Lenny's Podcast: Product | Career | Growth

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

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 podcast@lennyrachitsky.com.
—
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 podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com

Tom Verrilli is the chief product officer at Whatnot, a live shopping platform that’s become the fastest-growing U.S. marketplace business in history, with over $8 billion in GMV. Before joining Whatnot, Tom was CPO at Twitch and director of product growth at Twitter (during one of the most turbulent periods in the company’s history).

In our in-depth conversation, we discuss:
1. Why Whatnot’s product team was founded on the premise “we regret that product management exists”
2. How AI is reshaping the PM role
3. What Tom looks for when hiring PMs
4. The shift toward senior ICs doing the work
5. How AI has transformed data science at Whatnot
6. Tom’s “play the accordion” mental model
7. Why “hire great people and get out of their way” fails
8. His biggest lessons from his time at Twitter
—
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/this-cpo-regrets-that-product-management
—
Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
—
Where to find Tom Verrilli:
• X: https://x.com/tdrobbo
• LinkedIn: https://www.linkedin.com/in/tom-robertson-042
—
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
(02:40) “We regret that product management exists”: what it means and why
(08:30) When specialization makes sense, and when it doesn’t
(15:20) How Whatnot structures its PM org
(17:28) What 31,832 PM applications revealed about the function
(19:40) How to develop systems thinking
(22:10) The shift to senior ICs doing IC work
(32:26) Advice for PMs struggling in today’s market
(35:22) How AI has transformed work at Whatnot
(41:14) The data scientist problem
(42:48) Which roles are trending up and down
(44:48) What the product team of the future looks like
(46:29) Why core PM skills are the most durable in an AI world
(49:23) How to get the most out of the people you hire
(53:32) Navigating the CPO-founder relationship
(57:34) Advice for aspiring CPO’s
(59:16) How to know when to stand firm and when to step back
(01:01:38) Play the accordion: balancing strategic vision with fast iteration
(01:06:35) Agentic commerce vs. live commerce
(01:09:46) Lessons from Twitter
(01:13:07) Failure corner
(01:15:45) Lightning round and final thoughts
—
Referenced:
• Whatnot: https://www.whatnot.com
• Building, and Whatnot: https://www.linkedin.com/pulse/building-whatnot-tom-verrilli-bwkdc
• Twitch: https://www.twitch.tv
• Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO): https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future
• Peter Bailis on LinkedIn: https://www.linkedin.com/in/pbailis
• Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next
• Ben Kus on LinkedIn: https://www.linkedin.com/in/benkus
• Henry Shi on LinkedIn: https://www.linkedin.com/in/henrythe9th
• Hex Threads: https://hex.tech/product/threads
• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty
• Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine
• Logan Head on LinkedIn: https://www.linkedin.com/in/logan-head
• Emmett Shear on LinkedIn: https://www.linkedin.com/in/emmettshear
• Kara Swisher on X: https://x.com/karaswisher
• Jeff Bezos: Amazon and Blue Origin—Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY
• Star City on AppleTV+: https://tv.apple.com/us/show/star-city/umc.cmc.2l8p785osmtmiyk64bh6tfde1
• For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7
• Service NSW Mobile App: https://www.service.nsw.gov.au/services/service-nsw-mobile-app
• Rudyard Kipling: https://en.wikipedia.org/wiki/Rudyard_Kipling
• E-fish.com: https://www.e-fish.com
—
Recommended books:
• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/dp/0062273205
• The Purpose Driven Church: Every Church Is Big in God’s Eyes: https://www.amazon.com/dp/0310201063
• Babel: Or the Necessity of Violence: An Arcane History of the Oxford Translators’ Revolution―An Historic Fantasy of Dark Academia: https://www.amazon.com/Babel-Necessity-Violence-Translators-Revolution/dp/0063021439
—
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

Dianne Penn is Head of Product for Anthropic’s AI Research and Labs teams. She joined in 2023 as Anthropic’s first technical product manager, when the entire product team was five engineers, and has since helped ship every model from Claude 2 through Fable, and helped incubate Claude Code, MCP, Skills, computer use, tool use, and reasoning. Before Anthropic, she helped build Alexa’s AI at Amazon and, before that, traded high-yield bonds at JP Morgan Chase.

In our in-depth conversation, we discuss:
1. What Anthropic’s early days were like
2. The inflection points that turned Anthropic from an underdog into the fastest-growing company in history
3. How exactly Claude got so good at coding
4. The eval-driven development loop her team is pioneering
5. How to find joy in AI when everything is moving this fast
6. Why Claude’s willingness to push back is key to its success
7. Where human judgment remains irreplaceable
—
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/anthropics-first-technical-pm-on
—
Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
—
Where to find Dianne Penn:
• LinkedIn: linkedin.com/in/dianne-na-penn
—
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
(02:31) Early Anthropic days
(08:55) Big milestones
(13:50) Inside the exponential
(20:02) Token maxing
(23:30) Anthropic Labs and the incubation model
(27:30) How the research role works
(31:35) How to become a top researcher
(35:18) Frontier model safeguards
(39:38) Hiring in the AI era
(44:16) Building an eval set
(47:48) Evals vs PRDs
(49:55) The importance of hands-on leadership
(52:46) Finding joy in AI
(58:10) How Dianne uses Claude
(01:01:05) Avoiding overreliance on AI
(01:03:50) The constitution that makes Claude better
(01:07:11) AI writing and verification
(01:11:40) Where human brains will continue to be valuable
(01:14:10) Navigating AI with kids
(01:16:26) Alignment, the future of the PM role, and burnout
(01:21:54) Lightning round and final thoughts
—
Referenced:
• Anthropic: https://www.anthropic.com
• Golden Gate Claude: https://www.anthropic.com/news/golden-gate-claude
• Dario Amodei’s website: https://darioamodei.com
• Scaling Laws and Interpretability of Learning from Repeated Data: https://www.anthropic.com/research/scaling-laws-and-interpretability-of-learning-from-repeated-data
• Tokenmaxxing: How Top Builders Use AI To Do The Work Of 400 Engineers: https://www.ycombinator.com/library/Pa-tokenmaxxing-how-top-builders-use-ai-to-do-the-work-of-400-engineers
• Garry Tan on X: https://x.com/garrytan
• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next
• Introducing Labs: https://www.anthropic.com/news/introducing-anthropic-labs
• Louis CK | about airplane Wi Fi: https://www.youtube.com/watch?v=me4BZBsHwZs
• What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering
• The Anthropic Hive Mind: https://steve-yegge.medium.com/the-anthropic-hive-mind-d01f768f3d7b
• How to build a company that withstands any era | Eric Ries, Lean Startup author: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands
• Fallout on Prime Video: https://www.amazon.com/dp/B0CN4GGGQ2
• Fallout (video game): https://fallout.bethesda.net
• Claude Tag: https://www.anthropic.com/news/introducing-claude-tag
—
Recommended books:
• Crucial Conversations: Tools for Talking When Stakes Are High: https://www.amazon.com/dp/0071771328
• How to Raise an Adult: Break Free of the Overparenting Trap and Prepare Your Kid for Success: https://www.amazon.com/How-Raise-Adult-Overparenting-Prepare/dp/1627791779
• Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great: https://www.amazon.com/dp/B0FWZZBPZB
—
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