The GTMnow Podcast

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Jun 2026

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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.

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June 15, 202657 min

He's Seen 300+ Sales Comp Plans. 90% Make the Same Mistake | Siva Rajamani (Everstage CEO)

Most sales comp plans are quietly broken, and the people running them have no idea. Siva Rajamani, CEO of Everstage, has visibility into 300+ enterprise comp plans, and he says 90% of companies make the same mistakes. In this episode he breaks down what's going wrong, how to spot it, and what a comp plan that actually drives revenue looks like.Siva explains why sales compensation is not a back office cost center but the single biggest lever in your go-to-market strategy. It's the glue between what a company intends and what reps actually do. If your reps aren't doing what you want, the answer isn't in a 1-on-1. It's in your comp plan.We get into the over-complication trap, the hidden math that makes reps refuse your best deals, the base-to-variable ratios that actually work, why your top reps should out-earn almost everyone, and how AI is about to blow open the gap between your best and average sellers.Chapters:00:00 Intro00:30 Siva's RevOps background at Freshworks04:00 Scaling RevOps from 1 to 2504:50 Why he left to build Everstage06:30 Why incentives drive revenue, not tools08:00 Comp as the glue between intent and action10:30 The 1 to 2 mistakes almost every team makes12:00 "If your comp plan needs FAQs, it's a tax code"14:00 The 60-second test for a broken plan15:30 Designing comp to retain top talent16:50 How AI widens the gap between top and average reps18:00 The $1M sales rep is coming19:30 Why optimizing for top earners is better on margins21:30 Quota to OTE ratios that actually work23:00 Base vs variable: the 50/50 rule and exceptions24:00 What Everstage does and who it serves25:30 How Everstage structures its own comp plan28:00 The rise of the revenue architect48:00 CPQ and connecting margin to commissions50:30 When should reps earn commission in the deal cycle52:30 Six month vs twelve month comp cycles54:30 The most a sales rep has ever made55:20 Where to find SivaConnect with Siva Rajamani: Co-founder, CEO of EverstageTwitter/X: https://x.com/siva_rajamaniLinkedIn: https://www.linkedin.com/in/sivasrajamani/Host: Sophie Buonassisi, SVP at GTMnowFollow Sophie: https://x.com/sophiebuonaLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ABOUT GTMnowGTMnow 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.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_/Subscribe for more conversations with the operators and founders behind today's best go-to-market teams.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.

June 9, 202655 min

"We Don't Fund Good Companies" : A $1.5B VC Explains Why | Ben Lerer, Lerer Hippeau

Ben Lerer, Managing Partner and Founder of Lerer Hippeau, has built one of New York's most influential early-stage venture firms across nine funds and nearly $1.5B in AUM. In this VC edition of the GTMnow podcast, Ben sits down with Max and Paul to unpack how he actually picks founders, why he wants to be the "worst investor" at his own fund, and the contrarian belief that backing good, sensible businesses is a mistake.Ben got his start in media, building Thrillist before it merged into Group Nine, then turned those relationships and that operator empathy into a venture career writing early checks into companies like Warby Parker and Casper. He shares what's changed about winning deals in a more competitive, sharp-elbowed market, how Lerer Hippeau runs its investment committee on conviction rather than consensus, and the process failure behind passing on Peloton.We also get into the debate every investor is wrestling with right now: the crazy, fast-moving AI-native founder versus the second or third-time operator with deep domain expertise, and why the answer is rarely a silver bullet.A real venture-nerd conversation on firm building, IC decision-making, founder selection, and what it takes to chase the power law.Topics covered:- The "worst investor at my own fund" philosophy- Conviction vs. consensus in the investment committee- Why Lerer Hippeau funds "crazy" founders, not good companies- The Peloton miss and what it revealed about process- From Thrillist and digital media to venture capital- AI-native founders vs. domain experts- How to win competitive deals as a smaller firmChapters:00:00 Intro00:52 Max and Paul on the episode: IC process and founder selection14:36 Conversation with Ben Lerer begins15:02 Nine funds, $1.5B AUM, and the early-stage strategy23:00 From Thrillist to venture: the media springboard28:00 What's changed in picking founders and winning deals33:00 How the investment committee grew and evolved37:40 The "magic" deal and chasing high-conviction bets50:43 Why Ben wants to be the worst investor at his fund53:00 Funding crazy people, not good companies51:35 Yankees or Mets?Connect with Ben Lerer: https://x.com/BenjLererLinkedIn: https://www.linkedin.com/in/benlerer/Connect with Max: https://x.com/hackitmaxlinkedin.com/in/maxaltschulerListen on Apple and Spotify, and subscribe for more GTMnow VC editions.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 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.

June 4, 202631 min

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 Intro00:44 Two types of government policy (regulation vs internal)02:06 The NYPD 3,000-page policy problem03:23 Digitizing a paper-based, 20-person workflow04:12 Why policy is infrastructure05:23 Real impact: Tennessee healthcare & Arkansas hunting licenses07:45 Esper's ideal customer: complexity, catalyst, volume08:18 Going to market in GovTech (and why it's slow)10:16 Advice for founders entering GovTech: win trust first11:27 Why professional services are a moat12:38 In-house vs third-party services13:49 What DOGE actually looks like on the ground15:11 Is DOGE a tailwind for Esper?16:36 The new funding round & enterprise SaaS in the age of AI19:13 From VC to founder: why Maleka made the shift22:10 Advice for founders: read fiction, not productivity books24:14 AI, data quality, and the problem with vibe coding26:43 How Esper uses AI internally (meet "Poly")27:27 Building a high-agency culture while scaling29:00 Closing thoughtsConnect with Maleka Momand: Co-founder, CEO of EsperTwitter/X: @MalekaMomand LinkedIn: linkedin.com/in/malekamomandHost: Sophie Buonassisi, SVP at GTMnowFollow Sophie: https://x.com/sophiebuonaLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ABOUT GTMnowGTMnow 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.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_/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 #AIThe 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.

May 29, 202650 min

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) SoloBen 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 Forgot01:24 - How He Raised $30M at $250M Valuation with Himself as the Only Employee02:15 - The Origin Story: Building Polsia from Scratch04:13 - Why the Controversial Product Name Became Free Marketing ($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 Behalf12:00 - The Psychology of Single Founder Mode (Why It Scales Faster)14:45 - AI Agents Handling Customer Support, Refunds, & Bug Fixes16:30 - Email Automation: How Polsia Responds to 100% of His Emails20:15 - The Viral Fundraising Stunt (Live Dashboard + Agent-Led Investor Calls)25:00 - Why He Let His AI Agent Handle First Meetings with Investors28:30 - The Self-Fulfilling Prophecy of Distribution (More Visibility = More Traction)32:15 - How Distribution Strategy Becomes Your Go-To-Market35:45 - Building in Public While Running Everything Solo38:00 - Customer Obsession at Scale (Staying Close When You're Alone)42:56 - Founder Availability: Direct Phone Access to Customers44:00 - Manufactured Moments That Feel Authentic50:13 - Why Distribution Isn't an Afterthought AnymoreKey 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 leverageWhy 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 buildersConnect with Ben Cera:Founder & CEO of PolsiaTwitter/X: @bencera LinkedIn: https://www.linkedin.com/in/benbroca/Host: Sophie Buonassisi, SVP at GTMnowFollow Sophie: https://x.com/sophiebuonaLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ABOUT GTMnowGTMnow 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.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_/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.

May 26, 202634 min

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 TunguzThis 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 Anticipated02:13 - Data Center CapEx Could Hit 5-7% of US GDP by 203005:21 - 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 Playing09:48 - How the Data Stack & AI/ML Worlds Have Completely Fused12:33 - Product-Market Fit is No Longer Binary: It's Continuous Now15:17 - How AI is Changing Venture Capital & Portfolio Management17:09 - The Future: Image & Video Data is Going to Require MASSIVE Infrastructure18:25 - Pattern Recognition Across Winning Companies (Domain Expertise is Key)20:50 - Hot Take: Corporate Org Structure Will Transform in 5 Years21:00 - Final Advice to Founders: Nobody Knows the AnswerKey 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 seriouslyConnect with Max:https://x.com/hackitmaxhttps://www.linkedin.com/in/maxaltschuler/Connect with Paul:https://x.com/PaulGTMhttps://www.linkedin.com/in/paulsirving/Guest: Tomasz Tunguz, General Partnerhttps://www.linkedin.com/in/tomasztunguz/https://x.com/ttunguzHost: Sophie Buonassisi, SVP at GTMnowhttps://www.linkedin.com/in/sophiebuonassisi/https://x.com/sophiebuonaABOUT 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.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_/Brought to you by: AngelListFrom starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility, from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.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 gtmnow@gtmfund.comGTMnow 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.

May 20, 202624 min

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 productivityABOUT THE GUESTLinda 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 DaysGuest: Linda Tong, CEO Webflowhttps://www.linkedin.com/in/lktong/https://x.com/YayLTHost: Sophie Buonassisi, SVP at GTMnowhttps://www.linkedin.com/in/sophiebuonassisi/https://x.com/sophiebuonaABOUT 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.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: .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 gtmnow@gtmfund.comGTMnow 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 #aimarketingThe 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.

May 14, 202641 min

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 headcountIf 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 & leadersHost: Sophie Buonassisi, SVP Marketing at GTMnowhttps://www.linkedin.com/in/sophiebuonassisi Guest: David Zhu, Co-founder and CEO at Reevohttps://www.linkedin.com/in/zhuventures/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_/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.comFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow 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 #AutomationThe 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.

May 12, 202647 min

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 Intro01:14 Intro18:48 Tyler joins23:09 "Sell Jesus, sell anything"27:42 The $2.5B Divvy exit34:39 The "bent the odds" contract38:11 Startups vs. OpenAI and Anthropic39:05 "Software is worth zero"40:55 The death of per-seat pricing43:02 Lessons from raising 4 kids46:44 "LinkedIn is the trailer park"Connect with Tyler:https://x.com/thoggehttps://www.linkedin.com/in/thogge/Connect with Max:https://x.com/hackitmaxhttps://www.linkedin.com/in/maxaltschuler/Connect with Paul:https://x.com/PaulGTMhttps://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: AngelListFrom starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility, from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.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 gtmnow@gtmfund.comGTMnow 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 #FounderAdviceVisit 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 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.

May 6, 202612 min

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.TIMESTAMPS0:00 Intro0:58 Welcome to GTMnow at HumanX1:10 Why 2026 is when AI moves from pilot to production2:32 Influencing decisions vs. making decisions: the next 2 years3:18 Digital Impact: why fragmentation will stall the AI revolution5:01 "Get your data to the gym": the new slogan5:20 The 3 questions to know if your company is AI-ready6:47 Change happens at the speed of trust7:53 The internal protest behind Boomi's CSM agent9:32 From integration platform to data activation: the strategic shift10:50 Steve's most transformative AI workflow as a CEO11:12 Vibe coding with Claude on an airplane12:20 Where to follow Steve and BoomiHost: Sophie Buonassisi, SVP Marketing at GTMnowlinkedin.com/in/sophiebuonassisi Guest: Steve Lucas, CEO at Boomihttps://www.linkedin.com/in/nstevenlucas/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_/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.comFor inquiries about sponsoring the podcast, email gtmnow@gtmfund.comGTMnow 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 #futureofworkThe 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.

April 29, 202640 min

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 workHost: Sophie Buonassisi, SVP Marketing at GTMnowhttps://www.linkedin.com/in/sophiebuonassisiGuest: Jon Addison, CRO at Oktahttps://www.linkedin.com/in/jon-addison-3399175Timestamp:0:00 - Cold open1:19 - Welcome + Jon's background: from London to Silicon Valley1:52 - How Jon got into software and identity management4:08 - Okta for AI Agents launch announcement5:04 - 90% of customers live with agents, only 10% confident in securing them6:31 - What's driving the governance gap in the market7:53 - Speed of agent innovation must be matched by security and governance8:36 - 40% higher ACV on deals that include new products9:43 - Why consolidation around a single identity platform is resonating11:45 - How AI agents unlock a massive new TAM for Okta13:05 - Okta's turnaround: from $850M operating losses to $760M operating income13:36 - Key decision 1: GTM specialization drove productivity15:02 - Key decision 2: becoming a partner-first company16:14 - What cracking the partner-led model actually looks like19:08 - How long it takes to see ROI from a partner-led pivot20:12 - The path from $3B to $5B: enterprise, international, public sector21:49 - Using AI internally: launching "Apex," the AI-era sales methodology23:04 - What the Apex sales methodology entails24:25 - Buyers now show up with strong opinions before the first call25:44 - How discovery is changing: human-centric selling in the AI era27:33 - Headcount and AI: what skills matter in the future29:31 - Why relationships are Okta's core competitive advantage30:36 - The role of experiences: F1, events, and the 7-touchpoint rule31:47 - Broad GTM surface area: ABM, ecosystem, brand33:47 - The future of identity: SaaS disruption, consolidation cycles, and Okta's position37:06 - Jon's leadership style: coaching reps and unlocking potential39:01 - Positive vs. negative leadership and the 1-to-10 touchpoints frameworkVisit us on: https://gtmnow.comFollow us on LinkedIn: https://www.linkedin.com/company/gtmnowFollow us on X (TwitteThe 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.