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

Building beautiful products with Stripe’s Head of Design

9Frameworks
12Insights

Frameworks in this episode

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