Lenny's Podcast: Product | Career | Growth

Jeetu Patel is the president and chief product officer at Cisco, where he leads a team of 30,000 people and is playing a central role in the massive AI infrastructure buildout happening right now. Previously, he spent five years as CPO at Box and 17 years running his own startup. Recently Jeetu organized an AI summit featuring industry leaders like Jensen Huang, Sam Altman, Marc Andreessen, and Fei-Fei Li. We discuss: 1. How Cisco went AI-first across 90,000 employees 2. His six-part framework for building great companies: timing, market, team, product, brand, distribution 3. Why he says he couldn’t have done this job without AI 4. His “right to win” strategic framework 5. His communication framework for preventing “packet loss” across an organization 6. Why he flips “praise in public, criticize in private” and does the exact opposite 7. The important communication lesson his mother taught him — Brought to you by: Sentry—Code breaks, fix it faster: https://sentry.io/lenny Framer—Build better websites faster: https://framer.com/lenny Samsara—Saving lives with AI built for physical operations: https://samsara.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jeetu Patel: • X: https://x.com/jpatel41 • LinkedIn: https://www.linkedin.com/in/jeetupatel • Website: https://blogs.cisco.com/author/jeetupatel — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction and welcome (04:15) Insights from Cisco’s Al summit (08:45) Transforming Cisco into an Al-first company (15:33) What Cisco actually does in the Al infrastructure stack (19:09) The future of Al (24:36) Raising kids in the AI era (29:46) “Permission to play” framework (36:50) Lessons from great CEOs (42:02) Leading at scale (50:54) Why Jeetu inverts the ‘praise in public, criticize in private’ rule (57:45) Surrounding yourself with good human beings (58:35) Lessons from loss (01:03:21) Career advice: platforms, hunger, and preparation (01:10:21) The six-part framework for building great companies (01:19:05) Lightning round and final thoughts — Resources and episode mentions: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Boris Cherny is the creator and head of Claude Code at Anthropic. What began as a simple terminal-based prototype just a year ago has transformed the role of software engineering and is increasingly transforming all professional work. We discuss: 1. How Claude Code grew from a quick hack to 4% of public GitHub commits, with daily active users doubling last month 2. The counterintuitive product principles that drove Claude Code’s success 3. Why Boris believes coding is “solved” 4. The latent demand that shaped Claude Code and Cowork 5. Practical tips for getting the most out of Claude Code and Cowork 6. How underfunding teams and giving them unlimited tokens leads to better AI products 7. Why Boris briefly left Anthropic for Cursor, then returned after just two weeks 8. Three principles Boris shares with every new team member — Brought to you by: DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny Sentry—Code breaks, fix it faster: https://sentry.io/lenny Metaview—The AI platform for recruiting: https://metaview.ai/lenny — Episode transcript: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Boris Cherny: • X: https://x.com/bcherny • LinkedIn: https://www.linkedin.com/in/bcherny • Website: https://borischerny.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Boris and Claude Code (03:45) Why Boris briefly left Anthropic for Cursor (and what brought him back) (05:35) One year of Claude Code (08:41) The origin story of Claude Code (13:29) How fast AI is transforming software development (15:01) The importance of experimentation in AI innovation (16:17) Boris’s current coding workflow (100% AI-written) (17:32) The next frontier (22:24) The downside of rapid innovation (24:02) Principles for the Claude Code team (26:48) Why you should give engineers unlimited tokens (27:55) Will coding skills still matter in the future? (32:15) The printing press analogy for AI’s impact (36:01) Which roles will AI transform next? (40:41) Tips for succeeding in the AI era (44:37) Poll: Which roles are enjoying their jobs more with AI (46:32) The principle of latent demand in product development (51:53) How Cowork was built in just 10 days (54:04) The three layers of AI safety at Anthropic (59:35) Anxiety when AI agents aren’t working (01:02:25) Boris’s Ukrainian roots (01:03:21) Advice for building AI products (01:08:38) Pro tips for using Claude Code effectively (01:11:16) Thoughts on Codex (01:12:13) Boris’s post-AGI plans (01:14:02) Lightning round and final thoughts — References: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia’s fastest-growing founders as their in-house CEO coach. We discuss: 1. His LOCKS framework for evaluating founders 2. Why you should build your team like the 2004 Red Sox 3. Why hiring “spicy” candidates beats consensus picks 4. Why enterprise sales will be the last white-collar job AI replaces 5. Some of my favorite “Halliganisms” — Brought to you by: Sentry—Code breaks, fix it faster: http://sentry.io/lenny Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Brian Halligan • X: https://x.com/bhalligan • LinkedIn: linkedin.com/in/brianhalligan • Delphi: https://www.delphi.ai/bhalligan • Podcast: https://sequoiacap.com/series/long-strange-trip — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Brian Halligan (03:56) The perpetual state of constructive dissatisfaction (05:25) Coaching CEOs (07:49) The art of interviewing and hiring (11:21) Getting the most out of reference calls (13:10) Homegrown talent vs. big company hires (16:31) Traits of successful CEOs (19:40) Brian’s LOCKS framework for evaluating founders (21:34) Are great CEO’s born or made? (23:41) Giving effective feedback (25:54) The future of go-to-market strategies (31:56) Understanding forward deployed engineers (34:17) How the CEO role has evolved over the last 20 years (38:10) Halliganisms (01:01:18) The CEO’s role in scaling a company (01:02:41) Lightning round and final thoughts — Referenced: • Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria • HubSpot: https://www.hubspot.com • Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad • McKinsey & Company: https://www.mckinsey.com • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang • Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg • James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca • Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel • He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor • Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392 • OpenClaw: https://openclaw.ai • Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat • Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159 • Dalai Lama’s 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin • Glassdoor: https://www.glassdoor.com • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a • Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia • Bob Weir:...

Sherwin Wu leads engineering for OpenAI’s API platform, where roughly 95% of engineers use Codex, often working with fleets of 10 to 20 parallel AI agents. We discuss: 1. What OpenAI did to cut code review times from 10-15 minutes to 2-3 minutes 2. How AI is changing the role of managers 3. Why the productivity gap between AI power users and everyone else is widening 4. Why “models will eat your scaffolding for breakfast” 5. Why the next 12 to 24 months are a rare window where engineers can leap ahead before the role fully transforms — Brought to you by: DX—The developer intelligence platform designed by leading researchers Sentry—Code breaks, fix it faster Datadog—Now home to Eppo, the leading experimentation and feature flagging platform — Episode transcript: https://www.lennysnewsletter.com/p/engineers-are-becoming-sorcerers — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Sherwin Wu: • X: https://x.com/sherwinwu • LinkedIn: https://www.linkedin.com/in/sherwinwu1 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Sherwin Wu (03:10) AI’s role in coding at OpenAI (06:53) The future of software engineering with AI (12:26) The stress of managing agents (15:07) Codex and code review automation (19:29) The changing role of engineering managers (24:14) The one-person billion-dollar startup (31:40) Management lessons (37:28) Challenges and best practices in AI deployment (43:56) Hot takes on AI and customer feedback (48:57) Building for future AI capabilities (50:16) Where models are headed in the next 18 months (53:35) Business process automation (57:22) OpenAI’s ecosystem and platform strategy (01:00:50) OpenAI’s mission and global impact (01:05:21) Building on OpenAI’s API and tools (01:08:16) Lightning round and final thoughts — Referenced: • Codex: https://openai.com/codex • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • OpenClaw: https://openclaw.ai • The creator of Clawd: “I ship code I don’t read”: https://newsletter.pragmaticengineer.com/p/the-creator-of-clawd-i-ship-code • The Sorcerer’s Apprentice: https://en.wikipedia.org/wiki/The_Sorcerer%27s_Apprentice_(Dukas) • Quora: https://www.quora.com • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • Sarah Friar on LinkedIn: https://www.linkedin.com/in/sarah-friar • Sam Altman on X: https://x.com/sama • Nicolas Bustamante’s “LLMs Eat Scaffolding for Breakfast” post on X: https://x.com/nicbstme/status/2015795605524901957 • The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html • Overton window: https://en.wikipedia.org/wiki/Overton_window • Developers can now submit apps to ChatGPT: https://openai.com/index/developers-can-now-submit-apps-to-chatgpt • Responses: https://platform.openai.com/docs/api-reference/responses • Agents SDK: https://platform.openai.com/docs/guides/agents-sdk • AgentKit: https://openai.com/index/introducing-agentkit • Ubiquiti: https://ui.com • Jujutsu Kaisen on Crunchyroll: https://www.crunchyroll.com/series/GRDV0019R/jujutsu-kaisen?srsltid=AfmBOoqvfzKQ6SZOgzyJwNQ43eceaJTQA2nUxTQfjA1Ko4OxlpUoBNRB • eero: https://eero.com • Opendoor: https://www.opendoor.com — Recommended books: • Structure and Interpretation of Computer Programs: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871 • The Mythical Man-Month: Essays on Software Engineering:...

Lazar Jovanovic is a full-time professional vibe coder at Lovable. His job is to build both internal tools and customer-facing products purely using AI, while not having a coding background. In this conversation, he breaks down the tactics, workflows, and framework that let him ship production-quality products using only AI. We discuss: 1. Why having no coding background can be an advantage when building with AI 2. Why most of your time should go to planning and chat mode, not prompting 3. What to do when you get stuck: his 4x4 debugging workflow 4. The PRD and Markdown file system that keeps AI agents aligned across complex builds 5. Why kicking off four or five parallel prototypes is the best way to clarify your thinking 6. Why design skills and taste are going to be the most important skills in the future 7. His “genie and three wishes” mental model for making the most of AI’s limitations 8. How product, engineering, and design roles are converging—and what that means for your career — Brought to you by: Strella—The AI-powered customer research platform: https://strella.io/lenny Samsara—Saving lives with AI built for physical operations: https://samsara.com/lenny WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Lazar Jovanovic: • X: https://x.com/lakikentaki • LinkedIn: https://www.linkedin.com/in/lazar-jovanovic • YouTube: https://www.youtube.com/@50in50challenge • Starter Story course: https://build.starterstory.com/build/ai-build-accelerator?via=lazar (code LAZAR15 for 15% off) — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Lazar and professional vibe coding (04:53) What a professional vibe coder actually does day-to-day (09:26) Why non-technical backgrounds can be an advantage (12:24) The importance of self-awareness (14:42) His “genie and three wishes” mental model (17:43) Developing taste and judgment in the age of AI (21:46) The parallel project approach for better outcomes (29:30) Creating dynamic context windows with PRDs (36:56) Why elite vibe coders focus on planning, not coding (44:43) Creating MD files to guide AI development (50:57) Why prototyping still matters (56:50) Why “good enough” is no longer good enough (01:00:53) The future of engineering in an AI world (01:05:14) What to do when you get stuck: his 4x4 debugging workflow (01:14:27) Helping agents learn from their mistakes (01:15:35) Why watching agent output is more important than code (01:19:08) The incredible pace of AI development (01:22:55) Why emotional intelligence will become more valuable (01:28:30) How to become a professional vibe coder (01:30:10) Why building in public is the fastest path to opportunities (01:37:03) Final thoughts on focusing on quality over tech stack — Referenced: • The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna • Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company • The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led • 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna • Lovable:...

Dr. Becky Kennedy is a clinical psychologist, the bestselling author of Good Inside, and the founder of a parenting platform used by millions. Known for her practical, psychology-based approach to parenting, Dr. Becky shares how the same principles that help parents raise resilient children can make you a much more effective leader. In this conversation, she breaks down why all human systems—whether families or companies—operate on the same fundamental principles, and how understanding these dynamics can make you more effective in every relationship. We discuss: 1. Why repair—not perfection—defines strong leadership 2. Why you need to connect before you correct to build cooperation and trust 3. The “most generous interpretation” framework for handling difficult behaviors 4. How to correctly set boundaries (vs. making requests) 5. The power of “I believe you, and I believe in you” 6. What it looks like to be a “sturdy” leader — Brought to you by: Merge—Fast, secure integrations for your products and agents: https://merge.dev/lenny Metaview—The AI platform for recruiting: https://metaview.ai/lenny Framer—Builder better websites faster: https://framer.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/dr-becky-on-the-surprising-overlap — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Dr. Becky Kennedy: • X: https://x.com/GoodInside • LinkedIn: https://www.linkedin.com/in/drbecky • Instagram: https://www.instagram.com/drbeckyatgoodinside • TikTok: https://www.tiktok.com/@drbeckyatgoodinside • Website: https://www.goodinside.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Dr. Becky Kennedy (05:14) Connecting parenting and leadership (08:40) The power of repair (11:05) Connecting before correcting (17:45) Good Inside framework at work (22:08) The most generous interpretation (MGI) (25:46) Curiosity over judgment (27:07) Understanding behavior change (31:08) What potty training can teach us about workplace behavior (34:40) Naming your intention (35:41) Sturdy leadership (40:52) How to set boundaries well (46:33) The role of leadership and consensus (50:50) The importance of being “locatable” (52:40) A powerful story of betrayal and realization (57:12) Building resilience over happiness (01:00:34) The power of the phrase “I believe you, and I believe in you.” (01:09:08) The Good Inside community and resources (01:16:22) AI corner (01:19:52) Good Inside’s mission (01:22:26) Lightning round and final thoughts — Referenced: • Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng • Punch: https://en.wikipedia.org/wiki/Punch_(play) • Figma: https://www.figma.com • Andrew Hogan on LinkedIn: https://www.linkedin.com/in/ahhogan • Replit: https://replit.com • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Lovable: https://lovable.dev • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Claude: https://claude.ai • ChatGPT: https://chatgpt.com • Secrets We Keep on Netflix:...

Marc Andreessen is a founder, investor, and co-founder of Netscape, as well as co-founder of the venture capital firm Andreessen Horowitz (a16z). In this conversation, we dig into why we’re living through a unique and one of the most incredible times in history, and what comes next. We discuss: 1. Why AI is arriving at the perfect moment to counter demographic collapse and declining productivity 2. How Marc has raised his 10-year-old kid to thrive in an AI-driven world 3. What’s actually going to happen with AI and jobs (spoiler: he thinks the panic is “totally off base”) 4. The “Mexican standoff” that’s happening between product managers, designers, and engineers 5. Why you should still learn to code (even with AI) 6. How to develop an “E-shaped” career that combines multiple skills, with AI as a force multiplier 7. The career advice he keeps coming back to (“Don’t be fungible”) 8. How AI can democratize one-on-one tutoring, potentially transforming education 9. His media diet: X and old books, nothing in between — Brought to you by: DX—The developer intelligence platform designed by leading researchers Brex—The banking solution for startups Datadog—Now home to Eppo, the leading experimentation and feature flagging platform — Episode transcript: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Marc Andreessen: • X: https://x.com/pmarca • Substack: https://pmarca.substack.com • Andreessen Horowitz’s website: https://a16z.com • Andreessen Horowitz’s YouTube channel: https://www.youtube.com/@a16z — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Marc Andreessen (03:16) The historic moment we’re living in (05:21) The impact of AI on society (09:47) AI’s role in education and parenting (20:49) The future of jobs in an AI-driven world (34:41) The Mexican standoff of tech roles (39:10) The evolution of executive and admin roles (39:42) Adapting to changing job tasks (40:48) The future of coding and AI’s role (42:51) The shift to scripting languages (44:58) The importance of understanding code (50:12) The value of design in the AI era (52:02) The T-shaped skill strategy (01:01:11) AI’s impact on founders and companies (01:04:30) The concept of one-person billion-dollar companies (01:07:16) Debating AI moats and market dynamics (01:12:06) Complex adaptive systems and uncertainty (01:13:10) The rise of GPT wrappers (01:14:31) The rapid evolution of AI models (01:16:59) Indeterminate optimism in venture capital (01:21:00) The concept of AGI and its implications (01:22:49) Human IQ vs. AI capabilities (01:28:34) Media and product diets (01:34:51) Favorite movies and AI voice technology (01:41:59) Closing thoughts and recommendations — Referenced: • Linus Torvalds on LinkedIn: https://www.linkedin.com/in/linustorvalds • The philosopher’s stone: https://en.wikipedia.org/wiki/Philosopher%27s_stone • Alexander the Great: https://en.wikipedia.org/wiki/Alexander_the_Great • Aristotle: https://en.wikipedia.org/wiki/Aristotle • Bloom’s 2 sigma problem: https://en.wikipedia.org/wiki/Bloom%27s_2_sigma_problem • Alpha School: https://alpha.school • In Tech We Trust? A Debate with Peter Thiel and Marc Andreessen: https://a16z.com/in-tech-we-trust-a-debate-with-peter-thiel-and-marc-andreessen • John Woo: https://en.wikipedia.org/wiki/John_Woo • Assembly: https://en.wikipedia.org/wiki/Assembly_language • C programming language: https://en.wikipedia.org/wiki/C_(programming_language) • Python: https://www.python.org • Netscape: https://en.wikipedia.org/wiki/Netscape • Perl: https://www.perl.org • Scott Adams:...

Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team. We discuss: 1. Jason’s five-step framework: logo retention, pricing, NRR, marketing channels, target market 2. A small tweak that’ll double response rates on your cancellation surveys 3. Why “it’s too expensive” is almost never the real reason customers cancel 4. The “elephant curve” of growth 5. How repositioning the same product can increase revenue 8x 6. When to reconsider if growth is even the right goal for your business — Brought to you by: 10Web—Vibe coding platform as an API Strella—The AI-powered customer research platform Brex—The banking solution for startups — Episode transcript: https://www.lennysnewsletter.com/p/why-your-product-stopped-growing — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jason Cohen: • Preorder Jason’s book: https://preorder.hiddenmultipliers.com/ • X: https://x.com/asmartbear • LinkedIn: https://www.linkedin.com/in/jasoncohen • Blog: https://longform.asmartbear.com • Website: https://wpengine.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jason Cohen (05:19) Jason’s writing journey (08:25) Questions to ask when your product stops growing (18:17) Getting real customer feedback (20:27) Analyzing cancellation reasons (26:54) Onboarding and activation (29:35) Quick summary (35:46) Revisiting pricing strategies (41:46) Positioning strategies (47:52) Why pricing is inseparable from your strategy (52:06) The importance of net revenue retention (NRR) (01:00:25) Asking whether or not this is good for the customer (01:04:34) Leveraging existing customers (01:06:42) Are your acquisition channels saturated? The “elephant curve” (1:09:41) Why all marketing channels eventually decline (01:12:04) Direct vs. indirect marketing channels (1:13:36) Getting creative with new channels (01:19:04) Do you actually need to grow? (01:25:57) Deciding when to quit (01:29:27) Book announcement (01:33:21) AI corner (01:34:35) Contrarian corner (01:37:43) Lightning round and final thoughts — Referenced: • Tyler Cowen’s website: https://tylercowen.com • How to Perform a Customer Churn Analysis (and Why You Should): https://www.groovehq.com/blog/learn-from-customer-churn • Linear: https://linear.app • Jira: https://www.atlassian.com/software/jira • Patrick Campbell’s post on X about pricing: https://x.com/Patticus/status/1702313260547006942 • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam • Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy • M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs): https://www.lennysnewsletter.com/p/m-and-a-competition-pricing-and-investing • “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr • Buffer: https://buffer.com • AG1: https://drinkag1.com • How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com):...

Zevi Arnovitz is a product manager at Meta with no technical background who has figured out how to build and ship real products using AI. His engineering team at Meta asks him to teach them how he does what he does. In this episode, Zevi breaks down his complete AI workflow that allows non-technical people to build sophisticated products with Cursor. We discuss: 1. The complete AI workflow that lets non-technical people build real products in Cursor 2. How to use multiple AI models for different tasks (Claude for planning, Gemini for UI) 3. Using slash commands to automate prompts 4. Zevi’s “peer review” technique, which uses different AI models to review each other’s code 5. Why this might be the best time to be a junior in tech, despite the challenging job market 6. How Zevi used AI to prepare for his Meta PM interviews — Brought to you by: 10Web—Vibe coding platform as an API DX—The developer intelligence platform designed by leading researchers Framer—Build better websites faster — Episode transcript: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Zevi Arnovitz • X: https://x.com/ArnovitzZevi • LinkedIn: https://www.linkedin.com/in/zev-arnovitz • Website: https://zeviarnovitz.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Zevi Arnovitz (04:48) Zevi’s background and journey into AI (07:41) Overview of Zevi’s AI workflow (14:41) Screenshare: Exploring Zevi’s workflow in detail (17:18) Building a feature live: StudyMate app (30:52) Executing the plan with Cursor (38:32) Using multiple AI models for code review (40:40) Personifying AI models (43:37) Peer review process (45:40) The importance of postmortems (51:05) Integrating AI in large companies (53:42) How AI has impacted the PM role (57:02) How to improve AI outputs (58:15) AI-assisted job interviews (01:02:57) Failure corner (01:06:20) Lightning round and final thoughts — Referenced: • Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Product Lead at Riverside): https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv • Wix: https://www.wix.com • Building AI Apps: From Idea to Viral in 30 Days: https://www.youtube.com/watch?v=j2w4y7pDi8w • Riley Brown on YouTube: https://www.youtube.com/channel/UCMcoud_ZW7cfxeIugBflSBw • Greg Isenberg on YouTube: https://www.youtube.com/@GregIsenberg • Bolt: https://bolt.new • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Lovable: https://lovable.dev • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • StudyMate: https://studymate.live • Dibur2text: https://dibur2text.app • Claude: https://claude.ai • Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code • Bun: https://bun.com • Zustand: https://zustand.docs.pmnd.rs/getting-started/introduction • Cursor: https://cursor.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Wispr Flow: https://wisprflow.ai • Linear: https://linear.app • Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu • Cursor Composer:...

Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder who’s now teaching etiquette to Silicon Valley’s founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026—especially as technology becomes more central to society and trust becomes harder to build. His etiquette book and courses have become surprisingly popular, teaching founders how to “show up in a room with a low heart rate” and quickly build trust. We discuss: 1. Why etiquette matters 2. Sam’s framework for showing up confidently, with a low heart rate, in any room 3. How to navigate introductions, small talk, meetings, and meals like a pro 4. Simple hacks for remembering names and handling awkward social situations 5. 30+ specific etiquette tips — Brought to you by: 10Web—Vibe-coding platform as an API DX—The developer intelligence platform designed by leading researchers WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs — Episode transcript: https://www.lennysnewsletter.com/p/silicon-valleys-missing-etiquette-playbook — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Sam Lessin: • X: https://x.com/lessin • LinkedIn: https://www.linkedin.com/in/wlessin • Website: https://www.wlessin.com • Podcast: https://moreorlesspod.com • Lettermeme: https://lettermeme.com/lessin — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Sam’s background (04:18) The role of etiquette in business success (09:30) Introductions and entering a room (16:20) Engaging conversations and building relationships (23:55) Hygiene and dress code essentials (33:42) Dining etiquette (37:15) Tipping etiquette (41:36) The “B&D trick” (43:05) Humor in social settings (45:18) Self-deprecating humor (47:42) Winding down conversations (49:20) Scheduling etiquette (55:23) Communication and email etiquette (01:02:28) Meeting etiquette tips (01:04:03) Virtual meeting best practices (01:05:15) The importance of cleaning up after yourself (01:05:58) Exiting and follow-up etiquette (01:07:24) Final thoughts (01:09:20) AI corner (01:11:13) Contrarian corner (01:16:25) Lightning round — Referenced: • Y Combinator: https://www.ycombinator.com • Kleiner Perkins: https://www.kleinerperkins.com • “Lose Yourself” by Eminem on Spotify: https://open.spotify.com/track/7MJQ9Nfxzh8LPZ9e9u68Fq • Alison Gopnik on Childhood Learning, AI as a Cultural Technology, and Rethinking Nature vs. Nurture: https://conversationswithtyler.com/episodes/alison-gopnik • Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan • Bain & Company: https://www.bain.com • Evernote: https://evernote.com • Calendly: https://calendly.com • Morning Brew: https://www.morningbrew.com • Cursor: https://cursor.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • DigitalOcean: https://www.digitalocean.com • Cloudflare: https://www.cloudflare.com • SpaceX: https://www.spacex.com • Marc Andreessen on X: https://x.com/pmarca • Landman on Prime Video: https://www.amazon.com/Landman-Season-1/dp/B0D4D8RTMD • Dave Morin on X: https://x.com/davemorin — Recommended books: • Modern Etiquette in Technology, Finance, Society, and at Home: A Slow Ventures Handbook: https://www.amazon.com/Modern-Etiquette-Technology-Finance-Society-ebook/dp/B0G4HSKSY5 • Life, the Universe and Everything: https://www.amazon.com/Universe-Everything-Hitchhikers-Guide-Galaxy-ebook/dp/B001ODEQ7A • The Ancient City: A Study on the Religion, Laws, and Institutions of Greece and...

Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they’ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your team a lot of pain and suffering. We discuss: 1. Two key ways AI products differ from traditional software, and why that fundamentally changes how they should be built 2. Common patterns and anti-patterns in companies that build strong AI products versus those that struggle 3. A framework they developed from real-world experience to iteratively build AI products that create a flywheel of improvement 4. Why obsessing about customer trust and reliability is an underrated driver of successful AI products 5. Why evals aren’t a cure-all, and the most common misconceptions people have about them 6. The skills that matter most for builders in the AI era — Brought to you by: Merge—The fastest way to ship 220+ integrations: https://merge.dev/lenny Strella—The AI-powered customer research platform: https://strella.io/lenny Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs — Transcript: https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/183007822/referenced — Get 15% off Aishwarya and Kiriti’s Maven course, Building Agentic AI Applications with a Problem-First Approach, using this link: https://bit.ly/3V5XJFp — Where to find Aishwarya Naresh Reganti: • LinkedIn: https://www.linkedin.com/in/areganti • GitHub: https://github.com/aishwaryanr/awesome-generative-ai-guide • X: https://x.com/aish_reganti — Where to find Kiriti Badam: • LinkedIn: https://www.linkedin.com/in/sai-kiriti-badam • X: https://x.com/kiritibadam — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Aishwarya and Kiriti (05:03) Challenges in AI product development (07:36) Key differences between AI and traditional software (13:19) Building AI products: start small and scale (15:23) The importance of human control in AI systems (22:38) Avoiding prompt injection and jailbreaking (25:18) Patterns for successful AI product development (33:20) The debate on evals and production monitoring (41:27) Codex team’s approach to evals and customer feedback (45:41) Continuous calibration, continuous development (CC/CD) framework (58:07) Emerging patterns and calibration (01:01:24) Overhyped and under-hyped AI concepts (01:05:17) The future of AI (01:08:41) Skills and best practices for building AI products (01:14:04) Lightning round and final thoughts — Referenced: • LevelUp Labs: https://levelup-labs.ai/ • Why your AI product needs a different development lifecycle: https://www.lennysnewsletter.com/p/why-your-ai-product-needs-a-different • Booking.com: https://www.booking.com • Research paper on agents in production (by Matei Zaharia’s lab): https://arxiv.org/pdf/2512.04123 • Matei Zaharia’s research on Google Scholar: https://scholar.google.com/citations?user=I1EvjZsAAAAJ&hl=en • The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis • Gajen Kandiah on LinkedIn: https://www.linkedin.com/in/gajenkandiah • Rackspace: https://www.rackspace.com • The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper • Semantic Diffusion: https://martinfowler.com/bliki/SemanticDiffusion.html • LMArena: https://lmarena.ai • Artificial Analysis:...

Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth. We discuss: 1. “Give away your Legos”: a framework for scaling yourself as a leader 2. “J-curves vs. stairs”: the two paths of career growth, and why you should pick the scarier path 3. “The waterline model” for diagnosing team problems (and why you should “snorkel before you scuba”) 4. Six rules for creating effective goals (and aligning everyone around them) 5. Rules of thumb for leading through rapid scale and change 6. Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor — Brought to you by: DX—The developer intelligence platform designed by leading researchers Brex—The banking solution for startups GoFundMe Giving Funds—Make helping a habit — Transcript: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182877855/my-biggest-takeaways-from-this-conversation — Where to find Molly Graham: • X: https://x.com/molly_g • LinkedIn: https://www.linkedin.com/in/mograham • Substack: https://mollyg.substack.com • Website: https://glueclub.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Molly Graham (04:28) Molly’s background at Google, Facebook, Quip, and CZI (11:29) The “Give away your Legos” framework (16:44) Managing your inner monster (19:49) When not to give away your Legos (21:28) Embracing a long career (23:25) The J-curve vs. stairs approach to career growth (32:00) The gift of knowing yourself (34:28) Learning to be a professional idiot (38:30) The waterline model: snorkel before you scuba (47:16) Six rules for creating strong alignment around goals (57:15) Rules of thumb for leading through rapid scale (01:07:49) Investing in high performers vs. low performers (01:10:54) Lessons from Zuckerberg, Sandberg, and Bret Taylor (1:21:15) Pivoting from ambition to purpose (1:26:32) Finding stability in instability (01:29:44) Final thoughts — Referenced: • Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652 • Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage • Quip: https://quip.com • He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor • Chan Zuckerberg Initiative: https://chanzuckerberg.com • 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths • ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups • The Muppets: https://muppets.disney.com • Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell • J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve • Forget the corporate ladder—winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks • Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath • Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921 • Joseph...

Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed. We discuss: 1. How AI is fundamentally changing the sales function 2. Why most SDRs and BDRs will be “extinct” within a year 3. What Jason is observing across his portfolio about AI adoption in GTM 4. How to become “hyper-employable” in the age of AI 5. The specific AI tools and tactics he’s using that have been working best 6. Practical frameworks for integrating AI into your sales motion without losing what works 7. Jason’s 2026 predictions on where SaaS and GTM are heading next — Brought to you by: DX—The developer intelligence platform designed by leading researchers Vercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web Datadog—Now home to Eppo, the leading experimentation and feature flagging platform — Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation — Where to find Jason Lemkin: • X: https://x.com/jasonlk • LinkedIn: https://www.linkedin.com/in/jasonmlemkin • Website: https://www.saastr.com • Substack: https://substack.com/@cloud — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jason Lemkin (04:36) What SaaStr does (07:13) AI’s impact on sales teams (10:11) How SaaStr's AI agents work and their performance (14:18) How go-to-market is changing in the AI era (19:19) The future of SDRs, BDRs, and AEs in sales (22:03) Why leadership roles are safe (23:43) How to be in the 20% who thrive in the AI sales future (28:40) Why you shouldn't build your own AI tools (30:10) Specific AI agents and their applications (36:40) Challenges and learnings in AI deployment (42:11) Making AI-generated emails good (not just acceptable) (47:31) When humans still beat AI in sales (52:39) An overview of SaaStr's org (53:50) The role of human oversight in AI operations (58:37) Advice for salespeople and founders in the AI era (01:05:40) Forward-deployed engineers (01:08:08) What's changing and what's staying the same in sales (01:16:21) Why AI is creating more work, not less (01:19:32) Why Jason says these are magical times (01:25:25) The "incognito mode test" for finding AI opportunities (01:27:19) The impact of AI on jobs (01:30:18) Lightning round and final thoughts — Referenced: • Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org • SaaStr Annual: https://www.saastrannual.com • Delphi: https://www.delphi.ai/saastr/talk • Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/ • Vercel: https://vercel.com • What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Replit: https://replit.com • Behind...

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion. We discuss: 1. Why “extraordinary results demand extraordinary efforts” 2. Why you should deliberately understaff projects, and how to know when you’ve gone too far 3. Matt’s transition from COO to CPO and what surprised him about leading product 4. The “high alpha, low beta” framework for evaluating people, processes, and products 5. When founders should quit their startups (hint: much earlier than VCs want you to) 6. How to fight entropy in your organization through relentless energy and intensity — Brought to you by: Google Gemini—Your everyday AI assistant: https://ai.dev/ Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny — Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation — Where to find Matt MacInnis: • X: https://x.com/stanine • LinkedIn: https://www.linkedin.com/in/macinnis • Email: macinnis@rippling.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Matt MacInnis and Rippling (04:38) The importance of extraordinary efforts (08:37) The challenges and rewards of relentless effort (10:11) Your job as a leader is to preserve intensity (12:39) You learn far more from success than failure (16:34) Transitioning to chief product officer (19:54) Fixing product management at Rippling (25:27) The “high alpha, low beta” framework (28:55) The PQL framework (35:16) Hiring frameworks and team dynamics (36:52) A helpful interview tactic (40:00) Leading as a COO vs. a CPO (42:34) The reality of product-market fit (46:38) The problem with venture capital (49:29) When founders should quit their startups (41:48) The immutable market (54:13) Lessons from Notion’s success (57:43) Investment strategies and narrative violations (01:00:42) The power of compounding, power law, and entropy (01:07:02) Maintaining intensity and fighting entropy (01:11:33) The importance of feedback and escalations (01:14:31) Rippling’s vision and success (01:17:48) AI’s impact on SaaS and business software (01:23:42) AI corner (01:26:23) Final thoughts and lightning round — Referenced: • Rippling: https://www.rippling.com • Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman • Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill • Carvana: https://www.carvana.com • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad • Inkling: https://www.inkling.com • Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari • Notion: https://www.notion.com • Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law • Seeking Alpha: https://seekingalpha.com • Dennis Rodman’s website: https://dennisrodman.com • Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle • Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick • SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html • Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1 • Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits • New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling • Workday: https://www.workday.com • Matic robots: https://maticrobots.com •...

Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s spent more time than anyone alive studying how attackers break AI systems, and what he’s found isn’t reassuring: the guardrails companies are buying don’t actually work, and we’ve been lucky we haven’t seen more harm so far, only because AI agents aren’t capable enough yet to do real damage. We discuss: 1. The difference between jailbreaking and prompt injection attacks on AI systems 2. Why AI guardrails don’t work 3. Why we haven’t seen major AI security incidents yet (but soon will) 4. Why AI browser agents are vulnerable to hidden attacks embedded in webpages 5. The practical steps organizations should take instead of buying ineffective security tools 6. Why solving this requires merging classical cybersecurity expertise with AI knowledge — Brought to you by: Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny Metronome—Monetization infrastructure for modern software companies: https://metronome.com/ GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny — Transcript: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181089452/my-biggest-takeaways-from-this-conversation — Where to find Sander Schulhoff: • X: https://x.com/sanderschulhoff • LinkedIn: https://www.linkedin.com/in/sander-schulhoff • Website: https://sanderschulhoff.com • AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Sander Schulhoff and AI security (05:14) Understanding AI vulnerabilities (11:42) Real-world examples of AI security breaches (17:55) The impact of intelligent agents (19:44) The rise of AI security solutions (21:09) Red teaming and guardrails (23:44) Adversarial robustness (27:52) Why guardrails fail (38:22) The lack of resources addressing this problem (44:44) Practical advice for addressing AI security (55:49) Why you shouldn’t spend your time on guardrails (59:06) Prompt injection and agentic systems (01:09:15) Education and awareness in AI security (01:11:47) Challenges and future directions in AI security (01:17:52) Companies that are doing this well (01:21:57) Final thoughts and recommendations — Referenced: • AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff • The AI Security Industry is Bullshit: https://sanderschulhoff.substack.com/p/the-ai-security-industry-is-bullshit • The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0 • OpenAI: https://openai.com • Scale: https://scale.com • Hugging Face: https://huggingface.co • Ignore This Title and HackAPrompt: Exposing Systemic Vulnerabilities of LLMs through a Global Scale Prompt Hacking Competition: https://www.semanticscholar.org/paper/Ignore-This-Title-and-HackAPrompt%3A-Exposing-of-LLMs-Schulhoff-Pinto/f3de6ea08e2464190673c0ec8f78e5ec1cd08642 • Simon Willison’s Weblog: https://simonwillison.net • ServiceNow: https://www.servicenow.com • ServiceNow AI Agents Can Be Tricked Into Acting Against Each Other via Second-Order Prompts:...

Elena Verna is the head of growth at Lovable, the leading AI-powered app builder that hit $200 million in annual recurring revenue in under a year with just 100 employees. In this record fourth appearance on the podcast, Elena shares how the traditional growth playbook has been completely rewritten for AI companies. She explains why Lovable focuses on innovation over optimization, how they’ve shifted from activation to building new features, and why giving away their product for free has become their most powerful growth strategy. We discuss: 1. Why 60% to 70% of traditional growth tactics no longer apply in AI 2. Why you have to re-find product-market fit every 3 months 3. The specific growth tactics driving Lovable’s unprecedented growth 4. Why giving away product is a growth strategy that beats paid ads 5. “Minimum lovable product” as the new standard (not minimum viable product) 6. Why activation now belongs to product teams, not growth teams 7. Whether you should join an AI startup (honest tradeoffs) — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web Persona—A global leader in digital identity verification — Transcript: ⁠https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna⁠ — My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/181207556/my-biggest-takeaways-from-this-conversation⁠ — Where to find Elena Verna: • X: https://x.com/elenaverna • LinkedIn: https://www.linkedin.com/in/elenaverna • Newsletter: https://www.elenaverna.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Elena Verna (05:19) The scale and growth of Lovable (08:55) Confidence in Lovable as a business (12:17) Retention at Lovable (15:02) Lovable’s unique growth levers (28:13) The role of marketing in Lovable’s success (38:09) Launching new features (40:59) Hiring and team dynamics (43:17) The value of vibe coding (49:46) The importance of community (51:47) Giving away your product for free (56:26) Tripling their company size (01:00:23) Product-market-fit challenges (01:08:50) Advice for joining AI companies (01:12:00) Work-life balance (01:15:20) What it’s like to work at Lovable (01:19:45) Women in tech (01:25:29) Final thoughts and lightning round — Referenced: • Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company • The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led • 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna • Lovable: https://lovable.dev • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Stripe: https://stripe.com • What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess): https://www.lennysnewsletter.com/p/what-differentiates-the-highest-performing • How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra • “Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO): https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn • Eric Ries on...

Alexander Embiricos leads product on Codex, OpenAI’s powerful coding agent, which has grown 20x since August and now serves trillions of tokens weekly. Before joining OpenAI, Alexander spent five years building a pair programming product for engineers. He now works at the frontier of AI-led software development, building what he describes as a software engineering teammate—an AI agent designed to participate across the entire development lifecycle. We discuss: 1. Why Codex has grown 20x since launch and what product decisions unlocked this growth 2. How OpenAI built the Sora Android app in just 18 days using Codex 3. Why the real bottleneck to AGI-level productivity isn’t model capability—it’s human typing speed 4. The vision of AI as a proactive teammate, not just a tool you prompt 5. The bottleneck shifting from building to reviewing AI-generated work 6. Why coding will be a core competency for every AI agent—because writing code is how agents use computers best — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny Fin—The #1 AI agent for customer service: https://fin.ai/lenny Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc — Transcript: https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180365355/my-biggest-takeaways-from-this-conversation — Where to find Alexander Embiricos: • X: https://x.com/embirico • LinkedIn: https://www.linkedin.com/in/embirico — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Alexander Embiricos (05:13) The speed and ambition at OpenAI (11:34) Codex: OpenAI’s coding agent (15:43) Codex’s explosive growth (24:59) The future of AI and coding agents (33:11) The impact of AI on engineering (44:08) How Codex has impacted the way PMs operate (45:40) Throwaway code and ubiquitous coding (47:10) Shipping the Sora Android app (49:01) Building the Atlas browser (53:34) Codex’s impact on productivity (55:35) Measuring progress on Codex (58:09) Why they are building a web browser (01:01:58) Non-engineering use cases for Codex (01:02:53) Codex’s capabilities (01:04:49) Tips for getting started with Codex (01:05:37) Skills to lean into in the AI age (01:10:36) How far are we from a human version of AI? (01:13:31) Hiring and team growth at Codex (01:15:47) Lightning round and final thoughts — Referenced: • OpenAI: https://openai.com • Codex: https://openai.com/codex • Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Dropbox: http://dropbox.com • Datadog: https://www.datadoghq.com • Andrej Karpathy on X: https://x.com/karpathy • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Atlas: https://openai.com/index/introducing-chatgpt-atlas • How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna: https://www.lennysnewsletter.com/p/how-block-is-becoming-the-most-ai-native • Goose: https://block.xyz/inside/block-open-source-introduces-codename-goose • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennysnewsletter.com/p/lessons-on-building-product-sense • Sora Android app: https://play.google.com/store/apps/details?id=com.openai.sora&hl=en_US&pli=1 • The OpenAI Podcast—ChatGPT Atlas and the next era of web browsing:...

Edwin Chen is the founder and CEO of Surge AI, the company that teaches AI what’s good vs. what’s bad, powering frontier labs with elite data, environments, and evaluations. Surge surpassed $1 billion in revenue with under 100 employees last year, completely bootstrapped—the fastest company in history to reach this milestone. Before founding Surge, Edwin was a research scientist at Google, Facebook, and Twitter and studied mathematics, computer science, and linguistics at MIT. We discuss: 1. How Surge reached over $1 billion in revenue with fewer than 100 people by obsessing over quality 2. The story behind how Claude Code got so good at coding and writing 3. The problems with AI benchmarks and why they’re pushing AI in the wrong direction 4. How RL environments are the next frontier in AI training 5. Why Edwin believes we’re still a decade away from AGI 6. Why taste and human judgment shape which AI models become industry leaders 7. His contrarian approach to company building that rejects Silicon Valley’s “pivot and blitzscale” playbook 8. How AI models will become increasingly differentiated based on the values of the companies building them — Brought to you by: Vanta—Automate compliance. Simplify security. WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Coda—The all-in-one collaborative workspace — Transcript: https://www.lennysnewsletter.com/p/surge-ai-edwin-chen — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180055059/my-biggest-takeaways-from-this-conversation — Where to find Edwin Chen: • X: https://x.com/echen • LinkedIn: https://www.linkedin.com/in/edwinzchen • Surge’s blog: https://surgehq.ai/blog — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Edwin Chen (04:48) AI’s role in business efficiency (07:08) Building a contrarian company (08:55) An explanation of what Surge AI does (09:36) The importance of high-quality data (13:31) How Claude Code has stayed ahead (17:37) Edwin’s skepticism toward benchmarks (21:54) AGI timelines and industry trends (28:33) The Silicon Valley machine (33:07) Reinforcement learning and future AI training (39:37) Understanding model trajectories (41:11) How models have advanced and will continue to advance (42:55) Adapting to industry needs (44:39) Surge’s research approach (48:07) Predictions for the next few years in AI (50:43) What’s underhyped and overhyped in AI (52:55) The story of founding Surge AI (01:02:18) Lightning round and final thoughts — Referenced: • Surge: https://surgehq.ai • Surge’s product page: https://surgehq.ai/products • Claude Code: https://www.claude.com/product/claude-code • Gemini 3: https://aistudio.google.com/models/gemini-3 • Sora: https://openai.com/sora • Terrence Rohan on LinkedIn: https://www.linkedin.com/in/terrencerohan • Richard Sutton—Father of RL thinks LLMs are a dead end: https://www.dwarkesh.com/p/richard-sutton • The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html • Reinforcement learning: https://en.wikipedia.org/wiki/Reinforcement_learning • Grok: https://grok.com • Warren Buffett on X: https://x.com/WarrenBuffett • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong • Interstellar on Prime Video: https://www.amazon.com/Interstellar-Matthew-McConaughey/dp/B00TU9UFTS • Arrival on Prime Video: https://www.amazon.com/Arrival-Amy-Adams/dp/B01M2C4NP8 • Travelers on...

Tomer Cohen is the longtime chief product officer at LinkedIn, where he’s pioneering the Full Stack Builder program, a radical new approach to product development that fully embraces what AI makes possible. Under his leadership, LinkedIn has scrapped its traditional Associate Product Manager program and replaced it with an Associate Product Builder program that teaches coding, design, and PM skills together. He’s also introduced a formal “Full Stack Builder” title and career ladder, enabling anyone from any function to take products from idea to launch. In this conversation, Tomer explains why product development has become too complex at most companies and how LinkedIn is building an AI-powered product team that can move faster, adapt more quickly, and do more with less. We discuss: 1. How 70% of the skills needed for jobs will change by 2030 2. The broken traditional model: organizational bloat slows features to a six-month cycle 3. The Full Stack Builder model 4. Three pillars of making FSB work: platform, agents, and culture (culture matters most) 5. Building specialized agents that critique ideas and find vulnerabilities 6. Why off-the-shelf AI tools never work on enterprise code without customization 7. Top performers adopt AI tools fastest, contrary to expectations about leveling effects 8. Change management tactics: celebrating wins, making tools exclusive, updating performance reviews — Brought to you by: Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/ Miro—The AI Innovation Workspace where teams discover, plan, and ship breakthrough products: https://miro.com/lenny — Transcript: https://www.lennysnewsletter.com/p/why-linkedin-is-replacing-pms — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180042347/my-takeaways-from-this-conversation — Where to find Tomer Cohen: • LinkedIn: https://www.linkedin.com/in/tomercohen • Podcast: https://podcasts.apple.com/us/podcast/building-one-with-tomer-cohen/id1726672498 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Tomer Cohen (04:42) The need for change in product development (11:52) The full-stack builder model explained (16:03) Implementing AI and automation in product development (19:17) Building and customizing AI tools (27:51) The timeline to launch (31:46) Pilot program and early results (37:04) Feedback from top talent (39:48) Change management and adoption (46:53) Encouraging people to play with AI tools (41:21) Performance reviews and full-stack builders (48:00) Challenges and specialization (50:05) Finding talent (52:46) Tips for implementing in your own company (56:43) Lightning round and final thoughts — Referenced: • How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen • LinkedIn: https://www.linkedin.com • Cursor: https://cursor.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Devin: https://devin.ai • Figma: https://www.figma.com • Microsoft Copilot: https://copilot.microsoft.com • Windsurf: https://windsurf.com • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Lovable: https://lovable.dev • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • APB program at LinkedIn:...

Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy. We discuss: 1. Why GTM is becoming more strategically important in the AI era 2. The rise of the GTM engineer 3. A primer on segmentation 4. How to build a sales org that engineers and product teams respect 5. The changing calculus of build vs. buy for go-to-market tools in the AI era 6. Why most customers buy to avoid pain rather than to gain upside — Brought to you by: Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny Lovable—Build apps by simply chatting with AI: https://lovable.dev/ Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ — Transcript: https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation — Where to find Jeanne DeWitt Grosser: • X: https://x.com/jdewitt29 • LinkedIn: https://www.linkedin.com/in/jeannedewitt — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jeanne DeWitt Grosser (05:26) Defining go-to-market (08:43) The evolution of go-to-market roles (11:23) The rise of the go-to-market engineer (14:21) Implementing AI in sales processes (15:28) Optimizing sales with AI agents (23:47) Defining sales roles: SDRs and AEs (26:04) When to hire a GTM engineer (29:04) Hiring and scaling sales teams (30:50) The ideal go-to-market engineer (34:24) The go-to-market tool stack (40:39) Advice on building a great sales bot (44:34) Vercel’s unfair advantage (46:37) Go-to-market as a product (47:04) Innovative sales tactics at Stripe (52:38) Effective go-to-market tactics (01:00:37) Segmentation strategies (01:09:31) Building a sales org that engineers love (01:14:00) Thoughts on PLG and pricing (01:16:44) Sales compensation and hiring (01:19:24) Lightning round and final thoughts — Referenced: • Vercel: https://vercel.com • Stripe: https://stripe.com • Rosalind Franklin: https://en.wikipedia.org/wiki/Rosalind_Franklin • Ben Salzman on LinkedIn: https://www.linkedin.com/in/bensalzman • SDK: https://ai-sdk.dev/docs/introduction • Gong: https://www.gong.io • Lyft: https://www.lyft.com • Instacart: https://www.instacart.com • DoorDash: https://www.instacart.com • “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting • Kate Jensen on LinkedIn: https://www.linkedin.com/in/kateearle • Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics • Atlassian: atlassian.com — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com