Lenny's Podcast: Product | Career | Growth

Tara Seshan leads product for Codex and ChatGPT Work at OpenAI (alongside previous podcast guest Andrew Ambrosino, who’s her engineering manager). Before OpenAI, Tara spent over six years at Stripe, where she joined as one of the first five product managers. She went on to lead product for Watershed, which Time magazine named one of the best inventions of 2022, and she is also a founder and Thiel Fellow. Most personally meaningful to me: Tara is one of the three inaugural Lenny’s Newsletter Fellows, a program I ran a couple of years ago to spotlight the most exciting up-and-coming product leaders. In our in-depth conversation, we discuss: 1. The shift from “rowing” to “steering,” and why human judgment and ambition will become differentiators as AI takes on execution 2. How OpenAI thinks about building for model capabilities two to three months out 3. OpenAI’s best internal memes, such as “Is this maximally accelerated?” and “Are you mainlining it yet?” 4. Why ambition is the new bottleneck for companies, and why elevating others’ ambitions is now the key part of the PM job 5. Writing as thinking vs. writing as reporting — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Where to find Tara Seshan: • X: https://x.com/tarstarr • LinkedIn: https://www.linkedin.com/in/tarstarr • Newsletter: https://substack.com/@taraseshan — 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 (02:18) What makes OpenAI’s culture so different (06:42) Why AI product strategy is all about fast experimentation (09:02) How the PM role is changing (10:50) The shift from rowing to steering (15:35) What changes when agents become coworkers (20:05) Why ambition matters more than ever (26:39) Building products for models that do not exist yet (29:21) How ChatGPT’s Chat and Work modes differ (34:01) How OpenAI ships so quickly at scale (39:14) The vibe shift happening inside Codex (42:20) Why traditional roles are beginning to blur (45:59) Where humans will continue to provide unique value (48:20) How Tara uses AI in her own work (51:38) The magic of the /visualize command (52:39) Writing to think versus writing to report (57:10) How to use AI without losing your ability to think (01:00:15) Tara’s biggest lesson from Sutter Hill (01:04:16) ChatGPT’s site output (01:05:01) Why knowledge work is becoming more like coding (01:07:55) Lightning round and final thoughts — Referenced: • Codex: https://chatgpt.com/codex • ChatGPT Work: https://openai.com/chatgpt-work • Stripe: https://stripe.com • Watershed: https://watershed.com • Thiel Fellowship: https://thielfellowship.org • Meet your Lenny’s Newsletter Fellows: https://www.lennysnewsletter.com/p/meet-your-lennys-newsletter-fellows • The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir • The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennysnewsletter.com/p/the-nature-of-product-marty-cagan • Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty • Patrick Collison’s examples of fast projects: https://patrickcollison.com/fast • Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Andrew Ambrosino on X: https://x.com/ajambrosino • Tyler Cowen’s website: https://tylercowen.com • 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 • “Chop wood, carry water” quote: https://buddhism.stackexchange.com/questions/15921/what-is-the-meaning-of-the-zen-quote-before-enlightenment-chop-wood-carry-wat • 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google: https://www.lennysnewsletter.com/p/shreyas-doshi-live • Alan Kay: https://en.wikipedia.org/wiki/Alan_Kay • Brie Wolfson on X: https://x.com/zebriez • The playbook for building high-talent-density teams | Adam Ward, Head of Talent at Cursor: https://www.lennysnewsletter.com/p/the-playbook-for-building-high-talent • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • Sutter Hill Ventures: https://shv.com • Snowflake: https://www.snowflake.com • Mike Speiser on LinkedIn: https://www.linkedin.com/in/mikespeiser • Footnotes and Tangents: https://footnotesandtangents.substack.com • The Power Broker Book Club: https://www.robertcaro.org/copy-of-six-books-six-ny-times-book • The Odyssey: https://www.imdb.com/title/tt33764258 • Rashomon: https://www.imdb.com/title/tt0042876 • Akira Kurosawa: https://en.wikipedia.org/wiki/Akira_Kurosawa • Kevin Kwok on LinkedIn: https://www.linkedin.com/in/kevinakwok • The Work You Do, the Person You Are: https://www.newyorker.com/magazine/2017/06/05/toni-morrison-the-work-you-do-the-person-you-are • Ari Weinstein on X: https://x.com/AriX • Sky: https://sky.app • Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config — Recommended books: • Barbarian Days: A Surfing Life: https://www.amazon.com/dp/0143109391 • Anna Karenina: https://www.amazon.com/Anna-Karenina-LEO-TOLSTOY/dp/8175993421 • The Power Broker: https://www.amazon.com/dp/0394720245 • War and Peace: https://www.amazon.com/War-Peace-Leo-Tolstoy/dp/8175992832 • Wolf Hall: https://www.amazon.com/dp/0312429983 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jen Abel is the co-founder of JJellyfish and GM of enterprise sales at State Affairs. She is widely regarded as one of the sharpest practitioners in enterprise sales, and for that reason, this is her third visit to the podcast. In our first conversation we went deep on founder-led sales; in our second we mapped the $1M–$10M playbook. This time we do something I’ve never seen on another podcast: walk step by step through the full enterprise sales cycle. Most people think it’s five steps. Jen shows it’s closer to 15. In our in-depth conversation, we discuss: 1. Why the standard five-stage CRM pipeline is a forecasting tool, not a sales process, and what the real 15-step cycle looks like 2. The “pincer model” for landing the first meeting at the executive and N-minus-one level simultaneously 3. How to craft a two-to-three-sentence message around giving them “alpha” 4. How to run an intro call that extracts maximum intelligence before you ever show a demo 5. The two-to-three-day pilot structure, how to define success jointly, and when to charge for a longer pilot versus giving it away 6. Navigating pricing, procurement, redline negotiations, and the final signature without losing momentum — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Where to find Jen Abel: • X: https://x.com/jjen_abel • LinkedIn: https://www.linkedin.com/in/earlystagesales • Website: https://www.jjellyfish.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 (02:49) Why Jen is giving away her enterprise sales playbook (05:54) Example: selling AI legal tech to SpaceX (09:11) Step 1: Landing the meeting (18:44) Step 2: Running the intro call (30:00) Step 3: Running a follow-up call (36:30) Step 4: Prepping the pitch/frame for demo (38:36) Step 5: Running the demo (46:45) Step 6: Post-demo debrief (48:59) Step 7 through 9: Preparing for and running the pilot (01:03:44) Why the standard five-stage CRM pipeline doesn’t work (01:04:49) Step 10: Post-pilot session (01:07:48) What a healthy enterprise win rate looks like (01:11:45) Steps 11 through 14: Navigating procurement and getting the signature (01:18:01) How to think about expansion (01:19:18) How buyers can say no without wasting everyone’s time (01:21:53) Why enterprise sales is a lot like product management (01:22:27) Closing thoughts — Referenced: • State Affairs: https://stateaffairs.com • The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel • “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 • SpaceX: https://www.spacex.com • Lemlist: https://www.lemlist.com • Palantir: https://www.palantir.com • Jason Lemkin on X: https://x.com/jasonlk • We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents • Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org • Careers at State Affairs: https://stateaffairs.com/careers — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Ian Silber is the head of product design at OpenAI, where he has led the design of ChatGPT, Codex, and all of OpenAI’s product experience for the past three years. Before OpenAI, he was at Artifact, the AI-powered news app built by the founders of Instagram. Prior to that, he spent eight years at Instagram, where he worked on products including Reels. Ian is one of the most consequential designers working in AI today, and he takes us inside how OpenAI designs ChatGPT, Codex, and the future of how we will interact with AI. In our in-depth conversation, we discuss: 1. Why Ian believes this is the best time in history to be a product designer 2. Why engineers 10x’d with AI but design teams haven’t 3. What OpenAI looks for when hiring designers 4. “Just do less”: Ian’s counterintuitive advice to his designers 5. The future of ChatGPT as a super app 6. Where humans still win: user understanding, invention, and point of view — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Where to find Ian Silber: • X: https://x.com/iansilber • LinkedIn: https://www.linkedin.com/in/iansilber • Website: https://iansilber.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 Ian Silber (02:14) Why designers in general feel anxious about AI (09:01) What makes specific designers thrive in the AI era (13:41) Why Ian says it’s the best time in history to be a designer (17:13) How product roles are converging (22:24) Can AI design great products? (23:54) Where human judgment still matters (27:34) What Ian looks for when hiring designers (30:20) Why systems thinking matters (32:53) Balancing speed and craft (38:05) Designing for vastly different audiences (41:57) Solving the blank-box problem (43:31) How ChatGPT is evolving beyond chat (46:07) The vision for Codex (49:07) What Ian wishes he knew on day one (51:40) Why humility matters in AI (53:41) Advice for designers who are feeling overwhelmed (55:16) AI corner (57:43) Failure corner (01:00:45) Lightning round and final thoughts (01:05:52) Lessons from Groupon — Referenced: • OpenAI: https://openai.com • How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026 • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • 3 Spiderman Pointing meme template: https://www.kapwing.com/explore/3-spiderman-pointing-meme-template • OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape • Notion: https://www.notion.com • The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead • Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • ChatGPT Work: https://openai.com/chatgpt-work • 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 • Please Stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater • 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 • Maybe Happy Ending: https://www.maybehappyending.com • The Invite: https://www.imdb.com/title/tt14173636 • Rivian: https://rivian.com • Waymo: https://waymo.com • Groupon: https://www.groupon.com • How a VC and a tech founder used AI to launch a brick-and-mortar business in their spare time | Andrew Mason (CEO of Descript) and Nabeel Hyatt (General Partner at Spark Capital): https://www.lennysnewsletter.com/p/how-a-vc-and-a-tech-founder-used • Andrew Mason on X: https://x.com/andrewmason • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom • Sam Altman on X: https://x.com/sama — Recommended book: • The Design of Everyday Things: https://www.amazon.com/dp/0465050654 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Adam Ward is the Head of Talent at Cursor, one of the fastest-growing developer tools in history. Before joining Cursor, he founded Growth by Design, an independent recruiting and talent strategy firm that helped build teams at the most ambitious AI and technology companies in the world. Adam has spent more than 20 years building elite, high-talent-density teams across the industry and is widely regarded as one of the most effective and creative recruiters in tech. In our in-depth conversation, we discuss: 1. Inside today’s “tale of two cities” talent market 2. Why the traditional recruiting funnel—what Adam calls the “funnel of doom”—leads to mediocre hires 3. Adam’s three-step playbook: scoping, mapping, and relentless pursuit 4. The worst question to ask when sourcing great talent 5. The rise of the forward deployed engineer—and how to become one 6. The biggest mistake founders make when hiring their first recruiter — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Where to find Adam Ward • X: https://x.com/wardadamp • LinkedIn: https://www.linkedin.com/in/adampward — 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 (03:01) The state of the hiring market (06:41) What roles are trending up and what roles are trending down (11:25) The three-step hiring framework that changes everything (21:58) Getting the right people to actually respond (25:42) Keeping talent a top priority (29:16) Inside Cursor’s recruiting operation (32:19) How to relentlessly pursue top talent (35:42) “Caring is free” (38:33) The conversation most companies underestimate (39:19) Rethinking the atomic unit of a search (40:12) Other recruiting tactics (45:04) What the on-site is really for (49:35) The importance of work trials (53:10) The offer stage (57:53) Negotiations and comp (01:01:50) The details that actually close the deal (01:07:23) What it’s like working with an exec team who values recruiting (01:09:42) Talent density (01:11:18) The first recruiting hire most founders get wrong (01:15:00) Building incredible teams (01:18:12) The time between offer and acceptance (01:19:48) What’s next for the recruiting function (01:21:00) Lightning round — Referenced: • Cursor: https://cursor.com • Trilogy: https://trilogy.com • Brie Wolfson on LinkedIn: https://www.linkedin.com/in/brie-wolfson-17758724 • Inside Cursor: https://colossus.com/article/inside-cursor • SpaceX: https://www.spacex.com • Joe Gebbia’s website: https://joegebbia.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 • The Pitt on HBO Max: https://www.hbomax.com/shows/pitt-2024/e6e7bad9-d48d-4434-b334-7c651ffc4bdf • The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f • Granola: https://www.granola.ai • Wispr Flow: https://wisprflow.ai • 11 products I love, free for a year—the biggest Product Pass expansion in 2 years: https://www.lennysnewsletter.com/p/productpass-summer2026launch • How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working • The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham — Recommended books: • Emotional Intelligence: Why It Can Matter More Than IQ: https://www.amazon.com/dp/055338371X • High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100 • Scaling People: Tactics for Management and Company Building: https://press.stripe.com/scaling-people — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com