AEs, SCRs, like what are the big ones that stand out to you? Max Elster (09:10) I mean, we all become more intelligent, right? think that's kind of, we all essentially, we have ourselves and then we put an additional intelligence layer on top of that, which is gonna make us a smarter seller. It's gonna make us a smarter advisor to our customers. It's gonna make us more credible, more relatable because we can actually tell stories that are similar to what others have seen. So think that's very tactical. think sellers start to tap into those resources of previous deals, previous conversations. So do think about, Gong or the respective call recorder that you're using in the past, you didn't have an opportunity to get an account level overview of 150 plus conversations, Of like what actually is kind of the underlying executive summary around this particular account. Now it's possible, right? Because you have all those conversations that can feed into Gong summaries or kind of other tools that you're using in order to help prompt yourself for a business case, help yourself prompt for a better... code outbound, you're sending whatever you're doing in your sales process that can actually get leveraged by those individual call recordings. what we're seeing is that a lot of the forecasting providers are starting to open up their signals to more and more data points, which is interesting. If you think about your forecast, maybe in the past, it was limited by how well your Salesforce fields were filled out. think nowadays you can tap into many more signals and data sources around an individual account. Not just the conversations that you're having, but also Did they fire executives in the past two weeks, right? That could potentially impact your deal, right? Or it could risk the forecast. And all these different data points can now be merged and made accessible in your day to day, whether you're a chief revenue officer that runs the forecasting process with your sales manager. So whether it's an AE trying to become a more intelligent seller and more credible seller and advisor to your prospects. I think that's where AI is just getting started, started my first company back in 2019 where we built speech technology with natural language processing. And I remember back in the days that we were competing with Google and AWS on some first speech models. And it was incredibly difficult and almost hard to actually transcript a meeting. Nowadays, we talked six years later and we have almost perfect transcripts for almost every single language in the world. We can take those data points and put them into other sources, ask questions around it. It's pretty crazy, but also pretty exciting. I think opportunity for go-to-market teams to truly advance and be even more customer oriented than what they were a few years ago. Mark Petruzzi (11:23) So Max, what happens when every company has great AI building tools? What will still allow differentiation amongst the best revenue leaders? Max Elster (11:34) listening and building strong relationships. we're to go back to, core human strengths and qualities where we were social animals, And we want to come together and learn from each other. And I think that's what AI gives us more opportunity to not do cumbersome work that you would otherwise be spending a lot of time on and actually focus on how can you drive. better conversations with customers and how can you potentially show up more often, Maybe take that flight and just be with your customer and spend time with them, get to know them and make sure that you bring all the information that would be helpful with you. But all that information is there, You just need to tap into that and then you can focus on the actual conversation and trying to understand the other side better. it gives us an enormous ability to actually be closer to what we're supposed to be doing and not just typing letters on the computer. that's a great opportunity, but also it's a big opportunity will be to almost let the team run a little bit. Everybody's worried right now that teams are using chat, JBT and other systems. it gave everybody a first stint of what is possible with AI. And I often suggest to let people run and explore themselves. And at some point you grab everyone together and say, let's talk about the kind of individual projects that you've always tried out at home, On the weekends, during the week, like what are the things that have been, been working for you and how can we. now build a system around it that we can scale across the company because otherwise we're to be running around like headless chicken and everybody's going to be doing their own thing. But it's actually not solidified in one neutral story that you can execute on. And I remember a few years ago, everybody talked about great customer experiences. And I think we kind of come back to that again now where everybody had some internal runs on AI technology. And now it's probably getting everyone back in the room and thinking about what actually works. What do we want to deploy? What do we want to scale? KK Anderson (13:09) But after work, what is the point? Max Elster (13:11) I think that's kind of phase two of the AI go-to-market story right now. KK Anderson (13:15) I feel like AI is going to help the sales profession get back to what it originally was, which was building relationships and trust and credibility and having the time before we had all of these tools and technologies and everything had to be inputted into CRM. And, there was so much admin, before those days, was, your Rolodex and who you knew. And it was the relationships and that was the value, the value that you had as a salesperson. And now with AI being able to take so much of the busy work back, it's like you can focus again now on relationships. I always, mean, shoot, you can even use different generative AI tools as like your assistant, like your strategist and ask questions like, Hey, I'm thinking about this customer. I'm thinking about this challenge they have. Max Elster (13:56) Mm-hmm. KK Anderson (14:01) What are some questions that I can ask? what are some, just ask questions as if you're talking to like a sales coach, right? That's too. Max Elster (14:07) like different projects in ChatGBT and other tools where I kind of built those individual projects for me, I have a product coach who's advising me on how do I best navigate a new product idea. I have basically almost like a company coach that's helping me think about culture and strategy and then have a sales coach, That's helping me on some more tactical piece on go-to-market. And I'm kind continuously building that out as, we speak, I have an investor kind of related one where it helped me craft a good investor update. So there's many different sorts of these like micro projects that you can build. And you bring up a good point though of like, ultimately it's about the relationships. And I often compare that with what happened in coding, Which is actually moving at a faster pace right now as go to market, essentially what engineers are doing now is they work with cursor in order to automate some of the work around. writing code, And what happens is they come back to their core strengths, which is thinking about engineering problems and thinking about product problems and talking to your peers about that. And then the actual writing of code can be automated or at least partly automated, And you can have more time thinking about the solutions and the scoping of that, which is a more important task and the actual writing of it, So I think that's going to be an interesting. time where I coding kind of you can see that that's almost like a little bit of a headwind they already had of time and then go to market will follow. And it's going to be built around the relationships as you said, specifically in go to market, it's going to come to the core strengths of what the individual kind of people are actually doing in their function and department. Hopefully, I mean, that's maybe I'm an optimist hopefully in this regard. KK Anderson (15:33) the engines that you're using are selling the cloud listeners and reading our newsletter and recommending that you come and be on our podcast. We're so glad that you're here today. And I know that you have been a listener as well. So for the CROs that are listening today, what's the one thing, and it's gonna be hard to boil it down into one, but what's the one thing that they can do to future-proof their role? Max Elster (15:44) Thank you. KK Anderson (15:59) in the age of AI. The first thing they should do. Max Elster (16:01) I would say the first thing that they should do is I would pick 20 sellers and I would like the first thing I would probably do tomorrow if I would be a chief revenue officer right now, I would go into like a channel and say, Hey, I'm actually curious to learn from my team, whether it's 20 people or 50 people. What are the AI applications that they've built at home during the work time and have 15 minute conversations for every single one of them. and learn what they're doing and why they're doing it. And note every single action, note every single problem that they're trying to solve and then aggregate it at the end and think about a strategy that you can then deploy to everyone else. Because I think a lot of sellers are already doing something and they would love to, tell their story of what they have been experimenting with through the chief revenue officer and the chief revenue officer can future proof themselves to build a strategy around that, but also then guide and lead the managers below them to execute on that strategy. Often it's talking to the sellers. They're the ones that are testing a lot. I think actually reducing the width between the chief revenue officer and the AEs would help them get more future-proof and understand what's actually possible with AI. So that's probably what I would do tomorrow if I were a chief revenue officer. Mark Petruzzi (17:03) That's great. Well Max, this has been a great discussion. Do you mind if we jump into a few rapid fire questions? Our audience loves them Cool. So what was the first product or service you have ever sold? Max Elster (17:12) Of course. It was actually a ticket management software that was sold to event organizers and clubs in 2015. Mark Petruzzi (17:24) Nice. KK Anderson (17:24) Okay, who's your favorite CRO or CEO that you like to follow? Max Elster (17:29) That's a good question. I'm a big fan of Patrick Olsen at Stripe. I think they've done an incredible job building the company, the culture, the go-to market as well for a company that initially was built out of almost like a one bedroom apartment and now became, I think, is it now, 50, 60 billion company, Fintech. great company. The person that I admire for the work he has done in the team. Mark Petruzzi (17:51) What about a leadership or go to market practice that you believe every sales, marketing, executive leader should adopt? Max Elster (17:59) principles of the qualified sales leader. I've re-read it again, John McMahan's book. I think it's kind of the Bible and the principles for a lot of the thinking that we have building our product, Thinking about value and outcomes and making sure that it follows through. But the best go-to-market organizations have applied some form of the qualified sales leader's principles that John McMahan and the team. in the early days of BMC and Blade Logic and some of those companies have initially built and it still stays true today. he's on the board at Snowflake, Building the next $100 billion company plus and it stays true. So I think that's a great principle. would definitely read the book or take some summaries in order to develop our thinking. KK Anderson (18:38) I can't wait to check that one out. We'll put it in the notes as well. my favorite question. Advice that you would give your 21 year old self. Max Elster (18:44) I would probably say is to ask a lot of stupid questions and learn from others. when I look back over kind of the last like 10 years or so, think it's, I always try to kind of reach out to different people that were great in their qualities. And I try to just say, hey, I'm a person trying to learn about the field that you operate in, and I have a few questions and usually people are actually very happy to talk about themselves and in a good way. I think they, if you ask the right questions and they can tell about their stories and how they made decisions, they will open up and they will become mentors. They will become friends. And I think that's something where, if I think about the probably thousands of conversations I've had, think oftentimes it's just being curious and asking more questions that will help you become more curious about yourself, but then also you learn from others and you can apply those tactics in your day to day, whether it's on a professional or on personal site. And People are very open to help, you just need to ask for it. Mark Petruzzi (19:31) Excellent. Max, this has been so informative and so enjoyable. Thank you for taking the time with us. Where can our audience find you if they're looking to get in touch, learn more about the company? What are their best ways? Max Elster (19:46) Yeah, LinkedIn is great. So I'm available on LinkedIn, maxelster, or if you want to send me an email, it's max at minoa.io. So pretty easily accessible there. Just send me an email and happy to find some time. Mark Petruzzi (19:56) Perfect, thank you again, Max. Max Elster (19:58) Awesome. Thank you too. was great and incredible questions. KK Anderson (20:01) Thanks Max. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. | |||