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Podcast: Lenny's Podcast: Product | Career | Growth (LS 63 · TOP 0.1% what is this?)
Episode: AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)
Pub date: 2026-08-30

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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

The podcast and artwork embedded on this page are from Lenny Rachitsky, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.

Podcast: Lenny's Podcast: Product | Career | Growth (LS 63 · TOP 0.1% what is this?)
Episode: How we built Grok Bot in a month | Roman Ugarte (SpaceXAI)
Pub date: 2026-09-08

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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 [email protected].

—

Lenny may be an investor in the companies discussed.

To hear more, visit www.lennysnewsletter.com

The podcast and artwork embedded on this page are from Lenny Rachitsky, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.

Podcast: Lenny's Podcast: Product | Career | Growth (LS 63 · TOP 0.1% what is this?)
Episode: The grief, loneliness, and burnout sweeping through the tech industry right now | Molly Graham
Pub date: 2026-09-27

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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 [email protected].

—

Lenny may be an investor in the companies discussed.

To hear more, visit www.lennysnewsletter.com

The podcast and artwork embedded on this page are from Lenny Rachitsky, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.

Podcast: AI DevOps Podcast (LS 37 · TOP 2.5% what is this?)
Episode: Jeffrey Palermo: AI-Driven Software Projects - Episode 418
Pub date: 2026-09-07

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https://clearmeasure.com/developers/forums/

The podcast and artwork embedded on this page are from Jeffrey Palermo, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.

Podcast: Inside the Strategy Room (LS 49 · TOP 0.5% what is this?)
Episode: 321. M&A integration: PE’s new value creation playbook
Pub date: 2026-09-11

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Private equity is navigating one of its most challenging value creation environments in years, and winning firms are using M&A integration as a competitive weapon. Brian Dinneen and Matthew Maloney join us to discuss three high-impact integration strategies that leading sponsors are using to overcome these headwinds, based on their recent article.

Related insights

How private equity is using M&A integrations to overcome headwinds

Unlocking full potential: Five practices reshaping PE value creation

2026 Global Private Markets Report: Private equity−clearer view, tougher terrain

Beating the odds: How private equity firms can improve exit prospects

Transforming value creation in private equity portfolio companies (podcast)

Private Capital at McKinsey

Support the show: https://www.linkedin.com/showcase/mckinsey-strategy-&-corporate-finance/

See www.mckinsey.com/privacy-policy for privacy information

The podcast and artwork embedded on this page are from McKinsey & Company, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.

Podcast: Stellar Work
Episode: #65 Matt LeMay - The Low-Impact AI Death Spiral
Pub date: 2026-09-07

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Matt LeMay thought product teams had finally outgrown the feature factory. Then AI handed everyone a faster conveyor belt.Matt is a product consultant and author who has worked with Google, Spotify, and MailChimp. His book Impact-first Product Teams gave a name to what happens when teams optimize for safe, visible output: the Low-Impact Death Spiral. AI, he argues, is accelerating it.What you'll hear:- Why low-impact work compounds: every harmless little feature raises the cost of doing impactful work later- The rhinestone problem: decorate the car long enough and you can't open the hood anymore- Discovery theatre: how AI lets teams simulate discovery without learning anything- Why "trust is a feeling" and can't be automated- An actual impact-first AI story: how MailChimp's team reframed its subject line helper after qualitative researchLinks:Matt's website: https://mattlemay.comMatt on LinkedIn: https://www.linkedin.com/in/mattlemay/Impact-first Product Teams: https://www.amazon.com/Impact-first-Product-Teams-Success-Indispensable/dp/B0DVH4R3QJMore episodes & all platforms: https://stellarwork.start.pageNewsletter: https://substack.com/@stellarworkHost: Ben, founder of Stellar Work

The podcast and artwork embedded on this page are from Benjamin Igna, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.

Podcast: Lenny's Podcast: Product | Career | Growth (LS 63 · TOP 0.1% what is this?)
Episode: OpenAI Codex lead on the new shape of product work | Andrew Ambrosino
Pub date: 2026-06-28

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Andrew Ambrosino leads development of the Codex desktop app at OpenAI. Nearly 100% of OpenAI employees—not just engineers—now use Codex weekly. A lifelong builder with a background spanning engineering, design, product management, and founding companies, he is now responsible for turning the Codex desktop experience into what he calls “the best desktop app that has ever existed, full stop.”

In our in-depth conversation, we discuss:

1. Why AI has completely flipped the product development process

2. What “taste” really means as a professional skill, and why it is emerging as the most valuable capability in an AI-first workplace

3. Why Andrew believes the Codex app would have failed if they launched it last November (vs. in February)

4. The “zone defense” model for how product managers at OpenAI operate when everyone can build anything

5. How roles are collapsed on Andrew’s team, and why eliminating the concept of roles entirely is a big mistake

6. How Andrew uses Codex to run his own workflows

7. The vision for a home base that coordinates work across ChatGPT, Codex, and the tools people already use.

—

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/openais-codex-lead-on-the-new-shape

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Andrew Ambrosino:

• X: https://x.com/ajambrosino

• LinkedIn: https://www.linkedin.com/in/ajambrosino

• Website: https://ambrosino.io

—

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 Andrew Ambrosino

(02:30) How AI is changing the shape of product work

(06:32) When to use documents vs. prototypes

(10:25) What “taste” actually means

(12:06) Why AI is still bad at design

(16:18) Is the design process really dead?

(21:35) What the design process looks like on the Codex team

(23:41) Are product functions disappearing?

(27:22) Team structure

(30:12) IC vs. management

(31:37) Planning roadmaps

(35:16) Building features that don’t work yet

(38:13) The ambition problem: when you’re too AGI-pilled

(39:17) The latest frontier: loops and autonomous development

(52:05) How Andrew uses Codex to automate his entire job

(46:52) The power of computer use and browser automation

(49:10) Will we run all our SaaS apps inside Codex?

(52:05) The future vision for Codex

(57:20) The videographer who built a Premiere Pro extension with Codex

(59:30) Failure corner

(1:01:50) Lightning round

(1:07:03) BTS: How our producer uses Codex for editing

—

References: https://www.lennysnewsletter.com/p/openais-codex-lead-on-the-new-shape

—

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

The podcast and artwork embedded on this page are from Lenny Rachitsky, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.

Podcast: Lenny's Podcast: Product | Career | Growth (LS 63 · TOP 0.1% what is this?)
Episode: How tech workers actually feel about AI in 2026 | Annual AI sentiment survey (Noam Segal)
Pub date: 2026-07-12

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Noam Segal is a longtime research leader across Airbnb, Meta, Twitter, Zapier, Intercom, and Figma, a certified coach, AI builder, and my community research lead. Together, we run the annual Tech Worker Sentiment Survey, now in its second year and one of the largest of its kind: a quantitative study of how people in tech actually feel about their jobs, AI, burnout, and the future of their careers. This year’s survey captured responses from thousands of workers across product, engineering, design, research, marketing, data, and sales, and the results are striking.

In our in-depth conversation, we discuss:

1. Why AI has split the tech workforce almost exactly in half—one half that’s thriving, another that’s shaken

2. The four emotional archetypes defining tech workers right now (the Energized, the Conflicted, the Disoriented, and the Resentful)

3. Why burnout has jumped an alarming 11 points in a single year

4. Why nobody in tech would recommend their job to someone entering the industry today

5. The #1 fear in tech right now (it’s not job loss to AI)

6. Why managers are the single biggest lever for employee well-being

7. Concrete advice for what employees and leaders can do right now

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny

Mercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign

—

Episode transcript: https://www.lennysnewsletter.com/p/how-tech-workers-actually-feel-about

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Noam Segal:

• X: https://x.com/noamseg

• LinkedIn: https://www.linkedin.com/in/noamsegal

—

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 Noam Segal

(02:34) About the survey: methodology and scope

(06:04) The core finding: AI has split the tech workforce in half

(13:03) The AI identity stance

(14:40) The four archetypes: Energized, Conflicted, Disoriented, Resentful

(19:35) Burnout is surging (and why shipping faster is making it worse)

(22:53) A glimmer of hope

(24:55) Layoff worries

(29:15) The career recommendation NPS score

(36:45) The ladder metaphor: rungs disappearing beneath our feet

(45:14) AI is making us faster, not better

(52:53) The #1 fear: being squeezed to do more for the same pay

(55:55) The emotional landscape and “smiling exhaustion”

(01:01:02) Designers and researchers: the most negative group two years running

(01:06:27) Who’s happiest

(01:12:18) Managers: the single biggest lever on well-being

(01:18:47) The industry is “chaotic”

(01:24:53) What employees and leaders can do right now

(01:31:32) AI guilt and closing thoughts

—

Referenced:

• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026

• How tech’s most resilient workers handle burnout: https://www.lennysnewsletter.com/p/how-techs-most-resilient-workers

• Please stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater

• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp

• NPS Is The Worst: https://www.npsistheworst.com

• The Terminator: https://www.imdb.com/title/tt0088247

• Skynet: https://terminator.fandom.com/wiki/Skynet

• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu

• Devin: https://devin.ai

• An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union

• Redeploying Fable 5: https://www.anthropic.com/news/redeploying-fable-5

• Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble

• Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennysnewsletter.com/p/inside-linear-building-with-taste

• Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft): https://www.lennysnewsletter.com/p/building-beautiful-products-with

• 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

• OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape

• Elon Musk: ‘Chances are we’re all living in a simulation’: https://www.theguardian.com/technology/2016/jun/02/elon-musk-tesla-space-x-paypal-hyperloop-simulation

—

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

The podcast and artwork embedded on this page are from Lenny Rachitsky, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.

Podcast: Lenny's Podcast: Product | Career | Growth (LS 63 · TOP 0.1% what is this?)
Episode: Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO)
Pub date: 2026-07-19

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Elizabeth Stone is the Chief Product and Technology Officer (CPTO) at Netflix, where she oversees Engineering, Product, and Design. Since her first appearance on the podcast two years ago—which remained my second-most-popular episode for more than a year—she has expanded her role to lead product, in addition to engineering. Before Netflix, Elizabeth was VP of Science at Lyft, Chief Operating Officer at Nuna, an economist at Analysis Group, and a trader at Merrill Lynch.

In our in-depth conversation, we discuss:

1. Why “systems thinking” is now the most important skill she looks for

2. How to manage the flood of AI-generated output without losing quality or signal

3. How Netflix thinks about AI fluency as a universal expectation rather than a level-specific skill

4. What “excellence as an operating system” means

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WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny

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Episode transcript: https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Elizabeth Stone:

• LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754

—

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) AI and role confusion: the storming phase before the forming phase

(07:36) How roles have changed in the past two and a half years

(11:55) Will functions survive? The case for craft specialism

(13:26) What Netflix is hiring more of—and less of

(17:22) Why systems thinking is the rising skill across every function

(20:20) Is the design process dead?

(22:08) Skills trending down

(28:33) AI fluency and Netflix’s career ladder overlay

(31:00) AI use cases beyond coding

(35:12) Netflix’s AI history

(38:36) Excellence as an operating system

(41:11) The pillars of the excellence OS

(46:41) The keeper’s test—and why it’s mostly a positive conversation

(50:21) Attracting top talent in the age of frontier AI labs

(52:54) Junior talent, craft mastery, and the mentorship question

(56:25) Where engineering goes in 5 to 10 years

(59:45) The future of entertainment: beyond film and TV

(1:02:18) AI in Hollywood: Netflix’s creator-enablement position

(1:06:15) Lightning round and final thoughts

—

Referenced:

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• 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

• Claude Code: https://www.anthropic.com/product/claude-code

• Claude Cowork: https://www.anthropic.com/product/claude-cowork

• Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it

• Innovation for Filmmaking, By Filmmakers: Why InterPositive Is Joining Netflix: https://about.netflix.com/en/news/why-interpositive-is-joining-netflix

• InterPositive: https://weareinterpositive.com

• Netflix Prize: https://en.wikipedia.org/wiki/Netflix_Prize

• Quarterback on Netflix: https://www.netflix.com/title/81482895

• The Bill Simmons Podcast on Netflix: https://www.netflix.com/title/82186214

• Spencer Pratt on Instagram: https://www.instagram.com/spencerpratt

• Salman Rushdie’s Substack: https://salmanrushdie.substack.com

• Remarkably Bright Creatures on Netflix: https://www.netflix.com/title/81911351

• Eight Sleep: https://www.eightsleep.com

• Tour de France: https://www.letour.fr/en

—

Recommended books:

• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

• Into Thin Air: A Personal Account of the Mt. Everest Disaster: https://www.amazon.com/Into-Thin-Air-Personal-Disaster/dp/0385494785

• Liar’s Poker: https://www.amazon.com/Liars-Poker-Norton-Paperback-Michael/dp/039333869X

—

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

The podcast and artwork embedded on this page are from Lenny Rachitsky, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.

Podcast: Lenny's Podcast: Product | Career | Growth (LS 63 · TOP 0.1% what is this?)
Episode: Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn
Pub date: 2026-07-26

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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

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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

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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 [email protected].

—

Lenny may be an investor in the companies discussed.

To hear more, visit www.lennysnewsletter.com

The podcast and artwork embedded on this page are from Lenny Rachitsky, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.