Lenny's Podcast: Product | Career | Growth

Lenny Rachitsky
  • 4.9 (1.4K)
  • Technology
  • Updated Weekly

Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.

  1. 2d ago

    Why every company now needs to think and operate like a lab team | Josh Woodward (Google Labs, Gemini, AI Studio)

    Josh Woodward is the head of Google Labs, the Gemini app, and AI Studio. He has spent over 17 years at Google and oversees its longest-running and largest labs team, whose products include NotebookLM (now Gemini Notebook), Project Genie, and Flow. His job is to find, experiment with, and scale new AI products, and he has built one of the most distinctive product cultures in the industry for generating ideas, running experiments, and, even more importantly, knowing when to quit. In our in-depth conversation, we discuss: 1. Why every company now needs to think and operate like a labs team 2. Where the best ideas really come from 3. The “almost possible” framework 4. How to recognize genuine product-market fit early 5. When to kill an idea 6. What skills are rising in value in the AI era 7. Why roles are not actually blurring into one universal builder role 8. How to set up your internal labs team — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more DX—Engineering intelligence for the AI era — Episode transcript: https://www.lennysnewsletter.com/p/why-every-company-now-needs-to-think — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Highlights: https://lennyspodcast.com/mostreplayedmoments — Where to find Josh Woodward: • X: https://x.com/joshwoodward • LinkedIn: https://www.linkedin.com/in/joshwoodward — 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 (02:53) Why every company now needs to think like a labs team (05:43) Where great ideas come from (07:43) The “almost possible” framework (11:52) Finding product-market fit (16:09) Falling in love with the problem, not the solution (17:57) When to kill an idea (19:35) Overseeing Google Labs and the Gemini app (22:21) Next consumer AI breakthroughs (24:32) Google’s vision for a personal assistant (27:18) What is overhyped and underhyped in AI right now (31:36) Skills rising in value: unlearning rate, explosive endurance, trust (35:45) Why roles are not blurring into one universal builder role (38:59) Explosive endurance rhythms (41:31) How planning has changed: rolling windows and 100-day milestones (43:37) Labs lifecycle stages (47:37) Tips for setting up an internal lab (54:00) The future of products in an AI world (56:26) Google Labs culture, rituals, and closing thoughts — References: https://www.lennysnewsletter.com/p/why-every-company-now-needs-to-think — 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

    Why every company now needs to think and operate like a lab team | Josh Woodward (Google Labs, Gemini, AI Studio)

  2. Oct 4

    OpenAI’s Head of ChatGPT: We’re entering a new era of AI (again) | Tibo Sottiaux

    Tibo Sottiaux leads ChatGPT and Codex at OpenAI. Under his stewardship, OpenAI has shipped some of its most consequential consumer launches: Codex, ChatGPT Work, and most recently, the new Dots personal agent platform. He joined me at DevDay, hours after his team launched more than 20 new products, to talk about where things are heading. We discuss: 1. Dots, OpenAI’s new personal AI assistant 2. Why most actions on the internet will soon be taken by agents 3. Why loops, graphs, and fine-tuning agent workflows are a passing phase 4. Which skills are trending up and down in the AI era 5. How Tibo’s Dot warned him about a production outage five minutes before the launch 6. OpenAI’s approach to AI safety — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more DX—Engineering intelligence for the AI era — Episode transcript: https://www.lennysnewsletter.com/p/openais-head-of-chatgpt-were-entering — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Tibo Sottiaux: • X: https://x.com/thsottiaux • LinkedIn: https://www.linkedin.com/in/thibault-sottiaux-27195366 — 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 Tibo Sottiaux (01:12) How Tibo uses AI in his daily work (03:10) The vision for always-on AI agents (06:15) How AI will continue to change work (07:32) Bringing Codex, ChatGPT, and Dots together (08:20) The sci-fi inspiration behind the technology (09:02) Building AI with the community (10:13) Understanding the Dots structure (11:34) OpenAI’s open ecosystem and plugin revenue sharing (13:39) How plugins get discovered and recommended (14:39) The research behind Dots (16:20) Where humans will remain valuable (17:25) Agent fatigue, loneliness, and context switching (18:55) The pressure to do more with AI (20:09) An agent that spotted a production outage before a live demo (21:42) Agent guardrails and connecting multiple devices (23:25) The skills becoming more valuable in the AI era (25:56) Advice for people early in their careers (27:18) How teams build and ship inside OpenAI (28:59) Autonomy, trust, and learning from mistakes (30:45) Building for a future where agents dominate internet activity (32:41) What Tibo has changed his mind about (33:55) OpenAI’s approach to AI safety and alignment (36:15) Moving beyond model pickers toward simpler AI — Referenced: • OpenAI Dots: https://chatgpt.com/features/dots • Her on Netflix: https://www.netflix.com/title/70278933 • Star Trek: https://www.imdb.com/title/tt0060028 • Pi: https://pi.ai • OpenCode: https://opencode.ai • Notion: https://www.notion.com • Figma: https://www.figma.com • OpenClaw: https://openclaw.ai • Peter Steinberger on X: https://x.com/steipete • Grok Bot: https://x.ai/bot • Muse: https://muse.ai • Instinct: https://instinct.com • Ahmed Ibrahim on LinkedIn: linkedin.com/in/ahmedibrhm • The Hugging Face incident and the road ahead: https://openai.com/index/hugging-face-incident-and-the-road-ahead — Recommended book: • Neuromancer: https://www.amazon.com/Neuromancer-William-Gibson/dp/0441007465 — 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

    OpenAI’s Head of ChatGPT: We’re entering a new era of AI (again) | Tibo Sottiaux

  3. Sep 27

    The grief, loneliness, and burnout sweeping through the tech industry right now | Molly Graham

    Molly Graham is back for round two, and this one is even more powerful. Molly has spent more than 20 years helping organizations and the humans inside them navigate growth and change. She’s held leadership roles at Google, Facebook, Quip, and the Chan Zuckerberg Initiative and is the host of TED’s WorkLife podcast (which she took over from Adam Grant). She also runs Glue Club, a leadership community for senior operators, and writes a popular newsletter called Lessons. In our in-depth conversation, we discuss: 1. Why Molly’s famous “give away your Legos” career advice no longer holds true in an AI world 2. The grief, loneliness, and burnout sweeping through the tech industry right now 3. Why delegating to AI is fundamentally different from delegating to a human 4. The fear narrative around AI job displacement, and why it’s overblown 5. Which Legos you should never give to AI 6. What the best managers are doing right now — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more DX—Engineering intelligence for the AI era — Episode transcript: https://www.lennysnewsletter.com/p/the-grief-loneliness-and-burnout Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 Highlights: https://lennyspodcast.com/mostreplayedmoments — 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) Molly Graham returns (03:34) What is “Give away your Legos”? (05:44) The origin story: Google, Facebook, and rapid scale (11:27) What still holds true in an AI world (18:13) Engineering’s identity shift: from rowing to steering (22:09) Loneliness and the collapse of team structure (24:06) The centaur and the reverse centaur (25:36) The fear narrative: AI-branded layoffs and overblown doom (29:20) Survey data: burnout is up to 55%, but half of people are thriving (35:07) Cleaning up AI slop (40:01) What’s actually different: delegating to AI vs. giving Legos to a human (42:02) Why every worker is now a manager, whether they want to be or not (49:07) Why giving things away creates space for new opportunities (55:27) Advice for people in the age of AI (59:38) What Legos you should never give away (01:03:12) The human sandwich: vision at the top, AI in the middle, humans at the end (01:05:00) Holding on to the things you love: grief, funerals, and what comes next (01:09:39) Slow takeoff: why you’re not too late (01:13:32) The most important skill to build right now (01:18:58) A message for managers and leaders (01:24:17) Key takeaways (01:31:42) Final thoughts — References: https://www.lennysnewsletter.com/p/the-grief-loneliness-and-burnout — 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

    The grief, loneliness, and burnout sweeping through the tech industry right now | Molly Graham

  4. Sep 20

    90 minutes of unfiltered product advice from Snap and Discord’s product chief | Peter Sellis

    Peter Sellis was the first product manager at Snapchat, where he spent seven years building one of the most beloved consumer products in history. He went on to serve as Head of Product at Discord, where he helped drive some of the fastest user growth the platform had seen. Having left his role at Discord, he gets to be especially real and unfiltered — nothing to promote, no PR, no comms team. In our in-depth conversation, we discuss: 1. Why Peter designs teams like . . . terrorist organizations 2. What it was really like to manage Nikita Bier 3. Why the median PM is so bad 4. Why Snapchat’s ads business never reached its potential 5. Why growth almost always comes from the core product 6. Peter’s three “oxymorons” of great product management — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Episode transcript: https://www.lennysnewsletter.com/p/90-minutes-of-unfiltered-product — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Peter Sellis: • X: https://x.com/petersellis • LinkedIn: https://www.linkedin.com/in/disgruntled • Website: https://pjs.lol — 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 (02:48) Why Peter avoided podcasts until now (05:44) Designing teams like terrorist organizations (10:35) Cult versus terrorist org: the key distinction (11:19) Managing Nikita Bier (12:56) Building orgs that handle spiky talent (15:16) Why the median PM is probably bad (18:28) Is the PM profession getting better? (20:49) Snap’s three ads monetization challenges (25:03) Snap’s underrated product track record (27:57) Systems thinking (32:19) Instagram copying Snapchat’s worst features (33:32) Software moats (35:27) Taste, museum curators, and the art of saying no (40:05) OpenAI, ads, and the trust auction mechanism (46:25) Counterintuitive lesson: ride your best people hard (50:13) Why collaboration is often overrated (50:50) Growth lives in the core product (57:50) When to bet on something genuinely new (01:02:18) SpaceX and sunsetting the Falcon 9 (01:07:01) Ambition as a learnable muscle (01:10:26) Long-term greedy: the ads philosophy (01:13:36) The Core Product Value framework (01:16:33) The three oxymorons of a great PM (01:20:29) Contrarian corner (01:26:00) Lightning round and final thoughts — References: https://www.lennysnewsletter.com/p/90-minutes-of-unfiltered-product — 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

    90 minutes of unfiltered product advice from Snap and Discord’s product chief | Peter Sellis

  5. Sep 8

    How we built Grok Bot in a month | Roman Ugarte (SpaceXAI)

    Roman Ugarte helped incubate and build Grok Bot, the popular new knowledge-work agent from SpaceXAI. A small, isolated team took it from first line of code to a working internal product in four weeks, and to a hugely successful public launch just three weeks later. Before Grok Bot, Roman led Growth at Cursor, where he helped scale the company from 15 people to over 1,000 before its acquisition by SpaceX. In our in-depth conversation, we discuss: 1. The origin story of Grok Bot 2. The key decision to build it from scratch instead of adding it to Cursor 3. Why the team personally onboarded nearly 300 of its first users 4. The two early product decisions that made Grok Bot so successful 5. Their “colleague-pilled” product philosophy 6. Roman’s advice on moats, and what has allowed Cursor to keep winning in the most competitive market in the world — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Episode transcript: https://www.lennysnewsletter.com/p/how-we-built-grok-bot-in-a-month — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Roman Ugarte: • X: https://x.com/romanugarte_ • LinkedIn: https://www.linkedin.com/in/romanugarte • Website: https://x.ai — 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 (02:09) The origin story: building from scratch in one month (08:40) Why Grok Bot was built as a separate product (11:20) Manually onboarding a couple hundred people (14:29) Hiding internal mechanics from users (18:41) Timeline from beta to public launch (19:14) Unshipping features and simplifying (23:50) Early use cases and feedback (26:50) Product philosophy: “Grok Bot can now” (30:02) Cloud-first architecture (33:12) The fresh-start advantage (35:54) The vision: a true team of AI colleagues (39:20) The “colleague-pilled” framework (42:36) Work versus personal: one product or two? (47:14) Long-lived agents, persistent memory, and the computer abstraction (51:04) Grok Bot as an always-on infovore and chief of staff (53:35) How fast the team moves and what preserves the startup feeling (58:20) SpaceXAI pillars (1:00:44) The first 90% vs. the last 10% (1:03:30) Moving fast at scale (1:06:40) How Cursor kept winning in the most competitive market in the world (1:10:04) Company values: “deleting the product” and “just do the thing” (1:11:45) Moats: discovered, not planned (1:15:11) Tips for new users and power users (1:18:00) Lightning round and final thoughts — References: https://www.lennysnewsletter.com/p/how-we-built-grok-bot-in-a-month — 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

    How we built Grok Bot in a month | Roman Ugarte (SpaceXAI)

  6. Sep 6

    Why companies are becoming a series of loops | Anish Acharya (a16z)

    Anish Acharya is a General Partner at Andreessen Horowitz (a16z), where he has focused on consumer investing. Anish is one of the most insightful, thought-provoking, and in-the-weeds product investors I’ve met, and this conversation will get your mind buzzing. Before joining a16z, Anish was a serial founder and operator: he founded SocialDeck, which he sold to Google, then led multiple efforts inside Google before founding Snowball, which he sold to Credit Karma. At Credit Karma he rose to VP of Product and then GM of the consumer product and the broader credit card business. In our in-depth conversation, we discuss: 1. Why you don’t have to worry about becoming part of the “permanent underclass” 2. Why company building will now involve creating a series of loops 3. What’s happening in consumer right now 4. Why the biggest opportunity in consumer is “/loop, make me happier” 5. Why moats are discovered, not designed 6. The rising importance of distribution as a moat 7. Being a model sommelier — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Episode transcript: https://www.lennysnewsletter.com/p/why-companies-are-becoming-a-series — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Anish Acharya: • Andreessen Horowitz: https://a16z.com/author/anish-acharya/ • LinkedIn: https://www.linkedin.com/in/anishacharya/ • X: https://x.com/illscience • SoundCloud: https://soundcloud.com/illscience — 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 (02:25) The fear of AI creating a permanent underclass (05:25) Why AI takeoff may be slower than expected (08:02) How companies are actually adopting AI (11:25) Building AI products with loops (15:25) Why human intuition still matters (20:19) What the winners in AI are doing differently (21:41) Generalists vs. specialists (26:22) How to become a model sommelier (32:03) /loop make me happier (36:15) Why Anish is optimistic about the future of AI (42:47) What happens when models become too dangerous (46:29) How AI will change jobs and ambition (51:34) The state of consumer AI (54:30) How to build a durable moat in AI (59:25) The power of distribution and word of mouth (01:04:30) Making bigger bets and rethinking pricing (01:09:17) Advice for product builders in the AI era (01:11:48) Lightning round and final thoughts — References: https://www.lennysnewsletter.com/p/why-companies-are-becoming-a-series — 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

    Why companies are becoming a series of loops | Anish Acharya (a16z)

  7. Aug 30

    AI’s third era: the rise of persistent AI coworkers | Tara Seshan (Product Lead ChatGPT Work)

    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 podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    AI’s third era: the rise of persistent AI coworkers | Tara Seshan (Product Lead ChatGPT Work)

  8. Aug 23

    How to close $100K+ enterprise deals, step by step | Jen Abel

    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 podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

    How to close $100K+ enterprise deals, step by step | Jen Abel
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