The GTMnow Podcast

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  The Enterprise→PLG Playbook: Reversing the Motion Everyone Runs Backwards | Shensi Ding (CEO, Merge) 22.07.2026 47min

  Most companies start self-serve and grind their way up to enterprise. Shensi Ding did the opposite, then reversed course again. The co-founder and CEO of Merge joins Sophie Buonassisi on GTMnow to break down how she built a company that now powers integrations for OpenAI, Perplexity, Netflix, Uber, Mistral, and enterprise logos like Mastercard, JP Morgan, and Amex, backed by $75M from Accel and NEA. Shensi gets tactical on the GTM decisions behind that growth: why she went enterprise-first i...
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  The Blueprint for a High-Performing Sales Team | Brian Le, Notion 09.07.2026 45min

  Are your sales compensation plans driving the right behaviors or causing your best reps to quit? In this episode of GTMnow, Brian Le (Global Sales Compensation Partner at Notion) breaks down how to build a scalable sales comp operating system. Brian shares his firsthand experience scaling Notion's sales comp from 80 to over 400 employees and explains why trust is the ultimate currency in revenue operations. If you are a founder, revenue leader, or sales professional, this breakdown covers ev...
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  VC: How a 2-Person Fund Runs Like a Startup (Memos, KPIs, R&D) | Vanessa Larco, Premise (ex-NEA) 08.07.2026 48min

  "Investing in companies that OpenAI won't kill." That's Vanessa Larco's thesis, and in this VC bonus episode of GTMnow she breaks down exactly how she decides what survives. Vanessa, founder and GP at Premise (formerly a longtime partner at NEA, where she backed Robinhood from seed to IPO), joins Max to get into the nitty gritty of how AI is rewriting venture, distribution, and the entire go-to-market playbook. She makes the case for why "it's just a wrapper" got a lot of VCs in trouble, why...
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  Why a $1.2B exit felt like his biggest failure, and the customer-obsession thesis behind Agency 02.07.2026 52min

  A $1.2 billion exit is the dream. Elias Torres calls it his biggest failure. The Drift co-founder joins Sophie Buonassisi on GTMnow to unpack why the headline number felt hollow, what he learned in the quiet stretch afterward, and why he jumped straight back in to build Agency, an AI company that runs your entire customer organization. Elias gets honest about identity after the exit, the difference between chasing a title and building something enduring, and the operating thesis behind Agenc...
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  From DeepMind to 200 Customers in 20 Countries: Building the Execution Layer for Sales | Adam Liska, CEO of Airspeed 25.06.2026 32min

  The single most expensive sentence in sales is "I'll follow up on that." Adam Liska joins Sophie Buonassisi on GTMnow to break down the "execution gap," the space between knowing what to do in a deal and actually doing it, and why that gap is where most pipeline quietly dies. Adam left DeepMind's Gemini team in 2022, pre-ChatGPT, to build a native revenue execution platform now serving 200 customers across 20 countries (recently rebranded and fresh off a $20M Series A). In this conversation,...
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  VC: How Benchmark Picks AI Winners - Max 10 Bets a Year, 5 Partners | Chetan Puttagunta (GP) 24.06.2026 59min

  Benchmark's Chetan breaks down why the path from $0 to $100M has collapsed from five years to under two, and the one thing that is actually getting harder in the AI era: reaching your first million in revenue. In this VC bonus edition of the GTM Now Podcast, he sits down with Sophie Buonassisi to unpack how AI native companies are compressing 180 day sales cycles into 30 days, why direct sales is here to stay, and how value is shifting away from code toward the last mile of customer service. ...
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  Ads in ChatGPT Are Coming. What B2B Marketers Should Do Right Now | Keith Delany, CEO Primer 17.06.2026 45min

  LinkedIn CPMs just hit $800. AI is flooding every channel with content. Outbound is dying. So where should B2B marketers actually spend their ad budget right now? Keith Putnam-Delaney, co-founder & CEO of Primer, joins Sophie to break down the complete state of B2B paid advertising, what's broken, what's working, and where the real opportunities are hiding in 2025. What you'll learn: - Why LinkedIn & Google search are hitting a ceiling (and what to do instead) - How to get 80% match...
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  He's Seen 300+ Sales Comp Plans. 90% Make the Same Mistake | Siva Rajamani (Everstage CEO) 15.06.2026 57min

  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 betwe...
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  "We Don't Fund Good Companies" : A $1.5B VC Explains Why | Ben Lerer, Lerer Hippeau 09.06.2026 55min

  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 Gro...
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  How Esper Is Building the Operating System for Government Policy | Maleka Momand 04.06.2026 31min

  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 prof...
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  How He Built a $250M Company With Zero Employees | Ben Cera, Polsia 29.05.2026 50min

  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 cod...
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  The $575B AI Bet (Biggest Since the World Wars) and the New Two-Buyer Reality in Software | Tomasz Tunguz, Theory Ventures 26.05.2026 34min

  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 ...
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  SEO Is Not Enough Anymore: Webflow's CEO on the Rise of AEO | Linda Tong 20.05.2026 24min

  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 Optimizatio...
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  Inside Reevo's $80M Bet to Kill the $10B Frankenstein Stack | David Zhu, Cofounder & CEO 14.05.2026 41min

  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 ...
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  VC: "Software Is Basically Worth Zero Now" | Tyler Hogge, Ex-Pelion 12.05.2026 47min

  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 concentrate...
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  How AI Will Go From Influencing 20% to Making 90% of Your Decisions | Steve Lucas, Boomi CEO 06.05.2026 12min

  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 t...
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  Okta's CRO: From $850M in Losses to $760M Profit (The AI Agent Bet) | Jon Addison 29.04.2026 40min

  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...
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  VC: Inside a16z's $1.7B Infrastructure Bet | Jennifer Li, General Partner 28.04.2026 38min

  Jennifer Li, Partner at Andreessen Horowitz (a16z), breaks down why the firm allocated $1.7 billion of its latest $15 billion fund specifically toward AI infrastructure, and what she's betting on next. Jennifer has backed ElevenLabs from Series A all the way through Series D, watching it grow to an $11 billion valuation. In this episode, she explains what she saw in voice AI before anyone else did, what makes a founder worth backing regardless of the tech, and why the next wave of AI infrast...
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  How Figma Scaled From $2M to IPO | Kyle Parrish (First Sales Hire) 22.04.2026 47min

  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...
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  How AI Killed the Discovery Call | Sam Senior, Founder & CEO of TestBox 16.04.2026 57min

  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 TestBox, 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...