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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 era Timestamp: 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 next Guest: Kyle Parrish, former VP Sales at Figma LinkedIn: https://www.linkedin.com/in/kparrish8/ X: https://x.com/KyleHParrish Host: Sophie Buonassisi, SVP Marketing at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona Visit us on: 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/@GTM_now Follow 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.com For inquiries about sponsoring the podcast, email [email protected] GTMnow 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 Great Timestamps:0:00 - Cold open 1:09 - What Test Box does 2:43 - How buying has changed 5:48 - What founders/CROs should do now 7:05 - GEO: AI version of SEO 9:02 - Why mid-funnel is expanding 21:17 - Agent-to-agent procurement 26:02 - All procurement by agents in 3-5 years 29:09 - How vendors differentiate beyond product 33:30 - The croissant campaign breakdown 45:50 - 15 AI experiments per week 47:10 - Analyzing prospects via video AI 48:29 - Building AI culture in your team 52:39 - Book recommendations Guest: Sam Senior, Founder and CEO TestBox Linkedin: ⁠https://www.linkedin.com/in/samuelsenior/⁠ Test Box:⁠ https://www.testbox.com⁠ Host: Sophie Buonassisi, SVP Marketing at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ Newsletter:⁠ https://thegtmnewsletter.substack.com⁠ Visit us on:⁠ https://gtmnow.com⁠ Follow 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_  

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 founder Auren 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/maxaltschuler Connect with Auren:https://x.com/aurenhttps://www.linkedin.com/in/auren/https://www.youtube.com/@summationpod GTMnow 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 #Sales Visit 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 launched The one-week hackathon that took AI adoption from 10% to 50% overnight The AI fluency rubric Zapier built: Unacceptable, Acceptable, Adaptive, Transformative Why leaders who aren't using AI are the biggest bottleneck in their companies How to measure AI ROI: floor raisers vs ceiling raisers How AI now handles 50% of Zapier's customer support tickets Wade's personal "advisory council" of AI sub-agents he uses for every major decision Why building a company today is 10x cheaper but distribution is 10x harder The truth about fundraising: you're selling your company, not raising money How Zapier stayed profitable by only hiring when it hurt Guest: Wade Foster, CEO of Zapier LinkedIn: https://www.linkedin.com/in/wadefoster/ Company - Zapier: https://zapier.com Host: Sophie Buonassisi, SVP Marketing at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ Newsletter: https://thegtmnewsletter.substack.com Episode highlights0:00 - Intro 1:13 - The Seinfeld Quote & Kanye Text story 3:16 - Workflows vs. Agents: What's the difference? 6:09 - Zapier's Code Red moment 8:55 - The hackathon that moved AI adoption from 10% to 50% 12:06 - Making AI fluency a hiring requirement 13:47 - Building the AI fluency rubric 16:40 - Why leaders are the biggest AI bottleneck 18:12 - Revenue impact of going AI-first 22:09 - Would Wade build Zapier differently today? 23:20 - Is Zapier's moat at risk from agents? 24:59 - Staying profitable with minimal capital 28:37 - The riskiest contrarian bet that paid off 31:52 - Wade's 3 personal AI workflows 36:53 - Favorite books for founders GTMnow 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 episode Why engineering is no longer your bottleneck (and what is) The 5 P's Ed uses to evaluate every inception-stage investment The autonomous enterprise thesis and what it means for how companies are built Why AI-native leadership is now a survival reqxtuirement, not a nice to have The full Clay story: $600K to $100M ARR, how they stayed lean, and what actually unlocked growth The 3 CH's framework for being a great board partner to founders Why the best founders today are inside the AI jet stream, not chasing it What every board meeting sounds like right now Episode highlights0:00 Intro &  1:05 Episode Preview: Ed Sim & Key Takeaways 3:10 The Jet Stream Analogy: Two Types of Companies 5:43 How GTM Operators Should Evaluate Companies Like Angel Investors 7:20 The Collapsing of Moats & AI-Native Business Opportunities 10:00 Rebuilding Industries vs. Selling Software to Them 15:00 Why Old GTM Playbooks Are Dead 17:46 Ed Sim's Background: From Cutco to 30 Years in VC 21:43 The Five P's of Inception Investing 23:04 How to Evaluate Potential & TAM in a Fast-Changing Market 25:40 Staying Ahead of the Jet Stream as a Founder 26:32 The Autonomous Enterprise Thesis 28:44 Agent of the Week: How Companies Should Adopt AI Agents 29:10 How Agents Are Changing Engineering Bottlenecks 31:15 What Incumbents Must Do to Survive the AI Wave 32:53 Intercom, Snowflake & How Legacy Companies Are Adapting 36:43 The Clay Story: How They Found Their Footing 38:33 The Three C's of Working With Founders (Cheer, Challenge, Chill) 40:07 Clay's Growth Trajectory: $600K to $100M+ ARR 41:10 Clay's Agency GTM Model & Community Moat 43:50 Ed's Fund Model: $500K to $15M Checks at Inception 46:57 What's Hot in Enterprise IT & Venture Right Now 48:03 Closing Remarks Key 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 sponsor Connect 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/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/ - 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-commerce Transcript 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 slide For inquiries about sponsoring the podcast, email [email protected] GTMnow 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 Intro 1:54 Jason's Background at Foundation Capital 3:07 Why Jason Chose GTMfund 4:35 How Media Has Evolved in the VC Ecosystem 6:20 What Separates Winning Emerging Managers from the Rest 8:28 GTM Fund's Flywheel: Fund, Community & Media 10:41 Building a VC Firm Is Like Building a Startup 12:31 Emerging Managers vs. Mega Funds (a16z, Lightspeed) 14:01 Why Top Founders Are Picking Emerging Managers for Early Rounds 16:36 The LP Perspective: Emerging Managers vs. Platform Funds 18:39 The Barbell Strategy for LP Portfolio Construction 19:14 Early Stage vs. Growth Stage: Risk, Return & Why Early Stage Wins 20:18 Closing Thoughts & Welcome to the Team Visit us and subscribe: https://gtmnow.com Follow 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 seats Guest 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/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/ 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 & Charan For inquiries about sponsoring the podcast, email [email protected] GTMnow 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.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 – 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 deal For inquiries about sponsoring the podcast, email [email protected] GTMnow 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/, h Dan Wright - X: https://x.com/danwrightSF Armada - 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/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/ 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 builds 03:11 – From Saudi Arabia to the Arctic: recent deployments that redefine the edge 04:12 – AI's physics problem: why distance from data breaks everything 05:31 – How Starlink turned every remote location into a potential AI cluster 07:14 – What distributed intelligence means and why it's Armada's founding principle 08:14 – The global AI race: sovereign compute as a national security strategy 09:00 – The Genesis Mission, the White House, and Davos: why sovereign AI is mainstream 12:49 – GTM for a hardware company when the demo involves shipping a 40-foot container 15:18 – 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 own 18:51 – Category creation: the lesson Dan learned about specificity and business value 21:02 – What's next for Armada, SpaceX, and why Dan thinks we're two years from the moon 25:34 – The founder advice Dan wishes more people took seriously For inquiries about sponsoring the podcast, email [email protected] GTMnow 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.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 [email protected] GTMnow 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.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 [email protected] GTMnow 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/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 [email protected] GTMnow 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 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 [email protected] GTMnow 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 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 [email protected] 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_/