The GTMnow Podcast

Auren Hoffman (Flex Capital) joins the GTMnow podcast to share some of the most contrarian takes in tech today, from why AI moats are gone, to why your next VC meeting will be with a bot, to why AI is secretly going to trigger a baby boom.In this episode:- Why Auren runs 500+ AI agents to source deals, and what that means for founders raising capital- The "agent-to-agent" meeting prediction: by end of 2026, first VC conversations will be fully automated- Why every software moat has been "blown up" and what Salesforce, LinkedIn & DocuSign need to do to survive- The OpenAI x The Hustle acquisition breakdown: why it's the smartest (and cheapest) distribution play in AI- Why missing a great deal is 10x more painful than making a bad one, Auren's honest VC mistake framework- The baby boom thesis: why AI, IVF, self-driving cars & cheaper energy could reverse the fertility decline- Why companies won't sign yearly SaaS contracts anymore, and what that means for every B2B founderAuren Hoffman is the founder of Flex Capital, SafeGraph, and LiveRamp. He's an early backer of Replit, Perplexity, Rippling, Vercel, Coinbase, Chime, and AppLovin.Connect with Max: https://x.com/hackitmaxhttps://www.linkedin.com/in/maxaltschulerConnect with Auren:https://x.com/aurenhttps://www.linkedin.com/in/auren/https://www.youtube.com/@summationpodGTMnow shares how the best in tech build, scale and invest.Visit gtmnow.com for more episodes, The GTMnow Newsletter editions, and other content.GTMnow is run by GTMfund - we are an early-stage venture firm made up of 350+ go-to-market executives from the fastest-growing companies.Chapters:00:00 - Intro01:05 - GTMfund Q1 recap 02:38 - OpenAI x The Hustle breakdown 06:18 - Redpoint's optimal VC deployment period 11:24 - Auren Hoffman intro 13:04 - Why am I seeing this deal? 26:26 - Sizing up founders at Replit, Perplexity & Rippling 28:49 - What separates great founders 32:10 - 500+ AI agents for deal sourcing 33:40 - Agent-to-agent VC meetings by 2026 45:13 - Every software moat is blown up 49:09 - Who kills Salesforce next? 51:30 - Why no one signs yearly SaaS contracts anymore 51:50 - AI will trigger a baby boom 56:22 - Thinking generationally#AI #VentureCapital #GTM #StartupFunding #AurenHoffman #FlexCapital #SaaS #ArtificialIntelligence #Founders #SalesVisit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube: https://www.youtube.com/@GTM_nowFollow us on TikTok: https://www.tiktok.com/@gtmnow_Follow us on Instagram: https://www.instagram.com/gtmnow_/The GTMnow PodcastThe 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. 

Wade Foster is the CEO of Zapier, a company that sits between 7,000+ apps and runs millions of automations every single day. That gives him a front-row seat to how companies are actually adopting AI, not just talking about it.In this episode, Wade breaks down the exact decisions he made at Zapier to go from 10% AI usage to 97% company-wide, why agents and workflows are not the same thing, and what most leaders are getting completely wrong about AI fluency.What you'll learn:The difference between agents and workflows (and when to use which)What triggered Zapier's internal "Code Red" after GPT-4 launchedThe one-week hackathon that took AI adoption from 10% to 50% overnightThe AI fluency rubric Zapier built: Unacceptable, Acceptable, Adaptive, TransformativeWhy leaders who aren't using AI are the biggest bottleneck in their companiesHow to measure AI ROI: floor raisers vs ceiling raisersHow AI now handles 50% of Zapier's customer support ticketsWade's personal "advisory council" of AI sub-agents he uses for every major decisionWhy building a company today is 10x cheaper but distribution is 10x harderThe truth about fundraising: you're selling your company, not raising moneyHow Zapier stayed profitable by only hiring when it hurtGuest: Wade Foster, CEO of Zapier LinkedIn: https://www.linkedin.com/in/wadefoster/Company - Zapier: https://zapier.comHost: Sophie Buonassisi, SVP Marketing at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter: https://thegtmnewsletter.substack.comEpisode highlights0:00 - Intro1:13 - The Seinfeld Quote & Kanye Text story3:16 - Workflows vs. Agents: What's the difference?6:09 - Zapier's Code Red moment8:55 - The hackathon that moved AI adoption from 10% to 50%12:06 - Making AI fluency a hiring requirement13:47 - Building the AI fluency rubric16:40 - Why leaders are the biggest AI bottleneck18:12 - Revenue impact of going AI-first22:09 - Would Wade build Zapier differently today?23:20 - Is Zapier's moat at risk from agents?24:59 - Staying profitable with minimal capital28:37 - The riskiest contrarian bet that paid off31:52 - Wade's 3 personal AI workflows36:53 - Favorite books for foundersGTMnow is the media brand of GTMfund, sharing go-to-market insights from working with hundreds of portfolio companies backed by 350+ of the best GTM executives. Subscribe for weekly episodes with the operators, founders, and investors behind the fastest-growing software companies.

Ed Sim has been a VC for 30 years. He's backed companies like Clay, Front, BigID, and Snyk. He writes What's Hot in Enterprise IT every single Saturday, 489 weeks in a row. And right now, he says this is the most exciting and terrifying moment he's ever seen in his career.In this episode, Max and Ed break down what's actually happening inside startups and boards right now, why the old playbooks are dead, and what separates the companies that will survive this AI shift from the ones quietly getting killed by it.Discussed in this episodeWhy engineering is no longer your bottleneck (and what is)The 5 P's Ed uses to evaluate every inception-stage investmentThe autonomous enterprise thesis and what it means for how companies are builtWhy AI-native leadership is now a survival reqxtuirement, not a nice to haveThe full Clay story: $600K to $100M ARR, how they stayed lean, and what actually unlocked growthThe 3 CH's framework for being a great board partner to foundersWhy the best founders today are inside the AI jet stream, not chasing itWhat every board meeting sounds like right nowEpisode highlights0:00 Intro & 1:05 Episode Preview: Ed Sim & Key Takeaways3:10 The Jet Stream Analogy: Two Types of Companies5:43 How GTM Operators Should Evaluate Companies Like Angel Investors7:20 The Collapsing of Moats & AI-Native Business Opportunities10:00 Rebuilding Industries vs. Selling Software to Them15:00 Why Old GTM Playbooks Are Dead17:46 Ed Sim's Background: From Cutco to 30 Years in VC21:43 The Five P's of Inception Investing23:04 How to Evaluate Potential & TAM in a Fast-Changing Market25:40 Staying Ahead of the Jet Stream as a Founder26:32 The Autonomous Enterprise Thesis28:44 Agent of the Week: How Companies Should Adopt AI Agents29:10 How Agents Are Changing Engineering Bottlenecks31:15 What Incumbents Must Do to Survive the AI Wave32:53 Intercom, Snowflake & How Legacy Companies Are Adapting36:43 The Clay Story: How They Found Their Footing38:33 The Three C's of Working With Founders (Cheer, Challenge, Chill)40:07 Clay's Growth Trajectory: $600K to $100M+ ARR41:10 Clay's Agency GTM Model & Community Moat43:50 Ed's Fund Model: $500K to $15M Checks at Inception46:57 What's Hot in Enterprise IT & Venture Right Now48:03 Closing RemarksKey takeaways1. Engineering is no longer your bottleneck. Your people are. Code is shipping faster than your sales, marketing, and customers can absorb it. The constraint has flipped completely and most companies haven't noticed yet.2. Painkillers beat vitamins every time. The only startups worth backing at inception are solving a hair-on-fire problem someone desperately needs fixed, not a nice-to-have they can live without.3. The 3 CH's of being a great board partner. Know when to Cheer (when founders are getting beaten up), when to Challenge (when they feel invincible), and when to Chill (when they just need breathing room to figure it out). Elliot used all three with Clay to perfection.4. If your CEO came from sales, you are in trouble. Surviving this AI shift requires product-driven, agent-native leadership at the top. The companies that adapted, Snowflake, Intercom, Atlassian, all changed leadership first.5. The best founders are inside the AI jet stream, not chasing it. The question Ed asks every founder today: are you struggling to keep up, or are you the one constantly shipping and adapting faster than anyone can copy you?Thank you to our sponsorConnect with Ed: https://x.com/edsim  / edsim  Connect with Max: https://x.com/hackitmax  / maxaltschuler  Connect with Paul:https://x.com/PaulGTM  / paulsirving  GTM Now is the media extension of GTM Fund, a venture capital firm investing in early-stage B2B companies. Every episode features the operators, investors, and founders defining what modern go-to-market looks like.GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

This episode was recorded prior to Teresa Anania’s move to Chief Customer Officer at Verint. At the time of recording, she was SVP of Customer Experience at Sophos.Teresa Anania (CCO at Verint, formerly CCO at Sophos) joins GTMnow to share how she's built customer success into a true revenue engine at a company serving 600,000 customers across over $1 billion in annual revenue, and why the old reactive, relationship-based CS model is no longer cutting it.At Sophos, the threat landscape is compounding fast. AI is accelerating the speed and sophistication of attacks, which means response times, customer journeys, and success motions all have to evolve in lockstep in order to keep up. Teresa has spent her career at companies like Zendesk, Autodesk, and ON24 building the operational frameworks that make that possible at scale.Mentioned Resources: Cleverbridge: Merchant of Record for Software & SaaS​Guest links: Teresa Anania - LinkedIn: https://www.linkedin.com/in/teresa-anania/Sophos - LinkedIn: https://www.linkedin.com/company/sophos/Sophos - Website: https://www.sophos.com/Host links:Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Sophie Buonassisi - X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comSponsors: - HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/- Nooks - the AI workspace for outbound teams, where AI agents handle prospecting, research, and sequencing so reps can focus on conversations. Learn more at https://www.nooks.ai/- Cleverbridge – the digital commerce platform helping enterprises optimize post-sale revenue through renewals, winbacks, and add-ons with buyer-friendly purchasing experiences. Learn more at https://grow.cleverbridge.com/lp/digital-commerceTranscript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.com/Highlights:00:00 – Sophos at a glance: 600K customers, $1B+ in revenue, and why cybersecurity keeps growing when everything else slows down01:51 – AI vs. AI: how threat actors are using the same tools Sophos is building against03:02 – The 2026 Active Adversary Report: why attackers are logging in, not breaking in04:20 – Attackers move in 3-4 hours and how Sophos structures CS to respond before the customer even knows there's a problem06:05 – Connecting CS activity directly to retention and expansion: the attribution model08:45 – Advice for early-stage companies that want this kind of rigor but don't have perfect data yet10:06 – Automation as a scale lever: crawl, walk, run and why you should start at the end of the renewal cycle13:43 – The future of go-to-market: self-serve from first touch through win-back, powered by AI18:20 – "The customer should never feel your org chart": building a digital journey that meets people where they are20:39 – Going from legacy manual to digital without blowing up the business22:00 – Dynamic segmentation: why hard lines on ACV are the wrong way to assign CS coverage26:02 – The two-by-two that actually matters: risk, spend, and growth potential32:08 – The humble confidence hire: why Teresa looks for this specific combination across her entire org34:15 – The 5-to-1 scorecard and what Teresa has learned about earning customer trust over time36:14 – Inner and outer feedback loops: how Sophos turns NPS data into cross-functional action38:11 – Why retention has to be an all-company meeting, not a CS slideFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

Jason Demant just joined GTMfund as Partner, Head of Networks after 6 years at Foundation Capital where he reviewed over 1,000 emerging manager funds and invested in 100+.In this episode, Max (GP), Paul (GP), and Jason break down what separates the VC firms that survive from the ones that quietly die, why the best founders today are skipping mega funds at pre-seed, and what LPs are excited in about emerging managers.What we cover:The real reason raising from mega funds at pre-seed can backfireWhy less than 10% of VC firms ever make it to Fund 3What makes an emerging manager fundable (sourcing, founder support, durability)The media flywheel that gives certain funds an unfair advantageHow LPs should think about mega funds vs. emerging platforms (the barbell approach)Why founders are the ones now choosing their investors, not the other way aroundConnect with Jason:   / jasondemant   Connect with Max:   / maxaltschuler  Connect with Paul:   / paulsirving  GTMnow is the media extension of GTMfund, a venture capital firm investing in early-stage B2B companies. Every episode features operators, investors, and founders on the front lines of go-to-market.Timestamps:0:00 Intro1:54 Jason's Background at Foundation Capital3:07 Why Jason Chose GTMfund4:35 How Media Has Evolved in the VC Ecosystem6:20 What Separates Winning Emerging Managers from the Rest8:28 GTM Fund's Flywheel: Fund, Community & Media10:41 Building a VC Firm Is Like Building a Startup12:31 Emerging Managers vs. Mega Funds (a16z, Lightspeed)14:01 Why Top Founders Are Picking Emerging Managers for Early Rounds16:36 The LP Perspective: Emerging Managers vs. Platform Funds18:39 The Barbell Strategy for LP Portfolio Construction19:14 Early Stage vs. Growth Stage: Risk, Return & Why Early Stage Wins20:18 Closing Thoughts & Welcome to the TeamVisit us and subscribe: https://gtmnow.comFollow us on LinkedIn:   / gtmnow  Follow us on X (Twitter): https://x.com/GTMnow_Follow us on YouTube:    / @gtm_now  Follow us on TikTok:   / gtmnow_  Follow us on Instagram:   / gtmnow_  Sign up for the Newsletter: https://thegtmnewsletter.substack.com

NEW: @Paul Fipps (President of Global Customer Operations at @ServiceNow) joins GTMnow to break down how ServiceNow built the customer engine behind $10B+ in revenue and 20%+ growth for five consecutive years.From CIO at Under Armour overseeing a 300 million-member connected fitness ecosystem, to now leading global sales, customer success, field marketing, and partners at one of the most disciplined GTM organizations in enterprise software, Paul has seen what it takes to scale from both sides of the table.In this conversation, you'll learn:- Why complacency is a bigger threat than competition at scale- How to detect churn long before it shows up in a report- What a CIO cancelling 900 AI pilots tells you about where enterprise AI is actually headed- How ServiceNow unified sales, customer success, field marketing, and partners into one GTM motion so customers never feel the org chart- Why ServiceNow monitors customer health daily — and what signals their teams actually track- How community became a core GTM advantage, not just a marketing channel- How ServiceNow’s AI Control Tower governs agents across the enterprise stack- Inside “Now on Now”: how ServiceNow generated $335M in annualized AI productivity gains using its own platform- How integrating Claude into the GTM workflow cut account planning from days to minutes- What DTC product thinking from Under Armour unlocked in enterprise GTM- How ServiceNow shifted from 6-month product releases to monthly innovation cycles- Paul’s advice for building a world-class GTM organization: put the best people in the right seatsGuest links: Guest - LinkedIn: https://www.linkedin.com/in/paulfipps/Guest company - LinkedIn: https://www.linkedin.com/company/servicenow/Guest company website: https://www.servicenow.com/Host links:Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Sophie Buonassisi - X (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comSponsors:HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/Transcript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.com/Highlights:00:00 – How ServiceNow built one of the most disciplined GTM engines in enterprise software01:22 – 80B workflows, $10B+ revenue: what gets harder and easier at scale02:05 – Why complacency is the real threat at scale05:49 – Why ServiceNow unified sales, customer success, field marketing, and partners under one motion06:49 – The post-sale handoff problem: signing on Friday, new team showing up Monday08:22 – How to spot churn before it shows up in a report09:55 – How often ServiceNow teams check customer health12:25 – If you took away the dashboards, how would you know a customer is truly winning?15:35 – Why Paul blocks calendar time every week for direct customer conversations (and responds within 24 hours)17:53 – From Under Armour to ServiceNow: what DTC product thinking unlocks in enterprise B2B21:06 – The personalization gap in B2B enterprise software and how ServiceNow is closing it25:18 – The CIO with 900 AI pilots who cancelled every single one26:03 – How embedding agentic AI inside existing workflows drives measurable ROI32:39 – "Now on Now": $335M in productivity gains running on their own platform34:18 – Integrating Claude into the GTM motion for all 10,000 go-to-market team members36:44 – The AI control tower: governing every agent across the entire enterprise39:15 – Paul's one piece of advice for every GTM leader: get the best people in the right seats40:21 – The book that shaped Paul's career: Execution by Bossidy & CharanFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

Brett Queener (Partner at Bonfire Ventures) joins GTMnow to share what three decades across Siebel, early Salesforce, co-founding, and seed-stage investing has taught him about what actually wins now that software is cheaper and faster than he ever imagined.Brett was one of the earliest GTM hires at Salesforce when it had seven employees. He helped build the go-to-market playbook that defined a generation of SaaS: enterprise segmentation, sales motion design, product marketing, the whole works. He then co-founded SmartRecruiters, angel invested in companies like Outreach and Pando, and eventually joined Bonfire Ventures as a Partner to do early-stage investing the way he thinks it should be done: hands-on, operator-led, and built around founders who are ruthless about execution.Guest links:Brett Queener - LinkedIn: https://www.linkedin.com/in/brettqueener/Bonfire Ventures - LinkedIn: https://www.linkedin.com/company/bonfire-ventures/Guest company website: https://www.bonfirevc.com/Host links:Max - LinkedIn: https://www.linkedin.com/in/maxaltschuler/Max - X: https://x.com/HackItMaxPaul - LinkedIn: https://www.linkedin.com/in/paulsirving/Paul - X: https://x.com/PaulGTMNewsletter: https://thegtmnewsletter.substack.comBrought to you by: AngelListFrom 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 – Brett's career: Siebel, Salesforce employee #7, co-founder, angel investor, seed-stage VC06:58 – The big shift: from passive CRUD apps to agentic software that does the work for you08:07 – "Failing upwards" and what the fastest-growing companies taught Brett about investing in people10:58 – Why Brett moved into VC: 25 years of operators whose collective worth hit $25B16:50 – What Brett looks for in founders now and how it's changed over 6-7 years18:05 – Why anybody can build anything: Brett builds a fully functional travel app in 15 minutes19:20 – The last remaining moat in software26:20 – The real threat to Salesforce and HubSpot and why their ecosystem might be the boat anchor34:20 – How the entire GTM motion changes when the product does the job instead of just enabling it38:30 – Why communicating the right problem to the right ICP hasn't changed in 30 years39:20 – Deploy first, close later40:20 – Why face-to-face matters more now, not less41:00 – Why events are driving 75%+ of pipeline at Brett's early-stage portfolio companies42:10 – Pricing and packaging: the most important GTM lever nobody talks about enough46:35 – The death of the smooth-talking GTM leader47:25 – What happens to VC when software is no longer scarce to build52:00 – Why vertical software wins in the AI era: context, workflow, and the non-tech buyer55:20 – The rep who drove 65 miles to drop off donuts and closed an $80K dealFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

Dan Wright (Co-founder & CEO of Armada) joins GTMnow to unpack what it actually takes to bring AI infrastructure to the places the cloud was never built to reach.The cloud covers about 30% of the world. The other 70% (think: oil rigs, the Arctic tundra, military ships, remote mines) is where some of the most critical decisions happen, making latency a life-or-death and billions of dollars difference. Armada is building the infrastructure for that part of the world: modular, ruggedized AI data centers that go to the data, instead of the other way around.From the first offshore edge computing deployment with the US Navy, to cutting avalanche response times in Alaska from over a day to real time, to sovereign AI installations in Saudi Arabia with Aramco and Microsoft, Armada is redefining what operating at the edge even means.In this episode, we cover:- Why cloud infrastructure was built for a pre-AI world and what that gap costs- How Starlink turned every remote location into a potential AI cluster- What "distributed intelligence" means and why it's the founding principle behind Armada- The global race for AI sovereignty and why modular compute is the linchpin- How Armada goes to market when a product demo involves shipping a 40-foot container to a desert (yes, really)- Why customer champions are better than any sales rep- The Microsoft partnership and how Armada extends Azure to places Azure could never go on its own- Category creation lessons from building a company before the market had a name for the industry- What's next: SpaceX, sovereign AI, and why Dan thinks humans are on the moon in two years (yes, REALLY)Guest links: Dan Wright - LinkedIn: https://www.linkedin.com/in/wrightdh/, hDan Wright - X: https://x.com/danwrightSFArmada - LinkedIn: https://www.linkedin.com/company/armadaai/Armada - Website: https://www.armada.ai/Host links:Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Sophie Buonassisi - X: https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comSponsors: HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/Nooks - the AI workspace for outbound teams, where AI agents handle prospecting, research, and sequencing so reps can focus on conversations. Learn more at https://www.nooks.ai/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 the cloud only reaches 30% of the world and what Armada actually builds03:11 – From Saudi Arabia to the Arctic: recent deployments that redefine the edge04:12 – AI's physics problem: why distance from data breaks everything05:31 – How Starlink turned every remote location into a potential AI cluster07:14 – What distributed intelligence means and why it's Armada's founding principle08:14 – The global AI race: sovereign compute as a national security strategy09:00 – The Genesis Mission, the White House, and Davos: why sovereign AI is mainstream12:49 – GTM for a hardware company when the demo involves shipping a 40-foot container15:18 – Why Armada's customers do the selling for them (and do a better job than some reps)17:35 – The Microsoft partnership and extending Azure to the places it can't reach on its own18:51 – Category creation: the lesson Dan learned about specificity and business value21:02 – What's next for Armada, SpaceX, and why Dan thinks we're two years from the moon25:34 – The founder advice Dan wishes more people took seriouslyFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

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.comSponsors: - 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 eight03:55 – How Sheila defines brand: it's what people say when you're not in the room05:08 – Joining Dropbox as the second marketing hire06:07 – Space Race: the campaign that defined Dropbox's early strategy06:56 – What consumer marketing taught her about driving revenue08:29 – Measuring brand ROI through match market testing09:15 – How Figma thinks about brand building at a macro level11:21 – The PLG-to-enterprise equation: what Figma did early that Dropbox waited too long on15:02 – Why building the enterprise team is both operational and optical17:12 – How Figma ingests customer feedback at scale18:26 – AI at Figma: enabling human creativity, not replacing it21:13 – What the venture side taught her about staying sharp as an operator22:33 – Why the shift from SEO to GEO is inevitable and what to do about it23:24 – Why Reddit is back and social is a core growth lever24:51 – The mentors that changed her trajectory28:59 – One piece of advice: make good $h!tFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

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.comBrought to you by: AngelListFrom 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 hubs15:01 – Battery's approach: why there's no one-size-fits-all playbook19:56 – Outreach's accidental sales experiment: remote vs. in-person results21:23 – What nobody tells you about the transition from CRO to operating partner23:01 – Gold watch and slippers? Why operating partner is not a retirement plan27:15 – Three audiences: prospective investments, portfolio companies, and Battery internal31:42 – Investing in GTM tech: why Battery went 7 years between bets34:44 – 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 deployed40:05 – The mojo metric: 6 daily pipeline inputs that tell you everything43:16 – Helping technical founders sell: the one-eyed man in the land of the blind48:04 – Advice for operators who want to move into an operating partner role51:03 – The sales and marketing dance: what real GTM alignment sounds like in a board roomFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

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/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comSponsors: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 product01:25 – Why sales is fundamentally human (even in the AI era)02:39 – The Agent Workspace as the human–AI interface02:56 – Why legacy sequencing tools were built for a manual world04:14 – The sales chess analogy: understand the board before making the move05:02 – Reps spend too much time "making the move"06:00 – Nooks as a simulation engine: suggesting the next best move07:07 – The reason for the email isn't in the email07:45 – Signal vs. noise: reasoning like a rep10:00 – Why calls are the most data-rich outbound channel10:25 – Using calls to move up the org chart13:12 – The sales iceberg analogy: what's above vs. below the surface13:38 – Don't pay enterprise reps to find phone numbers14:15 – Doing more with less vs. doing more with more15:00 – Why sales remains competitive even with full automation16:38 – Owning the end-to-end prospecting workflow18:53 – How Nooks learns from rep decisions over time19:15 – The path from 40% → 90% AI-written emails19:58 – Reimagining sequences with org chart intelligence22:17 – Evolution from virtual classroom to virtual sales floor25:11 – Pivoting into the sales use case before ChatGPT26:08 – Near-death experiences and surviving the pivot graveyard27:03 – Nooks' six core values27:57 – "Ask why" as a core operating principle28:39 – Ruthless prioritization as a startup advantage29:25 – AI literacy as a hiring filter for GTM roles30:07 – Making sales sexy for top engineers31:31 – Hiring across the board in 2026For inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

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 companyGuest 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.comSponsors: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 systems01:50 – From attribution to a GTM operating system02:41 – Launching AI agents, blueprints, and the execution layer in 202603:57 – Building a single data foundation across the buyer journey05:09 – Why GTM must be rebuilt around AI (not layered with tools)06:23 – Doing "more with more" and increasing management leverage07:30 – Tool consolidation vs controlling the buyer journey08:48 – 2026–2028: the great GTM consolidation wave09:01 – The case for a winner-takes-all GTM platform10:10 – Moat: data foundation + application layer11:35 – Expanding horizontally across marketing, sales, and post-sales14:28 – Running GTM in weekly sprints like an engineering org14:46 – Content as a core investment and distribution strategy15:26 – Why connected TV works for B2B brand trust16:43 – Faster GTM iteration cycles in the AI era17:47 – LinkedIn as the top pipeline and opportunity channel18:12 – Product stories, personal stories, and data stories in content21:02 – How founders carve out time to create content22:43 – Generating first customers from LinkedIn with <100 followers23:45 – Founding journey: pivoting into market intelligence25:37 – YC lesson: make something people love before scaling27:18 – The 10-year commitment mindset from YC advice30:13 – Executive coaching and founder bottlenecks31:53 – In-person culture and competing in the AI era33:26 – Whiteboarding interviews vs AI-generated case studies34:35 – Final advice: build a good business and enjoy the processFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

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 LinksAmanda’s LinkedIn: https://www.linkedin.com/in/amanda-robson-7227685b/Amanda’s Twitter: https://x.com/robby_mtfModern 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/HackItMaxPaul - LinkedIn: https://www.linkedin.com/in/paulsirving/Paul - X: https://x.com/PaulGTMNewsletter: https://thegtmnewsletter.substack.comBrought to you by: AngelListFrom 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 founders02:15 – What actually defines a “technical founder” beyond coding ability03:45 – Why product judgment and customer instinct matter early05:05 – How early teams split engineering and go-to-market roles07:10 – When investor advice helps and when it gets in the way09:05 – Why calibrating the hiring bar matters more than providing playbooks12:40 – How network-driven support helps founders see what “great” looks like15:45 – Why valuation discipline sets the bar in today’s market17:10 – When first-time founders become too risky at certain prices19:40 – How early-stage defensibility often comes down to the team27:20 – Why TAM momentum matters more than static market size30:30 – How small markets quietly turn into billion-dollar categories39:55 – What separates real AI companies from AI theater41:40 – Why infrastructure and data tools benefit most from AI tailwindsFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow 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_AFollow us on TikTok:https://www.tiktok.com/@gtmnow_Follow us on Instagram:https://www.instagram.com/gtmnow_/

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 + AIGuest 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.comSponsors: 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 AI03:23 – What Fin is and how it changes customer support05:27 – How Fin scaled to a 67% resolution-rate06:38 – The thinking behind 99¢ outcome-based pricing08:54 – Why customers don’t want to pay for activity09:10 – How outcome-based pricing aligns incentives09:57 – What changed for sales, success, and revenue operations15:10 – How Intercom thinks about forward-deployed engineers16:22 – Why the future is humans + AI18:56 – The real moat: product feedback loops at scale19:32 – Why Intercom put a million-dollar guarantee behind results23:29 – Why enablement is now the GTM bottleneck32:24 – From $1M to nearly $100M: what Fin’s growth reveals38:26 – Hiring in a world with no playbooks42:20 – How Archana learns from podcasts, books, and customersFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

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 assetLou 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 great00:26 – Why early selling is about learning, not revenue01:47 – Why founders misunderstand customer pain02:06 – “If you build it, they will come” is a lie02:33 – Distribution as the real moat02:58 – What makes an “unlikely entrepreneur” succeed06:15 – Why age and experience increase founder success07:01 – Curiosity, coachability, and risk elimination09:29 – Why founders can’t outsource sales too early15:26 – Pattern recognition vs short-term ARR21:10 – Founder-led sales vs scalable systems29:12 – Leadership, culture, and delegation33:18 – Founder evolution from $1M to $100M38:24 – When product-market fit starts to break39:15 – Why churn is a lagging indicator39:54 – Why small teams outperform large ones44:22 – Lessons from Unlikely Entrepreneurs45:23 – Final advice for foundersSponsors:HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.comGuest 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.comFollow 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_AFollow us on TikTok:https://www.tiktok.com/@gtmnow_Follow us on Instagram:https://www.instagram.com/gtmnow_/

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 advantageHealey 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 distribution03:30 – Product vs distribution: what actually matters early06:45 – Why most startups fail from internal misalignment10:30 – Culture, communication, and focus as scaling constraints14:40 – Hybrid work broke alignment17:45 – Why offsites are becoming the new HQ21:30 – Events as a go-to-market strategy25:00 – AI, outbound fatigue, and inbox trust collapse28:40 – “In-person experiences are becoming a premium”32:30 – How to use events for customer and partner acquisition36:15 – What makes a high-impact event vs a wasted one39:50 – Dinners, summits, and unforgettable experiences43:30 – Leadership, kindness, and “don’t be a jerk”47:40 – Mental state as a competitive advantage52:30 – Final reflections and advice for foundersSponsors:HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.comGuest 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.comFollow 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_AFollow us on TikTok:https://www.tiktok.com/@gtmnow_Follow us on Instagram:https://www.instagram.com/gtmnow_/

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.Timestamps00:00 – Introduction01:00 – “Yes is great. No is great. Maybe will kill you.”02:00 – Why go-to-market should be treated like a product04:45 – Designing the experience of being sold to06:30 – Using AI to debug GTM process failures09:00 – Why “lost on price” usually isn’t about price12:00 – What go-to-market engineering actually is16:00 – The rise of the forward deployed engineer20:45 – AI, agents, and what still needs human judgment25:45 – What great sales reps do differently in the AI era29:30 – Why GTM roles are becoming more consultative33:30 – Will there be an AI reckoning?38:00 – What “joining early” really means42:00 – Career lessons from Google, Stripe, and Vercel44:00 – Closing thoughts

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 episodeWhy 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 highlights00:00 — “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: AngelListFrom 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 GoldbergLinkedIn: 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.

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 highlights00:00 — Why customer expansion is the real signal of product-market fit00:50 — Lagging revenue vs. leading indicators of endurance04:11 — Why the CS benchmark dropped from 10% to 7%08:41 — How AI moved from internal efficiency to customer-facing leverage11:41 — Why retention cost matters more than CAC in the AI era14:17 — The simplest framework for allocating the 7% CS budget18:53 — Founder-led CS, design partners, and early-stage PMF myths23:16 — The rise of AI-powered specialized generalists30:00 — When forward-deployed engineers actually make sense49:31 — The one rule for building a durable SaaS companyThis episode is brought to you by our sponsor: HockeyStackIf 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.comFollow Abbas Haider AliLinkedIn: 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.

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 episodeWhy 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 highlights00:00 — 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, ownership08:38 — Why Adam hires “architects” (system thinkers) instead of just sellers10:41 — The mindset shift: celebrate value realized, not contracts signed15:41 — Replacing CSMs with “go-to-market engineers” + an intervention model19:14 — Turning PLG signals into PQA/PQL routing (and reducing the “noise”)29:26 — “100M ARR is late” — when to start layering sales into PLGGuest linksLinkedIn (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 GTMnowWebsite: 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.