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1:02:42ENMercor’s Osvald Nitski on AI Training Data, Product and Customer ConcentrationGast: Osvald Nitski · Moderation: Harry StebbingsMercor’s head of product discusses how the company supplies expert data to AI labs, designs its marketplace and plans to reach more enterprise customers.
1:23:34EN20VC on Enterprise Sales Hiring, Compensation and AIGast: Chad Peets, Chris Degnan · Moderation: Harry StebbingsChad Peets and Chris Degnan discuss building sales teams, forecasting revenue and competing for talent while AI changes enterprise markets.
1:57:54ENCliff Weitzman on Speechify, AI Tools and Learning Through IterationGast: Cliff Weitzman · Moderation: Harry StebbingsThe Speechify founder discusses growth experiments, engineering culture, personal health experiences and the promise and risks he sees in AI.
1:14:23ENBecca Lindquist on Clay’s Sales Hiring, Compensation and AIGast: Becca Lindquist · Moderation: Harry StebbingsClay’s head of sales explains how she evaluates candidates, designs incentives and builds customer champions in a product-led business.
1:05:06ENShaunt Voskanian on Figma’s Sales Motion, Quotas and CoachingGast: Shaunt Voskanian · Moderation: Harry StebbingsFigma’s chief revenue officer explains how self-service adoption connects to enterprise sales, and why quota targets are only one part of evaluating a representative.
1:13:24ENWinston Weinberg on Building Harvey, Enterprise AI and the Art of DealsGast: Winston Weinberg · Moderation: Harry StebbingsHarvey’s co-founder explains how he thinks about founder focus, enterprise adoption, hiring and negotiating while legal AI changes.
1:06:10ENFuse CEO Alan Chang on Revolut, Energy and Building at SpeedGast: Alan Chang · Moderation: Harry StebbingsChang discusses his management approach, energy policy and Fuse’s growth while Harry Stebbings challenges several of his assumptions.
1:12:57ENMeta’s AI Talent Drive, Microsoft Layoffs and the Economics of Startup GrowthGast: Rory O’Driscoll, Jason Lemkin · Moderation: Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin examine talent competition, stock compensation, acquisitions and the changing market for venture-backed companies.
54:12ENJulian Teixeira on Hiring Sales Teams and Building a Repeatable ProcessGast: Julian Teixeira · Moderation: Harry StebbingsThe 1Password CRO discusses early hires, team goals, outbound prospecting, compensation and inspecting deals as a company scales.
52:59ENGeorge Bonaci on Growth Experiments, Hiring and Finding New ChannelsGast: George Bonaci · Moderation: Harry StebbingsRamp’s growth leader discusses balancing speed with rigor, measuring results and building a team that can find opportunities beyond an existing playbook.
46:23ENAdarsh Hiremath on Mercor, AI Recruiting and the Future of WorkGast: Adarsh Hiremath · Moderation: Harry StebbingsThe Mercor co-founder discusses expert labor for AI labs, automated interviews, fundraising and his vision for a global labor marketplace.
1:03:51ENMax Levchin on Hiring, Postmortems and Leading AffirmGast: Max Levchin · Moderation: Harry StebbingsThe Affirm founder discusses candid feedback, calculated risk, durable product work and staying focused through public-market volatility.
1:08:51ENAJ Tennant on Enterprise Sales, Customer Success and HiringGast: AJ Tennant · Moderation: Harry StebbingsGlean’s sales leader explains how to move upmarket, make AI deployments successful and evaluate sales candidates.
50:38ENZach Perret on Founder Mode, Product Expansion and Building PlaidGast: Zach Perret · Moderation: Harry StebbingsThe Plaid co-founder discusses delegation, difficult integration work, fundraising and the trade-offs of growing a multi-product company.
53:03ENMaria Angelidou-Smith on Product Reviews, Hiring and Building Better TeamsGast: Maria Angelidou-Smith · Moderation: Harry StebbingsThe Personio product and technology leader shares lessons from Meta on product careers, decision-making, resource allocation and leading distributed teams.
1:00:46ENJeetu Mahtani on International Expansion, Sales and Customer SuccessGast: Jeetu Mahtani · Moderation: Harry StebbingsThe former HubSpot sales leader explains how to test a new market, build partner ecosystems and align sales incentives with customer outcomes.
48:54ENAkshay Kothari on Notion’s Lean Team, Fundraising and Board DesignGast: Akshay Kothari · Moderation: Harry StebbingsThe Notion co-founder discusses staying focused, rebuilding sales and using cash-flow discipline to retain flexibility.
2:28:11ENPeople Are Easy to Predict — and They Hate Being Told SoGast: Charles Isbell · Moderation: Lex FridmanGeorgia Tech dean Charles Isbell talks with Lex Fridman about interactive AI, computing as a mindset, and race in America.
1:30:46ENSkip the Funnel of Doom: Cursor's Playbook for Hiring the Top 50Moderation: Lenny RachitskyAdam Ward, Cursor's head of talent, explains how to scope, map and relentlessly pursue the best people instead of hiring whoever survives a recruiting funnel.
1:42:04ENPaid Growth, Step by Step: Shopify's Performance Marketing Lead on Tests, Signal and Team DesignGast: Timothy Davis · Moderation: Lenny RachitskyTimothy Davis walks through when to start paid, how to run signs-of-life tests, which platforms to try, what to measure and who to hire first.
1:05:46ENHire for Balance, Fix Onboarding, Evaluate Companies Rigorously: Adam Fishman's Growth PlaybookGast: Adam Fishman · Moderation: Lenny RachitskyThe former Lyft, Patreon and Imperfect Foods growth leader lays out a four-part competency model for hiring growth talent, explains why onboarding is the most underrated retention lever, and shares a "people, mission, financials" framework for choosing where to work.
1:08:53ENPlay the Long Game: A Top Recruiter's Playbook for Hiring and Becoming a Product LeaderGast: Lauren Ipsen · Moderation: Lenny RachitskyRecruiter Lauren Ipsen explains how founders should hire their first senior product leader, how PMs should build their careers, and what recruiters often get wrong.
55:51ENHumble, Customer-Obsessed and Relentless: Inside DoorDash's CultureGast: Keith Yandell · Moderation: Lenny RachitskyDoorDash executive Keith Yandell explains how the company hires for culture, leads through crises, and manages people, from WeDash deliveries to a "how to work with me" document.
1:54:54ENSlow Down, Ask Questions, Sell the Vacation: An Executive Negotiator's PlaybookModeration: Lenny RachitskyJacob Warwick explains how senior operators win bigger offers by treating a job search like an enterprise sale and negotiating collaboratively rather than confrontationally.
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