The GTMnow Podcast

GTMnow
  • 4.6 (149)
  • TECHNOLOGY
  • UPDATED WEEKLY

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. GTM: Lessons from Figma, Dropbox, and Building Iconic Brands in the Age of AI with Figma’s CMO, Sheila Vashee

    2D AGO

    GTM: Lessons from Figma, Dropbox, and Building Iconic Brands in the Age of AI with Figma’s CMO, Sheila Vashee

    NEW: @Sheila Vashee (CMO of @Figma) joins GTMnow to share how she thinks about brand building across every stage. From selling brownies at age eight, to second marketing hire at Dropbox scaling to $1B+ in annualized revenue, to now leading marketing at one of the most beloved software brands in the world, Sheila has seen it all. In this conversation, you’ll learn what brand actually means (hint: it's not your logo), how PLG companies make the leap to enterprise, why being obsessively close to your customers is a compounding advantage, and how AI is reshaping the marketing playbook without replacing the human craft that sets great brands apart. Guest links:- Guest - LinkedIn: https://www.linkedin.com/in/sheilavashee/ - Guest company - LinkedIn: https://www.linkedin.com/company/figma/ - Guest company website: https://www.figma.com/ Host links: - Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ - Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona - Newsletter: https://thegtmnewsletter.substack.com Sponsors: - HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/ - Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/gtmfund  and get three months free with the code GTMFUND. Transcript available under the episode here: https://gtmnow.com/tag/podcast/ Subscribe to GTMnow for the latest episodes! https://gtmnow.com/ Highlights: 00:00 – The brownie stand: why brand building started at age eight 03:55 – How Sheila defines brand: it's what people say when you're not in the room 05:08 – Joining Dropbox as the second marketing hire 06:07 – Space Race: the campaign that defined Dropbox's early strategy 06:56 – What consumer marketing taught her about driving revenue 08:29 – Measuring brand ROI through match market testing 09:15 – How Figma thinks about brand building at a macro level 11:21 – The PLG-to-enterprise equation: what Figma did early that Dropbox waited too long on 15:02 – Why building the enterprise team is both operational and optical 17:12 – How Figma ingests customer feedback at scale 18:26 – AI at Figma: enabling human creativity, not replacing it 21:13 – What the venture side taught her about staying sharp as an operator 22:33 – Why the shift from SEO to GEO is inevitable and what to do about it 23:24 – Why Reddit is back and social is a core growth lever 24:51 – The mentors that changed her trajectory 28:59 – One piece of advice: make good $h!t For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

    31 min
  2. VC: 116 Quarters on Quota and What Every Sales Leader Should Be Tracking, with Bill Binch, Operating Partner at Battery Ventures

    3D AGO

    VC: 116 Quarters on Quota and What Every Sales Leader Should Be Tracking, with Bill Binch, Operating Partner at Battery Ventures

    Bill Binch (Operating Partner at Battery Ventures) joins GTMnow to share the operational frameworks he's built across 116 quarters on quota, and what actually changes when you move from driving revenue to advising an entire portfolio. Before Battery, Bill was employee #16 at Marketo, where he led sales from zero revenue through IPO and a Vista Equity acquisition. He then served as CRO at Pendo, helping scale ARR to nearly $100M in only three years. His career spans some of the most defining sales organizations in enterprise software, from Oracle to PeopleSoft. - Bill Binch - LinkedIn: https://www.linkedin.com/in/bill-binch-302a4a2/, - Battery Ventures - LinkedIn: https://www.linkedin.com/company/battery-ventures/ - Battery Ventures website: https://www.battery.com/ Host links: - Max - LinkedIn: https://www.linkedin.com/in/maxaltschuler/ - Max - X: https://x.com/HackItMax - Paul - LinkedIn: https://www.linkedin.com/in/paulsirving/ - Paul - X: https://x.com/PaulGTM - Newsletter: https://thegtmnewsletter.substack.com 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 https://angellist.com/gtmfund. Transcript available under the episode here: https://gtmnow.com/tag/podcast/ Subscribe to GTMnow for the latest episodes! https://gtmnow.com/ Highlights: 00:00 – Bill's career path: Oracle, Marketo employee #16, Pendo CRO, and choosing Arizona over tech hubs 15:01 – Battery's approach: why there's no one-size-fits-all playbook 19:56 – Outreach's accidental sales experiment: remote vs. in-person results 21:23 – What nobody tells you about the transition from CRO to operating partner 23:01 – Gold watch and slippers? Why operating partner is not a retirement plan 27:15 – Three audiences: prospective investments, portfolio companies, and Battery internal 31:42 – Investing in GTM tech: why Battery went 7 years between bets 34:44 – The Phil Fernandez warning: "your hand is on the wheel, now you're a passenger" 36:44 – Why every forecast should start with "my quota is" not "my forecast is" 38:33 – The metric most companies miss: plan vs. planned quota vs. actual quota deployed 40:05 – The mojo metric: 6 daily pipeline inputs that tell you everything 43:16 – Helping technical founders sell: the one-eyed man in the land of the blind 48:04 – Advice for operators who want to move into an operating partner role 51:03 – The sales and marketing dance: what real GTM alignment sounds like in a board room For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

    52 min
  3. GTM: BREAKING: Inside Nooks’ Launch: Why AI-Native Sales Tools Are Challenging Legacy Platforms, with Co-Founder & CEO Dan Lee

    FEB 24

    GTM: BREAKING: Inside Nooks’ Launch: Why AI-Native Sales Tools Are Challenging Legacy Platforms, with Co-Founder & CEO Dan Lee

    Dan Lee (Co-Founder & CEO of Nooks) joins GTMnow to give a behind the scenes on how Nooks is launching a new Agent Workspace and AI Sequencing layer designed to operate across the full action set of a rep’s day — calls, emails, research, prospecting, and strategy. The conversation explores why top of funnel is changing the fastest, why traditional sequencing tools optimize the “move” but not the strategy, and how AI systems that learn from rep behavior can compound advantage over time. As adoption deepens, automation can move from ~40% of outbound execution toward 70% and beyond, while switching away resets that intelligence. We also discuss the broader category shift: customers pushing AI-native tools to take on incumbents, the rise of agent workspaces as the new interface for GTM teams, and why calls remain the most data-rich channel in outbound compared to silent email non-responses. Guest links: Guest - LinkedIn: https://www.linkedin.com/in/dan9lee/ Guest company - LinkedIn: https://www.linkedin.com/company/nooksapp/ Guest company website: https://www.nooks.ai/ Host links: Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona Newsletter: https://thegtmnewsletter.substack.com Sponsors: HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/ Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/gtmfund and get three months free with the code GTMFUND. Transcript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.com/ Highlights: 00:00 – Announcing the Agent Workspace and AI sequencing product 01:25 – Why sales is fundamentally human (even in the AI era) 02:39 – The Agent Workspace as the human–AI interface 02:56 – Why legacy sequencing tools were built for a manual world 04:14 – The sales chess analogy: understand the board before making the move 05:02 – Reps spend too much time "making the move" 06:00 – Nooks as a simulation engine: suggesting the next best move 07:07 – The reason for the email isn't in the email 07:45 – Signal vs. noise: reasoning like a rep 10:00 – Why calls are the most data-rich outbound channel 10:25 – Using calls to move up the org chart 13:12 – The sales iceberg analogy: what's above vs. below the surface 13:38 – Don't pay enterprise reps to find phone numbers 14:15 – Doing more with less vs. doing more with more 15:00 – Why sales remains competitive even with full automation 16:38 – Owning the end-to-end prospecting workflow 18:53 – How Nooks learns from rep decisions over time 19:15 – The path from 40% → 90% AI-written emails 19:58 – Reimagining sequences with org chart intelligence 22:17 – Evolution from virtual classroom to virtual sales floor 25:11 – Pivoting into the sales use case before ChatGPT 26:08 – Near-death experiences and surviving the pivot graveyard 27:03 – Nooks' six core values 27:57 – "Ask why" as a core operating principle 28:39 – Ruthless prioritization as a startup advantage 29:25 – AI literacy as a hiring filter for GTM roles 30:07 – Making sales sexy for top engineers 31:31 – Hiring across the board in 2026 For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

    32 min
  4. GTM: The End of GTM Sprawl: How HockeyStack is Rebuilding Go-to-Market Around AI, with Co-Founder Emir Atli

    FEB 17

    GTM: The End of GTM Sprawl: How HockeyStack is Rebuilding Go-to-Market Around AI, with Co-Founder Emir Atli

    Emir Atli (Co-founder and CRO of HockeyStack) joins GTMnow to share how go-to-market is shifting in the AI era — from fragmented tools and GTM sprawl to unified, AI-native platforms built on a single data foundation. Originally known for attribution and market intelligence, HockeyStack is evolving into a central operating system for go-to-market, spanning marketing, sales, and post-sales through AI agents, blueprints, and an execution layer. We also explore weekly GTM sprints, founder-led content as a pipeline driver (even with 100 followers), and the long-game mindset behind building a generational company from age 20 after YC. In this episode, we cover:- Why you can’t layer AI onto legacy GTM — you must rebuild GTM around AI - The “sprawl crisis” and why siloed tools break without a single data foundation - HockeyStack’s evolution from attribution to a unified GTM operating system - AI agents, blueprints, and the shift from reporting to execution - Why consolidation is moving from tools to full buyer journey control - The case for a winner-takes-all GTM platform - How AI increases leverage across reps, managers, and pipeline reviews - Weekly GTM sprints and faster iteration cycles in the AI era - Founder-led content as a core growth engine and pipeline driver - LinkedIn as a top channel for MQL-to-opportunity and deal acceleration - The 10-year mindset, YC lessons, and building a generational company Guest links: Emir Atli - LinkedIn: https://www.linkedin.com/in/emiratli/ - HockeyStack - Website: https://www.hockeystack.com/ - HockeyStack - LinkedIn: https://www.linkedin.com/company/hockeystack/ Host links: - Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ - Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona - Newsletter: https://thegtmnewsletter.substack.com Sponsors:Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/?via=gtmfund&dub_id=ytmcNnCjtlqCbgH5 and get three months free with the code GTMFUND. Transcript available under the episode here: https://gtmnow.com/tag/podcast/ Subscribe to GTMnow for the latest episodes! https://gtmnow.com/ Highlights: 00:00 – The GTM sprawl crisis and why AI breaks in siloed systems 01:50 – From attribution to a GTM operating system 02:41 – Launching AI agents, blueprints, and the execution layer in 2026 03:57 – Building a single data foundation across the buyer journey 05:09 – Why GTM must be rebuilt around AI (not layered with tools) 06:23 – Doing "more with more" and increasing management leverage 07:30 – Tool consolidation vs controlling the buyer journey 08:48 – 2026–2028: the great GTM consolidation wave 09:01 – The case for a winner-takes-all GTM platform 10:10 – Moat: data foundation + application layer 11:35 – Expanding horizontally across marketing, sales, and post-sales 14:28 – Running GTM in weekly sprints like an engineering org 14:46 – Content as a core investment and distribution strategy 15:26 – Why connected TV works for B2B brand trust 16:43 – Faster GTM iteration cycles in the AI era 17:47 – LinkedIn as the top pipeline and opportunity channel 18:12 – Product stories, personal stories, and data stories in content 21:02 – How founders carve out time to create content 22:43 – Generating first customers from LinkedIn with 100 followers 23:45 – Founding journey: pivoting into market intelligence 25:37 – YC lesson: make something people love before scaling 27:18 – The 10-year commitment mindset from YC advice 30:13 – Executive coaching and founder bottlenecks 31:53 – In-person culture and competing in the AI era 33:26 – Whiteboarding interviews vs AI-generated case studies 34:35 – Final advice: build a good business and enjoy the process For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

    35 min
  5. VC: How VCs Evaluate Technical Founders (TAM, Moats & Diligence), with Amanda Robson, Founder and GP of Modern Technical Fund

    FEB 17

    VC: How VCs Evaluate Technical Founders (TAM, Moats & Diligence), with Amanda Robson, Founder and GP of Modern Technical Fund

    Amanda “Robby” Robson (Founder of Modern Technical Fund) joins GTMnow to break down how she evaluates companies at the very earliest stages and why discipline matters more than ever in today’s market. Amanda has spent over a decade in venture before launching Modern Technical Fund, investing across verticals ranging from security and compliance to developer tools at firms like Norwest and Cowboy Ventures. Her investment thesis is centered on backing elite technical founders early and helping them translate deep engineering talent into real products, real customers, and real momentum. In this conversation, we unpack how Amanda thinks about founder quality, market timing, and risk when there’s limited data and plenty of noise, which is more critical than ever in an AI-heavy investing environment. Guest Links Amanda’s LinkedIn: https://www.linkedin.com/in/amanda-robson-7227685b/ Amanda’s Twitter: https://x.com/robby_mtf Modern Technical Fund’s LinkedIn: https://www.linkedin.com/company/modern-technical-fund/ Modern Technical Fund website: https://moderntechnicalfund.com/ Host links: Max - LinkedIn: https://www.linkedin.com/in/maxaltschuler/ Max - X: https://x.com/HackItMax Paul - LinkedIn: https://www.linkedin.com/in/paulsirving/ Paul - X: https://x.com/PaulGTM Newsletter: https://thegtmnewsletter.substack.com 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. Transcript available under the episode here: https://gtmnow.com/tag/podcast/ Subscribe to GTMnow for the latest episodes! https://gtmnow.com/ Highlights: 00:00 – Why Modern Technical Fund exclusively backs technical founders 02:15 – What actually defines a “technical founder” beyond coding ability 03:45 – Why product judgment and customer instinct matter early 05:05 – How early teams split engineering and go-to-market roles 07:10 – When investor advice helps and when it gets in the way 09:05 – Why calibrating the hiring bar matters more than providing playbooks 12:40 – How network-driven support helps founders see what “great” looks like 15:45 – Why valuation discipline sets the bar in today’s market 17:10 – When first-time founders become too risky at certain prices 19:40 – How early-stage defensibility often comes down to the team 27:20 – Why TAM momentum matters more than static market size 30:30 – How small markets quietly turn into billion-dollar categories 39:55 – What separates real AI companies from AI theater 41:40 – Why infrastructure and data tools benefit most from AI tailwinds For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.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_/

    56 min
  6. GTM: How Intercom Built the Highest-Performing AI Agent on the Market Using Outcome-Based Pricing with Archana Agrawal, President at Intercom

    FEB 10

    GTM: How Intercom Built the Highest-Performing AI Agent on the Market Using Outcome-Based Pricing with Archana Agrawal, President at Intercom

    Archana Agrawal (President of Intercom) joins GTMnow to share how Intercom (founded in 2011) successfully restructured its product, pricing, and go-to-market to become AI-native at a speed and scale most legacy SaaS companies haven’t achieved. Their agent, Fin, now handles 80%+ of support volume, resolves 1M customer issues per week, and has grown from $1M to $100M+ ARR with a $0.99 outcome-based pricing model backed by up to a $1M performance guarantee if resolution targets aren’t met. In this episode, we cover:- Why customer support is fundamentally a 24/7 business - How Fin now handles 80%+ of customer queries through automation - Why human empathy often breaks down in real-world support workflows - How AI makes instant, individualized service possible for the first time - Why Intercom put a million-dollar guarantee behind its resolution rate - What it takes to confidently price software on outcomes - Why the future of support is humans + AI Guest links: - Archana Agrawal - LinkedIn: https://www.linkedin.com/in/archana-agrawal/ - Intercom - LinkedIn: https://www.linkedin.com/company/intercom/ - Intercom’s Fin Agent: https://fin.ai/ Host links: - Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ - Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona - Newsletter: https://thegtmnewsletter.substack.com Sponsors: HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/ Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/?utm_medium=podcast&utm_source=gtmfund&utm_campaign=intercom-episode  and get three months free with the code GTMFUND. Transcript available under the episode here: https://gtmnow.com/tag/podcast/ Subscribe to GTMnow for the latest episodes! https://gtmnow.com/ Highlights: 00:00 – Why Intercom went all-in on AI 03:23 – What Fin is and how it changes customer support 05:27 – How Fin scaled to a 67% resolution-rate 06:38 – The thinking behind 99¢ outcome-based pricing 08:54 – Why customers don’t want to pay for activity 09:10 – How outcome-based pricing aligns incentives 09:57 – What changed for sales, success, and revenue operations 15:10 – How Intercom thinks about forward-deployed engineers 16:22 – Why the future is humans + AI 18:56 – The real moat: product feedback loops at scale 19:32 – Why Intercom put a million-dollar guarantee behind results 23:29 – Why enablement is now the GTM bottleneck 32:24 – From $1M to nearly $100M: what Fin’s growth reveals 38:26 – Hiring in a world with no playbooks 42:20 – How Archana learns from podcasts, books, and customers For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

    46 min
  7. GTM: Why Most Founders Build the Wrong Company (And Realize It Too Late), with Lou Shipley, Former CEO and Co-Author of Unlikely Entrepreneurs

    FEB 3

    GTM: Why Most Founders Build the Wrong Company (And Realize It Too Late), with Lou Shipley, Former CEO and Co-Author of Unlikely Entrepreneurs

    Lou Shipley (three-time CEO, Harvard Business School professor, and author of Unlikely Entrepreneurs) joins GTMnow to break down why most founders struggle to turn good ideas into great companies. Lou has led companies through acquisitions, teaches sales and go-to-market at Harvard, and has spent decades studying what actually separates companies that scale from those that stall. In this conversation, we unpack why understanding customer pain and learning how to sell are still the two most important founder skills, especially as product moats decline and go-to-market becomes the real differentiator. In this episode, we discuss: - Why understanding customer pain matters more than having a great idea - Why early selling should optimize for learning, not revenue - Why founders can’t outsource sales too early - How distribution becomes a competitive advantage at scale - What makes “unlikely entrepreneurs” outperform expectations - Why small, high-quality teams beat large organizations - Why churn is a symptom, not the root problem - How product-market fit quietly changes as companies grow - Why founders must evolve from heroic sellers to system builders - How culture becomes a real go-to-market asset Lou also shares lessons from teaching sales at Harvard, profiling 13 unlikely entrepreneurs, and working with founders who realized too late that they were building the wrong company for the wrong customer. If you’re a founder, operator, or investor trying to avoid costly early mistakes and build a company that actually scales, this episode will give you a clearer mental model for what matters most. Timestamps: 00:00 – What actually makes a company great 00:26 – Why early selling is about learning, not revenue 01:47 – Why founders misunderstand customer pain 02:06 – “If you build it, they will come” is a lie 02:33 – Distribution as the real moat 02:58 – What makes an “unlikely entrepreneur” succeed 06:15 – Why age and experience increase founder success 07:01 – Curiosity, coachability, and risk elimination 09:29 – Why founders can’t outsource sales too early 15:26 – Pattern recognition vs short-term ARR 21:10 – Founder-led sales vs scalable systems 29:12 – Leadership, culture, and delegation 33:18 – Founder evolution from $1M to $100M 38:24 – When product-market fit starts to break 39:15 – Why churn is a lagging indicator 39:54 – Why small teams outperform large ones 44:22 – Lessons from Unlikely Entrepreneurs 45:23 – Final 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:LinkedIn: https://www.linkedin.com/in/loushipley/X: https://twitter.com/loushipleyHost (Sophie Buonassisi) links:LinkedIn:  https://www.linkedin.com/in/sophiebuonassisi/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_/

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

    JAN 28

    GTM: 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
See All (616)

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.

Information

  • Creator
    GTMnow
  • Years Active
    2018 - 2026
  • Episodes
    616
  • Rating
    Explicit
  • Copyright
    © GTMnow
  • Show Website
    The GTMnow Podcast

You Might Also Like