Katie Dill

@katie-dill · 12 positions · 0 changes of mind

Head of Design at Stripe; previously Head of Experience Design at Airbnb and Head of Design at Lyft.

Katie Dill did not write this page.

We collected these quotes from things they published elsewhere, and every quote links to where it was said. They have no account here and have not endorsed this site. Quotes are word for word; the short line under each one is our own restatement, not their wording. Their own site. Is this you? Claim it or ask us to remove it. Or tell us what is wrong here.

The shading behind a date shows how recently it was said: full within a month, empty after three years.

Our reading
Language models are good at giving the most probable answer and less good at giving what is original or specific to a brand and its users.

LLMs

Their wordsLLMs are really good at telling you the most probable answer, which essentially means that they're able to tell you what has been or is popular now, what has worked, what was in style. They're less good at telling you what's original or specific to you, your brand, and your users context.
spoken · machine transcript hear it at 2:17 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 1st of 12 in this recording
Our reading
AI makes work feel finished very fast, too often prematurely.

Their wordsAI makes things feel finished really really fast all too often prematurely.
spoken · machine transcript hear it at 2:57 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 2nd of 12 in this recording
Our reading
People building with AI need a point of view of their own, or the AI will supply one.

Their wordsFirst one, you have to have a point of view. If you don't, AI will give it for you.
spoken · machine transcript hear it at 5:44 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 3rd of 12 in this recording
Our reading
How something was made should not change its quality bar, because users care whether it is good, not how it was made.

Their wordsWhy should that matter how it was made? It doesn't matter to the users how it was made. It matters to them if it's good or not.
spoken · machine transcript hear it at 7:26 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 4th of 12 in this recording
Our reading
The object of design is no longer the screen but the system itself.

design

Their wordsSo, the object of design is no longer the screen. It is the system itself.
spoken · machine transcript hear it at 9:53 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 5th of 12 in this recording
Our reading
Design systems used to scale consistency; now they need to scale intent.

design

Their wordsNow, the old system scaled consistency, but the new system needs to scale intent.
spoken · machine transcript hear it at 10:50 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 6th of 12 in this recording
Our reading
Now that building is cheap, filtering has to happen after the build, which makes an editor's role ultra important.

Their wordsBut the filtering that used to be throughout the process now needs to happen post build when it is a lot harder to say no. This is where the role of an editor comes in and it is ultra important in this day and age.
spoken · machine transcript hear it at 13:06 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 7th of 12 in this recording
Our reading
Teams have to unlearn that built means done and that done means good.

Their wordsIt's a new behavior. We have to unlearn that built means done and that done means good.
spoken · machine transcript hear it at 13:27 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 8th of 12 in this recording
Our reading
AI can manufacture monotony, but it is also the greatest creative catalyst there has ever been.

Their wordsYes, AI can help us manufacture monotony, but it is also the greatest creative catalyst we've ever had.
spoken · machine transcript hear it at 16:32 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 9th of 12 in this recording
Our reading
It is time to invent new interfaces and new aesthetics; the best practices have not been written yet.

Their wordsIt is time to invent new interfaces. It is time to invent new aesthetics. The best practices have not been written yet.
spoken · machine transcript hear it at 17:16 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 10th of 12 in this recording
Our reading
Leaders should not just tell their teams to use AI but give them room to explore.

Their wordsSo, if you're leading a team, don't just tell them to use AI, but give them room to explore. Protect the strange.
spoken · machine transcript hear it at 19:42 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 11th of 12 in this recording
Our reading
Using AI only to make existing things faster misses its most interesting part: it can raise the ceiling, not just the floor.

Their wordsIf we only use AI to make the things that we already make just faster, then we are definitely missing out on the most interesting part. AI can help us raise the ceiling, not just the floor.
spoken · machine transcript hear it at 20:00 · all korrents from this recording
↗How to scale intent, quality, and artistry with Al | Katie Dill (Stripe) (Lenny & Friends Summit, San Francisco, 10 September 2026)youtube.com 12th of 12 in this recording

How recent

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