Katie Dill (Stripe, Airbnb, Lyft)15 October 2023

Building beautiful products with Stripe’s Head of Design

9Frameworks

12Insights

Episode overview

Stripe Head of Design Katie Dill explains why beauty and functionality reinforce one another, arguing that careful craft improves usability, trust, and business performance. She describes Stripe's “walk the store” practice: multidisciplinary leaders inspect important user journeys, log friction, assign qualitative scores, and calibrate the quality bar quarterly. Drawing on leadership lessons from Airbnb and Lyft, she also emphasizes earning trust through listening, embedding designers with product and engineering, sharing work early, and improving performance by increasing potential while removing interference.

Key ideas

Beauty is not opposed to functionality: thoughtful aesthetics can make products more approachable, understandable, compelling, and trustworthy.
Quality can directly drive growth; Stripe observed increased activation from onboarding improvements and a 10.5% revenue increase from a newer checkout experience.
High quality is a group responsibility requiring shared standards, an aligned vision, strong editing, and the courage to reject work that is not yet good enough.
Stripe's teams “walk the store” by experiencing critical end-to-end journeys, logging friction, filing issues, and scoring overall utility, usability, and desirability.
Product quality reviews calibrate qualitative journey scores across engineering, product, design, marketing, and company leadership.
Katie frames team performance as potential minus interference: hire and develop strong people while continually removing organizational obstacles.
Designers should remain embedded with engineering and product while also maintaining a strong design community and dedicated space for creative exploration.
Vision work should reach for an ideal end-to-end experience, then guide measured incremental delivery toward that North Star.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Leadership5 steps

Come In Listening, Not Swinging

New leader's first move: earn trust before inflicting the change you were hired to make.

Read →

Leadership5 steps

Performance = Potential − Interference

Two levers only: raise the team's ceiling, or remove the weight sitting on top of it.

Read →

Strategy5 steps

Quality Is Growth: Making the ROI Case

Kill the 'business goals vs design goals' framing by collecting the quality wins that moved your own metrics.

Read →

Strategy5 steps

Reach for the Stars, Land on the Moon

Sketch the ideal end-state journey, then work backwards and ship it in measurable pieces.

Read →

Leadership5 steps

Taste, Humility, Hutzpah: The Designer Hiring Lens

Hire for judgment, humility, and the courage to say 'not good enough' — tools and process you can teach.

Read →

Leadership5 steps

The Four Conditions for Operationalizing Quality

Group effort, vision + alignment, an editor, and the courage to say 'almost, but no'.

Read →

Innovation5 steps

The Levels of Quality Ladder

Rate every feature 1-5: works → error-free → usable → desirable → surprisingly great.

Read →

Communication5 steps

The Low-Maintenance Work-in-Progress Deck

One shared slide deck of screenshots, updated monthly, that kills redundant work and spreads patterns.

Read →

Leadership7 steps

Walk the Store: The Essential Journeys Quality Program

Name your 15 critical user journeys, give each a cross-functional owner, and score them on a fixed cadence.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 18

Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“today my guest is Katie Dill”
▶ Watch at ~0:30approx.
Katie DillMentionsKatie is head of design at stripe where she over product design brand and marketing creative web presence user research content strategy and design Ops
“Katie was previously head of design at Lyft and head of experienc design at Airbnb”
▶ Watch at ~1:00approx.
Joe GebbiaMentionsAt Airbnb, he discussed employees identifying with both their discipline and cross-functional team.
“Joe bot at Airbnb once said it's like what t-shirt are you do you wear like what team are you on”
▶ Watch at ~10:30approx.
Jessica WalshCoinedCo-author of Beauty.
“Stephan sagmeister and Jessica Walsh have a book called Beauty”
▶ Watch at ~22:00approx.
Stefan SagmeisterCoinedCo-author of Beauty.
“Stephan sagmeister and Jessica Walsh have a book called Beauty”
▶ Watch at ~22:00approx.
Brian CheskyMentionsBrian chesky at Airbnb there was a whole article where we unpacked this moment in their product development cycle
“at Airbnb you know Brian chesky is like the editor of all the things that you know come together”
▶ Watch at ~31:30approx.
David SingletonMentionsDavid is Chief Technology Officer at Stripe where he's responsible for guiding its engineering and design teams
“which I know David Singleton talked about on your podcast”
▶ Watch at ~35:30approx.
David SingletonMentionsDavid is Chief Technology Officer at Stripe where he's responsible for guiding its engineering and design teams
“David Singleton who you mentioned he and I do these things very regularly too”
▶ Watch at ~42:30approx.
Will GaybrickMentionsA Stripe leader participating in product quality reviews who leads product and business.
“will gabri um who you know leads product and business”
▶ Watch at ~44:00approx.
Rick RubinMentionsJack Clark is our you know head of policy and he got connected to Rick Rubin
“I think I found in the Rick Rubin book but it's by someone else”
▶ Watch at ~1:07:00approx.
Robert HenriCoinedCredited with the quotation about creating a state in which art becomes inevitable.
“the object isn't to make art it's to be in that wonderful state which makes art inevitable”
▶ Watch at ~1:07:00approx.
Brian CheskyMentionsBrian chesky at Airbnb there was a whole article where we unpacked this moment in their product development cycle
“I think Brian chesky talks about it I think it was like the 11 star experience”
▶ Watch at ~1:09:30approx.
Charlie MungerCoinedHis words and documents were assembled into Poor Charlie's Almanack.
“it's actually Charlie monger's words but Peter Kaufman a friend and a colleague of his assembled all of the these documents”
▶ Watch at ~1:16:00approx.
Peter KaufmanCoinedAssembled Charlie Munger's documents and remarks into Poor Charlie's Almanack.
“Peter Kaufman a friend and a colleague of his assembled all of the these documents over the years”
▶ Watch at ~1:16:00approx.
David PerellMentionsDescribed podcasting as maximizing usefulness per minute without removing humanity.
“I was actually on David perel's podcast recently”
▶ Watch at ~1:22:30approx.
Dale CarnegieCoinedmentioned
“how to win friends and influence people it's a oldie but a goodie”
▶ Watch at ~1:23:00approx.
David McCulloughCoinedAuthor of a book about the Wright brothers recommended by Katie Dill.
“it's about the right Brothers uh by David M MLL I think”
▶ Watch at ~1:24:00approx.
Charlie MackesyCoinedmentioned
“the boy the mule The Fox and the horse um this book was given to me”
▶ Watch at ~1:25:00approx.

Resources · 40

StripeMentionscompany · Patrick Collison and John Collison
“Katie is head of design and stripe”
▶ Watch at ~0:30approx.
AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk
“Katie was previously head of design at Lyft and head of experienc design at Airbnb”
▶ Watch at ~1:00approx.
LyftMentionscompany
“Katie was previously head of design at Lyft”
▶ Watch at ~1:00approx.
SidebarRecommendscompany · Sidebar
“with sidebar senior leaders are matched with highly vetted private supportive peer groups”
▶ Watch at ~2:30approx.
SidebarMentionscompany · Sidebar
“by visiting sidebar. c/ Lenny to learn more”
▶ Watch at ~3:00approx.
AtlassianCoinedcompany
“jira product Discovery the new prioritization and Road mapping tool built for product teams by atlassian”
▶ Watch at ~3:30approx.
Jira Product DiscoveryRecommendssoftware · Atlassian
“introducing jira product Discovery the new prioritization and Road mapping tool built for product teams by atlassian”
▶ Watch at ~3:30approx.
JiraUsessoftware · Atlassian
“it's all built on jira where your engineering team is already working”
▶ Watch at ~4:00approx.
AmazonUsescompany · Jeff Bezos
“larger organizations and Enterprises like Amazon and herdz Shopify Spotify X”
▶ Watch at ~18:00approx.
ShopifyUsescompany · Shopify
“larger organizations and Enterprises like Amazon and herdz Shopify Spotify X”
▶ Watch at ~18:00approx.
HertzUsescompany
“larger organizations and Enterprises like Amazon and herdz Shopify Spotify X”
▶ Watch at ~18:00approx.
StripeUsescompany · Patrick Collison and John Collison
“stripe is used by millions of businesses globally”
▶ Watch at ~18:00approx.
SpotifyUsessoftware · Spotify
“larger organizations and Enterprises like Amazon and herdz Shopify Spotify X”
▶ Watch at ~18:00approx.
XUseswebsite · X Corp.
“Shopify Spotify X which I believe you use”
▶ Watch at ~18:00approx.
Google BooksMentionswebsite · Google
“the use of word beauty in in books that have been digitized by Google has decreased like pretty dramatically”
▶ Watch at ~22:00approx.
BeautyRecommendsbook · Stefan Sagmeister and Jessica Walsh
“Stephan sagmeister and Jessica Walsh have a book called Beauty and is I would highly recommend it”
▶ Watch at ~22:00approx.
Grand Central TerminalMentionsplace
“the people tweeting from Pen Station was just like more negative than the people that were tweeting from Grand Central Station”
▶ Watch at ~23:30approx.
Penn StationMentionsplace
“they studied the tweets that came from people that were traveling through Penn Station versus Grand Central”
▶ Watch at ~23:30approx.
The BearRecommendstv show · Christopher Storer
“actually a perfect example of this have you seen the show The Bear”
▶ Watch at ~25:00approx.
The EconomistMentionswebsite · The Economist Group
“at The Economist you know there's a chief editor”
▶ Watch at ~31:30approx.
PaveUsescompany
“companies like scale Ai and pave are using one schema”
▶ Watch at ~53:00approx.
Scale AIUsescompany · Alex Wang and Lucy Guo
“companies like scale Ai and pave are using one schema”
▶ Watch at ~53:00approx.
OneSchemaRecommendssoftware · Christina Gilbert
“today's episode is brought to you by one schema the embeddable CSV importer for SAS”
▶ Watch at ~53:00approx.
Microsoft ExcelUsessoftware · Microsoft
“your customers don't have to spend hours in Excel just to get started with your product”
▶ Watch at ~53:30approx.
Google SlidesUsessoftware · Google
“they add this to a slide and Google slide deck every couple of weeks”
▶ Watch at ~57:30approx.
Stripe PressCoinedcompany · Stripe
“stripe prints books uh so stripe press”
▶ Watch at ~1:15:00approx.
Poor Charlie's AlmanackRecommendsbook · Charlie Munger
“we have a new book coming out that you can pre-order now uh and it is poor Charlie's Almanac”
▶ Watch at ~1:16:00approx.
Stripe PressRecommendscompany · Stripe
“it is uh press. stripe.com will be where you can see all the books that we have at strip press”
▶ Watch at ~1:17:00approx.
How to Win Friends and Influence PeopleRecommendsbook · Dale Carnegie
“how to win friends and influence people it's a oldie but a goodie”
▶ Watch at ~1:23:00approx.
The Wright BrothersRecommendsbook · David McCullough
“the other one is um a newer book I think actually still a couple years old it's about the right Brothers”
▶ Watch at ~1:24:00approx.
The Boy, the Mole, the Fox and the HorseRecommendsbook · Charlie Mackesy
“the boy the mule The Fox and the horse um this book was given to me”
▶ Watch at ~1:25:00approx.
OppenheimerRecommendsfilm · Christopher Nolan
“Oppenheimer was amazing”
▶ Watch at ~1:25:30approx.
ShrinkingRecommendstv show
“TV show uh shrinking and that one was really good”
▶ Watch at ~1:25:30approx.
TonieboxRecommendsproduct · tonies
“as a parent you should definitely know the Tony box”
▶ Watch at ~1:26:30approx.
Beauty and the BeastMentionsfilm · Disney
“it could be like um you know Belle from Beauty and the Beast”
▶ Watch at ~1:26:30approx.
FrozenMentionsfilm · Walt Disney Animation Studios
“or like Elsa from U Frozen”
▶ Watch at ~1:26:30approx.
Tribe of MentorsMentionsbook · Tim Ferriss
“the tribe of mentors version of Lenny's podcast”
▶ Watch at ~1:28:00approx.
SpotifyMentionssoftware · Spotify
“you can subscribe to the show on Apple podcast Spotify or your favorite podcast app”
▶ Watch at ~1:33:30approx.
Apple PodcastsMentionssoftware · Apple Inc.
“you can subscribe to the show on Apple podcast Spotify or your favorite podcast app”
▶ Watch at ~1:33:30approx.
LennyPodcast.comRecommendswebsite · Lenny Rachitsky
“you can find all past episodes or learn more about the show at Lenny podcast.com”
▶ Watch at ~1:33:30approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 2

Hot Take15:30

Quality Is Growth: How Stripe's Checkout Fixes Lifted Revenue 10.5%

Katie pushes back on the framing of growth versus quality, arguing that quality is growth. Stripe research found that 99% of top e-commerce sites have errors in their checkout flow that hurt conversion. By fixing small and large quality issues in the checkout experience, Stripe saw a 10.5% increase in businesses' revenue moving from an older checkout to a newer one.

Growth-versus-quality is a false trade-off; quality drives growth
99% of top e-commerce sites have checkout-flow errors that hinder conversion
Stripe's growth team is maniacally focused on building better experiences tied to business metrics
Checkout quality improvements produced a 10.5% revenue increase for businesses
Onboarding-flow quality improvements increased activations

“I know there's this saying of like it's growth versus quality but like quality is growth”
Katie Dill · 15:30

“we have seen a 10.5% increase in business's revenue from that you know an older form of checkout to a newer form of checkout”
Katie Dill · 17:00

#conversion#checkout#growth#stripe#roi

Hot Take1:07:30

Reach for the Stars, Land on the Moon: Why Incrementalism Fails

Katie warns against a fear of bold ideas, where teams default to safe, measurable incremental approaches that never make the whole experience better. Her alternative: reach for the stars and land on the moon. Vision work that sketches the ideal, comprehensive, journey-level version gives you a North Star to work back from, enabling measured, thoughtful big risk-taking rather than incrementing your way to a mediocre outcome.

Fear of bold ideas pushes teams toward safe, measurable increments
Incremental work scoped to your own area rarely improves the whole experience
Vision work should sketch the ideal, journey-level version of the product
This is not a beautiful deck that sits on a shelf; it's a North Star to build back from
You can still ship pieces incrementally while working toward the vision

“reach reach for the stars and land on the Moon”
Katie Dill · 1:08:30

“if you don't know what that is like what are the chances that you're going to increment yourself to the right outcome”
Katie Dill · 1:09:30

#vision#strategy#product#risk-taking

Explainer· 2

Explainer11:30

The Levels of Quality, From Baseline to Surprisingly Great

Katie rejects the idea that some disciplines just don't care about quality, reframing it as levels of prioritization. Level one is whether the thing works and delivers its value proposition; level two is error-free and well-rounded; levels three through five exceed expectations and deliver things the user wasn't even seeking. Which level you should aim for depends on user expectations.

Baseline quality: the product works and provides its value proposition
Next level: error-free and functioning in a well-rounded way
Higher levels: exceeds expectations, doing things the user never asked for
No discipline is indifferent to quality; it's a question of prioritization
The right level of quality should be set by user expectations

“the levels of quality should be based on user expectations”
Katie Dill · 12:00

#quality#product#prioritization

Explainer22:00

Why Beauty Matters Even for a B2B Financial Company

Katie argues functionality and beauty aren't opposites; beauty enhances functionality by making things easier, more approachable, and more compelling to use. Citing the book Beauty, she notes usage of the word declined in digitized books from the 1800s to 2000s as functionality was crowned king, and points to a study of tweets from Penn Station versus Grand Central to show how surroundings shape how people feel. For Stripe, beauty increases trust, improves outcomes, and begets more beauty.

Functionality and beauty are not opposites; beauty enhances functionality
Use of the word 'beauty' in digitized books dropped sharply from the 1800s to the 2000s
Study cited: tweets from Penn Station skewed more negative than those from Grand Central
Beautiful details signal care and increase user trust
Beauty begets beauty and is a matter of pride that attracts talent

“actually Beauty enhances functionality because it does make things easier to use more approachable”
Katie Dill · 22:30

“things that are more beautiful increase trust”
Katie Dill · 24:00

#beauty#design#trust#b2b

Story· 2

Story05:00

The Airbnb Design Team That Staged an Intervention on Katie Dill

A month into leading Airbnb's design org, Katie was called into a meeting where five designers and an HR partner read from prepared papers listing everything she was doing wrong. The core message: she hadn't earned their trust because she'd come in trying to inflict change rather than bringing the team along. She shifted her approach to listening first, and a couple of months later the design team had the best engagement scores in the company.

She was hired to lead a 10-person experience design team that had reported directly to a founder
Five designers plus an HR partner took turns reading criticisms aloud from papers
The theme across all feedback: she had not earned the team's trust
The lesson: you can inflict change on people, but doing it with them requires trust
After shifting to listen-first leadership, the team hit the company's best engagement scores

“you can inflict change on people but if you want to do it with them you you really you know trust is the the key…”
Katie Dill · 08:30

“instead of coming in swinging you know come in listening so that you can really you know set out to make change that actually has…”
Katie Dill · 09:00

#leadership#trust#design-teams#feedback

Story1:01:30

Breaking Down the Locked Door at Lyft's Design Team

At Lyft, Katie found the design team physically separated behind a locked door, in a beautifully designed creative space apart from engineering and product. It fostered creativity but produced wasted, misaligned work because designers were deciding things separately from PMs and engineers. She reorganized the teams, both literally and figuratively breaking down the wall so designers sat with their respective engineers and PMs, while preserving a protected creative space for crits and exploration.

Lyft's design team sat behind a locked door, separated from eng and product
The separation caused wasted work and misalignment with shared goals
She reorganized so designers sat embedded with their engineers and PMs
Changes were made together with eng and product after listening first
A protected creative space for crit and exploration was still preserved

“like literally and figuratively we broke down the wall and you know brought you the teams physically together so that they would work together”
Katie Dill · 1:05:30

#design-teams#org-design#collaboration#lyft

Tool· 1

Tool1:23:00

Katie Dill's Most-Recommended Books

In the lightning round, Katie shares the books she recommends most. How to Win Friends and Influence People, which she's read four times, for its timeless reminder that people care first about themselves. The Wright Brothers by David McCullough, relevant to entrepreneurs for its story of resolve against an impossible challenge. And The Boy, the Mole, the Fox and the Horse, a gift from Jenny Arden, for its gentle lessons like the freedom in how we react to things.

How to Win Friends and Influence People, read four times, on how you articulate things
The Wright Brothers by David McCullough, on resolve against an impossible challenge
The Boy, the Mole, the Fox and the Horse, given to her by Jenny Arden
A favorite quote from that book: one of our greatest freedoms is how we react to things

“the learnings from it you know are Timeless and I've actually read it four times”
Katie Dill · 1:23:30

#books#recommendations#reading

Takeaway· 5

Takeaway39:00

Trust Your Own Judgment When You Use the Product

Katie affirms that experiencing a product firsthand delivers a visceral understanding that even hearing a user describe it can't match. While she strongly supports user research and data as inputs, feeling the pain yourself surfaces problems users may not know how to articulate. Product people should trust their own reaction when something feels bad, because they're not that different from a potential user.

Firsthand use gives a next-level visceral sense that something could be better
This complements, but does not replace, user research and data
Users often can't say what's missing or that something could be improved
Your own point of view is a valuable additional input alongside research

“feeling the pain firsthand is just like this next level of visceral understanding of like oh this could be better”
Katie Dill · 40:00

#product#judgment#user-research

Takeaway54:30

The Formula Katie Uses to Lead Teams: Potential Minus Interference

A formula Katie learned at Airbnb has become a clarifying force for how she leads: performance equals potential minus interference. Increasing potential means hiring well and developing talent; decreasing interference means removing the obstacles that hold great people back. Even the best hires are like a muscle atrophying under a cast if interferences keep them from doing great work.

Performance = potential − interference
Raise potential by hiring well and developing talent
Reduce interference by removing what holds people back
Great talent held back by interference will burn out and underperform
As a company grows, processes break and must be continually re-designed

“performance equals potential minus interference”
Katie Dill · 55:00

“you can hire the best people in the world but like a muscle atrophying underneath a cast”
Katie Dill · 55:30

#leadership#teams#performance#management

Takeaway57:00

The Low-Maintenance Slide Deck That Keeps a Whole Design Team in Sync

For over a decade Katie has had designers drop a screenshot or prototype of their work into a shared Google Slides deck every couple of weeks, then emailed it to PMs, engineering leaders, and company leaders. It gives everyone visibility into what's being built across the org, surfaces overlapping or colliding projects early, and keeps teams aligned on the journey. The key to it working is keeping it low-maintenance and not treating it as a status check.

Designers add a screenshot or prototype to a shared deck every couple of weeks
The deck is shared with PMs, engineering leaders, and company leadership
It surfaces overlapping patterns and redundant or colliding projects early
Keeping it low-maintenance is critical; if it feels arduous it fails
It's framed as 'what projects are happening,' not a status check on everyone

“I'm strong believer that a Picture Tells a thousand words and a prototype tells you know saves a thousand meetings”
Katie Dill · 57:30

#design-teams#collaboration#process#alignment

Takeaway1:11:00

What to Look For When Hiring a Designer: Taste, Humility, Hustle

For non-designers hiring their first designer, Katie says it's easier to teach tools and process than taste and character, so weigh a candidate's hit rate for great judgment and taste heavily, even in the inexperienced. Beyond talent and high craft, look for humility, which makes people pay closer attention to users, and hustle or chutzpah, the courage to propose something better from a blank page. In early stages you likely need a doer, ideally paired with a senior design advisor for user-focused strategy.

Tools and process are teachable; taste and character are not
Weigh the candidate's hit rate for great judgment and taste
Humility makes designers pay more attention to users
Hustle and courage matter because creation from a blank page is scary
Early companies likely need a doer, ideally paired with a senior design advisor

“humility means that they're going to pay more attention to what the users are saying”
Katie Dill · 1:12:30

#hiring#design#taste#talent

Takeaway1:19:00

At Its Core, Design Is Simply Intention

Katie reframes design as intentionality: bringing deliberate thought to your decisions by considering who a thing is for and who it impacts. Whether you're designing a door knob, an org structure, or a strategy, anyone in any function can bring more care and intention. Great design also requires creativity and taste, which is why design expertise matters, but everyone can contribute intentionality from day one.

Design at its core is intention: being deliberate about decisions
Ask who a thing is for and who is impacted by it
The principle applies to a door knob, an org structure, or a strategy
Great design still requires creative skill and great taste
Anyone in any function can bring more care and intentionality

“at the core design is is simply intention you're bringing intentionality to the decisions that you make”
Katie Dill · 1:19:30

#design#intention#philosophy

Key ideas

Frameworks in this episode

Come In Listening, Not Swinging

Performance = Potential − Interference

Quality Is Growth: Making the ROI Case

Reach for the Stars, Land on the Moon

Taste, Humility, Hutzpah: The Designer Hiring Lens

The Four Conditions for Operationalizing Quality

The Levels of Quality Ladder

The Low-Maintenance Work-in-Progress Deck

Walk the Store: The Essential Journeys Quality Program

People & resources mentioned

People · 18

Resources · 40

Insights & moments

◆Hot Take· 2

Quality Is Growth: How Stripe's Checkout Fixes Lifted Revenue 10.5%

Reach for the Stars, Land on the Moon: Why Incrementalism Fails

✶Explainer· 2

The Levels of Quality, From Baseline to Surprisingly Great

Why Beauty Matters Even for a B2B Financial Company

❝Story· 2

The Airbnb Design Team That Staged an Intervention on Katie Dill

Breaking Down the Locked Door at Lyft's Design Team

✦Tool· 1

Katie Dill's Most-Recommended Books

▲Takeaway· 5

Trust Your Own Judgment When You Use the Product

The Formula Katie Uses to Lead Teams: Potential Minus Interference

The Low-Maintenance Slide Deck That Keeps a Whole Design Team in Sync

What to Look For When Hiring a Designer: Taste, Humility, Hustle

At Its Core, Design Is Simply Intention

Hot Take· 2

Explainer· 2

Story· 2

Tool· 1

Takeaway· 5