Tara Seshan
Product lead for ChatGPT Work at OpenAI; previously one of the first five product managers at Stripe, head of product at Watershed, and a Thiel Fellow.
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Their wordsthere's a lot of like theorizing that one can do before you ship something but nothing compares to like the actual empirical evidence of seeing users try it, use it, and then iterating from there.
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 1st of 18 in this recording
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Their wordsprobably most importantly in this era is this aiming for 2 to 3 months of like where the models will be rather than being overly anchored in the present or being overly like futuristic and unusable.
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 2nd of 18 in this recording
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Their wordsthere there are philosophical things one could have and opine on in this topic but to me there are just so many practical product considerations like the use case matters so much in deciding this.
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 6th of 18 in this recording
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Their wordsthe third thing that you just really need in addition to user empathy and systems thinking is like a relentlessness to like try it out and keep iterating
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 8th of 18 in this recording
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Their wordslearning how to write good evals and writing evals as much as possible is like the most important thing
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 9th of 18 in this recording
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Our reading
Building exactly for today means being left behind; the ideal horizon is two to three months.
Their wordsand then at the same time if you build exactly for today you're going to get left behind. So it's like I constantly repeat this but it's like two to three months out.
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 10th of 18 in this recording
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Their wordsmaybe it is appropriate to plan you know many many months out but I think it involves understanding like the pace of the market you're in
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 11th of 18 in this recording
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Their wordsnow if the you know agent is doing things semi-autonomously like you actually really need to make sure that at any given point a user can like predict what is probably going to happen with a feature or a primitive that you're introducing.
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 13th of 18 in this recording
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Their wordsall the usual stuff still applies except the importance of testing things empirically and moving faster has only increased.
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 14th of 18 in this recording
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Their wordsof course you should be in direct contact with your users.
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 15th of 18 in this recording
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Their wordsthe existence of voice like changed the game like it is such an intuitive interface for so many people.
↗Stop planning for 2027: how OpenAI builds product 90 days at a time | Tara Sesha and Nan Yu (OpenAI) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 17th of 18 in this recording
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Their wordsAnd so actually being prolific and being um more like empirical is way more important than being um like maybe more academic or theoretical.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 1st of 17 in this recording
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Their wordsAnd what that means is the thinking you need to do is being as pointed as possible about what your core hypothesis is. And that hypothesis definition is the most important thing.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 2nd of 17 in this recording
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Their wordsBut the core of it has always been about what is like the most essential question you need to ask about your product. Like what is the thing that will determine whether your product works or doesn't work?
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 3rd of 17 in this recording
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Our reading
Work will increasingly look like steering rather than rowing, with agents doing the rowing.
Their wordsI do think that increasingly the future of work will look more like steering than rowing in the sense that there will be agents that you'll you'll be able to work with that do a lot of the rowing and your role increasingly becomes steering the ship in the right direction and pointing it in the right direction.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 4th of 17 in this recording
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Our reading
People may underrate the power of intuition and of deciding what they want the future to be.
Their wordsI think sometimes that we underrate like that power of like intuition or even um sort of like positive like determinism of what we want the future to be like.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 5th of 17 in this recording
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Their wordsIdeally, work feels like a multiplayer game where all of us together are getting stuff done, steering our agents as our agents continue to take care of more and more of those like rowing tactical tasks.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 6th of 17 in this recording
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Their wordsbut a lot of it is also just really tactical like data access like cloud infrastructure and reliability pieces that feel um yeah, they feel much more prosaic than some of the the broader intelligence questions, but matter in some ways just as much for end effectiveness.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 7th of 17 in this recording
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Their wordsYour ambitions are no longer limited by like what you're capable of executing yourself, what you're capable of communicating.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 8th of 17 in this recording
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Their wordsUm, part of your job now is to elevate everyone's ambitions and say, "Actually, isn't the possibility ceiling meaningfully higher?"
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 9th of 17 in this recording
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Their wordsYou fail if you build for where the models are now. You fail if you build for where you think the models will be in a year. Like both outcomes are equally wrong.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 10th of 17 in this recording
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Their wordsBut I think what's been really compelling and interesting about this era and this product experience has been getting the product in the hands of users when you have so much conviction that hey it's transformative like is way better than perfect and that urgency and that uh introduction of that product is is so important.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 11th of 17 in this recording
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Their wordsI think humans will continue to be most valuable as a certainly as a um like an entity of accountability.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 12th of 17 in this recording
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Their wordsUm I also think the human brain continues to be valuable in like how we care for each other and relate to one another.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 13th of 17 in this recording
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Their wordsI think you should use the models as much as possible for writing as reporting and in as much as you think with writing as I really do and I think a lot of people do you should not use it you shouldn't replace your thinking with it
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 14th of 17 in this recording
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Their wordsI have like results where we tried this, we ran an AB, here's like the results. This is why I think we should like go in this direction. That is a way better communication tool than like the the doc itself.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 15th of 17 in this recording
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Their wordsBut knowledge work is different in that I can't simply look at the deck in the end and see the numbers. Oh, it's like 90% success or whatever in the deck and actually believe that. I really need to think about the process and the inputs and the reasoning and how it went along the way.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 16th of 17 in this recording
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Their wordsIt is exactly what I think the future should be which is people should make software that exactly meets their and their friends needs.
↗AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)youtube.com 17th of 17 in this recording
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