Explore every episode of the podcast The GTMnow Podcast
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Title
Pub. Date
Duration
VC 2: How Cassie Young Picks Winners Before They Even Leave Their Jobs
15 Dec 2025
01:09:20
Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage firm in New York backing category-defining SaaS, fintech, and vertical software companies. Before investing, she spent 15 years as a GTM operator, serving as Chief Revenue Officer at Sailthru and later Chief Customer & Commercial Officer at Marigold (Campaign Monitor, Sailthru, and other martech brands), where she scaled global sales, marketing, and customer success organizations.
Today, Cassie leads investments while also running Primaryās Impact program, giving founders access to a 30-person team across talent, GTM, and strategic finance, and she continues to teach operators through programs like Pavilion and Dukeās Innovation & Entrepreneurship board.
Discussed in this episode:
How Cassie āaccidentallyā became a VC after 15 years in GTM leadership.
The career advice Bill Gurley gave her that changed her trajectory.
Why Primary refuses to say āplatformā and instead built a 30-person Impact team.
How she actually sources pre-seed/seed founders before they leave their jobs.
Primaryās 5-part Founder Outcomes Framework (vision, talent, JDCE, and more).
The difference between real traction vs. āhappy earsā and fake design partners.
Why sheās picky on GTM/AI tools and looks for step-change, not incremental gains.
How operators can actually break into VC (hint: itās all about doing the work).
Episode highlights
00:35 ā Clay, usage-based pricing, and the $100M ARR rocketship
09:10 ā The real story on AISDR: where AI reps actually work (and where they really donāt)
14:02 ā Inside āThe Gross Retention Apocalypseā and why AI experimental budgets are a ticking time bomb
22:46 ā How Cassie accidentally became a VC and the Bill Gurley advice that changed her career path
27:17 ā Why Primary hates the word āplatformā and how Cassie built a 30-person Impact team for founders
36:10 ā Cassie breaks down her 5-part founder outcomes framework (including ājaw-dropping customer experienceā)
46:01 ā Avoiding āhappy earsā: how founders should really use design partners and MedPick-style rigor
57:48 ā Time to value as the new north star and why nailing a tight wedge beats peanut-buttering features
1:01:29 ā So you want to be a VC: Cassieās playbook for operators to break into venture (without delusion)
Brought to you by: AngelList
How did we build the GTMfund back office? Easy!
We leveraged AngelListās Rolling Fund product for Fund I, which was the perfect vehicle to scale up GTMfund in its first iteration. This structure allowed us to build our network, and add revenue leaders while we raised and deployed capital simultaneously, which was crucial for getting early points on the board and building relationships with founders.
For Fund II, we transitioned to a traditional closed-end fund structure through AngelList. This time with institutional investor support. This model allowed us to be more intentional about our portfolio construction. We worked closely with the AngelList team throughout this process, and they were incredible ā always there to support us and our LPs every step of the way.
If youāre raising a fund or are looking to migrate your fund, we highly recommend you check them out. You can do so at www.angellist.com/gtmfund.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Why Old Playbooks Are Breaking and How AI Assisted GTM Actually Works | Dave Boyce
10 Dec 2025
00:35:49
Dave Boyce is a go-to-marketāfocused technology executive, author of Freemium, and longtime SaaS operator and board member. Over two decades leading and advising B2B companies, heās helped founders navigate the shift from sales-led to product-led, from gut-driven to instrumented, and now from manual GTM to AI-assisted systems. Today, Dave teaches revenue architecture and PLG through Winning by Designās Growth Institute, works with leadership teams on Bow Tieābased growth models, and is all-in on how AI will reshape GTM as a true engineered system.
Discussed in this episode
Why classic sales & marketing playbooks havenāt caught up to how modern buyers actually buy.
How the Bowtie model exposes the real levers of growth that funnels hide.
Why PLG-style thinking is now essential even for sales-led and enterprise motions.
The 3 first principles of freemium: empathy, generosity, and metrics.
Where AI can reliably outperform humans across the customer journey, and where it absolutely shouldnāt.
How to design hybrid human + AI workflows using a clear data model, not vibes.
What RevOps should own in a modern revenue architecture (and why it canāt just serve the CRO narrative).
Hard-earned founder lessons from Fundly on reinvention, calling bets early, and letting go of old branches.
Episode highlights
00:00 ā GTM is still running 20-year-old playbooks
01:29 ā āSales, marketing, CSā¦ the last unengineered engineā
03:20 ā The myth of ājust add more headsā
05:50 ā The Fundly story: reinvention, too late
08:30 ā Why Freemium had to be written
11:01 ā Three first principles of freemium
15:25 ā Mapping AI across the entire customer journey
19:29 ā āAutomate the predictable, humanize the exceptionalā
25:18 ā What the Bowtie exposes that funnels hide
27:25 ā Building a āminimum viable Bowtie
This episode is brought to you by our sponsor: ZoomInfo
ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.
By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.
Itās trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 166: SEO ā AEO: The Next Big Shift in How People Discover Your Product
07 Oct 2025
00:35:29
Guy Yalif is Chief Evangelist at Webflow and a veteran B2B marketing leader with 20+ years across Twitter, Yahoo, BrightRoll, and as co-founder/CEO of Intellimize (acquired by Webflow). He champions AI-driven optimization for sites and content, bringing a rare blend of aerospace-engineer rigor and operator experience from four successful exits to help teams win the shift from SEO to AEO.
Discussed in this episode
Why AEO is an evolution of SEO (and what truly changes)
The shift from keywords to āclusters of questionsā as the new topic model
10:11 ā Case study: Add ~6 FAQs + inline schema to product pages ā half of new citations came from 6 pages; +24% organic in 2 weeks.
15:23 ā If you only do two things: (1) answer questions comprehensively, (2) add schema metadata.
21:46 ā Webflow data: AI-search traffic converts ~6x better than non-branded organic; unbranded share grew from 0% ā 42% in a year.
24:02 ā How buyers actually use LLMs in-flow; why your website still matters (to humans and machines).
29:58 ā The learning curve is back: why AEO is resetting the playing field and rewarding curiosity.
This episode is brought to you by our sponsor:
ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.
By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth.
With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.
Itās trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 77: Building a Top-Down Sales Strategy While Maintaining a Bottoms-Up Approach with Leena Joshi
17 Jan 2024
00:40:08
Leena Joshi is Co-Founder & CEO of CloseFactor, a GTM strategy and execution platform that helps enterprise tech hone in on the exact right prospective customers and accelerates their conversion by helping your sales and marketing teams be contextually relevant to them.Ā
She has led GTM teams at high scale B2B companies such as Splunk, VMware, Redis and has a unique perspective on the convergence of sales and marketing into an efficient, high performing GTM organization.
What You Will Learn:
The differences in go-to-market motions across different stages of organizations.Ā
The theme for the year is go-to-market convergence.
Leena's experience finding the right go-to-market motion at CloseFactor.Ā
Creating an outbound motion through inbound tracking.Ā
How selling value is a tactic that is working for CloseFactor.
Highlights: (14:08) Maintaining focus on the ICP in the early days, including turning revenue down.
(23:13) The importance of curiosity and a beginner's mindset.
(25:38) Finding a leader who has your back.
(28:19) Building a top-down sales strategy while maintaining a bottoms-up approach.
(32:28) The importance of hiring the right salespeople and balancing long-term and short-term thinking in sales.
(32:56) One thing revenue leaders believe to be true that Leena thinks is bull$***.
(36:03) One thing that is working for Leena in go-to-market right now.
Sponsor: Common Room enables you to turn any buyer activity into pipeline. It ingests all of your product usage data, intent data, social activity, community conversations, and CRM insights to automatically surface high-intent leads and timely, relevant context so your sales reps can convert more customers and hit revenue targets faster. You can try it for free today, or book a demo to go deeper at www.commonroom.io.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 76: 0 to $100M: You Need to Reinvent Yourself at Every Phase with Mike Molinet
09 Jan 2024
00:48:31
Mike Molinet is the Co-Founder of Branch (branch.io), where he was COO and President, leading the company to $100M in ARR. He oversaw all things GTM there, including G&A and Product. Now, he is the Co-Founder of Thena (thena.ai), a seed-stage startup backed by Lightspeed and First Round, where they're helping companies service and engage their customers in Slack. After taking Branch to $100M, he's doing it all over again, this time with a lot of learnings.
What You Will Learn:
The different micro-phases within each stage of growth (0-1M ARR, 1-10M ARR, etc) and how leaders need to level up and adapt through each one.
Hiring the right roles at the right time - AES vs leaders.
Maintaining an open and learning mindset even with growing success.
Relinquishing control as you scale while still providing oversight.
Balancing product requests from large customers vs your overall roadmap.
Highlights: (7:21) How your success comes from the people you hire and retain.Ā
(9:10) Evolving through micro phases through rapid growth.Ā
(15:50) Threading the needle on when to ask design partners for money in the early 0 to $1M stage.Ā
(23:11) Heuristic framework of evaluation for taking on bespoke build requests.Ā
(31:29) How hiring great people makes you feel excited to relinquish control.
(43:20) One thing revenue leaders believe to be true that Mike thinks is bull$***.
Sponsor: Common Room enables you to turn any buyer activity into pipeline. It ingests all of your product usage data, intent data, social activity, community conversations, and CRM insights to automatically surface high-intent leads and timely, relevant context so your sales reps can convert more customers and hit revenue targets faster. You can try it for free today, or book a demo to go deeper at www.commonroom.io.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 75: The AI Evolution: Cross the Chasm of First to Future Iterations with Gongās EVP Eran Aloni
02 Jan 2024
00:39:47
Eran Aloni is the Executive Vice President of Product Strategy and Ecosystem at Gong. Ā He has been a leader at Gong for eight years, previously holding titles of Chief Customer Officer and Chief Operating Officer.Ā
What You Will Learn:
Eran's career advice to younger go-to-market professionals.Ā
Two stages of AI advancements and which is more valuable.Ā
The role that data sets have in AI progressions.Ā
How to continuously solicit team feedback to level up as a leader.Ā
Highlights: (6:55) How AI solutions are still only scratching the surface in terms of driving deep, strategic value for customers.
(10:00) The competitive advantage players have with their access to rich, proprietary data sets to train AI.Ā
(18:12) Eran's biggest personal surprise from growing with Gong has been constantly challenging himself to develop new skills as the company scales.
(23:15) A story about early feedback Eran received as a young leader and how it shaped his future leadership.
(28:19) Why having core operating principles permeate through all levels of an organization builds trust.
(34:03) One thing revenue leaders believe to be true that Eran thinks is bull$***.
(37:22) One thing that is working for Eran in go-to-market right now.Ā
Sponsor: Common Room enables you to turn any buyer activity into pipeline. It ingests all of your product usage data, intent data, social activity, community conversations, and CRM insights to automatically surface high-intent leads and timely, relevant context so your sales reps can convert more customers and hit revenue targets faster. You can try it for free today, or book a demo to go deeper at www.commonroom.io.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 74: It's Bull$***. 50+ GTM Leaders Share Which Widely Held Beliefs They Disagree With
26 Dec 2023
00:31:39
To cap off the year, we have another special episode. Be warned: It's a spicy one!Ā
At the end of every weekly podcast episode, host Scott Barker asks guests the same two questions. Last week, you heard the compilation of guest responses to the first question. This week, youāll hear the compilation of their responses to the second question:
What is one widely held belief that revenue leaders have that you think is bull$*** or no longer serving us?
What You Will Learn:
The perspectives of go-to-market leaders that are counter to many others.Ā
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 73: 50+ GTM Leaders on Whatās Working and Career Learnings
20 Dec 2023
00:36:29
We have a very special episode this week.Ā
At the end of every weekly podcast episode, host Scott Barker asks guests the same two questions.Ā
Today, youāll hear the compilation of their responses to one of the questions.Ā
Spoiler alert: youāll get to tune into the other question next week, which is slightly spicier as itās full of hot takes.Ā
What You Will Learn:
Whatās working and learnings for these go-to-market leaders.Ā
The questions that 50+ go-to-market leaders answer in this episode:Ā
Whatās one tactic or strategy thatās working for you or the companies that youāre serving?
If you can sum up your learnings in a few sentences, whether itās something discussed on the podcast or general learnings you would want to impart in folks, what would those sentences be?
Highlights: (2:36) The first question above.Ā
(25:50) The adaptation to the question, which is question #2 above.
Sponsor: Todayās episode is sponsored by Demandbase, Demandbase helps B2B companies hit their revenue goals using fewer resources. How? By using the power of AI to identify and engage the accounts and buying groups most likely to purchase. They combine your sales and marketing data with our validated B2B data and AI to create Account Intelligence that informs every step of your buyerās journey. They deliver accurate company, contact, technographic, engagement, and intent data right where you work every day ā CRM, collaboration tools, browsers, and more. Start spotting opportunities earlier and orchestrate smarter sales and marketing motions with Demandbase. See this live in action: https://www.demandbase.com/product-tour/sales-intelligence/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 72: Avoiding Agency and Fractional Roulette: How to Pick the Right Partner with Daniel Weiner
12 Dec 2023
00:54:43
Daniel Weiner is a former agency executive turned Founder. He started YouShouldTalkTo in 2020 amidst the madness of the pandemic and 3 years later has turned it into a 7-figure business. He also hosts a podcast and private CMO dinners in Atlanta. Outside of work he enjoys all things food/cooking, playing basketball, and working on renovating his loft.
What You Will Learn:
How to assess what type of external support is the best fit is for you (agency/fractional/freelancer).Ā
Insight behind the story of founding a company during the 2020 pandemic.Ā
Why your network is your net worth and tactics for navigating business with this philosophy.Ā
Advice for posting on LinkedIn consistently.Ā
A playbook for vetting agencies upfront andmaking process as efficient as possible.
Highlights: (3:18) Starting with a strong foundation in order to partner with external support.Ā
(4:43) The danger of asking peers which agencies / fractional / freelancer partners they work with.
(18:39) The two biggest mistakes that brands make.
(22:22) The use case for fractional work compared to agency work.
(28:04) Daniel's journey starting YouShouldTalkTo, which began in 2020.Ā
(34:16) The biggest lesson learned in growing his business.
(36:18) Advice for posting on LinkedIn, derived from three years of putting out content.
(40:46) Tactical advice for vetting agencies upfront and how to make the process as efficient as possible.
(48:16) One thing revenue leaders believe to be true that Daniel thinks is bull$***.
(50:00) One thing that is working for Daniel in go-to-market right now.Ā
Sponsor: Todayās episode is sponsored by Flex, a finance super app built around a credit card with unique Net-60 day terms that enables businesses to make an investment today and pay it back 60 days later with zero percent interest. If your business growth is constrained by the cashflow you need for inventory, advertising, or something else, Flex could provide you with an interesting growth lever.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 71: Writer CEO Tells All: Securing Enterprise Customers with a PLG Motion | May Habib (Revisited Bonus Episode)
05 Dec 2023
00:45:58
May Habib is CEO and Co-Founder of Writer, the full-stack generative AI platform for enterprises. Writer empowers your entire organization to accelerate growth, increase productivity, and ensure compliance.Ā
May has worked in NLP and ML for 10 years, and before Writer, she founded and built Qordoba, a localization software company. She is an expert in AI-driven language generation, AI-related organizational change, and the evolving ways we use language online.
She sits on the board of TechWadi, an organization that bridges MENA-based entrepreneurs with Silicon Valley-based VC and talent networks, and is a MELI Fellow with the Aspen Institute.
May graduated from Harvard University and spends her time between San Francisco, where Writer is based, and London, where her two children live.
What You Will Learn:
May's perspective on the economy now compared to that of 2008/2009.Ā
Writer's decision to make PLG table stakes and how they leverage their motion to secure enterprise customers.Ā
AI use cases - what they are and how they continue to progress.Ā
Tips for recruiting the best possible team members and how patience factors into that.Ā
Career insight from years of operating.Ā
Highlights: (6:12) Mayās learnings from Lehman Brothers and the economic crisis of 2008/2009.
(14:11) How much attention the average business leader should spend thinking about AI and how much of a near-term impact AI will have. Ā
(25:17) Writer's PLG motion, including self-serve and sales-assisted, and how it's used to turn small downloads into big enterprise accounts.
(31:07) A consultative sales process and messaging considerations.Ā
(36:56) May's strategy for recruiting A players.Ā
(42:55) Personal career learnings distilled by May.
Sponsor: Todayās episode is sponsored by Flex, a finance super app built around a credit card with unique Net-60 day terms that enables businesses to make an investment today and pay it back 60 days later with zero percent interest. If your business growth is constrained by the cashflow you need for inventory, advertising, or something else, Flex could provide you with an interesting growth lever.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 70: The ā5 Psā Winning Formula Behind Crunchbaseās Sales Leader Ang McManamon
28 Nov 2023
00:50:27
Ang McManamon is a tenured sales leader who puts culture first, helps build high-performing SaaS teams, and executes with urgency across all areas of an organization. She is currently the VP of Sales at Crunchbase, where she leads a high-growth team out of New York City. She previously served as a sales leader for Amazon, Knotel, and Stack Overflow.
What You Will Learn:
Retrospective sales career and overall career insight.Ā
Ang's 5 Ps: Professionalism, Preparation, Process, Performance, Play - and why they are important.Ā
Inspiration for women leaders and aspiring leaders.
Go-to-market perspectives.
Highlights: (9:28) Angās 5 Ps - 5 principles that make up her foundation, created to remind herself of who she wants to be and how she wants to lead to then expose team to them to make sure there is transparency and trust.
(13:37) How to approach preparation, including in a remote-first workplace.Ā
(30:12) An impactful career story on becoming a strong woman leader.Ā
(38:43) Advice to women facing challenges with fellow women in the workplace.Ā
(40:28) What Ang would do differently now being able to reflect retrospectively on her career.Ā
(43:46) One thing revenue leaders believe to be true that Ang thinks is bull$***.
(47:15) One thing that is working for Ang in go-to-market right now. Ā
Sponsor: Todayās episode is sponsored by Flex, a finance super app built around a credit card with unique Net-60 day terms that enables businesses to make an investment today and pay it back 60 days later with zero percent interest. If your business growth is constrained by the cashflow you need for inventory, advertising, or something else, Flex could provide you with an interesting growth lever.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 69: Behind the Scenes on Building and Selling Wisely for $187 Million with Mike Vichich
21 Nov 2023
00:57:39
Mike Vichich is the Co-Founder and CEO of Wisely, which he successfully sold to Olo for $187 million in 2021. Currently contemplating his next move, it will involve embarking on the journey of being a second-time founder. With the experience of building Wisely under his belt, he is looking to avoid making mistakes from his first venture and avoid common traps. He resides in Ann Arbor, Michigan with his wife and three sons.Ā Ā
What You Will Learn:
Insight on the behind the scenes to Mikeās journey building a company that sold for $187M.Ā
What worked and what did not in building Wisely.Ā
How to evaluate product-market fit from experience trying to find it for 4.5 years, including early indicators. Ā
Tactics to encourage resilience and determination and how Mike maintained a strong mindset throughout the journey, even when times got tough.Ā
Highlights: (3:45) Evaluating entrepreneurial ideas, including Mike's process of moving from first-time to second-time founder.
(6:33) Mike's entrepreneurial journey.Ā
(9:46) Differentiating product-market-timing fit from product-market fit.
(14:58) The Wisely story - building and growing the company.Ā
(21:22) Balancing personal life and self-identity when cash is running out and times get tough.Ā
(28:54) Leveraging a network of decision making, rather than a hierarchy of decision making.
(31:37) Defining moments and things that Mike got right while building Wisely.Ā
(38:41) First things Wisely did to accelerate growth once product-market fit was found.Ā
(47:05) One thing revenue leaders believe to be true that Mike thinks is bull$***.
(51:49) One thing that is working for Mike in go-to-market right now.Ā
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 68: Klaviyoās Blueprint for Sales Success of $25M to $450M+ Growth with Sean Marshall
14 Nov 2023
00:53:54
During Sean's most recent operating role he spent 4.5 years as SVP, Global Sales at Klaviyo. He helped scale the sales organization from 15 to 300 people, while growing annual recurring revenue from $25m to over $450m.Ā Prior to Klaviyo, Sean served in enterprise sales roles at Localytics, Yammer (acquired by Microsoft for $1.2B) and SuccessFactors (IPO & acquisition by SAP for $3.4B). He was one of the first few reps hired at Yammer to sell into the Fortune 500, responsible for closing some of their largest, 7-figure contracts. In 2022 Sean made the switch from operator to investor, currently serving as Managing Partner at Perkins Cove Partners. Over the last few years he has advised and invested in many B2B SaaS companies, particularly focused on helping with Go-To-Market.
What You Will Learn:
The importance of leveraging your connections.
Strategically pulling in every sales team within your org to orchestrate deals.
How to hire the best AEās for your company.
How to be an effective storyteller.
Optimizing different parts of your funnel in order to extract incremental dollars.
Highlights: (2:57) Sean Marshallās success attributor.
(5:35) Moving up to enterprise from a PLG focused company.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 165: Vibe prompting, AI fluency, and the new rules of go-to-market | Kieran Flanagan
30 Sep 2025
00:48:52
Kieran Flanagan is the SVP of Marketing at HubSpot and Co-Host of Marketing Against the Grain. A longtime operator and investor, heās at the forefront of how AI is reshaping go-to-market. With a background in engineering and years leading growth and marketing teams, Kieran now spends his time building, experimenting, and sharing lessons on how prompting, agents, and personality-led growth will define the next era of software companies.
Discussed in this episode
Why prompting and context engineering are the most important skills for GTM operators
How āvibe promptingā accelerates learning and output with LLMs
The three keys to building AI fluency inside teams
Measuring ROI from AI across sales, marketing, and operations
Why every professional is now a manager (of AI agents)
How websites will evolve into multimodal closing mechanisms
The rise of personality-led growth in B2B marketing
Why curiosity and persistence matter more than ever in an AI-first world
Episode highlights
00:46 ā The 100x difference between good and bad prompting
03:57 ā The rise of ācontext engineeringā as a GTM skill
07:22 ā Kieranās 3-part framework for AI fluency inside teams
09:31 ā Why āvibe promptingā is as powerful as vibe coding
11:00 ā How AI boosts conversions & deal velocity in sales workflows
15:10 ā Using ChatGPT memory as a personalized prompting coach
22:19 ā Everyone now manages a PhD-level AI intern
31:12 ā The 3 biggest shifts coming to GTM: influence, AI optimization, multimodal
37:42 ā Why AI makes human creativity more valuable than ever
43:06 ā The grind, reps, and curiosity as the ultimate AI skills
Brought to you by: Mutiny
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Thatās where Mutiny comes in. Mutiny is the fastest place to launch breakthrough campaigns for your target accounts.Ā
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The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 67: Stop and Celebrate Your Wins with Scott Gifis
07 Nov 2023
01:01:35
Scott Gifis is currently the CEO at NoFraud, formerly the President and COO at frame.io (bought by Adobe) and prior to that, he was the president at AdRoll for 6 years.Ā Scott is an experienced executive operator, investor, advisor, and board member with a proven track record of building and scaling great companies, globally, from near zero to $100M plus. Today Scott advises for nearly a dozen SaaS companies.
What You Will Learn:
Stop and celebrate your wins.
The power of your influence.
Unlocking team building successfully as a leader.
Knowing when to part ways with your early employees.
When to bring on a COO / Head of RevOps and the common pitfalls.
Highlights: (4:51) balancing work / life priorities.
(10:03) Impactful moments in Scotts career that led him to run large behemoths.
(16:01) Flying back to his younger self.
(22:18) Knowing where your influence affects your employees.
(29:32) The best team building strategies.
(42:48) When to bring on a COO / Head of RevOps.
(54:37) The problems with hiring an enterprise leader to run your startup.
Our Sponsor Todayās episode is sponsored by Demandbase, Demandbase helps B2B companies hit their revenue goals using fewer resources. How? By using the power of AI to identify and engage the accounts and buying groups most likely to purchase. They combine your sales and marketing data with our validated B2B data and AI to create Account Intelligence that informs every step of your buyerās journey. They deliver accurate company, contact, technographic, engagement, and intent data right where you work every day ā CRM, collaboration tools, browsers, and more. Start spotting opportunities earlier and orchestrate smarter sales and marketing motions with Demandbase. See this live in action: https://www.demandbase.com/product-tour/sales-intelligence/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 66: How to Land your Dream Role in a Competitive Market with Sophie Buonassisi
31 Oct 2023
00:48:25
Sophie Buonassisi is the Vice President of Marketing at GTMfund, overseeing GTMnow - the media arm of the GTMfund brand - and the internal community. Sheās passionate about empowering go-to-market leaders and founders with access to insight through GTMnowās channels, like this podcast, the newsletter, and more. Before joining the GTMfund team, she built and scaled GTM at a predictive conversion optimization company. She enjoys advising SaaS companies as they build out and optimize their marketing and overall GTM strategies.
What You Will Learn:
How to be proactive with your references.
The need for speed throughout your interview process.
Showcasing skill and character effectively.
Highlights: (3:45) Whoās Sophie and how she ended up at GTMfund.
(6:31) How Sophie stood out during an application process of 400+ people.
(11:15) How to be proactive about finding a new role when you havenāt identified what that role is exactly.
(17:21) Knowing how to navigate the interview process systematically.
(22:41) How to leverage your community to endorse you.
(26:49) How to effectively nail a take home assignment.
(32:30) The importance of understanding your future employer deeply.
(35:35) How to hit the ground running before your start date.
(40:05) Top tips for landing page conversion optimization.
Sponsor: Todayās episode is sponsored by Demandbase, Demandbase helps B2B companies hit their revenue goals using fewer resources. How? By using the power of AI to identify and engage the accounts and buying groups most likely to purchase. They combine your sales and marketing data with our validated B2B data and AI to create Account Intelligence that informs every step of your buyerās journey. They deliver accurate company, contact, technographic, engagement, and intent data right where you work every day ā CRM, collaboration tools, browsers, and more. Start spotting opportunities earlier and orchestrate smarter sales and marketing motions with Demandbase. See this live in action: https://www.demandbase.com/product-tour/sales-intelligence/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 65: Consultative Selling Mastery, and The Positive Snowball Effect of Building Strong Relationships with Zach Lawryk
24 Oct 2023
00:50:26
Zach Lawryk is currently the Head of Global Solutions Consulting at Rippling, previously the VP of Solutions Consulting at Slack, Director of Sales Engineering at Box, and really began his career in tech at Salesforce as a Sales Engineer in 2005.
What You Will Learn:
The importance of building long-term relationships at work.
The beginning of SaaS SEās.
How the SE/SC role will evolve with AI.
Knowing when to bring in SE's as a founder.
Highlights: (3:41) How Zach has successfully landed at powerhouse companies and how to identify those companies.
(8:16) Zachās snowball effect of building relationships in the workplace.
(11:10) The energy you put out always comes back to you.
(19:30) When the sales engineer role got pioneered.
(21:43) The SE/SC role evolving with AI.
(29:11) AI experiments that Rippling is currently running.
(34:49) When to invest in solution engineers.
(37:30) Benchmark for the bump in win rate after bringing in SC/SEās.
(42:07) Gauging the complexity high water marker.
(44:35) Practicing transparency with the value you provide.
(48:07) The power of video content that Rippling is currently leveraging.
Our Sponsor Todayās episode is sponsored by Demandbase, Demandbase helps B2B companies hit their revenue goals using fewer resources. How? By using the power of AI to identify and engage the accounts and buying groups most likely to purchase. They combine your sales and marketing data with our validated B2B data and AI to create Account Intelligence that informs every step of your buyerās journey. They deliver accurate company, contact, technographic, engagement, and intent data right where you work every day ā CRM, collaboration tools, browsers, and more. Start spotting opportunities earlier and orchestrate smarter sales and marketing motions with Demandbase. See this live in action: https://www.demandbase.com/product-tour/sales-intelligence/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 64: Hiring Ethereal Talent with Chuck Brotman and David Teichner
18 Oct 2023
00:50:46
This week we have a special 2 guest episode, with the best hiring guru's in the game, Chuck Brotman & David Teichner.
Chuck is the co-founder of Blueprint Expansion, a GTM roles recruiting firm that has helped over 50 VC-backed companies make amazing Sales, Marketing, & Customer Success hires. Prior to starting Blueprint in 2020, he worked for over fifteen years in various sales and sales management roles, building teams across presales, partnerships, SMB, Mid-Market, & Enterprise Sales. Chuck lives in the Bay Area with his wife and has two daughters, a junior at UCLA and a freshman at UC Santa Barbara.
David has 25 years under his belt as a serial entrepreneur. Built and exited companies in MarTech, FinTech and Media. He's invested and advised for over a dozen companies, and launched AccelerateHC seven years ago to help companies think through the organization they need and ultimately help them recruit high performing talent.
What You Will Learn:
Understanding your business goals before expanding your team.
Utilizing a āWhite Boardā exercise throughout the interview process.
How to hire the most ethereal talent in an oversaturated market.
Knowing which role to hire for when budgets are tight.
How to avoid making a bad hire at the early stages.
Highlights: (1:35) How Chuck initially started his career in recruiting.
(4:40) How David got drawn into recruiting.
(9:10) Generalists vs Specialists for Seed/SeriesA startups, which should you pick?
(14:00) How to decrease the chance of making a bad hire at the early stage.
(21:00) The importance of implementing a strong process when hiring talent.
(22:38) Maximum number of skills/behaviours you can test for during an interview process.
(25:27) Optimal length for an interview process.
(30:05) How to test for ethereal factors that you canāt put on paper in an interview.
(35:10) When budgets are tight, who do you opt in for, another AE or a sales leader.
(38:29) How to navigate the āleadā roles / player coaches.
(40:50) Hot Take: The āHire slow and Fire fastā mentality no longer serves us.
(41:45) Hiring people for their titles and hot logoās on their resume does not guarantee success.
If you're looking for any help with your hiring process, fill out This 3 Question Typeform and we'll connect you directly with Chuck and David.
If you're a talented go-to-marketer on the job hunt, fill out
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 63: Community Mashup with The Best in the Game ft. Kathleen Booth, Erica Kuhl, & Holly Firestone
10 Oct 2023
00:51:54
We have a special episode this week, a community mashup with the best community leaders in the game! Pavilion's SVP of Marketing, Kathleen Booth, The founder of Salesforce's Trailblazer's Community, Erica Kuhl, and The Former Director of Community for Salesforce's Trailblazer Community as well as The Former Head of Global Community at Atlassian, Holly Firestone.
What You Will Learn:
The importance of community in 2023.
How to stand out as a community in an oversaturated market.
How to maintain quality members in the community as you scale.
Centralizing user groups for the community: how to scale, track, and optimize for monumental growth.
Highlights: (1:15) Kathleen Booth explains why community is more important than ever.
(6:34) How to advise early-stage SaaS companies on how to leverage community to drive revenue and demand.
(16:00) Erica Kuhl unpacks the oversaturation of community today and how to overcome that.
(20:00) Maintain quality members as you scale.
(25:07) Building Salesforce Trailblazers: walking through what worked and what didn't.
(33:00) Holly Firestone's time at Atlassian: scaling, tracking, and optimizing for significant growth.
(42:00) Some mistakes that Holly made as the Director of Community with Salesforce's Trailblazers.
(46:20) Mistakes that Erica Kuhl made during her time at Salesforce.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 62: The Revenue Viking Shares his Competitive Edge & Winning Culture Tactics with Mark Cranney (Revisited Bonus Episode)
03 Oct 2023
00:43:39
Mark Cranney is an enterprise go-to-market operator and three-time unicorn creator. Most recently, he was the COO at Skydio. He's also a founding operating partner at Andreessen Horowitz (a16z) and has been involved in the acquisitions of Opsware and Aster Data Systems by HP and Teradata, respectively. Mark specializes in developing winning playbooks, cultures, and strategies that put his competition on the back foot.
What You Will Learn:
How to create a winning culture.
How to keep your competition at bay.
How to hire talent that culturally fits your organization.
Highlights: (03:48) The books that shaped Mark's winning culture.
(10:39) How to keep your competition at bay.
(14:10) Three questions to ask when scouting for culture-fit talent.
(15:46) How to keep recruited talent motivated.
(16:16) "Process triumphs heroics." How Mark created and used playbooks to create winning cultures.
(23:00) Why you need to get more granular in your competitive strategy.
(35:17) How to create a winning culture without turning your team's culture toxic.
(37:18) "If it's not a competitive environment, for me, that's toxic."
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 61: Two M&A Exits in One Calendar Year by Harnessing the Power of Deep Relationships with Dan Reich
26 Sep 2023
00:49:13
Dan Reich is a serial entrepreneur, investor, and writer and has been building companies since he was a teenager. Some of the companies that he founded include: TULA Skincare which was acquired by Proctor & Gamble - Troops.ai which was acquired by Salesforce - Spinback which was acquired by Buddy Media and then acquired by Salesforce. Dan is now a co-founder of Dibs Beauty, which is backed by LCatterton and is building more companies. He also invests through his family office, Reich Capital. He has a background in electrical engineering and volunteers as a member of national ski patrol.
What You Will Learn:Ā
The power of influencer marketing.
Leveraging B2C strategies for B2B companies.
Maintaining authenticity across all business plays.
The importance of building strong relationships in business.
How to keep your team motivated when momentum takes a hit.
Highlights: (6:33) Influencer marketing in B2B.
(8:34) Tactics and strategies that B2B companies can steal from B2C companies today.
(13:00) How Dan structured a designated BDR team for influencer marketing.
(17:00) How to maintain authenticity when partnering with influencers.
(21:32) How to effectively compensate influencers: Equity vs Cash.
(24:20) Danās experience with 2 M&A exits.
(30:08) How to keep your team motivated in moments of momentum loss.
(32:28) How each acquisition began its first conversations.
(42:30) Why email marketing is dead today.
(44:50) Finding gratitude and happiness within yourself will ultimately lead you toward success.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 60: 261% More Likely to Trust a Company When Their Founders are Posting on LinkedIn with Sam McKenna
19 Sep 2023
00:52:22
Sam McKenna is the founder of SamSalesConsulting, previous to that she spent 6 years at On24 ending up as their VP of Enterprise Sales, She then jumped over to LinkedIn as their Head of Enterprise Sales. Sam is also an advisor for high growth companies. She now leads an all women team of 11, has over 180 clients, multiple million dollars in revenue, all under 4 years.
What You Will Learn:
Knowing when to outsource talent as a founder.
Using strategic hooks to capture engagement on social.
The power of dark social and leveraging it to increase impressions.
How to monetize your social presence.
Learning to scale things you do well effectively.
How to effectively implement the "show me you know me" framework in sales.
Highlights:
(3:40) Why building your digital footprint is more important than ever for founders
(8:30) How to carve out time for thought leadership throughout busy times.
(13:00) Strategies from Samās playbook that people should implement when building their social.
(20:00) High-impact strategies that Sam used to excel throughout her sales career.
(26:00) Walking the line between doing what works for you vs following playbooks given by your leaders.
(29:00) A framework for āshow me you know meā in Sales.
(33:42) Hot take: Shorter e-mails are not the way to earn your ICPās time.
(35:51) How to successfully hire for key roles.
(40:30) Hot take: Cold calling isn't the way to approach your ICP anymore.
(44:10) How to leverage data to prospect efficiently.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 59: Weekly Active Users Up 33% by Making the Hard Decisions Faster with Melanie Fellay
05 Sep 2023
00:49:47
Melanie Fellay is the CEO and Co-Founder of Spekit, a just-in-time platform that is transforming how we learn at work. Spekit meets reps with the process guidance, enablement and knowledge they need, right when they need it, in their flow of work to help them be more efficient, drive more revenue and eliminate the friction of change.
Sheās a Forbes 30 Under 30 recipient, Top 100 Female Entrepreneur to watch (Entrepreneur) and has been featured across Forbes, Entrepreneur, Fast Company, Business Insider and more. Mel co-founded Spekit with Zari Zahra to solve a simple challenge: how do we make sure employees know what they need to know, when and where they need to know it. Hundreds of the world's most innovative companies, including Uber Freight, Snowflake, Southwest Airlines and Invesco, rely on Spekit to empower their employees with real-time knowledge and training, without disrupting their day-to-day workflows.The company has raised $60M in venture funding from notable investors Craft Ventures. Felicis, Operator Collective, Matchstick Ventures, Renegade Partners, Foundry Group and Bonfire Ventures and more.
What You Will Learn:
Narrowing the playing field and going where people aren't as a founder.
Always be strategic and intentional when you go wide.
The importance of customer-facing as a founder.
Making hard decisions faster will only benefit your team's success long term.
Product momentum comes from working well as an executive team.
Highlights: (2:40) The importance of allowing your mind to rest.
(9:37) Melās founder journey that inspired her to build Spekit.
(15:44) How to go-to-market with a tool that tackles multiple categories.
(22:33) Customer-facing as a founder shouldn't be overlooked.
(24:10) How Mel ended up having to step in as Spekit's CTO during the pandemic and her experience sitting in the engineering seat.
(34:08) How Mel took the mental strength to show up for her team when things were difficult.
(39:38) What Mel would tell her 25-year-old self.
(42:06) The importance of networking and building your brand as a first-time founder.
(46:44) Figuring out how you work best as an executive team to increase product momentum.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 58: How Stripe SuperCharged their SMB Team with Meka Asonye
29 Aug 2023
00:45:53
Meka Asonye is a Partner at First Round Capital based in San Francisco. Before moving into venture, Meka was an active angel investor backing companies such as Coda, Alchemy, Rimeto (acq. by Slack), Snackpass and Stytch.
Previously, he served as the VP of Sales & Services at Mixpanel, where he ran the more than 100-person global revenue team. Before Mixpanel, Meka spent four years at Stripe and scaled and matured its sales organization during the company's rapid growth from 250 to 2000 people. Prior to joining Stripe, Meka served as Case Team Leader at Bain in San Francisco, partnering with the C-Suites of Fortune 50 companies across different verticals.
Meka started his career working in Player Development & Baseball Operations for the Cleveland Indians. Meka earned a Bachelor of Arts degree cum laude in Economics and Finance from Princeton and his MBA from Harvard Business School
What You Will Learn:
Long-term orientation for lead distribution at Stripe.
Investing in the person, and then the product, is most important in angel investing.
Best tips to start out in angel investing.
Compensation structures that early-stage companies should implement.
Highlights: (3:44) How Meka started his career in player development and baseball ops for the Cleveland Indians.
(8:50) Mekaās biggest challenges during his time at Stripe as the Head of Sales.
(10:15) How the SMB team measured success at Stripe and how it evolved over the years.
(13:14) Balancing lead distribution at Stripe.
(16:28) Practicing āDumpster Divingā at Stripe.
(18:00) Setting up long-term incentive structures at Stripe.
(22:48) How Meka began angel investing.
(28:10) What Meka learned from his first angel investing experience.
(36:22) The best way to start out in angel investing.
(39:42) Why traditional sales compensation models at early-stage companies are flawed.
(42:00) The importance of educating your customers effectively through each touch.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Cristina Cordova is a seasoned operator who has scaled some of the most iconic companies in tech. At Stripe, she built and led partnerships that became a foundational revenue engine, including the pivotal deal with Shopify. At Notion, she helped turn viral adoption into a durable distribution strategy powered by community. Today, Cristina is the Chief Operating Officer at Linear, where sheās applying her experience building high-velocity GTM engines to the next generation of developer-first tools.
Discussed in this episode
Why Cristina joined Stripe without knowing what an API was
Building Stripeās early partnerships and salvaging the Shopify deal
How Notion pioneered community-driven growth
Lessons on brand, design, and investing for the long term
What Cristina looks for in exceptional founders and operators
How Linear is scaling GTM with AI-driven prioritization
The difference between ākeeping the lights onā and transformative leadership
Cristinaās frameworks for evaluating product resonance and customer love
Episode Highlights
00:43 ā The rare superpower behind Cristinaās career: joining breakout companies early
2:46 ā Why Cristina joined Stripe without knowing what an API was
12:22 ā On Cristinaās first day, Shopify walked away from Stripeās deal ā and how she won them back
16:55 ā How Notion scaled by making consumer use free and fueling community-driven growth
20:52 ā Why investing in brand early is a leading indicator of durable growth
25:27 ā Cristinaās framework for spotting beloved products in the market
37:53 ā How Cristina applied lessons from Stripe to build Linearās GTM from scratch
47:30 ā Where AI fits into GTM: prioritizing opportunities, not replacing humans
56:01 ā Why Linear built high-quality swag kits for early customers
58:28 ā Where to follow Cristinaās journey today
This episode is brought to you by our sponsor
Harmonic helps you discover the best startups way ahead of the competition. We use it at GTMfund, as do thousands of investors at firms like USV and Insight. GTM teams at companies like Notion and Brex also rely on the platform to stay ahead.
Harmonic tracks millions of startups and lets you search using simple filters or natural language to match exactly what youāre looking for. When you find a company that looks interesting, Harmonic pulls everything into one place (founder backgrounds, traction, and market data) so you can quickly evaluate and understand if itās a fit.
At GTMfund, we even have a private Slack channel called #companywatchlist powered entirely by Harmonic.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 57: The Real/Raw Version of Selling a Start-Up with Eli Rubel
22 Aug 2023
00:42:38
Eli Rubel is the CEO of MatterMade and NoBoringDesign, and has served as a Marketing advisor for companies like Dropbox, Loom, Productboard, Calm, and many others. Prior to MatterMade & NoBoringDesign, Eli was the founding CEO of Glider.com which he led through a successful acquisition to FPX.
What You Will Learn:Ā
The importance of leveraging Demand Efficiency for your business.
Being aware of the bad actors that exist in business.
Extreme diligence on contract work should not be overlooked.
Setting yourself up successfully post-acquisition changes.
Highlights: (3:39) Defining Demand Efficiency.
(7:30) Shared data around good efficiency through channels.
(10:10) Common micro-surfaces that are often overlooked.
(13:10) Companies revisiting their brand guidelines and brand identity.
(15:24) Good conversion rates on ad spend for B2B SaaS companies.
(17:10) Things people should think about when analyzing their demand efficiency
(18:10) Eliās acquisition that went wrong.
(25:30) How to combat against acquisitions going wrong.
(28:00) Post-acquisition shift - how to set yourself up.
(30:10) Founder Question: What your first marketing hire should look like.
(25:00) Hot take: LinkedIn is dying!
(38:00) Operational excellence will set your team up for success every time.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 56: The Pioneer of Account Based Sales Development with Lars Nilsson *Revisited Bonus Episode*
18 Aug 2023
00:46:23
This is a revisited episode from the early GTM Podcast days, and our highest streamed episode. So much value to take away from the Pioneer of the BDR name!
Lars Nilsson is the VP of Global Sales Development at Snowflake. Prior to Snowflake, Lars was the CEO of SalesSource, a premier RevOps consulting firm. Before that he was the VP of Global Inside Sales for Cloudera. Lars and his team at Cloudera developed the Sales methodology known as Account-Based Sales Development, which has transformed how businesses approach high-value targets, and is an integral part of most teams playbooks today.
Lars has also served in sales exec roles at ArcSight, Hewlett Packard, Riverbed Technology, and Portal Software, all three of which achieved IPOs.
Lars starts this episode by sharing what he learned early in his career at Xerox and the world-famous Xerox Management Training Program. He then talks about Cloudera's account-based sales development method, including how it started and why it was successful.
What You Will Learn:
How to use personalization to your advantage.
How to speak among people in a way that brings them together.
What to look for when hiring a BDR.
Highlights:
(05:00) Insights on nurturing young talent while fostering loyalty.
(14:40) Cloudera's account-based sales development methodology: origins and early successes.
(21:40) Insights on the power of personalization.
(27:30) How to create a lasting impression in front of people and bring them together.
(31:00) Why you should express gratitude or tell a story in front of people more often.
(32:49) How to overcome fear and nervousness and find the courage to speak among people.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 55: Contagious B2B Messaging Mastery with Dave Gerhardt
17 Aug 2023
00:50:01
Dave Gerhardt worked as a Senior Marketing Manager at Drift in 2015 and quickly grew into their VP of Marketing. Dave left Drift in 2019 to join Privy as their CMO for just under 2 years, then returned to Drift as a Chief Brand Officer. Dave now runs Exit Five, The #1 community for B2B Marketers.
What You Will Learn:Ā
How to successfully set yourself up as a one-person team.
Evolving your strategy and goals as your company's goals change.
How to nail your company's messaging.
Effectively building a founder brand.
The importance of niching down to drive growth.
Highlights (3:25) Shifting from a āYes mindsetā to a āNo mindset.ā
(12:10) How Dave grew into a VP-level role at Drift.
(12:58) How Dave started his career at Drift.
(24:00) Moments in Daveās career where he didnāt achieve his goals.
(28:48) Aligning revenue goals between Sales and Marketing.
(31:50) Getting people excited and engaged in Driftās product at an early stage.
(36:50) The pros and cons of starting a founder brand.
(40:39) How Dave measured success for his podcast as they started out.
(43:00) Hot take: Measuring everything in Marketing is no longer relevant.
(45:00) The importance of niching down to drive growth.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 54: Resilience is Your Willpower with Anna Baird
15 Aug 2023
00:51:02
Anna Baird started her career in Accounting helping with IPOs of companies like Google. She then moved to become an SVP at McAfee and when they sold to Intel she decided to work at start-ups so that she could help build the foundations at scale from the beginning. She became a CFO and then a COO and finally a CRO. Anna is now working on Boards to help other executives take advantage of the opportunities that they saw earlier and avoid some of the mistakes that she's faced at early stages. ā”Ģ
What You Will Learn:
The importance of leveraging your relationships to bring in revenue.
Practicing resilience to surpass those who doubt your capabilities.
Knowing when to walk away from a company.
Understanding where your hires' skillsets are to be successful within your organization.
Highlights: (6:13) What Anna has learned throughout her career selling into large strategic accounts.
(11:45) A walk through of Outreachās deal review calls as a successful strategic tactic.
(15:45) How to prepare folks to make a strong ask that garners results.
(19:20) Annaās impactful story that fueled her.
(22:55) A moment in time where Anna faced a struggle with misalignment.
(32:40) Annaās advice to female leaders struggling to get promoted.
(37:40) Understanding where your hires' skillsets are to be successful in your organization.
(42:10) Working in silos no longer works.
Quotes: āI just wanna work with interest people, solving interesting problems, with people I enjoy and respect being around.ā
āThe only reason why we exist as a company, is because weāre solving a pain. Never lose track of why you exist and what is it that youāre building for.ā
āEveryone wants to work for a place where they feel has a great foundation of innovation, great ideas, and different perspectives, and I feel thatās what the younger generation is excelling at.ā
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 53: Hire Slow & Fire Fast with Justin Welsh
08 Aug 2023
00:45:53
Justin Welsh helped scale ZocDoc as the Director of Strategic Sales, and later joined PatientPop as the SVP of Sales. Justin currently has over 440k followers on Linkedin and Twitter, and 150k subscribers on the Saturday Solopreneur Newsletter. Justin is also an Angel investor and an advisor for early stage startups.
Justin has bundled all of his learnings into 2 courses that he offers today: The Operating System Digital Course, teaching you how to build a viable meaningful business on Linkedin and the TheContent OS Digital Course, which gives you a more holistic strategy around content.
What You Will Learn:
How to nail your LinkedIn presence and strategy.
Common mistakes and misconceptions folks come across when building their social presence.
How to navigate burnout.
How Justin cracked the Twitter code on growth.
The importance of giving yourself KPIs as a thought leader.
The best hacks on how to use your social channels to drive an abundance of inbound leads.
Highlights: (3:18) The evolution of Justinās career growth as a solopreneur.
(4:48) The courses Justin built on how to excel as a thought leader on LinkedIn.
(6:33) How to crack the Twitter code.
(13:25) Outsourcing creativity.
(14:50) Using a scheduler for content - which platforms Justin uses for scheduling.
(16:40) Justinās take on threads.
(19:15) The impactful results that Justin saw as he kickstarted his solopreneur journey.
(22:17) Tips for executives and founders looking to build on LinkedIn.
(25:00) Common mistakes that folks should avoid on LinkedIn.
(27:00) Justinās experience with burnout before he decided to bet on himself.
(31:35) Justinās best advice to his younger self.
(33:26) How to motivate your hires to be more active on social.
(37:48) Hot take: Fire Fast!
(41:55) Actionable tips that SaaS teams can implement to drive more inbound.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 52: *Special Edition* Monthly Jam Session (August 2023)
03 Aug 2023
00:07:11
Presenting you with a very special bonus episode this month...
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 51: A Dream to a Nightmare, and Now a Multi Million Dollar Company with James Isilay
01 Aug 2023
00:44:54
James Isilay founded Cognism a B2B sales intelligence company together with Stjepan Buljat in 2015. James had previously worked as a quantitative trader and analyst and studied Information Systems Engineering. Cognism helps you identify your ideal customers globally, find others like them, and reach out when they are most likely to buy.
What You Will Learn:
The power of networking as you build your career.
The importance of making top-tier hires when scaling your business.
Scaling internationally is how you win in today's market.
Why SDRs should be working in the office.
Highlights: (3:05) Jamesā career journey that led him to become a founder.
(8:09) Factors that drew James into being a financial trader early on in his career.
(14:55) Jamesā inflection point quitting his 9-5 to start Cognism.
(18:12) Jamesā learnings from his early days building Cognism.
(20:33) How James calibrated excellence across his team.
(27:08) Cognism's take on in-office vs remote work.
(31:28) Listener question: The āneed to havesā on a go-to-market tech stack.
(36:40) Hot take: Every company should be expanding and building a sales capacity globally.
(42:38) Value loops and ungated content are the way to succeed.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 50: Solving the Age Old Problem, A Sales & Marketing Misalignment with Nicole Wojno Smith
25 Jul 2023
00:38:29
Nicole Wojno Smith is the VP of Marketing at Tackle, where she oversees the strategy and execution across brand, demand gen, content, product, customer, and partner marketing. Sheās passionate about building GTM programs aligning cross-functional teams while scaling revenue. Before Tackle, she built and scaled the marketing team from the ground up at two previous SaaS companies.She enjoys advising early-stage SaaS companies as they build their marketing team and strategy.
What You Will Learn:
The importance of taking ownership as a business and leaning on your team for support.
Building the strongest possible cross-functional team in order to collectively tackle the problem you're solving.
Nicole's 4-part framework: 1 shared revenue goal, executing integrated campaigns across the org, and a multi-touch attribution model.
The importance of infusing an integrated theme across the organization.
Highlights: (3:17) The meaning of alignment between sales, marketing, & partnerships.
(5:35) The framework Nicole built to create better alignment between sales & marketing.
(11:03) How to extract data and diagnose a breakdown where problems are happening.
(13:10) The impact on Nicoleās company after rolling out her framework.
(16:08) What led Nicole to make changes within the sales and marketing org.
(17:45) How Nicole motivated her team to adjust to these changes.
(20:40) The importance of leading with data in every situation.
(23:47) Nicoleās operational shift error.
(26:53) Nicoleās biggest learnings and takeaways.
(28:07) Listener question: Where to allocate marketing dollars in demand gen today.
(30:15) Decreasing ad performance in todayās market.
(31:35) Hot take: 1 Marketer with 10 different roles isnāt the way to succeed.
(33:59) How to leverage AI for every possible role today.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 49: "What Got You Here Won't Get You There" with Adam Schoenfeld
18 Jul 2023
00:42:34
Adam Schoenfeld is the Co-Founder & CEO at Keyplay, as well as the Co-Founder & Analyst at PeerSignal.org. Adam is a 4th time SaaS founder. His past includes Siftrock (acquired by Drift), Simply Measured, Product & Strategy VP at Drift, and a board member at Bizible.
What You Will Learn:
The importance of having alignment with your cofounder.
The concept of building a media channel as a part of every brand.
Being overly structured doesn't bring you the best outcomes over time.
Never stop interfacing with your customers as a founder.
Highlights: (2:57) The thinking and execution behind Keyplay.
(6:06) How to get people to care about your early-stage startup.
(10:28) Adamās advice to founders building a Media and community arm.
(13:50) Adamās pivotal career story.
(20:44) The importance of the Co-founder relationships.
(23:30) Not losing track of your customer.
(27:25) How to get past the 1M mark as a startup.
(33:30) Gating content is no longer needed in tech.
(36:30) What's replacing gated content.
(38:17) Offering a free version of your product will help your company's growth at the earlier stage.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 48: Monthly Jam Session (July 2023)
13 Jul 2023
00:28:05
Guest appearance from the one and only Paul Irving again this month as him and Scott discuss the general trends in the macro environment, predictions and paving the path forward for todays economy. They also dive into the asset class comparisons and their latest US Trade Mission trip to HongKong... Don't miss out!
Highlights: (0:45) Little Summer Update.
(2:14) Why the VC landscape is different this year.
(5:00) Paulās take on the private and public markets right now.
(8:44) Scott and Paulās recap on the US Trade Mission in Hong Kong last month.
(13:45) Last month's GTM dinners in Toronto and NYC.
(15:57) A GTMfund Portfolio Company story/update from Paul.
(21:00) Expanding on the concept of āflight to quality.ā
(26:00) Whether founders are going to start rethinking their value propositions.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 163: From $2M to $50M ARR to Unicorn: How Owner Scaled with AI & Talent Density | CRO Kyle Norton
16 Sep 2025
01:08:32
Kyle Norton is the Chief Revenue Officer at Owner, the fast-scaling restaurant SaaS platform valued at over $1B. Since joining from Shopify, Kyle has helped grow the company from $2M to $50M+ in ARR by instilling a high bar for sales talent, building RevOps early, and driving a disciplined go-to-market strategy. A podcast host himself, Kyle shares deep expertise on sales hiring, leadership, and GTM AI, while keeping his focus on building a generational company.
Discussed in This Episode
Why Kyle let go of half the sales team just 45 days in
The importance of setting a high bar for sales talent and cultural fit
Investing in RevOps and data foundations far earlier than conventional wisdom
How to reduce churn by narrowing ICP and saying no to misfit customers
Lessons from running hiring retros to assess interview process effectiveness
The balance between remote vs. in-office roles for scaling GTM teams
How Owner approaches AI in go-to-market, starting with data over āshiny toolsā
Kyleās leadership philosophy: servant leadership and building for growth
Episode Highlights
00:44 ā Ownerās journey from $2M ARR to unicorn
02:01 ā Kyle explains why he fired half the sales team just weeks into the role
04:56 ā Why Owner set a sky-high bar for early sales hiring
08:13 ā Kyleās case for bringing in RevOps ātoo earlyā and why it paid off
12:39 ā Reducing churn by saying no to 30% of potential customers
15:57 ā Why hiring fit matters more than a candidateās āpedigreeā
21:49 ā What Kyle learned from running hiring retros on interview data
30:25 ā Ownerās AI GTM transformation: starting with third-party data
48:34 ā Kyleās take on the remote vs. in-office debate for sales teams
54:53 ā His leadership philosophy: servant leadership + relentless coaching
59:19 ā Kyleās essential reading list for sales leaders
This episode is brought to you by our sponsors:
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The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 47: Elena's "Pinch Me" Moment Going Public with Medallia
11 Jul 2023
00:47:59
Elena Hutchison has over 15 years of B2B SaaS experience, including a 10-year run at Customer Experience leader Medallia where she supported the company's growth from Series B through IPO.As Medallia's Chief Strategy Officer, Elena led Product Marketing, Analyst Relations, and PreSales functions, and contributed significantly to the company's M&A and product strategy. Elena has particular expertise in scaling global PreSales functions - she joined Medallia as one of its first Sales Engineers and eventually led the 150-person org.S he has also built a reputation as an elite Analyst Relations practitioner, with multiple leading Forrester Waves and Gartner MQs under her belt.
Prior to Medallia, Elena spent 5 years in Professional Services and Customer Success roles. (She also earned some phenomenal stories from her days as a political pollster and focus group moderator).
What You Will Learn:
How to stay motivated and stick with a company for 10+ years.
Defining the role of Analyst Relations.
Learning to step into an era of āyesā and an era of ānoā equally in business.
The importance of a peer group that gives you strength.
Distinguishing which companies need Sales Engineers and which donāt.
Highlights: (3:48) How Elena built her way up from Sales Engineer to C-Suite at Medallia.
(7:22) How to fill the gaps when starting a new role.
(13:10) Elenaās transition from engineering to analyst relations at Medallia.
(18:24) Defining analyst relations.
(25:16) Analyzing the concept of āPay to Playā.
(30:00) The metrics that matter for analyst relations.
(31:41) Elenaās biggest mistake sitting at the executive table.
(35:00) The power of outside mentorship.
(37:20) The importance of bringing on Sales Engineers early on.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 46: "Rest at the End, Not in the Middle" with The CEO and Co-Founder of Outreach, Manny Medina
27 Jun 2023
00:43:59
Manny Medina is the CEO and Co-Founder at Outeach. Prior to Outreach, Manny was employee number three on Amazon's AWS team, and led the Microsoft mobile division from launch to $50M in annual revenue. He holds an MBA from Harvard and a Masters in Computer Science from the University of Pennsylvania.
What You Will Learn:
How to stay driven and motivated while building a multi-billion-dollar company.
The importance of staying small in headcount as you begin to scale.
Finding product-sales fit as fast as you can as a first-time founder.
Manny shares his first sale that helped pivot the company from recruiting to sales.
Why managing by forecast has changed in the last year.
The best sales fundamentals to help founders succeed in todayās down market.
Highlights: (2:42) Where Mannyās sustained motivation to win comes from.
(5:14) Mannyās take on AIās impact on rev tech.
(9:35) Mannyās take on the competitive landscape with the emergence of AI.
(19:40) An impactful story that happened to Manny recently came across.
(27:24) How to maintain a strong company culture as you start to scale.
(33:35) Mannyās valuable advice to first-time founders.
(35:03) The story of Mannyās first memorable sale.
(37:08) 2 fundamental things that have changed in SaaS over the last couple of years.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 45: Employee 36 at Salesforce Built His Career off a Network Approach with Drew Sechrist
20 Jun 2023
00:49:53
Drew Sechrist is the Co-founder and CEO at Connect The Dots. Drew spent over 10 years at Salesforce.com as the VP of their High Tech vertical. He started his career in late 1999 as employee number 36 at Salesforce, beginning as the number one AE globally, and later to the number one Sales Manager globally.
What You Will Learn:
The importance of having a centralized point of contact who can act as a trusted liaison for your business.
Leveraging your network to drive revenue.
Knowing when to make strong asks in sales.
Introducing a Sales Ambassador role in your company.
Highlights (2:50) The premise behind Connect The Dots & Drewās story building his career.
(12:56) The evolution of LinkedIn and problems we face with it today.
(19:05) The importance of patience and creativity to elevate your career.
(21:05) Scott's infamous play that he rolled out at Outreach that brought in hundreds of millions of dollars.
(27:35) How they built Connect The Dots.
(32:25) Drewās successful play he ran at Salesforce.
(39:34) Knowing when to leverage your network.
(42:15) Introducing a Sales Ambassador to your sales organization.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
How to Activate Customer Data and Drive Business Growth
14 Jun 2023
00:38:21
Episode Summary
There's no doubt that companies must become more data-driven if they want to stay relevant in the market. However, in reality, that data sits in silos while the data team and marketing or sales teams rarely communicate. Therefore, companies must bridge the gap between these departments by enabling teams to access and use data in their preferred tools.Ā
In this episode of Sales Hacker, we welcome Kashish Gupta, the co-founder and co-CEO of Hightouch, a simple tool enabling businesses to transfer customer data from warehouses to their tools of choice.Ā
Kashish discusses the mission and vision of his company and why they decided to be an inbound-driven business, at least at the early stage. He also shares his take on AI and whether teams, especially sales teams, should use tools like ChatGPT. Finally, Kashish explains how his teams use Hightouch internally and the sales team's role as consultants in providing value, building trust, and maintaining long-term customer relationships.Ā
Guest-at-a-Glance
š” Name: Kashish Gupta
š” What he does: Kashish is the co-founder and co-CEO of Hightouch.
š” Noteworthy: Along with his team, Kashish is on a mission to help businesses transfer customer data easily from their data warehouses to their chosen tools.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 44: Taking Tableau from $5 million in Revenue to over $1 Billion with Elissa Fink
13 Jun 2023
00:50:43
Elissa Fink serves on several not-for-profit and corporate boards. Retired from Ā Tableau Software in 2019 after 11+ years as their CMO, she helped grow the company from ~$5 million to over $1 billion in revenue and helped lead it through IPO and enterprise growth, leaving right before acquisition by Ā Salesforce. She earned a BA in English and an MBA in Marketing. She now enjoys time with her husband, teenaged daughter and 9 year old son.
What You Will Learn:
Exercising the power of no.
The importance of surrounding yourself with exceptional individuals.
Always hire folks whose best years are ahead of them.
Highlights: (4:00) What made Elissa stay at Tableau for 11 years.
(7:27) Elissa explains her experience as a leader at Tableau and having to adapt as a marketer.
(12:56) What Elissa attributes her career growth to.
(17:42) Elissa explains Tableauās decision to start the Tableau conference at 12M in revenue.
(33:10) The importance of exercising the power of no.
(36:08) Elissaās vital mistake attacking a competitor.
(39:37) How to make a big impact in your first 90 days at a new role.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 43: Monthly Jam Session (June 2023)
08 Jun 2023
00:10:34
Max Altschuler back at it this month leading our monthly bonus episode solo while Scott & Paul take Hong Kong for a US trade mission.
Max hits us with some internal company updates, this months PortCo announcements, qualities that we're looking for in founders as we invest in new early stage startups, and a little topical discussion around moats and distribution.
Don't miss out!
Highlights: (1:30) Update on the fund, network & candidate growth.
(3:03) Tailwinds, economic changes, and micro qualities that we continue to look out for at the fund.
(4:30) Types of entrepreneurs/founders that stand out to us when evaluating an investment.
(6:22) PortCo announcements.
(7:04) "We have no moat, and neither does OpenAI." Unpacking the concept of moats and how to succeed through distribution.
(9:13) Max's 4-part Series on the GTM Newsletter (Decoding Community).
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
How to Make an Established Process Work Instead of Replacing It With a Trendy One
07 Jun 2023
00:52:41
Episode Summary
Sales teams use various methodologies, including MEDDIC, MEDDPIC, and NEAT, and often switch between them based on the dominant trend. But, as our guest Richard Harris says, one size doesn't fit all, and it's not as simple as rip-and-replace if a process doesn't bring immediate or quick results.Ā
In this episode of Sales Hacker, Richard shares how he approaches processes from creation to implementation. Richard also discusses manager-employee relationships and how we can learn plenty, even from bad leaders.Ā
Richard may be the founder of The Harris Consulting Group, but he is still fighting impostor syndrome. As a result, he reminds everyone ā including himself ā to be kind and friendly to themselves, prioritizing self-care and mental health.Ā
Guest-at-a-Glance
š” Name: Richard Harris
š” What he does: Richard is the founder of The Harris Consulting Group and the co-founder of Surf and Sales.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 42: Earn the Right to Side Hustle with Scott Leese
06 Jun 2023
00:53:35
Scott Leese is a 6x Sales Leader, 4x Founder, 3x Author, a Sales Consultant, Advisor, Solopreneur, and Community Builder. Scott Leese Consulting was founded in 2016 with a focus on companies scaling from $0 - $25m ARR.
Scott founded Surf and Sales in 2017 with the mission to bring valuable events and conferences around the globe to help sales professionals and executives grow and expand their skills.
Most recently Scott founded GTM United, which is a private community of go-to-market professionals united by a mission to put their development first. Get feedback, ask questions, practice self-care, and make real connections.
What You Will Learn:
How to land advisory work & how to hire the best advisors.
Identifying which early-stage startups to join.
The importance of asking deeper questions in your career.
The 'Go-To-Network' approach.
Highlights: (4:40) Defining advisory work in SaaS.
(7:57) What to look for when bringing on an advisor.
(11:07) How to land an advisory role.
(17:21) The big resume blip that Scott encountered in his career.
(25:50) Building strategies to discover different sales archetypes.
(32:35) Earning the right to side hustle.
(34:45) What Scott would've done differently throughout his career.
(41:30) Scott's advice on hiring the best sales individuals.
(44:20) Hot take: Go-to-market strategies won't be relevant in a couple of years.
(48:54) Creating a partner channel to accelerate your business.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Boosting Sales Performance: Unearthing the Potential of Women in Sales
31 May 2023
00:53:31
Episode Summary
In this insightful episode, Colin Campbell of Sales Hacker engages Lauren Bailey from Sales Bar, Factor Eight, and Girls Club in a thoughtful discussion on the dynamics of the sales industry. They delve into the underrepresentation of women in sales and the initiatives aimed at bridging the gender gap. The conversation emphasizes the importance of mentorship and community in fostering a more inclusive and diverse sales force.
Lauren Bailey shares personal experiences in the sales industry, discussing the challenges and triumphs that have marked the journey. The conversation also explores imposter syndrome, a common occurrence among sales professionals, and ways to overcome it. Lauren Bailey highlights the essential role of confidence in navigating sales.
The episode wraps up with a light-hearted discussion about the prospect of men joining initiatives traditionally designed for women, underlining the importance of inclusivity in all professional development programs. This episode is a must-listen for sales professionals seeking to understand and navigate the complexities of the sales landscape.
Guest-at-a-Glance
š” Name: Lauren Bailey
š”What they do: Founder and President
š”Company: The Sales Bar, Factor Eight, Girls Club
š”Noteworthy: Lauren Bailey builds happy teams, powerful online experiences, learning cultures, engaging workshops, and solutions to help people fall in love with sales and look forward to coming to work.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 41: Selling The Easy Button Through to Multi Million Dollar Deals with Jamal Reimer
30 May 2023
00:43:46
Over the past 20 years, Jamal closed multiple $50m deals as an individual contributor enterprise seller, authored the best selling book, Mega Deal Secrets, coached hundreds of ambitious sellers to sell the largest deals of their lives, and founded the Enterprise Sellers Community, a community of practice for individual contributors.
What You Will Learn:
The psychology on how to sell to executives.
Knowing which deals to prioritize.
Multi-threading and aligning your sellers to your product market message.
Earning clout and respect from executives.
Highlights: (3:09) Things to think about when starting to sell to larger enterprises.
(5:48) The story behind Jamal's best-selling sales book āMega Deal Secretsā.
(9:36) How to get access to the right people in the room when closing a deal.
(15:12) The framework for identifying and prioritizing the right deals.
(18:00) How to earn clout and respect from executives.
(22:31) How to keep executives invested in your relationship.
(31:26) Key components necessary in an enterprise sales playbook.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 162: From PLG to Enterprise: How to Layer Sales Without Breaking What Works | Ghazi Masood
09 Sep 2025
00:27:48
Ghazi Masood is the Chief Revenue Officer at Retool, where he leads the go-to-market engine for the low-code developer platform. Previously he served as SVP & GM, Americas at Auth0 after leadership roles at Microsoft, Oracle, Polycom, and Nintex K2, and he advises several high-growth startups on GTM. A field-first operator, Ghazi specializes in layering sales onto product-led motions and building enterprise upgrade paths without breaking self-serve growth.
Discussed in this episode
The moment inbound stops being enoughāand how to size the outbound gap
Why to bifurcate SDRs (inbound vs. outbound) and how to define lead sources
Profiling inbound (more technical, SE-adjacent) vs. outbound (AE-track) talent
Structuring self-serve as a permanent home vs. a stepping stone to enterprise
āUngate to upgradeā: using sustained overage/feature use as a right-sizing trigger
Pricing & packaging that pulls larger accounts to annual, committed plans
The āGTM engineerā model for AI-native, high-velocity companies
Hiring pace, capacity planning, and the leadership principles that scale
Episode highlights
00:00 ā Inbound eventually caps out; annual planning exposes the pipeline gap that outbound must fill.
00:45 ā What it really takes to add sales to a product-led motionāwithout breaking PLG.
03:23 ā First move: bifurcate SDR into dedicated inbound and outbound to drive focus and outcomes.
04:18 ā Nail definitions with Marketing: what counts as inbound vs. outbound (e.g., events ā inbound).
06:37 ā Decide the role of self-serve: permanent home for some segments vs. stepping stone to enterprise.
09:41 ā Ungated features as signals: after ~3 months of sustained overage/premium use, āright-sizeā the plan.
12:09 ā Why frictionless adoption beats hard gatesāand how clear web docs make the convo non-adversarial.
15:10 ā When to move from pay-as-you-go to annual: sophistication and committed usage, not arbitrary timing.
18:51 ā Enter the āGTM engineerā: one person spans SDR ā SE ā AE ā AM to capture massive inbound demand.
25:36 ā Frameworks that still work: MEDD(P)ICC and Solution Selling 2.0 for complex, multi-product deals.
Sponsor ā Pursuit
The best talent isnāt actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers.
If youāre hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Master the Art of Knowing Who to Call and How to Ask
24 May 2023
00:50:56
In the highly competitive B2B tech space, it's easy to market your offer with so many tools and channels available. But, we can't help but notice the increased interest in referrals as more and more companies realize that word of mouth is the path to growth.Ā
In this episode, we dive into this renewed trend with Tito Bohrt, the CEO of AltiSales, the one-stop shop for world-class sales development. Tito explains when it makes sense to prioritize customer acquisition vs. retention and vice versa. He also shares how company culture impacts productivity and morale, primarily within sales teams.Ā
Tito and host Colin Campbell also touch upon the concept of a sales champion and how to find the ideal champion within a prospect's organization. Finally, we asked Tito to talk about how he got into angel investing and his consulting endeavors.Ā
Guest-at-a-Glance š” Name:Ā Tito Bohrt š” What he does:Ā Tito is the CEO of AltiSales. š” Company:Ā AltiSales š” Noteworthy:Ā Tito is an expert in sales development and all things sales. š” Where to find Tito:Ā LinkedIn
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 40: Refresh Your Mindset, Because the Numbers are Different Today with Sam Jacobs
23 May 2023
00:49:25
Sam Jacobs is the founder & CEO of Pavilion and was Host of The Sales Hacker Podcast, Sam is focused on helping people unlock and achieve their professional potential. He believes there is greatness within all of us and sometimes it just needs a mechanism through which it can be brought forth. This philosophy led him to build a company called Pavilion and the purpose of that company is to help members, employees, and stakeholders realize the greatness within themselves.
Pavilion is a paid membership for leaders of all levels dedicated to providing support, assistance, education, and career growth. TheyĀ are a global organization with over 9,000 members and hubs in every major city in the world. Sam created Pavilion based both on his personal experience and the experiences of friends, partners, and colleagues in the high growth community.
What You Will Learn:
Pre-negotiating your severance pay and equity when joining a company.
Adjusting comp plans and aligning each contributor's goals to the company's.
Pivoting away from the zero-interest rate era.
Highlights: (3:16) SVB banking analysis.
(11:06) Pavilionās origin story.
(15:00) Stepping into Pavilion's next chapter.
(23:48) What people should be thinking about and negotiating for in their contract as they move into their next roles.
(35:41) How to handle getting paid not at market rate.
(41:29) Hot take: Sales people donāt actually generate the money in the business.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
How to Write Sales Emails That Stand Out
17 May 2023
00:47:52
Writing good emails is vital in sales, and every salesperson has their own email tactic. But you only get one shot at getting your sales emails opened, so it's critical to do it right.
In this episode of the Sales Hacker podcast, our host Colin Campbell welcomes Will Allred, the co-founder and COO of Lavender. They talk about the potential application of ChatGPT in sales, why frameworks are better than templates, and how to personalize your email sequence.
Check out Will's killer series "1 email. 2 takes." https://www.youtube.com/playlist?list=PLGXnz4Tyz3-SFxoZNp8RijB-qnKWZMcNU
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.