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20VC with Harry Stebbings· Aug 15, 2026Podcast · 2 speakersMatt Swulinski on Building and Measuring a Product-Led Growth EngineGuest Matt Swulinski · Host Harry StebbingsThe growth leader shares lessons from Superhuman, Wispr Flow and Viktor on paid acquisition, creative testing, referrals and AI-assisted workflows.
1:02:42EN20VC with Harry Stebbings· Jul 25, 2026Podcast · 2 speakersMercor’s Osvald Nitski on AI Training Data, Product and Customer ConcentrationGuest Osvald Nitski · Host 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.
57:42EN20VC with Harry Stebbings· Jun 6, 2026Podcast · 2 speakersJacob Lauritzen on AI Engineering, Legal Work and Building LegoraGuest Jacob Lauritzen · Host Harry StebbingsLegora’s CTO discusses code review, token budgets, enterprise adoption and how legal workflows might change.
1:57:54EN20VC with Harry Stebbings· May 9, 2026Podcast · 2 speakersCliff Weitzman on Speechify, AI Tools and Learning Through IterationGuest Cliff Weitzman · Host Harry StebbingsThe Speechify founder discusses growth experiments, engineering culture, personal health experiences and the promise and risks he sees in AI.
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No Priors: AI, Machine Learning, Tech, & Startups· Aug 21, 2025Podcast · 2 speakersHire the AI First: Andrew Ng on Agentic Workflows and the Scarcity of JudgmentHost Sarah Guo, Elad GilOn No Priors, Andrew Ng argues that agentic AI has made software cheap and fast, which moves the bottleneck to product judgment, error analysis, and the instinct to try an AI before adding headcount.
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Jane Street· Jul 16, 2025How Jane Street’s Strategy and Product Team Works Across the FirmLily, Andrew, Basma · Jane StreetTeam members describe rotations, cross-functional projects and the skills they use to tackle ambiguous problems.
46:53EN20VC with Harry Stebbings· Feb 7, 2025Podcast · 2 speakersBrian Tolkin on Hiring Product Teams and Finding the Problem That MattersGuest Brian Tolkin · Host Harry StebbingsOpendoor’s head of product draws on Uber and Opendoor to discuss user choice, AI prototypes, decision-making and hiring.
1:06:04EN20VC with Harry Stebbings· Jan 8, 2025Podcast · 2 speakersDan Gill on Carvana’s Unit Economics, Product Decisions and TurnaroundGuest Dan Gill · Host Harry StebbingsThe Carvana product leader discusses financing, logistics, prioritization and leading through a dramatic market-cap decline.
1:00:24EN20VC with Harry Stebbings· Nov 15, 2024Podcast · 2 speakersRaman Malik on Perplexity’s Growth: Retention, Partnerships and ExperimentsGuest Raman Malik · Host Harry StebbingsPerplexity’s growth leader explains how he evaluates activation, organic acquisition, paid channels and a growing team.
53:03EN20VC with Harry Stebbings· Oct 4, 2024Podcast · 2 speakersMaria Angelidou-Smith on Product Reviews, Hiring and Building Better TeamsGuest Maria Angelidou-Smith · Host Harry StebbingsThe Personio product and technology leader shares lessons from Meta on product careers, decision-making, resource allocation and leading distributed teams.
1:09:13EN20VC with Harry Stebbings· Sep 13, 2024Podcast · 2 speakersMike Hudack on Product Simplicity, Experimentation and Building TeamsGuest Mike Hudack · Host Harry StebbingsThe Sling Money founder shares lessons from Facebook, Deliveroo and Monzo on customer choice, data and product leadership.
1:05:48EN20VC with Harry Stebbings· Aug 14, 2024Podcast · 2 speakersKaz Nejatian on Shopify: Building Complete Products and a Company for the Long TermGuest Kaz Nejatian · Host Harry StebbingsShopify’s COO explains its product culture, internal tools and partnerships, and reflects on remote work, information flow and leadership.
1:06:40EN20VC with Harry Stebbings· Jun 14, 2024Podcast · 2 speakersJanie Lee on Product Judgment, Hiring and Enterprise ExpansionGuest Janie Lee · Host Harry StebbingsThe Loom product leader discusses customer problems, clear writing, product reviews and the shift from self-serve adoption to enterprise sales.
58:18EN20VC with Harry Stebbings· May 17, 2024Podcast · 2 speakersJiaona Zhang on Product Scorecards, Strategy and Faster LearningGuest Jiaona Zhang · Host Harry StebbingsLinktree’s product leader explains how KPI trees, weekly scorecards and collaborative rituals connect customer needs to business outcomes.
52:54EN20VC with Harry Stebbings· Apr 17, 2024Podcast · 2 speakersVickie Peng on Building Less, Measuring Customer Value and Finding Product-Market FitGuest Vickie Peng · Host Harry StebbingsThe Sequoia product leader explains how to learn with less product, choose meaningful metrics and recognize different customer mindsets.
59:25EN20VC with Harry Stebbings· Feb 21, 2024Podcast · 2 speakersScott Williamson on Hiring Product Managers and Writing Better StrategyGuest Scott Williamson · Host Harry StebbingsThe former GitLab product leader explains his hiring process, written strategy tools and routines for coaching and reviewing product work.
57:49EN20VC with Harry Stebbings· Feb 2, 2024Podcast · 2 speakersWill Wu on Human-Centered Product Design, Snap and AIGuest Will Wu · Host Harry StebbingsThe Match Group CTO shares lessons from Snapchat Discover and Snap Games, and explains how he combines user empathy, rapid prototyping and technical judgment.
1:06:31EN20VC with Harry Stebbings· Dec 8, 2023Podcast · 2 speakersSanjit Biswas on Product-Market Fit, Sales and Building Samsara for the Long TermGuest Sanjit Biswas · Host Harry StebbingsThe Samsara co-founder discusses lessons from Meraki, customer-led product expansion, hiring and capital allocation.
59:36EN20VC with Harry Stebbings· Dec 6, 2023Podcast · 2 speakersGeoff Charles on Product Teams, Sprint Velocity and Strategy at RampGuest Geoff Charles · Host Harry StebbingsRamp’s product leader explains customer discovery, two-week sprints, reusable systems and hiring for execution.
1:01:17EN20VC with Harry Stebbings· Nov 22, 2023Podcast · 2 speakersJeff Seibert on Product Pivots, AI Infrastructure and Angel InvestingGuest Jeff Seibert · Host Harry StebbingsThe Digits founder discusses decisive product pivots, the risks of thin AI applications and the difference between paper gains and cash returns.
1:16:06EN20VC with Harry Stebbings· Nov 1, 2023Podcast · 2 speakersDavid Meyer on Product Management, Customer Curiosity and Building TeamsGuest David Meyer · Host Harry StebbingsThe Databricks product leader explains why product work is a balancing act, how to test assumptions with customers, and what he looks for when hiring.
1:01:06EN20VC with Harry Stebbings· Oct 25, 2023Podcast · 2 speakersEly Lerner on Startup Advisors, Growth Strategy and FocusGuest Ely Lerner · Host Harry StebbingsThe former Yelp and Chime product leader explains how to choose and compensate advisors, identify a growth lever, and balance strategic bets with essential defensive work.
1:14:20EN20VC with Harry Stebbings· Oct 6, 2023Podcast · 2 speakersGuillermo Rauch on Product Focus, AI Interfaces and InvestingGuest Guillermo Rauch · Host Harry StebbingsThe Vercel founder explains how he evaluates talent, chooses product battles and thinks about AI’s impact on software and business models.
50:35EN20VC with Harry Stebbings· Sep 29, 2023Podcast · 2 speakersKevin Niparko on Hiring Product Leaders, Demos and Customer OutcomesGuest Kevin Niparko · Host Harry StebbingsThe Twilio product leader shares lessons from Segment on building product teams, running reviews and deciding when to invest in a second product.Load moreShowing 24 of 195