AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)
Lenny's Podcast: Product | Career | Growth
10 HOURS AGO
AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)
AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)

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