
57 segments available
Katie Dill is the Head of Design at Stripe. Previously, she was Head of Experience Design at Airbnb and Head of Design at Lyft. Katie has been named one of Business Insider’s 10 People Changing the Tech Industry as well as one of Fast Company’s 100 Most Creative People in Business and received the Girls in Tech “Creator of the Year” award. In today’s episode, she shares: • What makes a design great • Advice on building high-performing teams in hyper-growth environments • A pivotal lesson in leadership she learned at Airbnb • Stripe’s focus on quality and how it’s tied to growth • A formula for removing organizational friction • How to increase productivity • What to look for when hiring a designer — Brought to you by Sidebar—Catalyze your career with a Personal Board of Directors | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | OneSchema—Import CSV data 10x faster Find the transcript and references at: https://www.lennysnewsletter.com/p/building-beautiful-products-with Where to find Katie Dill: • X: https://twitter.com/lil_dill • Threads: https://www.threads.net/@lil_dilly • LinkedIn: https://www.linkedin.com/in/katie-dill-79168b3/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Katie’s background (04:47) Katie’s pivotal leadership moment at Airbnb (10:55) Advocating for design ROI (16:07) Stripe’s quality focus (17:50) Stripe’s vast scope (18:45) How design enhances utility (21:39) Defining beauty and its role in product growth (26:19) Operationalizing quality (28:44) Katie’s insights from dialogues with diverse organizations (34:47) 15 Essential Journeys: Stripe’s method for holistic UX understanding and unified vision (44:35) Stripe’s PQR quality review (46:25) Stripe’s prioritization philosophy (48:29) Measuring impact beyond metrics (50:28) Performance = potential – interference (54:09) Building and managing large teams (1:01:46) Removing interference at Lyft: a practical example of Katie’s leadership impact (1:06:10) Stripe’s physical workspace design (1:07:41) Embracing bold ideas (1:11:07) Qualities of great designers (1:15:15) Stripe Press (1:19:19) Katie’s parting wisdom (1:23:17) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.
Katie Dill discusses the declining use of the word 'beauty' in digitized literature and how this reflects a broader misconception that functionality and beauty are opposing forces. She argues that beauty enhances functionality by making products easier to use and more trustworthy, emphasizing the importance of aesthetics in design.
"the use of the word beauty in in books that have been digitized by Google has decreased like pretty dramatically and it it's aligned with this idea of like well functionality is King functionality is ..."
Katie Dill introduces herself as the Head of Design at Stripe, sharing her extensive background in leading design teams at Airbnb and Lyft. She highlights her experiences in scaling design organizations in hyper-growth environments and the lessons learned from her leadership roles.
"short word from our sponsors this episode is brought to you by sidebar are you looking to land your next big career move or start your own thing one of the most effective ways to create a big leap in ..."
Katie recounts a significant learning experience during her early days at Airbnb when the design team staged an intervention to address her leadership style. She reflects on the importance of trust and communication in building effective teams and how this moment shaped her approach to leadership.
"focused tactical feedback at every step of your journey Journey if you're a listener of this podcast you're likely already driven and committed to growth a sidebar personal board of directors is the m..."
In this segment, Katie emphasizes the importance of listening to team members to build trust and engagement. She shares how her initial approach to leadership needed to shift towards inclusivity and collaboration, ultimately leading to improved engagement scores within her team.
"Lenny Katie thank you so much for being here welcome to the podcast thanks for having me good to be here it's absolutely my pleasure so as we were preparing for this podcast you hinted at a story that..."
Katie discusses the ongoing challenge of demonstrating the return on investment (ROI) of design in product development. She explains how high-quality design can lead to better user experiences and ultimately drive growth, emphasizing the need for companies to prioritize quality alongside new features.
"you know a necessary part of building a high functioning organization is that one you know Building Together is important so like having engineers and product managers and designers be together have s..."
Katie articulates the idea that quality is not just an aspect of product development but a crucial driver of growth. She shares insights on how improving user experiences can lead to increased engagement and customer satisfaction, reinforcing the connection between quality and business success.
"and I I recognize that you or customers don't always ask for it I mean you might see it in you know support cases for example like clearly they don't know how to use this next step and that is probabl..."
Dill highlights the importance of a seamless checkout experience in e-commerce, revealing that 99% of top sites have errors that hinder conversions. She shares how Stripe's focus on improving checkout quality has led to a significant increase in revenue, demonstrating the tangible benefits of prioritizing quality in user experience.
"like I know there's this saying of like it's growth versus quality but like quality is growth and if you think about how you can make your product easier to use and more understandable you know that w..."
Katie Dill outlines Stripe's extensive involvement in powering checkout flows for major companies like Amazon and Shopify. She explains how Stripe provides tools for financial automation, helping businesses manage subscriptions and revenue recognition, thereby simplifying complex financial processes for users.
"customers and these small things it really like they're quality issues they're just that if you really understand what a consumer is trying to get out of the experience then you can make it better and..."
Dill addresses the common misconception that design goals and business goals are separate. She argues for a unified approach where quality products serve customers effectively, leading to stronger business outcomes. The discussion emphasizes the importance of emotional experience in design and the need for collaboration between designers and product managers.
"through you know powerful tools that hope to make your job easier so you don't have to sweat the details of how these things work I just want to follow this thread a little bit you talked about these ..."
Katie Dill explores the concept of beauty in design, asserting that functionality and beauty are not opposing forces but rather complementary. She references a book that discusses how beauty enhances usability and user experience, highlighting the importance of creating products that are not only functional but also aesthetically pleasing.
"and that is an important lens to bring on it whereas you know somebody else might just be like well you know just make the button bigger and they'll click it more often and you know that's what the ou..."
Dill shares insights from research showing that beautiful designs can lead to more positive user experiences. She discusses how aesthetics can influence user perceptions and outcomes, using examples from public spaces to illustrate how design impacts emotions and interactions.
"Paramount you mentioned this word beauty and I wanted to follow on this a little bit of just it's a big question but just like what what is great design what is beauty is there like a objective defini..."
Katie Dill emphasizes that beauty in design fosters trust among users. She explains how attention to detail in design communicates care and reliability, which is crucial for a financial infrastructure company like Stripe. Dill argues that beautiful, well-crafted products lead to better user outcomes and stronger business relationships.
"shared understanding and you know the other piece of it that you yes I can imagine is not talked about in business as often is just the importance of how people feel and you know and a good example of..."
Dill discusses the pride that comes from creating high-quality products. She believes that when teams invest in the beauty and quality of their work, it attracts clients who appreciate craftsmanship. This segment highlights the intrinsic value of quality in design and its impact on business success.
"will lead them to better out outcomes thirdly I strongly believe Beauty begets Beauty and so when you know our business users or the consumers see you know the the Beauty and the the care and the crea..."
Katie Dill shares insights on how Stripe operationalizes quality in design. She discusses the collaborative efforts between design, engineering, and product teams to ensure high standards are met. This segment emphasizes the importance of teamwork and shared vision in achieving exceptional design outcomes.
"part of it all amazing speaking of beauty I think when I think of stripe and beautiful I think of your website and some of the specific landing pages you have which are just incredibly nice I'm just c..."
Dill stresses that achieving quality in design is a collective effort rather than the responsibility of a single individual or team. She highlights the need for a shared commitment to quality across the organization, ensuring that everyone is aligned towards common goals for product excellence.
"technical kind of power of the way that we show it how we've actually operationalize the way we do that is that we have design and engineering and our product partners and product marketing work reall..."
Katie Dill discusses the necessity of vision and alignment in design teams. She compares the process of creating cohesive products to building a house, emphasizing that without a unified direction, even the best talents may produce disjointed results. This segment underscores the importance of collaboration and shared objectives in achieving great design.
"you know we can build better things uh at stripe is actually I've been just talking to people talking to different you know design leaders product leaders engineer engineer leaders at different organi..."
Katie discusses the necessity of having an editor-like figure in product development to ensure that all elements come together effectively. She shares her experience at Airbnb, where leadership played a critical role in maintaining design quality and coherence across projects.
"a big pair on that is then the next piece which is editing and you know you might call that your your GC or your architect or somebody that you know kind of sees how all these things fit together and ..."
Dill highlights the importance of viewing product quality through the lens of the user experience. She introduces the concept of 'Journeys' to illustrate how users interact with products and emphasizes the need for empathy in design to ensure high-quality outcomes.
"you know the kind of the fitness of what you do and then lastly the thing that I've learned that will lead me to the the example that you were asking about is that in order to build quality you really..."
Katie explains the challenges of maintaining product quality after launch, using the analogy of home renovations. She discusses how different teams can inadvertently affect the overall quality of a product and the importance of a holistic approach to product management.
"piece of building teams that have empathy for their users so we have been operationalizing that you know all all the things that I just mentioned but like one of the the key pieces is to you know kind..."
Dill describes Stripe's innovative approach to quality assurance through a process called 'Walking the Store.' This involves team leaders reviewing critical user journeys to identify friction points and improve the overall user experience.
"and so that is you know something that can happen to products is actually they you know kind of get worse over time and then you organize a company oftentimes in you know parts to be able to focus on ..."
Katie elaborates on how teams at Stripe collaborate to assess product quality through regular reviews. She emphasizes the importance of diverse perspectives in these discussions to ensure a comprehensive understanding of user experiences.
"highest level of quality possible and so those 15 things then each have engineering product and design leaders that are responsible for the quality of the products and they review these Journeys what ..."
Dill discusses the calibration process for quality scores at Stripe, where teams come together to evaluate their findings and ensure consistency in quality assessments across the organization. This process fosters a shared understanding of quality standards.
"and then they score it and then on a you again a regular Cadence we come together in almost like a calibration where we meet and we talk about the score of their work and it it kind of relates to perf..."
Katie highlights the benefits of involving multi-disciplinary teams in the quality review process. She shares her experiences with team members from different functions collaborating to enhance product quality and user satisfaction.
"when people see the state of products in the wild as a user would they learn a lot about you know what are you know some of the bigger opportunities that we can make to make the product better what ar..."
Dill encourages product managers to trust their instincts when evaluating product quality. She emphasizes that firsthand experience with the product can provide valuable insights that complement user research and data.
"to better craft in the end oh man what an awesome process I have a million questions I want to ask to better understand how you operationalize this I'll try to ask just a few but one thing that stood ..."
Katie explains the importance of establishing a regular cadence for quality reviews at Stripe. She shares how quarterly assessments help teams stay accountable and continuously improve their products.
"point 100% like they're all just forms of input like I'm not definitely not saying like do this instead of user research do this instead of data it's like you know these things an additional sense and..."
Dill discusses the role of leadership in the quality review process, highlighting how leaders participate in discussions to provide insights and ensure that quality remains a top priority across the organization.
"know you're not missing that perhaps you know there's been a step back since but of course my real hope is that these happen you know they're happening weekly just perhaps in different parts of the or..."
Katie Dill discusses the importance of collaboration across disciplines in product design. She shares her experiences with David Singleton, emphasizing the value of diverse perspectives in product quality reviews. The segment highlights how team members from various backgrounds contribute to a holistic understanding of user experiences and the significance of maintaining a consistent design system.
"like that the load time didn't feel really good there and like oh whoa that like the the way we're stating this is not consistent per page um and Ah that's not on our design system uh so you know it i..."
In this segment, Katie explains the Product Quality Review (PQR) process used at Stripe to evaluate product quality. She details how teams score different aspects of user journeys using a color-coded system, allowing for qualitative assessments that prioritize user experience. This method encourages open discussions about product performance and fosters a culture of continuous improvement.
"sense in terms of scoring are you scoring individual steps of these Journeys or is it yellow for like segments what are you scoring the way the rubric works is so that and we we have a template for th..."
Katie Dill shares insights on how Stripe operationalizes feedback from product reviews to enhance quality and drive growth. She discusses the balance between fixing existing issues and developing new features, emphasizing the importance of hiring individuals with strong judgment and a commitment to quality. This segment underscores the cultural approach Stripe takes towards prioritizing quality in product development.
"to you know quicker but like straightforward uh opinions and decisions had a lot of companies you have these reviews and the founders like share all this like oh this is broken this is busted and as a..."
Katie highlights the correlation between product quality and business outcomes. She provides examples of how improving user experience can reduce support inquiries and enhance customer satisfaction. This segment reinforces the idea that investing in quality not only benefits users but also positively impacts the bottom line, challenging the misconception that quality improvements do not affect metrics.
"business part of it though is showing how it moves metrics because I I think that is a dangerous belief that is absolutely out there as we we talked about earlier but that actual quality improvements ..."
In this segment, Katie discusses how to evaluate team performance at Stripe, emphasizing the need for a broader definition of impact. She explains that not all quality efforts yield immediate measurable results, yet they are crucial for long-term success. This approach encourages recognition of contributions that may not directly influence metrics but are vital for the organization's growth.
"is there anything you do in how you evaluate performance of teams that helps prioritize this sort of thing so generally it's just like cool you te moved this metric by ton they're doing great I guess ..."
Katie Dill shares her philosophy on the importance of meticulous craft in design and product development. She explains how this principle is embedded in Stripe's culture and performance evaluations, ensuring that every team member takes pride in their work. This segment emphasizes the significance of attention to detail in creating exceptional user experiences.
"talk about the importance of things like quality uh and that that you know what we pursue is building these you know things that are are great and another part of that is also the operating principles..."
Katie reflects on her experiences leading design teams in hypergrowth environments. She introduces a formula for performance: potential minus interference, highlighting the need to foster talent while minimizing obstacles. This segment provides valuable insights into effective leadership and team management in rapidly scaling organizations.
"podcast one schema is offering $1,000 discount learn more at on schema. c/l I'm going to shift to a different topic and this is just the last area I want to spend some time on which is team building l..."
In this final segment, Katie discusses strategies for improving awareness within design teams at Stripe. She advocates for sharing prototypes and updates in a collaborative environment to ensure alignment across departments. This practice fosters communication and helps teams stay informed about ongoing projects, ultimately enhancing the overall design process.
"in terms of as you improve the processes one of the things that I've been working on since I worked back at Airbnb was this idea of improving awareness of the things that are happening what happens at..."
In this segment, Katie Dill shares her strategy of using prototypes and visual aids to enhance communication within design teams. By creating a shared deck where team members can showcase their work, she fosters a culture of collaboration and transparency. This method not only keeps everyone aligned but also encourages creative discussions and reduces the risk of duplicated efforts.
"really important for all the designers because they could see you know whether or not they're a team of 10 or 170 or whatever it might be what is happening and they can say like oh my gosh like you're..."
Katie recounts her experience at Lyft, where she identified and addressed organizational interference caused by physical separation of design teams from engineering and product teams. By bringing these teams together, she improved alignment and efficiency, allowing for faster iterations and clearer communication. This transformation highlights the importance of physical workspace design in fostering collaboration.
"and especially knowing designers they'd want to make sure it's the best version of what they've done and it takes all this extra time to like okay we got to make this beautiful mock that's actually an..."
Katie Dill explains how she evolved the workspace at Lyft to enhance collaboration between design, engineering, and product teams. By breaking down physical barriers and fostering a culture of shared goals, she facilitated better communication and alignment, ultimately leading to more efficient workflows and innovative outcomes.
"I joined Lyft as I mentioned to you earlier I was like oh I had learned from the experience that I had at Airbnb and I came in and you needing to transform the organization and was hopefully much bett..."
In this segment, Katie discusses the balance between maintaining creative spaces for design exploration and ensuring collaboration with other teams. She emphasizes the need for both environments to coexist, allowing designers to thrive creatively while also working closely with product managers and engineers to achieve shared objectives.
"approach about listening and you know came into that with a you know kind of better understanding of getting to know the team and getting to know engineering a product and and see what our goals were ..."
Katie Dill addresses the tendency of organizations to shy away from bold ideas due to fear of risk. She advocates for a vision-driven approach that encourages teams to think big and innovate, while also being mindful of incremental progress. This mindset is crucial for fostering a culture of creativity and quality in product design.
"interesting that that was a recurring pattern at the places you went I imagine stripe was not like that there was not all designers sitting in a locked room not in a locked room and when I joined stri..."
Katie shares her philosophy on the importance of vision in design work. She encourages teams to aim high and conceptualize the ideal user experience, which serves as a guiding star for incremental improvements. This approach not only inspires creativity but also ensures that all team efforts align towards a common goal.
"happen at small sizes and it can happen at large sizes actually it's just that like you know a fear of kind of like you know shaking things up too much or you know big ideas with lots of things changi..."
In this final segment, Katie Dill offers insights on what to look for when hiring designers. She emphasizes the significance of taste and character over technical skills, suggesting that a designer's judgment and aesthetic sensibility are crucial for success in a collaborative environment.
"get there you know day one and you know likely know end up giving up I love that reach for the stars land on the Moon that could be a metaphor for so many things um let me try to squeeze in one more t..."
In this segment, Katie discusses the challenge of hiring in early-stage companies, weighing the benefits of hiring junior doers versus senior thinkers. She suggests a balanced approach, advocating for a mix of execution and strategic thinking to build a user-focused organization from the start.
"piece would just be you know hustle or or hutzpah not sure exactly what's the right way to put it but you know the design and you know the creative functions is you know it's the act of creation and i..."
Katie reflects on the difficulty of measuring design quality and the importance of context in evaluating design effectiveness. She suggests that understanding user needs and the specific context of a product is crucial for assessing what constitutes great design.
"cool tip on the craft and taste piece a lot of times people don't have that themselves necessarily any tip for how to measure that is there I don't know book you'd Rec or trick or is it just trust you..."
Katie introduces Stripe Press, a project that aims to publish books that embody ideas of progress. She discusses the upcoming release of 'Poor Charlie's Almanac' and the creative process behind the book's design, highlighting the intersection of design and engineering in delivering engaging content.
"hard to kind of quote an individual book but yeah I mean I can think on it and we can put it in the show notes there there are definitely books that talk about like the principles of great design U an..."
Katie elaborates on the design philosophy behind Stripe Press's website, which aims to provide a bookstore experience that is engaging and user-friendly. She emphasizes the importance of intentional design decisions that enhance user interaction and satisfaction.
"linear story so much and so we have reprinted this book uh we also have we created a teaser site that I strongly recommend you all check out it's really fun man it's unreal I remember when you launche..."
Katie explains how Stripe's mission to increase the GDP of the internet aligns with the goals of Stripe Press. She discusses the importance of creativity and excellence in their work, emphasizing that sharing great ideas is part of their identity and contributes to their broader mission.
"know would be aligned with what a reader would want to pursue I can't help but ask but how did that even come together was it just like this passion project of like oh this book's coming out I just wa..."
In this segment, Katie discusses the essence of design as intentionality. She explains how every design decision should consider the user and the impact it has, advocating for a culture of care and thoughtfulness in design processes across all functions.
"thing for so like if you're designing a door knob let's say say and it's like okay does the door knob speak to whether or not I'm going to push or pull or turn uh is it comfortable in the hand is it e..."
Katie praises the podcast's approach to delivering valuable content, emphasizing the importance of quality and usability in every episode. She highlights the balance between providing concrete advice and maintaining a human touch, which is essential for engaging listeners.
"it so great wow Katie what a nice way to end it I really appreciate that that's exactly how I think about it actually you cracked my my whole strategy of just making it as concretely useful as possibl..."
Katie shares her top book recommendations, including 'How to Win Friends and Influence People' and a biography of the Wright Brothers. She discusses the timeless lessons from these books that can inspire personal and professional growth, emphasizing the importance of relationships and perseverance.
"but yes I mean the cover is funny you know you might be embarrassed to read it on a bus I don't know but uh the learnings from it you know are Timeless and I've actually read it four times uh and I ge..."
Katie introduces 'The Boy, the Mole, the Fox and the Horse,' a beautifully illustrated book that imparts life lessons through its charming narrative. She highlights a key quote about the freedom of choice in how we react to situations, linking it to personal growth and resilience. This segment is a reminder of the power of storytelling in conveying profound truths.
"then third book I would just say is actually I brought it over because I knew you were gonna ask me this question um I don't know if you could read that but uh the boy the mule The Fox and the horse u..."
In this segment, Katie shares her recent favorite movie, 'Oppenheimer,' and the TV show 'Shrinking.' She expresses surprise at the humor and positivity of 'Shrinking,' contrasting it with its trailer. This discussion reflects on the impact of storytelling in film and television, showcasing how narratives can resonate deeply with audiences.
"best quotes in it is one of our greatest freedoms is how we react to things very Buddhist yes yes awesome what is a recent favorite movie or TV show that you've really enjoyed um Oppenheimer was amazi..."
Katie reveals her favorite interview question: asking candidates about the work they are most proud of. She explains how this question helps her gauge a candidate's taste, motivation, and values. This segment provides valuable insights for hiring managers looking to understand potential team members better.
"candidates tell me what work you are most proud of and the reason I ask that is because well it helps me understand their taste and their judgment um what motivates them what uh work they view as good..."
Katie introduces the Tony Box, an innovative speaker designed for children that uses figurines to control stories and songs. She highlights its interactive features and the ability for parents to record their voices, making it a unique tool for storytelling. This segment showcases the intersection of design and functionality in creating engaging products for families.
"favorite product you recently discovered the an appp or physical thing anything yeah well as a parent you should definitely know the Tony box oh I don't know this the Tony box so good the Tony box I s..."
Katie shares her personal motto, 'Tomorrow is today,' emphasizing the importance of taking action in the present rather than procrastinating. She reflects on how this mindset can lead to better decision-making and accountability. This segment serves as a motivational reminder to seize the day and prioritize meaningful actions.
"box pretty awesome I just texted my wife to check this out forget amazing great very handy And Timely do you have a favorite life motto that You' like to share come back to find meaningful I don't say..."
Katie discusses the lessons she learned from her parents about merit and hard work, particularly in the context of raising her twin daughters. She reflects on a conversation with a Lyft driver about gender roles and the importance of not limiting children's potential based on gender. This segment highlights the ongoing conversation about equality and empowerment in parenting.
"tomorrow is now love that one I feel like I need to take all these mottos which are amazing I love this question that I just invented uh and just put them all my wall here in this office yes that's a ..."
Katie draws a powerful metaphor from her experience learning to fly, where her instructor demonstrated trust by stepping back from the controls. She emphasizes the importance of showing trust in team members and empowering them to take on challenges. This segment encapsulates a key leadership lesson about fostering autonomy and confidence in others.
"actually I thought about that the other day because I was riding in a a lift to the airport this was also at like 400 am so it was like a really hard time to be in in a lifted got into the airport and..."
In the closing segment, Katie shares how listeners can connect with her online, including her social media handles and job opportunities at Stripe. She invites engagement and collaboration, reinforcing the theme of community and continuous improvement in design and leadership. This segment encourages listeners to reach out and share their experiences.
"and so you whether it's like you know learning a language or whatever like that that is awesome and highly recommended but um no one of the key things that has definitely sat with me from the experien..."