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AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)

Shownote

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 [https://workos.com/lenny]—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury [https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign]—Radically different banking, now with Command — Where to find Tara Seshan: • X: https://x.com/tarstarr [https://x.com/tarstarr] • LinkedIn: https://www.linkedin.com/in/tarstarr [https://www.linkedin.com/in/tarstarr] • Newsletter: https://substack.com/@taraseshan [https://substack.com/@taraseshan] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com [https://www.lennysnewsletter.com] • X: https://twitter.com/lennysan [https://twitter.com/lennysan] • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ [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 [https://chatgpt.com/codex] • ChatGPT Work: https://openai.com/chatgpt-work [https://openai.com/chatgpt-work] • Stripe: https://stripe.com [https://stripe.com] • Watershed: https://watershed.com [https://watershed.com] • Thiel Fellowship: https://thielfellowship.org [https://thielfellowship.org] • Meet your Lenny’s Newsletter Fellows: https://www.lennysnewsletter.com/p/meet-your-lennys-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 [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 [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 [https://www.lennysnewsletter.com/p/product-management-theater-marty] • Patrick Collison’s examples of fast projects: https://patrickcollison.com/fast [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 [https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley] • Andrew Ambrosino on X: https://x.com/ajambrosino [https://x.com/ajambrosino] • Tyler Cowen’s website: https://tylercowen.com [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 [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 [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 [https://www.lennysnewsletter.com/p/shreyas-doshi-live] • Alan Kay: https://en.wikipedia.org/wiki/Alan_Kay [https://en.wikipedia.org/wiki/Alan_Kay] • Brie Wolfson on X: https://x.com/zebriez [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 [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 [https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein] • Sutter Hill Ventures: https://shv.com [https://shv.com] • Snowflake: https://www.snowflake.com [https://www.snowflake.com] • Mike Speiser on LinkedIn: https://www.linkedin.com/in/mikespeiser [https://www.linkedin.com/in/mikespeiser] • Footnotes and Tangents: https://footnotesandtangents.substack.com [https://footnotesandtangents.substack.com] • The Power Broker Book Club: https://www.robertcaro.org/copy-of-six-books-six-ny-times-book [https://www.robertcaro.org/copy-of-six-books-six-ny-times-book] • The Odyssey: https://www.imdb.com/title/tt33764258 [https://www.imdb.com/title/tt33764258] • Rashomon: https://www.imdb.com/title/tt0042876 [https://www.imdb.com/title/tt0042876] • Akira Kurosawa: https://en.wikipedia.org/wiki/Akira_Kurosawa [https://en.wikipedia.org/wiki/Akira_Kurosawa] • Kevin Kwok on LinkedIn: https://www.linkedin.com/in/kevinakwok [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 [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 [https://x.com/AriX] • Sky: https://sky.app [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 [https://www.lennysnewsletter.com/p/dylan-field-live-at-config] — Recommended books: • Barbarian Days: A Surfing Life: https://www.amazon.com/dp/0143109391 [https://www.amazon.com/dp/0143109391] • Anna Karenina: https://www.amazon.com/Anna-Karenina-LEO-TOLSTOY/dp/8175993421 [https://www.amazon.com/Anna-Karenina-LEO-TOLSTOY/dp/8175993421] • The Power Broker: https://www.amazon.com/dp/0394720245 [https://www.amazon.com/dp/0394720245] • War and Peace: https://www.amazon.com/War-Peace-Leo-Tolstoy/dp/8175992832 [https://www.amazon.com/War-Peace-Leo-Tolstoy/dp/8175992832] • Wolf Hall: https://www.amazon.com/dp/0312429983 [https://www.amazon.com/dp/0312429983] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com [podcast@lennyrachitsky.com]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com [https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language]

Highlights

This conversation examines how AI is changing the way products are imagined, built, and managed. It focuses on the emerging partnership between people and increasingly capable AI systems, and on the human qualities that will matter most as execution becomes faster and more automated.
00:00
Persistent AI coworkers may define a new product era
05:16
OpenAI turns breakthroughs into feedback almost instantly
06:42
Fast learning beats elaborate strategy in AI
09:03
AI makes problem definition the PM’s core advantage
13:33
Human value comes from distinctive perspective
15:35
AI handles execution; humans provide judgment
20:05
AI makes ambition the key differentiator.
26:39
Today’s models are the worst they’ll ever be.
29:26
AI should help teams choose bigger ambitions
34:10
Ship transformative products before they are perfect
39:22
Human judgment drove Codex’s success
45:27
Engineering is shifting from coding to directing AI
45:59
Human value lies in judgment, care, and collaboration.
48:20
AI turns static artifacts into malleable software
51:39
Clear visuals make complex data compelling
52:41
Writing to think remains deeply human
57:10
AI should strengthen thinking, not replace it
1:03:00
Test the message before building the product
1:04:16
Playful design makes AI-generated websites memorable
1:05:02
Knowledge work requires visible reasoning and context
1:15:35
Ambition grows when you challenge your limits

Chapters

Introduction
00:00
What makes OpenAI’s culture so different
02:18
Why AI product strategy is all about fast experimentation
06:42
How the PM role is changing
09:02
The shift from rowing to steering
10:50
What changes when agents become coworkers
15:35
Why ambition matters more than ever
20:05
Building products for models that do not exist yet
26:39
How ChatGPT’s Chat and Work modes differ
29:21
How OpenAI ships so quickly at scale
34:01
The vibe shift happening inside Codex
39:14
Why traditional roles are beginning to blur
42:20
Where humans will continue to provide unique value
45:59
How Tara uses AI in her own work
48:20
The magic of the /visualize command
51:38
Writing to think versus writing to report
52:39
How to use AI without losing your ability to think
57:10
Tara’s biggest lesson from Sutter Hill
1:00:15
ChatGPT’s site output
1:04:16
Why knowledge work is becoming more like coding
1:05:01
Lightning round and final thoughts
1:07:55

Transcript

Tara Seshan: If you think about the first era of AI products as chat, the second era of these products working with agents, that third era that might come soon is. How do you work with a persistent co-worker who is able to get things done with you? Lenny ...