The GTMnow Podcast

Kyle Parrish joined Figma as the first-ever sales hire when the company was doing $2M in ARR and helped scale it to $950M ARR. Figma then went on to IPO (FIG). But the path there was anything but smooth.In this episode, Kyle breaks down what it actually took to build Figma's enterprise sales motion from scratch, including the no-discount rule that made procurement teams furious, the 40-hour interview weeks when hiring felt impossible to keep up with, and what it was like to lead a 300-person team through a failed $20B Adobe acquisition, and then have their best year immediately after.We cover:- Why Figma refused to discount, even when Microsoft pushed back- How to hire the right first sales rep as a founder- The PLG to enterprise transition most companies get wrong- What the Adobe deal collapse actually felt like from the inside- How Figma went from 3 products to 8 overnight and launched into an IPO- What great sales look like in the AI eraTimestamp:0:00 – Intro 1:02 – Guest intro: Kyle Parrish 1:35 – Joining Figma at $2M ARR in 2018 5:01 – First meeting with Dylan (Figma CEO) 6:13 – How to find your first sales hire 9:05 – Stage alignment in early hiring 11:43 – Early-stage operators need "scar tissue" 13:19 – Northstar metric at Figma 14:13 – Obsessing over customer conversations 16:44 – Building Figma's brand through community 17:31 – Scaling the "unscalable" 20:08 – In-person GTM vs. digital 22:47 – Was there a moment Figma might not make it? 24:48 – Pivoting after the Adobe deal collapsed 28:10 – Figma's no-discount rule 31:05 – Enterprise ELAs replacing discounting 34:47 – What makes a great salesperson in the AI era 36:56 – Missionaries vs. mercenaries in AI-era GTM 39:47 – Spotting the next Dropbox or Figma 43:46 – Kyle's post-Figma investing focus 45:58 – Family, travel & what's nextGuest: Kyle Parrish, former VP Sales at Figma LinkedIn: https://www.linkedin.com/in/kparrish8/X: https://x.com/KyleHParrishHost: Sophie Buonassisi, SVP Marketing at GTMnowLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/X: https://x.com/sophiebuonaVisit 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_/Sponsors: Nooks - the AI workspace for outbound teams: https://www.nooks.ai/gtmfund.Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice. Transcript available under the episode here: https://gtmnow.com/tag/podcast/Subscribe to GTMnow for the latest episodes! https://gtmnow.comFor inquiries about sponsoring the podcast, email [email protected] is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

AI isn't just changing how we sell. It's changing how buyers make decisions before they ever talk to you.Sam, Founder and CEO of Test Box, joins Sophie on GTMnow to break down exactly what's happening to the B2B software buying process right now, and what go-to-market leaders need to do about it immediately.If you're a founder, CRO, or AE wondering why your pipeline feels different, this conversation will give you a clear framework for what's happening and what to do next.What we cover:Why 70-80% of purchase decisions are already made before the first call (and it's accelerating)The shift from discovery calls to validation calls, and how to prepareCEO (AI-version of SEO): how LLMs are shaping what buyers believe about your productThe "day one shortlist" shrinking from 3-4 vendors to 1-2 vendorsAgent-to-agent procurement: Sam's timeline for when AI agents fully take over buyingWhy the mid-funnel is actually getting longer, not shorterThe "Fake Nothing, Prove Everything" campaign that went viral post-Series AHow Test Box runs 15 AI experiments per week across the entire companyUsing Google Vertex video analysis to read prospect body language on sales callsHow to build an AI-first culture without burning out your teamBooks: The 15 Commitments of Conscious Leadership, No Ego, Courageous Marketing, Good to GreatTimestamps:0:00 - Cold open1:09 - What Test Box does2:43 - How buying has changed5:48 - What founders/CROs should do now7:05 - GEO: AI version of SEO9:02 - Why mid-funnel is expanding21:17 - Agent-to-agent procurement26:02 - All procurement by agents in 3-5 years29:09 - How vendors differentiate beyond product33:30 - The croissant campaign breakdown45:50 - 15 AI experiments per week47:10 - Analyzing prospects via video AI48:29 - Building AI culture in your team52:39 - Book recommendationsGuest: Sam Senior, Founder and CEO TestBoxLinkedin: ⁠https://www.linkedin.com/in/samuelsenior/⁠Test Box:⁠ https://www.testbox.com⁠Host: Sophie Buonassisi, SVP Marketing at GTMnowLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter:⁠ https://thegtmnewsletter.substack.com⁠Visit us on:⁠ https://gtmnow.com⁠Follow us on LinkedIn: / gtmnowFollow us on X (Twitter):⁠ https://x.com/GTMnow_⁠ Follow us on YouTube: / @gtm_now Follow us on TikTok: / gtmnow_ Follow us on Instagram: / gtmnow_  

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/