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53:08ENManage Up, Get Specific, Say No by Trading Off: Wes Kao's Playbook for Clearer WorkGuest Wes Kao · Host Lenny RachitskyMaven co-founder Wes Kao walks Lenny Rachitsky through five ideas on writing, teaching, managing your boss and declining requests, after a tour of her path from the Gap to Seth Godin's altMBA.
59:20ENFrom Trello to The Knot: Roles, Velocity and the Question "What Are You Optimizing For?"Guest Nikita Miller · Host Lenny RachitskyNikita Miller, head of product at The Knot Worldwide, on aligning cross-functional roles, shipping with urgency, working remotely and balancing life and work.
1:22:34ENSimplify, Follow Up, Carry the Water: What Separates Great Product ManagersGuest Maggie Crowley · Host Lenny RachitskyToast VP of Product and former Olympic speed skater Maggie Crowley on the three habits of the best PMs, how she writes strategy, and why "data-driven" can be a red flag.
43:44ENRoblox's 20-Year Bet: Building the Holodeck with Native AI ModelsHost Sarah Guo, Elad GilRoblox CEO Dave Baszucki explains how 13 billion monthly hours of 3D interaction data could power smarter NPCs, virtual doppelgängers and a cloud-native future for games.
1:24:56ENPeople Hire Products: Bob Moesta on Struggling Moments, Context and the Real Jobs to Be DoneGuest Bob Moesta · Host Lenny RachitskyThe co-creator of Jobs to Be Done explains how to find the moment customers change behavior, how to interview them, and where the framework doesn't fit.
1:02:56ENThink Rigorously, Decide Fast: Lessons from Stripe's Culture and Retool's Innovation MachineGuest Eeke de Milliano · Host Lenny RachitskyRetool's head of product and early Stripe PM Eeke de Milliano on first-principles thinking, protecting innovation, right-sizing process and building a balanced product team.
1:31:34ENHow Snyk Grew from a Node.js Niche to a Developer Security GiantGuest Ben Williams · Host Lenny RachitskyBen Williams, VP of Product at Snyk, explains the community, loops, team structure and data foundations behind the company's product-led growth.
1:12:29ENLazy, Vain, Selfish Users and the Rule of Three: An Indian Product Leader's PlaybookGuest Anuj Rathi · Host Lenny RachitskyAnuj Rathi of Jupiter Money walks through how product management took shape in India, and the frameworks he uses for onboarding, working backwards, strategy and marketplaces.
1:07:36ENMake a Podcast to Build for Podcasters: Maya Prohovnik on Dogfooding, Gut Calls and Anchor's Unscalable HacksGuest Maya Prohovnik · Host Lenny RachitskySpotify's head of podcast product and Anchor's employee number one explains how she dogfoods, balances intuition with data, and keeps a startup mindset inside a giant company.
29:03ENNotion's Simon Last on Rewriting the AI Harness Every Six Months and Managing a Swarm of AgentsHost Sarah Guo, Elad GilThe Notion co-founder traces the product's path from a writing assistant to custom background agents, and describes how coding agents changed the way he builds.
1:25:08ENRahul Vohra on Superhuman: Product-Market Fit Engines, Game Design and a CEO's TimeGuest Rahul Vohra · Host Lenny RachitskyThe Superhuman founder explains how he measures and optimizes product-market fit, why he treats products like games, and how he redesigned his own job to speed up the company.
1:01:49ENFocus Wisely: How Calendly Grew from a Free Viral Tool into a Product-Led Business with a Sales TeamGuest Annie Pearl · Host Lenny RachitskyCalendly's chief product officer Annie Pearl explains how the company picks its customers, plans its roadmap, and layers sales on top of product-led growth.
1:30:53ENObviously Awesome in Practice: April Dunford's Playbook for B2B Product PositioningGuest April Dunford · Host Lenny RachitskyThe author of Obviously Awesome explains how to tell whether positioning is broken, how to rebuild it step by step, and why one persona matters more than the rest.
1:06:10ENColumn B Thinking: How Melanie Perkins Built Canva by Starting From the DreamGuest Melanie Perkins · Host Lenny RachitskyCanva's co-founder and CEO explains how working backward from a wild vision, rejection from over a hundred investors and a two-year rewrite shaped a company valued above $42 billion.









