The GTMnow Podcast

GTMnow

The GTMnow Podcast interviews well-known tech executive, VC, and founders - the expert operators in the trenches who have ‘been there, done that’ to build some of the fastest-growing software companies. Every week, a guest joins Sophie Buonassisi to dissect their stories, revealing expert insights around what worked, what didn’t, and how things actually went down.This podcast is produced by GTMnow, the media brand of GTMfund - sharing insight on go-to-market from working with hundreds of portfolio companies backed by over 350 of the best go-to-market executives. GTMfund is an early-stage VC fund focused on investing in the most exciting, up-and-coming B2B SaaS companies across the world. The LP network consists of VP and C-level Sales, Marketing, and Customer Success leaders from companies like DocuSign, Salesforce, LinkedIn, Snowflake, Okta, Zoom, and many more.Visit gtmnow.com for more details and to sign up for our newsletter and other content resources.

  1. Why AI Is Killing Your Outbound and Making In-Person GTM Inevitable, with Healey Cypher, CEO at BoomPop

    2D AGO

    Why AI Is Killing Your Outbound and Making In-Person GTM Inevitable, with Healey Cypher, CEO at BoomPop

    Healey Cypher (multi-time founder and CEO of BoomPop) joins GTMnow to unpack one of the fastest growing channels for company growth: in-person events. As AI floods digital channels with perfectly personalized messages, trust is becoming harder to earn online. Healey explains why events, dinners, and in-person experiences are becoming a premium GTM channel, not a nice-to-have, and how founders can use them intentionally for distribution, alignment, and acquisition. In this episode, we discuss: - Why in-person events are becoming a premium GTM channel in an AI-first world - How founders can de-risk distribution before building the product - The most common internal missteps that derail startups early - Why offsites are the new HQ for remote and hybrid teams - How to design offsites that drive alignment, not just fun - What makes a dinner actually work — including overlooked details like acoustics - How teams use events for customer acquisition and partnerships - Why kindness and positivity can be a real leadership advantage Healey also shares a powerful insight from Sam Altman that reframes how we should think about AI’s impact on trust and human connection. If you’re interested in scaling events as a growth channel, this episode will give you all the details you need and an understanding of what is working in today’s world. Timestamps: 00:00 – Why founders underestimate distribution 03:30 – Product vs distribution: what actually matters early 06:45 – Why most startups fail from internal misalignment 10:30 – Culture, communication, and focus as scaling constraints 14:40 – Hybrid work broke alignment 17:45 – Why offsites are becoming the new HQ 21:30 – Events as a go-to-market strategy 25:00 – AI, outbound fatigue, and inbox trust collapse 28:40 – “In-person experiences are becoming a premium” 32:30 – How to use events for customer and partner acquisition 36:15 – What makes a high-impact event vs a wasted one 39:50 – Dinners, summits, and unforgettable experiences 43:30 – Leadership, kindness, and “don’t be a jerk” 47:40 – Mental state as a competitive advantage 52:30 – Final reflections and advice for founders Sponsors: HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.com Guest links:Instagram: https://www.instagram.com/healeycypher/?hl=enHealey’s podcast: https://www.dontbeajerkpodcast.com/ Mentioned Resources: Host (Sophie Buonassisi) links: X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comHost (GTMnow) links: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow/ Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/channel/UCGQM23b5lZbcfLtHAe87J_A Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/

    47 min
  2. Why Most Go-To-Market Motions Collapse at Scale, with Jeanne DeWitt Grosser, COO at Vercel

    JAN 22

    Why Most Go-To-Market Motions Collapse at Scale, with Jeanne DeWitt Grosser, COO at Vercel

    Why do so many go-to-market motions fall apart right when a company starts to scale? In this episode of GTMnow, Sophie Buonassisi sits down with Jeanne DeWitt Grosser, former GTM leader at Google and Stripe and now COO at Vercel, to unpack why GTM fragility is one of the most underdiagnosed risks in startups and scaling companies. This is a deep, operator-level conversation about what actually breaks in sales, why AI won’t magically fix it, and how the best teams treat go-to-market like a product that must be designed, tested, and iterated. If you are a founder, operator, or investor navigating growth, this episode will give you clearer mental models for building GTM that actually holds up under pressure. In this episode, we cover: Why most GTM motions fail at scale, even with strong productsWhat it really means to treat go-to-market like a productHow AI changes execution without changing fundamentalsThe rise of the forward deployed engineerWhy “lost on price” is usually a lieWhat great sales reps still do better than anyone in the AI eraHow to think about joining companies “early” without getting timing wrongListen if GTM feels fragile, unpredictable, or overly dependent on heroes. Timestamps 00:00 – Introduction 01:00 – “Yes is great. No is great. Maybe will kill you.” 02:00 – Why go-to-market should be treated like a product 04:45 – Designing the experience of being sold to 06:30 – Using AI to debug GTM process failures 09:00 – Why “lost on price” usually isn’t about price 12:00 – What go-to-market engineering actually is 16:00 – The rise of the forward deployed engineer 20:45 – AI, agents, and what still needs human judgment 25:45 – What great sales reps do differently in the AI era 29:30 – Why GTM roles are becoming more consultative 33:30 – Will there be an AI reckoning? 38:00 – What “joining early” really means 42:00 – Career lessons from Google, Stripe, and Vercel 44:00 – Closing thoughts

    45 min
  3. VC 3: Investing Philosophy for 2026: What Founders Should Know

    JAN 20

    VC 3: Investing Philosophy for 2026: What Founders Should Know

    Mark Goldberg is a Managing Partner and Co-Founder at Chemistry, a new early-stage venture firm with a $350M debut fund backing standout software companies from Seed to Series A. Prior to Chemistry, Mark was a Partner at Index Ventures, where he led early-stage investments across software and fintech for nearly a decade. Before Index, Mark was one of the first business hires at Dropbox, helping the company navigate hypergrowth.  Discussed in this episode Why Mark studied international relations, and why venture feels like “the liberal arts of jobs”Index’s US “invisibility” era and what that taught him about building a new firmThe Chemistry spinout thesis: “take great multi-stage DNA, reconstitute it with focus”Fund design: pre-seed → seed → A, light reserves, and concentrated doubling-downHiring strategy: network access > spreadsheet diligenceCulture principles: excellence, performance, “no one takes themselves too seriously”Conviction-based investing vs consensus IC, and why omissions are the real killerThe hardest lesson in venture: managing co-founder dynamics (and when to just listen)Episode highlights 00:00 — “A+ people want to work with A+ people.” 01:46 — GTMfund’s 2026 prediction: big players come roaring back (Google, Meta, Microsoft, Uber/Waymo). 14:51 — GTMfund platform metrics: thousands of support items, intros, hires, and fundraising connects. 26:29 — Why Mark left Index to build Chemistry: big-fund lessons, rebuilt with focus. 33:39 — Chemistry’s strategy: early-stage focus, light reserves, and building for “product-market discovery.” 44:05 — “Venture doesn’t scale well.” Why Chemistry stays small to avoid bureaucracy. 49:59 — Events that actually work: chess tournaments, surfing, and hobby-driven gathering > happy hours. 54:56 — Investment process: conviction, not consensus—optimize for outliers, not averages. 1:10:32 — Hardest lesson in venture: co-founder dynamics, and learning when to listen (not “advise”). Brought to you by: AngelList From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility — from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved. As we expanded from Fund I to Fund II, AngelList took care of the back-office operations, allowing us to stay focused on what matters most: investing in world-class founders and building the strongest go-to-market network in venture.  They’ve scaled with us across funds and into the future. If your fund is growing in size or complexity, check them out at www.angellist.com/gtmfund. Follow Mark Goldberg LinkedIn: https://www.linkedin.com/in/mark-goldberg-25458110X (Twitter): https://x.com/Mark_Goldberg_X (formerly Twitter)Chemistry (website): https://www.chemistry.vc/ChemistryThe 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.

    1h 12m
  4. GTM 174: The 7% Rule: How AI Is Rewriting Customer Success Budgets (From 10% to 7%) with Abbas Haider Ali

    JAN 14

    GTM 174: The 7% Rule: How AI Is Rewriting Customer Success Budgets (From 10% to 7%) with Abbas Haider Ali

    Abbas Haider Ali is SVP of Customer Success at GitHub, where he leads a 550+ person post-sales organization supporting a $2B+ ARR business serving over 150 million developers, including more than 90% of the Fortune 100. Previously, Abbas was VP of Customer & Partner Success at Twilio following its acquisition of Segment, and has held executive roles at xMatters, Opnet Technologies, Managed Objects, and IBM. He is also a General Partner at GTM Operators Network, investing from seed through growth, and is deeply committed to mentorship and advancing underrepresented leaders in tech. Discussed in this episode: Why “AI-led growth” can hide churn and value erosionLagging vs leading indicators for retention enduranceWhy the CS investment benchmark is shifting from 10% → ~7%A simple “waterfall” for allocating post-sales budget: support → onboarding → outcomesHow to “lever up” the envelope with premium support + professional servicesWhy expansion (not renewals) is the early signal of product-market fitThe rise of AI-powered specialized generalists in post-salesWhen forward deployed engineers make sense (and when they’re just a fad)Episode highlights 00:00 — Why customer expansion is the real signal of product-market fit 00:50 — Lagging revenue vs. leading indicators of endurance 04:11 — Why the CS benchmark dropped from 10% to 7% 08:41 — How AI moved from internal efficiency to customer-facing leverage 11:41 — Why retention cost matters more than CAC in the AI era 14:17 — The simplest framework for allocating the 7% CS budget 18:53 — Founder-led CS, design partners, and early-stage PMF myths 23:16 — The rise of AI-powered specialized generalists 30:00 — When forward-deployed engineers actually make sense 49:31 — The one rule for building a durable SaaS company This episode is brought to you by our sponsor: HockeyStack If you run go-to-market, you already know the problem: your data lives everywhere. Spreadsheets, CRMs, sales calls, ad platforms… yet you’re still guessing what to do next. HockeyStack is the AI platform for modern GTM teams. It unifies all your sales and marketing data into a single system of action. Built-in AI agents help teams prospect the right accounts, improve conversions, close and expand deals, and scale what works. That’s why teams like RingCentral, Outreach, ActiveCampaign, and Fortune 100 companies rely on HockeyStack to eliminate wasted spend, take better decisions, and make space to think. Learn more at hockeystack.com Follow Abbas Haider Ali LinkedIn: https://www.linkedin.com/in/abbashaideraliX (Twitter): https://x.com/abbashaideraliGitHub: https://github.com/AbbasHaiderAliFollow Sophie Buonassisi (Host) LinkedIn: https://www.linkedin.com/in/sophiebuonassisiX (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.com  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.

    53 min
  5. GTM 173: The PLG→Enterprise Playbook: Turning Product Signals into 9-Figure Revenue with Adam Carr

    JAN 7

    GTM 173: The PLG→Enterprise Playbook: Turning Product Signals into 9-Figure Revenue with Adam Carr

    Adam Carr is the Chief Revenue Officer at Apollo, where he’s scaling revenue by layering sales on top of a $150M+ ARR product-led growth engine. Previously, Adam helped scale Miro from a PLG-led company into a global sales organization, contributing to its growth into a $17.5B business. He’s known for building systems-driven GTM teams that turn product signals into durable revenue. Discussed in this episode Why PLG is gravity (signals + acquisition) and sales is the monetization layerThe “one-team” model to prevent PLG vs. sales cannibalizationBuilding talent density (and why slowing hiring can be the fastest path)Hiring for curiosity, coachability, ownership, and team-first executionThe “architect / systems thinker” profile for modern sellersA new post-sales model: CSMs → technical GTM Engineers + intervention-led journeyUsing customer journey milestones to drive expansion and prevent churn proactivelyAI in GTM: streamlining manual work so humans focus on better conversationsEpisode highlights 00:00 — PLG is about signaling + acquisition (not monetization) 01:30 — “PLG isn’t the monetization way… it’s layering sales.” 02:41 — Talent density: hire for the next 12–18 months, not just “today” 04:50 — The soft skills that scaled Miro: curiosity, coachability, ownership 08:38 — Why Adam hires “architects” (system thinkers) instead of just sellers 10:41 — The mindset shift: celebrate value realized, not contracts signed 15:41 — Replacing CSMs with “go-to-market engineers” + an intervention model 19:14 — Turning PLG signals into PQA/PQL routing (and reducing the “noise”) 29:26 — “100M ARR is late” — when to start layering sales into PLG Guest links LinkedIn (Adam Carr):https://www.linkedin.com/in/adamhcarrFollow Sophie Buonassisi (Host) LinkedIn: https://www.linkedin.com/in/sophiebuonassisiX (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comWhere to Find GTMnow Website: https://gtmnow.comLinkedIn: https://www.linkedin.com/company/gtmnowX (Twitter): https://x.com/GTMnow_YouTube: https://www.youtube.com/@GTM_nowPodcast Directory: https://gtmnow.com/tag/podcastThe 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.

    37 min
  6. VC 2: How Cassie Young Picks Winners Before They Even Leave Their Jobs

    12/15/2025

    VC 2: How Cassie Young Picks Winners Before They Even Leave Their Jobs

    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 Primary’s 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 Duke’s Innovation & Entrepreneurship board. Discussed in this episode: How Cassie “accidentally” 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 “platform” and instead built a 30-person Impact team.How she actually sources pre-seed/seed founders before they leave their jobs.Primary’s 5-part Founder Outcomes Framework (vision, talent, JDCE, and more).The difference between real traction vs. “happy ears” and fake design partners.Why she’s picky on GTM/AI tools and looks for step-change, not incremental gains.How operators can actually break into VC (hint: it’s all about doing the work).Episode highlights 00:35 — Clay, usage-based pricing, and the $100M ARR rocketship 09:10 — The real story on AISDR: where AI reps actually work (and where they really don’t) 14:02 — Inside “The Gross Retention Apocalypse” and why AI experimental budgets are a ticking time bomb 22:46 — How Cassie accidentally became a VC and the Bill Gurley advice that changed her career path 27:17 — Why Primary hates the word “platform” and how Cassie built a 30-person Impact team for founders 36:10 — Cassie breaks down her 5-part founder outcomes framework (including “jaw-dropping customer experience”) 46:01 — Avoiding “happy ears”: how founders should really use design partners and MedPick-style rigor 57:48 — Time to value as the new north star and why nailing a tight wedge beats peanut-buttering features 1:01:29 — So you want to be a VC: Cassie’s 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 AngelList’s 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 — always there to support us and our LPs every step of the way. If you’re 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.

    1h 9m
  7. Why Old Playbooks Are Breaking and How AI Assisted GTM Actually Works | Dave Boyce

    12/10/2025

    Why Old Playbooks Are Breaking and How AI Assisted GTM Actually Works | Dave Boyce

    Dave Boyce is a go-to-market–focused technology executive, author of Freemium, and longtime SaaS operator and board member. Over two decades leading and advising B2B companies, he’s 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 Design’s Growth Institute, works with leadership teams on Bow Tie–based 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 haven’t 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 shouldn’t.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 can’t 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 — GTM is still running 20-year-old playbooks 01:29 — “Sales, marketing, CS… the last unengineered engine” 03:20 — The myth of “just add more heads” 05:50 — The Fundly story: reinvention, too late 08:30 — Why Freemium had to be written 11:01 — Three first principles of freemium 15:25 — Mapping AI across the entire customer journey 19:29 — “Automate the predictable, humanize the exceptional” 25:18 — What the Bowtie exposes that funnels hide 27:25 — Building a “minimum 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. It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence. Learn more at zoominfo.com. Follow Dave Boyce (Guest) LinkedIn: https://www.linkedin.com/in/boycedaveSubstack: https://daveboyce.substack.comWhere to Find GTMnow Website: https://gtmnow.comLinkedIn: https://www.linkedin.com/company/gtmnowX (Twitter): https://x.com/GTMnow_YouTube: https://www.youtube.com/@GTM_nowPodcast Directory: https://gtmnow.com/tag/podcastThe 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.

    36 min
  8. GTM 171: How to Build a Partner Ecosystem That Sells for You | Brian Weinberger

    12/03/2025

    GTM 171: How to Build a Partner Ecosystem That Sells for You | Brian Weinberger

    Brian Weinberger is the Chief Revenue Officer at Sisense, a leading analytics platform helping companies embed intelligence into every product experience. With over 30 years in sales leadership across New York’s tech scene, Brian has built and scaled go-to-market teams at every stage—from early-stage startups to category-defining giants like Yext, Segment, and Salesforce. Discussed in this episode The evolution of partner selling — from VARs to SIs to ecosystemsHow to know if partner selling fits your GTM modelThe delivery-first mindset that drives retentionDirect vs. partner motion: Microsoft vs. SalesforceWhy enablement is the #1 green flag for partner successPartner marketing: how to make resellers self-sustainingUsing AI to power future-ready GTM modelsThe case for hybrid work in high-performance sales culturesEpisode Highlights 00:00 — The “year four” moment when partners are selling for you 01:07 — 30 years of selling through partners in New York 03:22 — Start partner strategy with delivery, not distribution 06:32 — Why partner selling creates “superhuman” sellers 09:59 — Salesforce vs. Microsoft: direct vs. reseller — and why the future is hybrid 12:13 — The startup hack: sell delivery on your paper, subcontract partners 17:16 — A 90-day playbook for integration partnerships 21:39 — Hiring the right people to build a partner business 27:18 — How Sisense runs delivery partners and an Australian reseller 29:55 — White-labeling Snowflake: using resell to get the giant’s attention This episode is brought to you by our sponsor: BoomPop We’re deep in event planning right now, as no doubt many of you are. Whether it’s an offsite, conference, or any other kind of event, BoomPop makes that happen with end-to-end planning all in one place. They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics. Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events. Follow Brian Weinberger LinkedIn:https://www.linkedin.com/in/brianweinbergerRecommended Books What Great Salespeople Do by Michael Bosworth & Ben Zoldan — The power of storytelling in salesThe Power of Nice by Linda Kaplan Thaler & Robin Koval — Why kindness compounds in businessSacred Hoops by Phil Jackson — Coaching and leadership lessons from the Bulls dynastyReferenced Sisense: https://www.sisense.comSnowflake: https://www.snowflake.comAWS: https://aws.amazon.comSalesforce: https://www.salesforce.comMicrosoft: https://www.microsoft.comAccenture (SI example): https://www.accenture.comThe 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.

    39 min
4.6
out of 5
149 Ratings

About

The GTMnow Podcast interviews well-known tech executive, VC, and founders - the expert operators in the trenches who have ‘been there, done that’ to build some of the fastest-growing software companies. Every week, a guest joins Sophie Buonassisi to dissect their stories, revealing expert insights around what worked, what didn’t, and how things actually went down.This podcast is produced by GTMnow, the media brand of GTMfund - sharing insight on go-to-market from working with hundreds of portfolio companies backed by over 350 of the best go-to-market executives. GTMfund is an early-stage VC fund focused on investing in the most exciting, up-and-coming B2B SaaS companies across the world. The LP network consists of VP and C-level Sales, Marketing, and Customer Success leaders from companies like DocuSign, Salesforce, LinkedIn, Snowflake, Okta, Zoom, and many more.Visit gtmnow.com for more details and to sign up for our newsletter and other content resources.

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