Dan Slagen is the CMO & Chief AI Transformation Officer (CAITO) at Zapier. He joined just over a year ago as SVP Marketing, and recently got promoted to own the company-wide AI transformation mandate.
Before Zapier, he was CMO at Tomorrow.io, where he helped grow the company from $2M ARR to a $1B+ valuation, CMO & Chief Culture Officer at ThriveHive, and Head of Global Advertising at HubSpot.
In this episode, we talk about the future of the CMO role, why the CMO should (?) own the company-wide AI mandate, his “red alert” for Zapier’s marketing team, strategies to speed up your team’s AI adoption, and much more.
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We discuss:
* Why Dan took on Zapier’s company-wide AI transformation mandate as the CMO
* Dan’s case for fewer CMOs
* The “red alert” he called on Zapier’s marketing team
* The first step to making your company (and marketing org) more AI-native
* Zapier’s internal AI policy
* LLM jail, automation debt, and why only 24% of GTM workflows need AI
* Why AI is causing “generation loss” & what it has to do with your approval processes
* What every CMO behind on AI should do this weekend
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Show Notes:
Connect with Dan Slagen:
Dan Slagen’s LinkedIn: https://www.linkedin.com/in/dan-slagen-718675a/
Dan Slagen’s website: https://www.danslagen.com/
Zapier: https://zapier.com/
Connect with Finn:
Finn’s LinkedIn: https://www.linkedin.com/in/finnthormeier/
Thormeier.co - Founder Brand & LinkedIn Advisory: https://thormeier.co/
Mentioned in the episode:
ZapConnect (Zapier’s annual conference): https://zapier.com/zapconnect
Dan Slagen’s “LLM jail” & “Automation Debt” post: https://www.linkedin.com/posts/dan-slagen-718675a_our-team-keeps-hearing-the-same-two-words-activity-7490753511693930499-8NRJ
Zapier’s AI Workflow Index (Q2 2026): https://zapier.com/ai/workflow-index/q2-2026-report
Tomorrow.io: https://www.tomorrow.io/
Tom Wentworth (CMO at incident.io) episode: https://www.founderbrand.org/p/the-most-ai-pilled-cmo-in-tech-shares
Don Jeter (CMO at Torq) episode: https://www.founderbrand.org/p/how-to-radically-stand-out-w-don
Torq: https://torq.io/
Paul Roetzer’s SmarterX: https://smarterx.ai/
MAICON: https://www.maicon.ai/
Clay’s AI writing policy: https://www.clay.com/blog/ai-writing-policy
Claude Code: https://claude.com/product/claude-code
Cursor: https://cursor.com/
Codex: https://openai.com/codex/
Midjourney: https://www.midjourney.com/
HeyGen: https://www.heygen.com/
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Full Transcript:
Finn Thormeier: All right. My guest today is Dan Slagen. He is the Chief Marketing and Chief AI Transformation Officer at Zapier. Zapier, I’m sure given my audience, everyone will know it’s an automation platform, or as they say, it’s the most connected AI orchestration platform. Dan joined Zapier a little Over a year ago as SVP of Marketing and recently was promoted to CMO and CAITO, Chief AI Transformation Officer, which is a very interesting combination and we’ll discuss that.
Before joining Zapier, Dan was CMO at Tomorrow.io, where he helped grow the company from $2 million in ARR to $1 billion plus valuation in five years. CMO at ThriveHive, where he led the team through a $1.3 billion acquisition. CMO at Alignable, Head of Global Advertising at HubSpot and many other roles including founder of a video tech company for a year and he was also named one of Forbes top 50 entrepreneurial CMOs of 2024.
Dan thank you for joining and anything to correct or amend there in the intro?
Dan Slagen: No, appreciate it. Very, very kind words, but happy to be here.
Finn Thormeier: Cool. What’s the story behind the new title and is it disconnected or is there a reason why the company-wide AI transformation chief officer title was given to the CMO?
Dan Slagen: Good question. So I joined Zapier about a year ago and it’s a, you know, 13, 14 year old company, a lot of history. And so, you know, first and foremost, I think they want to make sure that someone coming in at this level is not going to stick around for a little while and leave. They want to make sure that someone who’s going to be really invested in the company and all that. And so it’s funny, you know, any Any executive marketing role these days, I feel like it’s a one-year trial, essentially. It’s a test. I’m going to see if I like the company, if I like working for the CEO with the exec team, and they’re going to do the exact same thing back to me.
And so as we were nearing the one-year mark, Wade and I... Got together, Wade’s the CEO, co-founder of Zapier, and we sort of had the conversation of is this a one-year deal or do we want to try and sign a multi-year contract? What do we want to do? And we both felt like the relationship was going well and this had been a fruitful experiment so far and it felt like something we both wanted to invest in moving forward.
And so as we did that, We also sort of talked about how else could the role expand and what else could you do outside of marketing. And so I’ve been extremely fortunate in the past to work for some smaller startups that went through hyper growth where you own everything. You know, I can remember roles where I owned marketing and sales and CS, BD, like everything, just building those systems from the ground up. Certainly not at the scale that Zapier is at, but I had some good familiarity. The one common factor with all of that was growth and pushing the limits on the technology that we’re using.
And so with AI, you mentioned my last company, it was a really, really small marketing team. With a very small budget. And so when AI came out, that was an aha moment for me of being this thing that we can finally compete with the biggest companies in the world. The playing field is finally level. I can do all these things I haven’t even been able to do. I wasn’t so excited about AI at first because it made the things I was doing better. I would tell you because I could literally do things that I couldn’t do before. I just told my CEO, can’t do that, can’t do that, can’t do that unless we, you know, get headcount or budget.
So I’ve stayed really close to that. And I’ve also stayed really, really close to the culture. In another previous role, you mentioned ThriveHive, I was the chief culture officer as well as the CMO there. So I started to learn a lot about that. And at my last company, the culture team and I partnered so closely together. So I’ve had all this experience that was sort of building towards something I didn’t quite know what it was. And it fruitfully ended up being this dual role of marketing and AI transformation at Zapier.
Finn Thormeier: Do you think marketers are somehow better suited for that type of role or was it just really this unique mix that you personally had that will not apply to other marketers as related to their peer leaders?
Dan Slagen: That’s an excellent question. I truly believe that someone sitting in The head of marketing role is in the best position in the company to lead it.
However, A lot of the personas that I see within marketing either have not had the experience that I just went through or do not have the mindset to be able to do it. They’re too focused on one thing. They know how to tell a really, really good brand story, but they have no idea how to think about pipeline and demand generation or the inverse of that. And it is hard to find someone that truly can spike across all three areas. Happy to dig more into that. I think if you can find the person with the right background, someone sitting in the marketing and growth department is an incredibly dangerous persona that can help the business immensely.
Finn Thormeier: Not to go on too much of a tangent, but you said At Tomorrow.io, you had a very small team. I think I saw you gave a presentation where you had four people reporting into you and that when AI happened, you felt like you could finally do these things that you hadn’t been able to do because of lack of headcount. Are there any specific ones that you can mention here where, again, things that you wanted to do but really couldn’t and now finally you were able to do?
Dan Slagen: Sure. One example that I like to tell is, you know, when I was at the company, we got included in an RFP from a major entertainment brand. They own theme parks around the world. They have lots of movies. You can probably guess who I’m talking about. And the RFP was really, really last minute. And we had a week or two to get something to them. And we knew there were 10 other companies all pitching. And we were added late. And they’re like, what are we going to do to stand out?
What we ended up doing was we created this video using AI where we went to all of the movies that the entertainment company had created and we saw where all of the characters were impacted by weather. And we’d be like, what if they had had access to our technology? They would know when to leave the dock. They would know when to go fly. They would know when to go outside. They wouldn’t be at risk. Literally use the exact scenes from the movies and the characters and all that.
And when we showed it to them, the response was literally, we love how much you just love our brand. You stood out so much compared to everyone else. We’re going to move you guys to the next round. We haven’t even looked at your technology yet. We’ll worry about that in the next round. But just they’re one of those companies that they want to see that people love their brand and get involved in their brand.
And so, you know, that’s something that, again, I wouldn’t have even proposed that prior. And, you know, we did this when, you know, Midjourney was really getting good. The video creator was starting to get good. We were using things like HeyGen AI to do all of our product marketing videos. So we were getting good at that really, really quickly. And so, again, it was sort of a new thing we could even offer the sales team that we wouldn’t have even thought about.
Finn Thormeier: The CMO role, I’ve seen so many posts about this recently, and even Tom Wentworth, a fellow Boston CMO who sends his regards, by the way, when I interviewed him about how he thinks the CMO role is evolving, Even he said he could see a future where the CMO title or role doesn’t exist. What’s your take? Is the CMO role dead?
Dan Slagen: No, not at all. I love Tom. Look, I go back to... Honestly, I go back to a couple things. One, you look at the education system and you look at colleges and universities. And when I was in school, the truth of the matter is I didn’t have the brain to go into finance, accounting, right? These are majors where you have to know your stuff. You have to know your numbers. You can’t BS your way through a finance degree. You can’t BS your way through an accounting degree. And a lot of kids Fall into the business school because they just think that’s what I’m supposed to do. I’m going to do business. And you know, the entrepreneurial tracks, not for everyone. That’s its own thing.
And so a lot of people fell into marketing because it was seen as a little bit of a fluff experience. You could kind of BS your way through these classes. What’s creative? How do you judge creativity? What’s good? What’s bad? No college professor is going to sit there and tell a kid their creative thinking is not right. Everyone kind of got a free pass. And so one, I think you had an extremely low bar of people getting into marketing just because. And there wasn’t so much of that like rigor.
Two, how do you think about marketing? There’s so many ways to think about marketing. You can appeal to people through creative. You can appeal to people through direct response, through really good product marketing, positioning fit. Like there’s so many parts of the job and depending on where the company’s at and what they’re trying to do, you need to be able to call on different parts of those things.
You don’t see that in other roles on the C team. CFO sort of knows what to do, you know? Head of Sales kind of knows what to do. Marketing, whenever I talk to a CEO and they want a marketing lead, my first question is, well, what does the company need? You know, you would never ask that question if you’re asking about like a CFO role. You kind of know for the most part what’s going on. So there’s so much ambiguity and it’s very hard to find someone that can just run across all those things. You have to have extreme width and enough depth to be dangerous and that’s really hard for people.
Again, I think I’ve been extraordinarily fortunate the way I was raised, the jobs I’ve been able to have, where I have the analytical side, the creative side, I’m connected to the business, I know what’s going on with sales, but I can also take creative moonshots and do really silly things and turn around the next minute and do something that’s really buttoned up and directly focused on ROI. And it all lives in your head. There’s just a lot you have to think about and the composure. So it’s just a really, really hard role.
All that to say, There’s no way the CMO role is dead. It’s possible that we’ll see fewer CMOs, but I think the ones that retain the title are absolutely at the top of their game, and these companies cannot be living without them. I also think we could see a role where companies come back to wanting a CMO as well.
Finn Thormeier: I mean, that makes a ton of sense to me, and there’s obviously a lot of people doing clickbait stuff, and maybe you answered this question, but Is there a deeper reason why there’s even a conversation about the CMO role being dead or obsolete? I’ve not seen similar takes about the CFO role is dead.
Dan Slagen: One thing is I think you see way too much celebration in marketing without knowing if it improved the business. And you could have a great brand campaign. You could have an innovative way to think about positioning, but were you able to connect it to ROI? Were you able to connect it to revenue?
I remember my very, very first day at Tomorrow.io. We had got the whole team together. We were at all hands, and I’m introducing myself to the company for the first time. The first thing I said to that company was, I am a sales-oriented CMO. First and foremost. And this is coming from someone who loves big brand play. I do a ton on PR. I told you about video creation. And we’ve done a lot at Zapier this year. We did Super Bowl. I love brand.
But I am also talking to my CFO every single week. We have a shared spreadsheet with the numbers. We talk the same language. I know ARR. I know our time to close and our ACV. I know our churn rate. I am... First and foremost, living in finance world. Then I’m living in sales world. Then I’m living in marketing world. And so having that understanding, you know, my CEO can watch my CFO and I have a conversation and he knows we’re speaking the same language. There’s no confusion around that.
But I think one, not understanding the business. Two, not being real with yourself about the impact of marketing. I’ve done some campaigns in the past that looked fantastic that had no impact on the business. I’ve also done things almost in silence that have grown huge ARR. And so there’s just this notion of sort of celebrating. And then the last thing again is every company thinks what they want for marketing is different and what they need is different.
Finn Thormeier: Right. So if the CMO role is not dead, what is the future of it? How is it changing? I mean, you’ve been a marketing leader for a long time. Now at Zapier, how is the skill set changing? How is the role changing? Talk to me about the future of how you see it evolving.
Dan Slagen: Yeah, it’s a really good question. Paul Roetzer, who runs SmarterX and the MAICON Conference, has done some really, really good work around sort of how AI is impacting marketing. And he had a post sort of this week talking about the Astra release and just, you know, how his level of optimism got a little bit lower when this came out because he’s just not sure how much people are going to be able to adopt this stuff.
First and foremost, what I try and do is I think you have to call a shock and awe moment with your people. And I think you have to do a little bit of fear-based leadership, which is not my style at all. I hate it. But every once in a while, you got to wake people up and say, hey, if you don’t learn this technology, I’m genuinely not sure what the future holds for you. And I’m also not sure what the future holds for me. So... Full stop. Let’s start there.
The first thing I do is make sure anyone coming through the front door to join the marketing team now is at a level of AI that I’m comfortable with, and it’s got to be on the cutting edge. So we have an AI fluency bar that we hold people to in the interview process, and we’re pretty nuts about it. So you have to stop the bleeding of people coming into your organization that might not be at the bar that you’re trying to build into.
Two is you gotta get in with your people. And like I said, it’s gotta be a shock and awe moment. So earlier this year, You really started to see non-developers using traditional developer tools for go to market. Claude Code, Cursor, Codex. You could see where it was going quickly. And I felt like the Zapier marketing team could potentially be at risk of falling off from being the most innovative, you know, AI thinking marketing team. We were at risk of falling down at least like one rung on the ladder.
So I called a red alert, got the whole team together, and I essentially brought someone in to do a presentation and show people how they thought about the future of AI marketing, how they built their digital twin, how they were building agents, everything, the whole deal. And it was pretty technical. We were almost in a terminal the whole time. And it was a 45-minute presentation.
After that, I asked the marketing team, who’s feeling overwhelmed right now? Everyone’s hand went up. And I said, yeah, you guys didn’t know that this person existed when you woke up this morning. Like you don’t even know that you’re interviewing against this person for a future role at Zapier or for a future role that you want outside of Zapier.
You’re going to have three weeks to go learn any coding tool that you want. Cursor, Claude Code, Codex, whatever it might be. After that, we’re going to do a build-a-thon. And what I told them was, I know you’re feeling overwhelmed right now, but for the next couple weeks, I’m going to give you access to five coaches. We had five power users on the marketing team. And you can ask them any question you want. Spend as much time with them as you want. I’m not going to know who’s asking what question, what question is being asked. I have no idea. But in three weeks, you’ve got to show up ready to build.
The team did that. I think we were like 95% ready to go. The team heard me loud and clear. Then we did a two-week build-a-thon and everyone built something. At the most basic level, someone built an interactive dashboard showing leads or impressions or whatever. Other end of that, someone built a fully functioning app that our events team is using to run our ZapConnect conference, which happens later this month. It’s our big annual flagship conference. We’re now using a homegrown app to manage 100 plus speakers and the majority of the conference. Really, really cool.
It then broke the team up into essentially three tiers. Tier one, you got the most basic builders. They’re doing the dashboards. Tier two, people starting to build systems and roles. And then tier three, you got full functions and almost companies being built within the marketing team. Now I can go to each of those tiers and give them different business challenges that I would like them to solve, and each tier I’m giving them challenges that are at their level, tier one, tier two, tier three, versus just saying the whole marketing team try and get better.
First, stop the bleeding. Make sure your hiring’s in a much better place. Two, you got to get in the weeds and build with your people. You know, when I did the build-a-thon, I got about 60 plus projects that came in. Everyone recorded a two-minute Loom. I watched every single one. I gave handwritten notes to every single person. We gave awards. I also built my own thing. And that was a really, really big moment for the team. And now they are on just a different building trajectory.
So you asked about what are the skills I’m looking for? Resilience, adaptable, curious, willing to learn, willing to change. I’m not going to sit here and say that 100% of the people on the marketing team loved what I was doing. Not everyone stayed, right? We also said, hey, you might not like this new way of working. This might not be for you. The way I’m working now is so different than it was five or 10 years from now. Fully understandable if you don’t like this. But this is where we’re going. And you’re either on the ride or you’re off the ride. And it’s okay if you’re off the ride. But we have to be honest about it. So those are kind of the big, big cultural shifts that we made this year.
Finn Thormeier: How do you... I guess you just enforce it. I’m just thinking, I’m sure there’s a lot of resistance that a lot of marketing leaders will face if they will try to do this. I guess you need to get the buy-in of your CEO beforehand. How do you recommend them to think through and deal with the resistance?
Dan Slagen: It’s a good question. A couple of years ago, I would have told you top-down is the most important thing. At this point, what CEO doesn’t? We are extremely fortunate at Zapier. We have access to every single AI tool in the world. There is no So Zapier is like an AI playground where you can come in and use any tool you want. And it’s very unique, but it’s a really, really great place to be. But as long as you can give your people access to the most interesting tools that they need, that would be a good step one.
You know, two, we try and be as transparent of a company as possible. And for those that follow Zapier, you know, you’ll see us posting as much stuff about the company and what we’re seeing in benchmarks, but we also do that internally. So when I call this Buildathon, it is in the public marketing channel that anyone in the company has access to. Everyone’s project is in there. If you didn’t do a project, you’re going to be on the side of the line that says no project. And so there’s a little bit of FOMO and, you know, competitiveness that we’re driving there.
And like I said, you know, not everyone stayed and that’s okay. But the thing that I needed to solve for was I don’t want anyone in the middle. That’s the worst part where you have those people that are just kind of doing what they can to stay by, but they’re probably pretty toxic for the culture. In or out. That’s just a decision we’ve made. It’s also more fair to your A players who want those types of other peers to build and get inspired with.
So working in public is a huge, huge part of it. You know, Zapier, we go so crazy as to, we do most of our communication on Slack. And so every month we have a Slack transparency leaderboard that gets published in front of the whole company and it’s just for the executives but it shows the company what percentage of Slacks an executive did public or private that month. The reason we do it is one culturally it de-risks you from things hiding or toxic stuff or drama but on the more positive side when you’re trying to build this AI brain and institutional AI you need to have Your conversations in public so the AI can actually see it and pull from it and move it forward.
And so when I joined the company, I was about 50% public, 50% private. I’d never really measured myself. That’s just sort of where I netted out. And then I made a big, big push to change that. I’m now 98% public, 2% private each month.
Finn Thormeier: The number one exec.
Dan Slagen: They say I’m number two in the company, although we have yet to meet number one.
Finn Thormeier: You need to know who’s number one.
Dan Slagen: I know. They didn’t want to reveal themselves last month. We’ll see. But yes, by far and large, number one for how much I Slack.
The other thing we do is we built a marketing OS and marketing brain. And so every morning I ask the marketing team, this is the first thing you need to look at. It looks like an interactive dashboard, but it shows you What happened yesterday? What’s happening today? What’s happening tomorrow within marketing? What you need to care about? How are we doing against goals? And that was a change for the team. I said, you need to look at this every single morning because once you start to understand what’s going on within the business, now we can start to run agentically off this in a much more exciting way.
I have tracking in place so I know who’s looking at it and who’s not. And so it’s very easy. Again, it’s very easy for me to tell who’s paying attention and who’s not. I’m not here to Shame anyone. We’re not here to call people out, but we are here to enforce a behavioral change and you’ve got to be pretty strict on it.
Finn Thormeier: Do you, I mean, I love all of this. Do you think you’re losing something by almost, I mean, you talked about the kind of interview questions and the AI fluency score. Do you think you’re losing anything by forcing every marketer to be deeply AI native?
One of my favorite interviews I did with Don Jeter, the CMO at Torq, and I mean, They’re obviously crushing, incredible brand, very experiential. They do a lot of field marketing. And I asked him about kind of AI and he’s like, I don’t do a lot. You know, an AI, he himself, and they also have a rule that you’re not allowed to use AI to create any kind of design that’s customer facing, anything that the world sees. And they’re obviously crushing because they focus on the brand, the storytelling, the experience. Does every single marketer have to be AI native?
Dan Slagen: It’s an excellent question. I think... I’m gonna say yes. I’m gonna say yes on that one. I think it’s easy to say no. The safe answer is to tell you no.
Finn Thormeier: Yeah, yeah.
Dan Slagen: I think... And look, Zapier... We do a ton of in-person events. It’s extraordinary. We are pretty much doing an in-person event every single week somewhere in the world. I was in New York last week with 20 or 30 major companies that you’ve heard of just in a room for five or six hours just talking AI transformation. What’s going on? We love the in-person stuff. We do these amazing events called Outposts where we get people to We had them at Zion National Park. We’re at a castle in the UK this week. We do awesome stuff because we believe in communities so much.
We also have tons of checks on what actually goes out to a customer. I personally don’t write with AI, especially for internal comms. I actually think that’s a superpower now that I...
That said, the way that our company works and the amount that we can speed up when these systems are in place is so important to us that I want people that are at least curious enough to go explore that. Now, I’m willing to hire someone that’s not Currently at the cutting edge of AI. That’s fine. And we’ve done it. What we look for is what’s the thing that’s going to be your hockey stick moment to really, really make you understand how to use systems. And I think the AI thing, the terminology gets overused. It’s like, would anyone on the team want a couple more headcount to help them do things? Of course they would.
So I have someone on the team that when we interviewed, They weren’t great on AI, but man, they were curious. They were so creative. The way they thought about it was interesting. And they were like, yeah, I think I’m getting to the unlock moment. And I felt like if we can bring you into Zapier, I can very quickly get you that unlock moment. And we did. And now that person is doing so much great stuff because they are creative first. But they have access now to essentially a much bigger team and resources and output that they can get stuff done with. And they think about what the customer is going to see first, not how much the AI can generate. And so I think that’s a very important distinction.
Now I’m speaking specifically for Zapier. There’s certainly, I can imagine, other... Other companies, other industries where maybe it’s not as important, but for us it’s something that we’re currently not really willing to bend on.
The last thing I’ll say is I think you’ve got to understand something to be able to ignore it and to be able to ignore certain parts of it or speak out against what parts you think are really dangerous. Unless you really spend the time getting in the weeds of what can be done, what should be done, Then how do you really know? You’re just reading headlines and you’re getting, you know, you’re kind of being led by clickbait to some degree. So I want my team to understand the pros and cons, the inspiring, the ethical concerns, all that thing. I want them to know that and master it so then we can make informed decisions.
Finn Thormeier: I’ll have a follow-up question on that, but before that, I’m thinking on the spot here, and maybe this is a stupid question, but when we’re talking about the future of the CMO role, it definitely seems like, at least from your point of view, systems thinking will be more important because you will be working more with AI, and for that, I think systems thinking is very important.
I don’t know who I talked to. I think it was Sydney Sloan, but there’s basically three tracks towards the CMO role. There’s the product marketing track, the brand track, and then the demand gen track. And I think she said most come from the product marketing track. Will that change where maybe because of that people who have more of a demand gen background, data background, engineering background, sales engineering background, where there’s a little bit more emphasis on this kind of systems thinking, will have an easier time thriving in that new world?
Dan Slagen: To some degree, yes, but Sometimes that mindset can also stop you from doing things that don’t scale. And that continues to be an important thing. There are parts of our in-person events motions that don’t make sense from a systems standpoint. They just don’t. But I fully believe in them and I would do it. There’s parts of our brand work that doesn’t quite make sense from a systems mindset. But we do it and we think it’s a good idea. So I think the problem with systems mindset people is sometimes they’re not as flexible as you need them to be.
This is where the role gets really, really hard. You know, again, I was extremely fortunate. I think the way I was raised, like I go back to like my parents, my mother was a nurse and my father was a psychologist. It’s the perfect combination of watching two people work. One is like helping people like with their heart and the other person helping people with their brain. You could see both like the left side and the right side working and you could try and find the perfect mix.
And so if you’re only systems thinking, you might not be able to go deep enough on one part. You might not be able to go deep enough on the brand and the emotional part. Or if you’re overly thinking on that you might not be able to connect it back to the demand or the product and the positioning. So again it kind of goes back to these people that can understand what a company needs and try and harmonize what the right balance of each three might be. So it is systems thinking but it’s the ability to Work in a flexible system as opposed to a rigid system. And I do see a lot of systems thinkers be too rigid. And that’s when I think you usually see marketing really fall flat.
Finn Thormeier: To come back to the previous topic, do you guys have any hard rules or published guardrails around how you allow your marketing org to use AI? What’s allowed? What’s not allowed? I believe Clay recently published their AI writing policy. Do you guys have anything in place? And if not, what’s your personal stance on where it’s useful and where you shouldn’t?
Dan Slagen: Yeah, yeah, yeah. You got internal, external. I’ll say for internal, again, we’re almost 800 people on Slack as our primary form of communication. So there’s a lot of comms. We started to notice it earlier this year. It’s like I saw my first Harry Potter wizard fight, essentially, at Zapier. This is a while ago. But someone had their AI create a doc, and they fired it over into the channel. And the other person clearly didn’t read it. They had their agent read it, and they fired their response back. They did this back and forth three or four times. And at some point, you can tell, guys, stop. Both of you. Turn it off, go read the docs, and we’ll come back and we’ll discuss this in person. But you could just see that stuff was starting to happen. And it wasn’t malicious behavior. It’s just there’s so much going on with more things being created. You’re trying to keep up, and people are just, they think something’s good enough, and they’re doing their best there. So you can start to see it.
We did implement an internal policy. It was really just rooted in respect. And this was a while ago. But it would be things like, it started with, You need to be honest with people when you send something, whether or not you read it and who wrote it. Like, hey, because there’s times when I’ve said, hey, I took what was going on. I just tossed in this prompt here. Let’s just, I don’t even know what’s in it. Let’s just start working on it together, brainstorm. Great. Then the person or the people I send, they know where I’m coming from. In my role, if I send something, people are probably going to read it or feel compelled to read it. So out of respect for them, I need to let them know, okay, I actually took time to write this. This is real. I need you on it. Or, hey, this is just a thing I made. Let’s just, I don’t know, we’ll jam on it later. So that was good to see.
Two, we look at, for external, we look at any comms that would ever go out. And there’s a lengthy testing period. And we are more than happy to keep humans writing when and where. It makes sense. Because I think the second AI takes the excitement out is really when you start to see, I think, diminishing returns.
So yes, internal, external policies, we’re pretty rigid about it. I think we’re, on the exec team, I’ll also say, I think we’re We are perfectly honest with each other and we have no problem shaming each other when someone clearly, I’ve been shamed before, we all have. But just being honest about that right from the start was the thing that really, really quickly improved the behavior.
Finn Thormeier: Yeah, especially because AI likes to go for the 12 page report rather than the quick and concise feedback.
Dan Slagen: 12 page report, I also think there’s times when we’ll embark on A step function change in the way we operate as a team or a company and we’ll acknowledge the fact that it’s going to be really messy. And we’re looking for feedback and we say, if you ever need something, you know, just raise your hand and let’s have a real discussion about it.
But, you know, for instance, we do a monthly check of the business where we look at all the numbers, all the stuff that happens and we kind of have a mini all hands. The department leaders would sort of write their narrative and they’d get their numbers and they’d kind of all present. We moved that to an agentic motion where we just have the whole report written, sent ahead of time, and we show up and talk.
We were very honest with the company that, hey, the first time we do this, it might not work. The data might be wrong. The narrative might be wrong. But we were honest about the vision we had and where we wanted to go and why. And so if you can get people bought in as to why we’re doing this and they feel bought in, inspired, and most importantly, safe, then they’re more enthusiastic about it and they’re more willing to help improve it versus just throw stones.
Finn Thormeier: I’ve seen some of your recent posts. I’d like you to explain and or expand on a few terms. Let’s start with automation debt and LLM jails.
Dan Slagen: Sounds good. The LLM jail is one that I find happening quite a bit at the enterprise level. One of the reasons that we love Zapier and our customers love Zapier is because it gives you this notion of interoperability where, you know, one, different models are good at different things. We see that. We have our automation benchmarks where you can see certain models spike And so you want to be able to make sure that you can actually pick the right model and the right LLM for the thing that you’re trying to do.
The other thing is that you don’t feel lock-in if something happens that you don’t like, if they make an announcement that you don’t like, if they start to make an announcement that you don’t like. Make data decisions that you don’t like or you’re not comfortable with. And the other thing is that you are not bound to their rate of acceleration. You’re bound to your own rate of acceleration and you’re more in the owner’s seat there. So I think it’s pretty rare for me to meet an enterprise that says we’re going all in on this one. This notion of interoperability is pretty clear there. So that’s kind of what we meant by automation jail. You want to make sure that you’re LLM jail. You want to make sure that you’re not Not able to do things because of the system that you’ve put in place.
You know, automation depth, you know, there we really start to look at what gets automated and essentially like how deep we’re able to go. So for instance, you know, we all started by automating little things like, let’s say our communications. I now have it automated where if an email comes in, it goes into a folder, it drafts up my reply, but it doesn’t respond yet. So it’s not fully end-to-end. The depth isn’t fully realized. That will happen when I feel so comfortable with my system that I get an email in, it can craft up a reply, and it sends without me even looking at it. Now, when will that happen? This year? Next year? Never? I don’t know. It’s just kind of dependent. That’s where sort of the judgment call is. Do you want to take your hands fully off the wheel, or is that something where you do want to stay involved at the human level?
So I think the depth, one... It relies on the technology being at a place where we feel comfortable, but it also relies on the place where we have to make our own calls as humans as to what we want to still be in the loop on or fully own or turn over to AI.
I think, you know, I was on a panel last week at a conference and they’re asking about the predictions for next year. And my biggest prediction a year from now is that we’re going to see people pushing back on AI more versus AI pushing on people. Like right now, AI is pushing on all of us in the tech world and in marketing. It’s like if you aren’t up to speed on the latest model and the latest thing, it’s as if you’re going to be viewed upon as obsolete. And there’s a lot of pressure being put on you by Just the marketing campaigns coming out from the LLMs. It is rare to see marketing campaigns taken with as much... It’s as if there’s like whatever they put out is destiny and the world is responding to that. That’s what it feels like sometimes. Which we know is not the case.
And I think you’re now starting to hear and see, especially in the in-person communities, you’re starting to see the uprising. And you’re starting to see people pushing back on it and saying, you know what? Wait a minute. I don’t want to do that. I don’t think that’s the right thing to do. And it’s good to see because I think people have been getting pushed around for the last two years with this tech push. And it’s time for us to start pushing back.
Finn Thormeier: Yeah, and I think part of that automation debt was also that you guys figured out that for a lot of workflows, you don’t need any AI. And I believe in that post, you wrote about only 24% of kind of the workflows, the things that you want to automate, the things that you build in, let’s say Zapier, actually need AI at any given step, and the rest you can just do without AI.
Dan Slagen: It’s the interesting thing. We call this fluid determinism. And so one of the things that Zapier is so good at is deterministic workflows. And it’s really what the company has scaled on in a lot of ways. And now as we’ve seen so many of these agents get built, ultimately what they are is fancy workflows. And the reason that token cost is so much and they’re spinning out of control is because they’re using AI for everything where you don’t really need it. For the most part, the workflow needs to do the same thing every single time. And it needs the ability to call AI when it needs to, but not run the whole thing like that.
And so that’s where we’ve been able to improve efficiency, drastically improve costs, reduce risk. And that’s the thing that people are really starting to warm up to. And that’s one thing that’s unique to Zapier. So yeah, that’s one part where I expect to see Big area of growth and almost like a resurgence of nostalgia and almost like going back to the original reason that Zapier existed. But in this new chapter of AI, when people are starting to come back to their senses and say, OK, we need to do this in a sustainable way.
Finn Thormeier: Right. Yeah. The other term that I saw that I loved that I want you to explain is generation loss.
Dan Slagen: Yeah, this was a really interesting one. So, you know, for those of you that maybe remember old VHS tapes, like movies, people used to make copies of them. Anything you make a copy of, you know, every time you make a copy of something, the quality gets worse and worse and worse. And back in the day, it was something like if you made nine copies of the same VHS tape, by the ninth version, it was completely blurry and fuzzy. And you didn’t even know what you were looking at.
And we see this in marketing, we see this in other departments, but you start with an idea or a brief, and it goes through so many different iterations of approval processes or changes that by the time it goes live, it doesn’t even look like the idea that you had initially.
Finn Thormeier: And it took me a little too long, but just so people can see on the screen now what that looks like, what you’re talking about, the first generation of a VHS and then... Third generation, fifth generation, and by the time you do the ninth copy, you get a bunch of ghosts.
Dan Slagen: Yeah. And so... As we started to build out our marketing brain and our marketing OS, we were really worried about generational loss because what we wanted was the most honest version of opportunity for Zapier to be the thing that goes live.
And so every month we have a meeting that includes the CEO and head of sales and our product marketing leaders. And we look at the last 30 days in everything, what happened in the world, what happened inside of Zapier, outside of Zapier with competitors. What deals that went well? What deals that did not go so well? What campaigns worked? What didn’t? And then we synthesize all that, and we think about the next 30 days. And we say, how much needs to change in our go-to-market? Do we have new messaging we need to test? Did something happen that we need to go jump on? Now sometimes, nothing really changes, and the next 30 days look very similar to the last 30 days. Other times, it’s time for a big change. Starts new motions.
The output of that meeting, you can imagine getting filtered as it goes from team to team to team and finally goes live. Where you just want the most honest version of the next 30 days will be this, go. And so as we took that and mirrored it with the marketing brain and the marketing OS, what we were trying to solve for was generational loss and not having that. We want the most honest version of the outcome of that meeting to go directly into the marketing brain and OS and immediately start to power our go-to-market. The content we’re going to create, the ads we’re going to run, the emails we’re going to send, the decks we’re going to show in the next sales meeting. And that’s really what we were trying to solve for there.
Finn Thormeier: Where does your marketing OS live?
Dan Slagen: Our marketing OS, we built it on Zapier. And so essentially people log into Zapier every morning and they go through it.
Finn Thormeier: But it’s like, it’s an interactive tool that you kind of build into the platform or?
Dan Slagen: It’s an interactive, it looks, to most people, it looks like an interactive dashboard.
Finn Thormeier: Okay. And I believe part of that is also, I don’t know if this is like a separate thing, but one thing I saw that you guys built Synthetic personas, but they’re built on actual sales conversations and product, how people act, behave inside of the product that then your team can ask and prompt to kind of get feedback on marketing copy and stuff like that.
Dan Slagen: Yeah, this one, we do it. I don’t think we’re, we’re not unique on this one. And it’s helpful, but it’s not at a level where I would replace real motions. But yes, the idea being is that you can build synthetic audiences to get a sense of what’s going on.
I think where it’s been the most helpful is actually with internal... Things where, you know, if the team knows they’re gonna present something to the CEO, they present it to a synthetic CEO first, or like AI CEO first, trained on all the things that our CEO is currently thinking about, talking about, posting about on Slack, pushing team for, and you can get a sense of, hey, If I give this to Wade, how is he likely going to respond? And so that’s been very helpful for the team. Before you go to anyone at the company, but definitely the C-level or CEO, make sure you’ve run this through. These are the expected reactions. You might want to think about doing this or that. That’s been a good kind of check step for people.
Finn Thormeier: Which is, again, that comes back to the transparency score that you have. Because if you, as the CMO, write 98% of your messages in the public account, Slack channels, someone can pull out of all of that and say, you know, look at all the things that Dan has been discussing and prioritizing and then cross compare that to what I’m trying to present here and give me a sense of if this fits anywhere to where Dan’s mind seems to be at right now in the last 30 days.
Dan Slagen: Exactly. And I will say the thing that the way that that works and the reason that works is because my CEO and I have trust. Because I’m willing to have conversations in front of the whole company. I am wrong a lot of times. I have ideas in public Slack channels where the CEO or someone else will say, that’s a horrible idea, that’s wrong, no. It’s okay. We’re all here. We’re learning together. We’re building in public. That’s part of being transparent is getting more comfortable with just being honest about the fact that people will be wrong sometimes and it’s okay to correct them in public and we respect each other and we trust each other.
But if I didn’t have that kind of trust with the CEO, I’d be having those conversations in private because I don’t want anyone to see this because what if I’m wildly off about, okay, does this new product launch mean XYZ for the industry or am I wrong? I can have those conversations in public, but it all boils down to trust.
Finn Thormeier: Now, last question. Obviously, AI transformation inside of your org starts with the head of the org, with the CMO. There’s so much pressure. There’s so much FOMO. There’s burnout. If a CMO is listening to this, they acknowledge that they are behind, that they need to do more, both personally as well as for their org. And they want to spend the next weekend getting ahead. Where would you point them to? What should they do? What should they read? Which specific resources should they get into? If they had, let’s say five to 10 hours to like get kickstarted, what’s that next thing?
Dan Slagen: The thing I would do is, marketers are notorious for measuring everything. We have a dashboard, a chart, a spreadsheet for everything. AI, I have not seen as many marketers think about how to measure it.
What I would do, especially if you’re leading the team, is I would go directly to your CEO and CFO and get a real agreement and a sense of what are the things that we want to measure with AI? Do we want to look at how fast campaigns go to market or how fast we get value from things we build with AI? Our success rate of pilots, The AI fluency of our people. It’s going to be different for every single company and every single CEO. The easy ones are, okay, token usage and ROI. Fine, but what does that actually mean? Boil it down to specific metrics that you care about and build a dashboard that’s connected to your system and report on it every single week and every single month.
If you don’t have the alignment with your CEO and CFO and then you don’t put that into a consistent structure that you look at every day, your mind is just going to spin and rot around the what ifs, I’m so behind, what do they care about? You’re never going to know. And then if you can keep that updated with your CEO and CFO and say, hey, the things we measured last month were this. Are we still measuring these things? Do we still think this is the most important thing? Maybe you have a new idea. Maybe they have a new idea. But work off a numerical dashboard that everyone’s in agreement on to the best of your ability. That’s a thing that for me has allowed a lot of structure and the ability to ignore a lot of noise.
Finn Thormeier: I love that. Cool. Dan, this was amazing. If people want to learn more about you or Zapier, I’ll link your LinkedIn and the website in the show notes. Thank you so much for taking the time. And that’s it.
Dan Slagen: All right. Thank you.
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