The GTMnow Podcast

GTMnow

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

  1. How Esper Is Building the Operating System for Government Policy | Maleka Momand

    1h ago

    How Esper Is Building the Operating System for Government Policy | Maleka Momand

    Maleka Momand, co-founder and CEO of Esper, joins Sophie Buonassisi on GTMnow to break down what it actually takes to build and sell software to government. Esper is the operating system for government policy, serving as the system of record for the regulation and internal policy that shapes daily life, from NYPD procedures to nurse practitioner licensing in rural Tennessee. Maleka shares hard-won lessons from 8 years in GovTech: why winning trust matters more than winning business, why professional services are a moat (not a cost center), and how Esper turns slow, paper-based policy processes into live digital workflows. She also covers the DOGE effect across red and blue states, why enterprise SaaS still has defensible moats in the age of AI, and her advice to founders entering regulated markets. Whether you're a founder, GTM leader, or operator selling into complex, slow-moving markets, this conversation is packed with practical playbooks on trust, go-to-market, and building durable enterprise software. Chapters: 00:00 Intro 00:44 Two types of government policy (regulation vs internal) 02:06 The NYPD 3,000-page policy problem 03:23 Digitizing a paper-based, 20-person workflow 04:12 Why policy is infrastructure 05:23 Real impact: Tennessee healthcare & Arkansas hunting licenses 07:45 Esper's ideal customer: complexity, catalyst, volume 08:18 Going to market in GovTech (and why it's slow) 10:16 Advice for founders entering GovTech: win trust first 11:27 Why professional services are a moat 12:38 In-house vs third-party services 13:49 What DOGE actually looks like on the ground 15:11 Is DOGE a tailwind for Esper? 16:36 The new funding round & enterprise SaaS in the age of AI 19:13 From VC to founder: why Maleka made the shift 22:10 Advice for founders: read fiction, not productivity books 24:14 AI, data quality, and the problem with vibe coding 26:43 How Esper uses AI internally (meet "Poly") 27:27 Building a high-agency culture while scaling 29:00 Closing thoughts Connect with Maleka Momand:  Co-founder, CEO of Esper Twitter/X: @MalekaMomand  LinkedIn: linkedin.com/in/malekamomand Host: Sophie Buonassisi, SVP at GTMnow Follow Sophie: https://x.com/sophiebuona LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ ABOUT GTMnow GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market. 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_/ Subscribe to GTMnow for the latest episodes on AI, founder strategy, fundraising, and go-to-market from the best builders in tech. #GovTech #GoToMarket #EnterpriseSaaS #StartupAdvice #GTM #SaaS #FounderAdvice #GovernmentTechnology #PolicyTech #AI 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.

    31 min
  2. How He Built a $250M Company With Zero Employees | Ben Cera, Polsia

    5d ago

    How He Built a $250M Company With Zero Employees | Ben Cera, Polsia

    One Person, $10M+ ARR, $30M Raised: How Ben Cera Built Polsia (AI Operating System) Solo Ben Cera, founder of Polsia, just raised $30M at a $250M valuation while running the entire company alone. His AI agent handles his emails, manages customer support, even led his fundraising calls. This is what a solo founder with an AI operating system looks like at scale. Polsia is an AI operating system that builds and runs companies autonomously. Give it an idea and it builds the product, writes code, conducts research, creates tweets, sets up company infrastructure, and works 24/7 on your behalf. Users are hitting $10M+ ARR using Polsia to scale their businesses. In this episode we cover: 00:00 - Intro & The Viral Launch Nobody Forgot 01:24 - How He Raised $30M at $250M Valuation with Himself as the Only Employee 02:15 - The Origin Story: Building Polsia from Scratch 04:13 - Why the Controversial Product Name Became Free Marketing ($Millions in Earned Media) 05:55 - What Polsia Actually Does (AI Operating System for Founders) 06:25 - How He Hit $10M+ ARR Running Solo (No Cofounders, No Hires) 10:30 - Building a Company OS That Works 24/7 on Your Behalf 12:00 - The Psychology of Single Founder Mode (Why It Scales Faster) 14:45 - AI Agents Handling Customer Support, Refunds, & Bug Fixes 16:30 - Email Automation: How Polsia Responds to 100% of His Emails 20:15 - The Viral Fundraising Stunt (Live Dashboard + Agent-Led Investor Calls) 25:00 - Why He Let His AI Agent Handle First Meetings with Investors 28:30 - The Self-Fulfilling Prophecy of Distribution (More Visibility = More Traction) 32:15 - How Distribution Strategy Becomes Your Go-To-Market 35:45 - Building in Public While Running Everything Solo 38:00 - Customer Obsession at Scale (Staying Close When You're Alone) 42:56 - Founder Availability: Direct Phone Access to Customers 44:00 - Manufactured Moments That Feel Authentic 50:13 - Why Distribution Isn't an Afterthought Anymore Key Insights: - One founder + AI operating system beats small teams without leverage (speed, decision-making, equity concentration) - Polsia lets you build multiple products simultaneously without hiring (products work 24/7 on your behalf) - The more controversial your positioning, the more people talk (free marketing from debate) - AI agents can handle 80% of founder work: emails, support, customer refunds, even investor screening - Live dashboards showing real-time growth create self-fulfilling prophecies (transparency = conviction) - Distribution is how you reach product-market fit faster (not an afterthought) - AI agents leading first investor meetings works (validates the product claim + generates buzz) - Customer intimacy at scale = founder still takes direct texts from users - Retention matters more than naming: customers don't complain about the name, they just use it - One person with AI tools > 5 people building without leverage Why This Matters: This is the playbook for next-generation founders in 2026. Ben shows you how to: scale solo using AI agents, multiply your output without hiring, go viral intentionally, raise capital through distribution, and stay close to customers at scale. If you're a founder thinking about AI leverage, autonomous systems, or scaling lean, this is essential. Watch This If You're: - Solo founders scaling without a team - Founders interested in AI agents and autonomous systems - Learning about AI-first product development - Studying modern GTM and distribution strategy - Raising capital in 2026 (fundraising case study) - Building products with AI agents doing the work - Curious about the solo founder + AI agent trend - Following autonomous company builders Connect with Ben Cera: Founder & CEO of Polsia Twitter/X: @bencera  LinkedIn: https://www.linkedin.com/in/benbroca/ Host: Sophie Buonassisi, SVP at GTMnow Follow Sophie: https://x.com/sophiebuona LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ ABOUT GTMnow GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market. 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_/ Subscribe to GTMnow for the latest episodes on AI, founder strategy, fundraising, and go-to-market from the best builders in tech. 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.

    51 min
  3. The $575B AI Bet (Biggest Since the World Wars) and the New Two-Buyer Reality in Software | Tomasz Tunguz, Theory Ventures

    May 26

    The $575B AI Bet (Biggest Since the World Wars) and the New Two-Buyer Reality in Software | Tomasz Tunguz, Theory Ventures

    AI Infrastructure Spending is Insane: Hyperscalers Betting $575B on the Data Center Race | Tomasz Tunguz This year's data center infrastructure spending will be the 5th largest infrastructure project in history (bigger than everything except railroads and the two world wars). Tomasz Tunguz breaks down what nobody appreciates about the scale of the AI boom. Tomasz Tunguz, General Partner at Theory Ventures, and one of the most insightful voices on AI infrastructure, data stacks, and founder strategy. In this episode we cover: 00:00 - Intro & The Scale Nobody Anticipated 02:13 - Data Center CapEx Could Hit 5-7% of US GDP by 2030 05:21 - For Every $1 AI Companies Make, They Spend $12 on Infrastructure ($575B Bet) 06:20 - Market Share Capture vs. Margin Games: The Chicken Game Big Tech is Playing 09:48 - How the Data Stack & AI/ML Worlds Have Completely Fused 12:33 - Product-Market Fit is No Longer Binary: It's Continuous Now 15:17 - How AI is Changing Venture Capital & Portfolio Management 17:09 - The Future: Image & Video Data is Going to Require MASSIVE Infrastructure 18:25 - Pattern Recognition Across Winning Companies (Domain Expertise is Key) 20:50 - Hot Take: Corporate Org Structure Will Transform in 5 Years 21:00 - Final Advice to Founders: Nobody Knows the Answer Key Insights: - Hyperscalers are spending ALL free cash flow + borrowing heavily to fund data center CapEx (Meta, Google, Oracle levered 7:1 on cash flow basis) - The dominant metric: intelligence per watt of electricity - Anthropic rumored to have very high gross margins (first wave competition) - Data teams are now reporting to heads of engineering (huge organizational shift) - Inference demand is infinite: models are growing 5-10x in size - Foundation models broke product-market fit: it's now continuous, not static - Second-time founders win because they understand domain history & distribution - PR is now a major distribution channel for AI companies (unlike software era) - Building for images & video is the next frontier (1,000-10,000x larger than text data) Watch this if you're: - Founders building AI/data companies - Investors analyzing the AI infrastructure play - Product leaders understanding AI's organizational impact - Anyone following the AI market seriously Connect with Max: https://x.com/hackitmax https://www.linkedin.com/in/maxaltschuler/ Connect with Paul: https://x.com/PaulGTM https://www.linkedin.com/in/paulsirving/ Guest: Tomasz Tunguz, General Partner https://www.linkedin.com/in/tomasztunguz/ https://x.com/ttunguz Host: Sophie Buonassisi, SVP at GTMnow https://www.linkedin.com/in/sophiebuonassisi/ https://x.com/sophiebuona ABOUT GTMnow  GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market. 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_/ 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. 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 gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.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.

    35 min
  4. SEO Is Not Enough Anymore: Webflow's CEO on the Rise of AEO | Linda Tong

    May 20

    SEO Is Not Enough Anymore: Webflow's CEO on the Rise of AEO | Linda Tong

    The future of websites isn't a builder problem anymore. It's an agent problem. In this episode of GTMnow, Sophie Buonassisi sits down with Linda Tong, CEO of Webflow, to unpack how the entire web is being rewritten for a world where humans AND AI agents are your audience. Linda breaks down why Webflow is no longer "just a website builder" (it's an agentic web marketing platform), what the Vidoso acquisition unlocks for AI-generated brand assets, and how the rise of Answer Engine Optimization (AEO) is forcing marketers to rethink content from the ground up. She also shares the practical playbooks her team uses to "vibe" sites into production with the Webflow MCP server, why human creativity is the only real moat left, and how she built her own personal CRM using Claude Code. If you run a GTM team, lead marketing, or are trying to figure out what your website should even look like in 2026, this one is essential. WHAT YOU'LL LEARN -Why your website is now the #1 source of truth for humans, bots, and agents -The shift from static sites to continuously optimizing, dynamic experiences -How "vibe coding" with MCP is changing the way teams build on the web -Inside the Vidoso acquisition and what "brand-governed AI" actually means -AppGen: going from prompt to production without losing brand consistency -Answer Engine Optimization (AEO): the non-obvious mistakes marketers are making -How to structure a marketing team made of humans plus agent swarms -The "5 words" exercise every CEO should run inside their company -Linda's personal CRM built with Claude Code (and how Webflow scales internal AI) -Why "unlimited credits" and Builder Days unlock real AI productivity ABOUT THE GUEST Linda Tong is the CEO of Webflow, the agentic web marketing platform powering some of the most respected brands on the internet. Before stepping into the CEO role, Linda served as President and COO at Webflow, and previously led product at Cisco's AppDynamics and held senior roles at Google. CHAPTERS  00:00 Intro  01:41 From static to dynamic  03:12 Inside the Vidoso acquisition  05:38 The human moat  07:17 Beyond the website builder  08:55 Structuring human + agent teams  09:58 AppGen, explained  10:45 Prompt to production  12:11 AEO misconceptions  14:40 Holistic AEO strategy  16:38 The 5 words exercise  18:10 Linda's personal CRM  19:31 Central vs. individual AI  20:44 Inside Webflow's Builder Days Guest: Linda Tong, CEO Webflow https://www.linkedin.com/in/lktong/ https://x.com/YayLT Host: Sophie Buonassisi, SVP at GTMnow https://www.linkedin.com/in/sophiebuonassisi/ https://x.com/sophiebuona ABOUT GTMnow  GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market. 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:  .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 gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/ #GTMnow #Webflow #AI #LindaTong #AnswerEngineOptimization #AEO #GoToMarket #B2BMarketing #AgenticAI #VibeCoding #AIAgents #FutureOfWeb #MarketingPlatform #SaaS #aimarketing 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.

    25 min
  5. Inside Reevo's $80M Bet to Kill the $10B Frankenstein Stack | David Zhu, Cofounder & CEO

    May 14

    Inside Reevo's $80M Bet to Kill the $10B Frankenstein Stack | David Zhu, Cofounder & CEO

    AI is rewriting go-to-market and most companies are still operating with a “Frankenstein stack.” In this episode of GTMnow, we sit down with David, founder & CEO of Reevo, to unpack how AI-native companies will replace legacy GTM systems, why the future of sales teams looks radically different, and how AI agents are becoming the new operating layer for revenue teams. David shares why Reevo stayed in stealth while building a vertically integrated AI revenue operating system, the problem of institutional knowledge loss in sales organizations, and why the old playbook for SaaS and GTM is breaking in 2026. We also dive deep into: - AI-native go-to-market strategy - The death of the legacy SaaS tech stack - Revenue operating systems explained - AI agents for sales, marketing, and customer success - How founders should think about AI adoption - Building startups in the age of AI - Why “failure is the cornerstone of innovation” - AI-driven sales productivity and revenue efficiency - Founder-led sales in 2026 - The future of CROs, CMOs, and RevOps - AI copilots, Jarvis-style workflows, and GTM automation - Scaling teams without scaling headcount If you're a founder, CRO, CMO, GTM leader, SaaS operator, AI builder, or investor trying to understand where B2B software and go-to-market are headed next, this episode is for you. Timestamps:  00:00 Intro  01:20 Why Reevo built in stealth  04:50 Why AI can finally disrupt GTM tech stacks  09:20 What Reevo actually does  11:10 AI outcomes vs headcount growth  15:00 How AI changes leadership & innovation  19:00 Why legacy GTM teams are vulnerable  23:00 The future of AI-native GTM organizations  29:00 Running an AI-native company internally  34:00 David’s favorite AI workflows & tools  37:40 Advice for introverted founders & leaders Host: Sophie Buonassisi, SVP Marketing at GTMnow https://www.linkedin.com/in/sophiebuonassisi   Guest: David Zhu, Co-founder and CEO at Reevo https://www.linkedin.com/in/zhuventures/ 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:  .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 gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/ #AI #Sales #GTM #SaaS #ArtificialIntelligence #RevenueOperations #Startup #B2B #RevOps #AIAgents #Founder #SalesLeadership #CMO #CRO #GoToMarket #AIStartup #TechPodcast #SalesTech #FutureOfWork #Automation 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.

    42 min
  6. VC: "Software Is Basically Worth Zero Now" | Tyler Hogge, Ex-Pelion

    May 12

    VC: "Software Is Basically Worth Zero Now" | Tyler Hogge, Ex-Pelion

    Tyler Hogge helped take Divvy from zero to a $2.5B acquisition by Bill.com. Now, as General Partner at Pelion Ventures, he argues that charging for software is dead, per-seat pricing is collapsing, and the next decade of venture-scale companies will be built on outcomes, not subscriptions. In this episode of the GTMnow VC Podcast, Tyler sits down with Max to break down what comes after SaaS pricing, why founder intensity is the only trait that still matters in 2026, and how Pelion concentrates capital into its biggest winners (Cloudflare alone returned over $1B to the fund). He also shares why most startups won't survive going head-to-head with OpenAI and Anthropic, the "bent the odds" contract he signed with Redo's CEO, and the lesson from raising four kids that changed how he leads. This is an honest, no-fluff conversation about where venture is going as AI commoditizes software. Chapters: 00:00 Intro 01:14 Intro 18:48 Tyler joins 23:09 "Sell Jesus, sell anything" 27:42 The $2.5B Divvy exit 34:39 The "bent the odds" contract 38:11 Startups vs. OpenAI and Anthropic 39:05 "Software is worth zero" 40:55 The death of per-seat pricing 43:02 Lessons from raising 4 kids 46:44 "LinkedIn is the trailer park" Connect with Tyler: https://x.com/thogge https://www.linkedin.com/in/thogge/ Connect with Max: https://x.com/hackitmax https://www.linkedin.com/in/maxaltschuler/ Connect with Paul: https://x.com/PaulGTM https://www.linkedin.com/in/paulsirving/ About Tyler Hogge: Tyler Hogge is a General Partner at Pelion Ventures, Utah's oldest and largest venture fund with $500M AUM across eight funds. Before Pelion, Tyler was VP of Product at Divvy, which sold to Bill.com for $2.5B in 2021. Earlier in his career, he was a product leader at Wealthfront under Andy Rachleff and Adam Nash. He's based in Utah and one of the most active venture capitalists on X. About GTMnow: GTMnow is the media arm of GTMfund, a pre-seed and seed-stage B2B SaaS venture firm backed by an LP base of 300+ C-suite and VP-level operators from the best go-to-market organizations in tech. The GTMnow VC Podcast publishes every other week with the investors and operators shaping the next decade of B2B software. 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. 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 gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/ Subscribe for new episodes every week #VentureCapital #VCpodcast #SaaS #AI #B2BSaaS #GTMnow #StartupFunding #TylerHogue #PelionVentures #FounderAdvice 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_/ 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.

    48 min
  7. How AI Will Go From Influencing 20% to Making 90% of Your Decisions | Steve Lucas, Boomi CEO

    May 6

    How AI Will Go From Influencing 20% to Making 90% of Your Decisions | Steve Lucas, Boomi CEO

    Boomi was founded in the early 2000s by Rick Nucci, acquired by Dell in 2010, and then spun out to Francisco Partners and TPG Capital in 2021. Today it powers 30,000+ enterprise customers globally and moves more data per second than the entire Visa card network, times two. What started as an integration platform has evolved into something bigger: the leading data activation company, purpose-built for the agentic AI era. Steve Lucas took over as CEO in early 2023, just as ChatGPT was about to reshape the entire software landscape. A three-time CEO with nearly 30 years in enterprise software, Steve previously led Marketo through its $4.75B acquisition by Adobe (the largest in Adobe's history at the time), scaled iCIMS into the world's leading talent acquisition cloud, and held senior roles at SAP, Salesforce, Adobe, and BusinessObjects. He's also the author of "Digital Impact: The Human Element of AI Driven Transformation," a book arguing that the AI revolution will stall unless companies fix the fragmentation of their data first. In this episode, Sophie Buonassisi sits down with Steve at HumanX in San Francisco to unpack why 2026 is the year AI moves from pilot to production, the three diagnostic questions every CEO should ask before deploying agentic AI, and why "change only happens at the speed of trust." Steve also gets candid about the internal protest that erupted when Boomi rolled out its first CSM agent, his prediction that AI will go from influencing 20% of executive decisions to making 90% of them within 2 years, and how he picked up Claude Code on an airplane to vibe-code a contracts agent for his sales team. If you're a founder, operator, or GTM leader trying to figure out whether your business is actually ready for agentic AI (or just chasing the buzzword), this one is for you. TIMESTAMPS 0:00  Intro 0:58  Welcome to GTMnow at HumanX 1:10  Why 2026 is when AI moves from pilot to production 2:32  Influencing decisions vs. making decisions: the next 2 years 3:18  Digital Impact: why fragmentation will stall the AI revolution 5:01  "Get your data to the gym": the new slogan 5:20  The 3 questions to know if your company is AI-ready 6:47  Change happens at the speed of trust 7:53  The internal protest behind Boomi's CSM agent 9:32  From integration platform to data activation: the strategic shift 10:50 Steve's most transformative AI workflow as a CEO 11:12 Vibe coding with Claude on an airplane 12:20 Where to follow Steve and Boomi Host: Sophie Buonassisi, SVP Marketing at GTMnow linkedin.com/in/sophiebuonassisi   Guest: Steve Lucas, CEO at Boomi https://www.linkedin.com/in/nstevenlucas/ 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:  .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 gtmnow@gtmfund.com GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/ Keywords: #AI #AgenticAI #Boomi #SteveLucas #GTMnow #DataActivation #HumanX #EnterpriseAI #AIStrategy #B2BSaaS #ClaudeCode #VibeCoding #CEOInterview #DigitalTransformation #futureofwork 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.

    13 min
  8. Okta's CRO: From $850M in Losses to $760M Profit (The AI Agent Bet) | Jon Addison

    Apr 29

    Okta's CRO: From $850M in Losses to $760M Profit (The AI Agent Bet) | Jon Addison

    Okta's CRO Jon Addison joins GTMnow host Sophie to break down the full story behind Okta's remarkable revenue turnaround, the launch of Okta for AI Agents, and the go-to-market playbook that's carrying them from $3B toward a $5B ARR target. From nearly $850M in operating losses to over $760M in operating income, Okta's transformation is one of the most significant turnaround stories in enterprise SaaS. In this episode, Jon pulls back the curtain on exactly how it happened. In this episode: - Why 91% of enterprises are already deploying AI agents but only 10% have a security strategy for them - How Okta's "AI governance gap" insight became the foundation for their biggest product launch in years: Okta for AI Agents - The GTM restructure around specialization that unlocked productivity and drove 40% higher average contract value on new product deals - How Okta became a partner-first company: 95% of their top 100 deals in the last fiscal year were partner-led, and what operationally made that possible - Why the first discovery call no longer exists, and how sellers need to show up differently in the AI era - Jon's new internal sales methodology, APEX, built on Command of the Message for the AI era - How Okta is using AI internally to transform their own go-to-market motion, from conversational intelligence to pre-sales assistants - What the path to $5B ARR actually looks like: enterprise expansion, international growth, public sector, and the massive new TAM unlocked by non-human identity - Jon's leadership philosophy: why human-centric selling is becoming more critical as AI takes over the repetitive work Host: Sophie Buonassisi, SVP Marketing at GTMnow https://www.linkedin.com/in/sophiebuonassisi Guest: Jon Addison, CRO at Okta https://www.linkedin.com/in/jon-addison-3399175 Timestamp: 0:00 - Cold open 1:19 - Welcome + Jon's background: from London to Silicon Valley 1:52 - How Jon got into software and identity management 4:08 - Okta for AI Agents launch announcement 5:04 - 90% of customers live with agents, only 10% confident in securing them 6:31 - What's driving the governance gap in the market 7:53 - Speed of agent innovation must be matched by security and governance 8:36 - 40% higher ACV on deals that include new products 9:43 - Why consolidation around a single identity platform is resonating 11:45 - How AI agents unlock a massive new TAM for Okta 13:05 - Okta's turnaround: from $850M operating losses to $760M operating income 13:36 - Key decision 1: GTM specialization drove productivity 15:02 - Key decision 2: becoming a partner-first company 16:14 - What cracking the partner-led model actually looks like 19:08 - How long it takes to see ROI from a partner-led pivot 20:12 - The path from $3B to $5B: enterprise, international, public sector 21:49 - Using AI internally: launching "Apex," the AI-era sales methodology 23:04 - What the Apex sales methodology entails 24:25 - Buyers now show up with strong opinions before the first call 25:44 - How discovery is changing: human-centric selling in the AI era 27:33 - Headcount and AI: what skills matter in the future 29:31 - Why relationships are Okta's core competitive advantage 30:36 - The role of experiences: F1, events, and the 7-touchpoint rule 31:47 - Broad GTM surface area: ABM, ecosystem, brand 33:47 - The future of identity: SaaS disruption, consolidation cycles, and Okta's position 37:06 - Jon's leadership style: coaching reps and unlocking potential 39:01 - Positive vs. negative leadership and the 1-to-10 touchpoints framework Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitte 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.

    40 min
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About

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

Information

  • Creator
    GTMnow
  • Years Active
    2018 - 2026
  • Episodes
    637
  • Rating
    Explicit
  • Copyright
    © 2026 The GTMnow Podcast
  • Show Website
    The GTMnow Podcast

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