Katie Dill: Quality Control › First of Kind

When I was at ArtCenter, I had a teacher named Norm Sherman, and he used to say to me multiple times that it's all about mileage. And what he meant was that I had to essentially do the time, get in there with the work and, you know, and spend some time in the pixels and, you know, with your hand skills and like really, you know, get close to the craft.

First of Kind is a new series about design and tech told by its pioneers, sponsored by Framer, Cursor, Vercel, and Profound. Katie Dill has led design at Stripe, Lyft, and Airbnb. She's built world-class teams at 3 iconic companies, proving that thoughtful design can shape quality at scale. Katie, thank you so much for doing this. It is such an honor to be here in your beautiful headquarters at Oyster Point in San Francisco. Stripe is the home to an incredible design team and an incredible design legacy. But the thing I'm most excited about talking about today is your career path to this role. This whole series is about first-of-a-kind designers. It's about telling the story of modern design through conversations with its pioneers. And when I think about your career thus far, you've been at the helm of not one, not two, but three storied design organizations, design organizations that have been the stage for incredible work and incredible designers to produce that work. And, you know, to use an NFL analogy, it's like helming a championship team across 3 franchises. And so when I, when I sat down and started making a shortlist of people to talk to for the second season of First of a Kind, your name was super high on that list because I feel as though you are a singular person in the tech ecosystem. And I just think it's such a privilege to get to chat with you about your biography, your story. And learn more about what brought you here.

Well, thank you. Geez, wow. It is not often that people align me and the NFL. So thanks for that. But no, that is extremely flattering. And I wouldn't say I necessarily deserve that, but I appreciate it very much. And I'm so glad you're here. This is a real treat. I'm such a big fan of First of Kind. So to be a part of it is an honor.

Awesome. So I wanted to start off with a little anecdote. I've learned recently that you are now piloting planes. And once I got past the, like, why would you do that? Um, I, I started wondering to myself, it's like, well, anytime you take on a new hobby, a new capability, it folds itself back into the rest of the work that you do. And I'm really curious to know out of the gate, what is flying teaching you about design? What, how is it shaping the way that you lead and the way you operate in the world? Why did you decide to learn how to fly?

I love this topic. Uh, and, and so much to, to your questions there. Well, I grew up, uh, in back in New York. Uh, my father was a pilot. He went to the Air Force and later in his life he was a private pilot. And so, on the weekends, we would fly from Westchester, New York, just outside of the city, up to the Adirondacks. So, basically, it's kind of like in the San Francisco ratio, it's like, you know, the Marin to Tahoe. And spending time in little planes was, I mean, an incredible privilege and joy. And it was just, you know, a wonderful way to grow up and got me excited about that. I think also in my family, we just had a penchant for vehicles and driving. And, you know, my mom used to say when I'd leave the house, she'd be like, "Drive fast, take chances." A joke, but it was, you know, kind of a part of our family is just like driving and being a part of, kind of exploring the world in different ways.

I love that because when I first met you, you were in like a biker outfit, pulling your biker helmet, and you came visited the Dropbox office. And I'm like, who is this woman?

Motorcycles are a great way to get around.

Yeah, as it turns out.

Yes, yes. But yeah, actually, so I rode motorcycles for quite a while. I used to ride with my dad. And actually, the last time I saw him was on a motorcycle trip through the Rockies. We did 2,000 miles, me and his biker gang. It was amazing. But the story ends in a sad note where that was the last time I saw him and he passed away on a motorcycle. And I rode for a little bit longer after that. It was still, you know, it somehow kind of like drew me to him and, you know, it felt like, you know, it was something I loved to do. But then as I had kids, I realized it was just like, it kind of felt hypocritical to keep riding. Like, I don't think my father would've kept riding if, you know, I had gone. And, you know, I thought about the, like, just being there for my family and the risks involved. And so I, you know, sold my bike and then made the decision to learn to fly.

So you traded structural risks.

Yes, exactly.

I did this less frequently.

Yes, yes, exactly. I did a little bit of data on like, you know, what is the risks involved? But yeah, I guess I still needed the adrenaline rush. And it was one, became a new addiction about learning. And what an incredible feeling going from not really knowing how to do something to being able to speak this new language and being able to understand it. I mean, that was just like, it was an incredible feeling. And, you know, it was also just like a wonderful thought of like, I can do this. I can learn things wholly new. So I think your other question of just like, well, what does that do for you and work and what do you, where do you take that? I think that's one. It's just like, I feel less intimidation about things that I don't understand because now I've proved to myself that I can go from knowing nothing to being, you know, capable of, of of flying a plane over San Francisco. I think secondly, you know, kind of maybe related to your point about it was like your own time is that, you know, people always tell me I gotta meditate. You know, apparently that's a thing people do and it's a good idea. Every time I try, I am just like going through the to-do list.

I fall asleep. Really? That's all I do.

That's a moment of zen. So that's, you know, maybe working for you. But yes, I couldn't, you know, relax and just not be busy in my brain. But with flying, I have no choice. I have to be in the moment. I have to really just like lean into that and not be distracted with the, the pressures and the concerns that I have about work or whatever it might be. And so it actually is my moment of zen. I was definitely nervous when I was driving to the airport, thinking about it, thinking about all the things that could go wrong, but kind of related to the moment of zen, like when you actually get in the plane, you can't really focus on your, what you're nervous about. And instead you, you just kinda have to focus on what you're doing. And that I think is a correlation for things that I need to be doing in work as well, where, you know, you could stay like nervous, like, I'm gonna sit there and have to talk to Soleio ​ and oh my goodness, we're gonna have this interview. Is it gonna go terribly wrong? It's just like, well, right now we're just here, you know, and we're just having a conversation. And I've, I've talked about this with my team as well. It's just like, you could do this. And like once you're, you know, in that conversation, it's the nerves can fall away. And so you, you're usually the most nervous before you even get there.

So the thing I've always loved about the field of design is that unlike being a lawyer or even being like a software engineer, when you look at people's backgrounds, it's such a wide gamut. The minority of people even go to design school. And I'm always particularly drawn to people who are coming from areas of study that are way afield of design. Uh, I'm a music major. That's what I studied in undergrad. Yeah. I was just really proficient with web browsers and, and Photoshop on the side. And that sort of spiraled into a full-time job for me. And in the process of kind of preparing for this conversation, I learned that you studied history. I really wanna know what that transition was like to go from studying history to finding your way into the world of design and ultimately in in-house roles as a, as a tech executive. That's not the most obvious pathway, right? That's not a playbook that you would typically hand over totally to somebody who's starting off their career path. Yes. Yes. Um, so I'd love to hear a little bit about like how you, how you arrived at that field of study and where design kind of emerged for you as a path in life.

I totally agree. I think it is so interesting about design and, you know, because perhaps it's defined as a bit of a newer discipline, but yes, we all have such circuitous paths to it. The reason why I chose to study history in my undergrad was because I just wanted to know why things are the way they are. I'm just infatuated with the stories of, you know, where, you know, lines were divided between countries and the stories of how different cultures came to be and, you know, why, you know, the architectural direction went that way versus this and how it's ended up impacting the way we live and how we are. And, you know, of course, if I speed up to the future, it's like, well, of course the next exposition was then like, well, why can't it be a different way? Why can't it be better? And that is, of course, design. But the real story about how I ended up transitioning to that was that I was studying in Florence, study abroad while I was in college on my junior year. And of course, I mean, in Florence, you can't help but be just taken by the art and the architecture.

You're surrounded by beauty.

Yeah, exactly. And it's just like there's something here and it's like it is, of course, you know, history and beauty interwoven. But I remember a vivid example of where we were on a class trip to Santa Maria Novella, the church in Florence. And we were there, we were talking about the history of the space and the area, but I was just taken by the beauty of this building, you know, from the 1400s. And the facade is done by Alberti and it like just really, it is a perfection of harmony and balance and proportion. And, you know, when you just spend some time with that, you just like think about what people are capable of, you know, in the 1400s and, you know, what the impact of these things can have on people's lives and actually even, you know, shape history made me just, I wanna, I wanna spend time on that. That's all, that's all I wanna do. I wanna be closer to that. And so I thought I wanted to be an architect and I decided to finish my degree at Colgate in upstate New York, a liberal arts school. And then I thought, okay, after this I'm gonna go and study architecture. Moved to Boston with that as my aim. Started talking to architects like, how do I get into this? This is amazing. And it was, you know, interesting to hear about their profession and what they did. And, you know, could definitely hear some stories about like, well, and you're doing outlets in a hotel room and they're all the same. You know, I was like, oh, that doesn't sound very exciting. But there was definitely, you know, something to it. But at the same time, my roommate who I lived with back at school and then again in Boston, her name was Tiffany. She saw the 60 Minutes special on IDEO about making the shopping cart. And so she learned about product design. And this was not something people talked a lot about on the East Coast. You know, I think we were a little bit behind. We, we knew about interior design and architecture and fashion, but not about product design. And so she told me about it 'cause she knew about the little things that they'd call Dillisms, which were my little inventions that I would make at, you know, the house or back at college. But she's like, "Dilysms is product design. You should check this out." And so I started talking to product designers and it's just like, wow, you get paid to do this? You get paid to solve problems, try to understand, you know, why things are the way they are and why can't they be better and, you know, come up with little things that are just gonna make people's lives better. Like, that is what I need to do. And so I just, you know, went on the hunt for how do I get into that? And they're like, well, you gotta go back to school because you know nothing about design.

Turned right back around.

Exactly, exactly. Yeah. So I, I mean, honestly, one of the hastiest decisions of my life. I essentially, you know, fell in love with design and moved to California. And so I went to ArtCenter and studied industrial design and, uh, that kind of took me to this path now.

It's amazing. And, and I love that sometimes the most consequential decisions in life can be that impulsive. It's kind of instinctive. So when you look at your relationship to architecture, to industrial design, even these fields are very far removed from software. What have those disciplines taught you about product making quality in a software and digital context? Because again, it's like I can theorize how music has shaped the way that I approach design, right? This idea of spontaneity around structure, inventiveness. There's a songwriting quality that I can never really escape with design and that sometimes it is an act of courage of just do the thing that feels best. Like do the thing that's right. Don't overthink it. But with fields as storied and with as established a set of patterns as architecture, or even with industrial design, when you are taking into serious regard the constraints, the materials, the legality, the regulations, all the things that are essential to making something that's both like really useful and desirable. How have those fields informed the way you think about software? How has that sort of been, uh, a conduit to your foray in, into digital design?

Yeah, for sure. Architecture, there's so much that we can learn from just because it's an older profession. One thing that's a fantastic concept is the idea of parti. Have you ever heard of that? No. Uh, it's spelled with a I, P-R-T-I. And basically what it means is like the core design, the core concept. And so you can imagine like drawing with a really thick Sharpie. What's the concept of the building? It's like, oh, well, it's like it's an L-shape or spokes on a wheel all around a center. And so a great architect is going to think about like, well, what's the core design of what I'm doing here? And then like holding that true as you build out the details kind of helps to create the integrity of that design and like keep that concept whole. That I think is something that we should think about from the design side as well. It's so easy to think about like, well, I do this part of this thing, or when you get down into the details, you can lose sight of like, well, what's the big idea here? What are we really trying to achieve? What's the core concept? So I love that, like, party. Secondly, I think on the architecture front, architects, it is like exactly what you just said, like the legality, the safety, that like really taking ourselves seriously, like stamping our documents that like I put my pride and my integrity behind this work. I think sometimes with product design, you know, we whip something up and, you know, cool. But like, it impacts people's lives. Like, people's work, their business, their, their day is impacted by the decisions we make. We should take them as seriously as an architect takes their work too.

Yeah. I want to make sure we, we, we, we, we go back to this gap still where, um, I think when I met you, you were working in venture or in some venture capacity. Yeah. And when we powwow, you were really interested in navigating, well, what are the design leadership opportunities within software companies? And I never really got filled in on how you went from point A to point B. Mm-hmm. And so I'd love to, to kind of go through that because I see it as central to the golden thread of your career.

Yeah, you have a great memory. I cannot believe you remember that, uh, from when we first met. Uh, but yes, I went to Art Center studying industrial design. And what I thought I wanted to do going into that was that I wanted to come out and I wanted to work on products like OXO, right? It's just like they figured out how to make the best hand peeler or the best measuring cup, but whatever it was. And I was like, I wanna, you know, make products that are just gonna make people's lives better. But while I was at ArtCenter, there were two major shifts in my thinking, one of which was I went to INSEAD, a business school, while I was at ArtCenter. Really an incredible opportunity to better understand the business side of building products. But I took away something in addition to that that I think changed the course of my life, which was the power of working with people that thought a very different way than I did. So like, for example, in one of the classes that I was in, which was creating new products, I was on a team of 5 people and I was one designer and they were 4 MBA students. And we somehow got on the, the thought that we were gonna build a water bottle. We wanted to create a water bottle and solve the plastic problem. So good luck with that. But we set out to do this. 4 of them had just awesome data on what is the water bottle industry today, you know, who's buying, what's the TAM, you know, all that stuff. What did I come back with? I had user interviews, I had user journeys about like, well, when, you know, when are people drinking and what is the role the bottle plays in their life. And so you lay this all out and that is a full set of insights that will help to drive the next idea. And so that has definitely contributed greatly to the way I think about teams and the way I think about design, working with engineering and product management and data science and just the value that different mindsets bring to the work and you know, how it's great that we all have a different way of looking at it, but even better when we, you know, bring those things together in how we work. With that, I was looking for my next job. And so that's where I ended up at that VC you mentioned. It was called GreenStart. And one, we were focused on early-stage organizations that were basically in the green space and trying to, you know, build better products and services that, you know, had a positive impact on the earth. And that's where, yes, you met me. And I mean, it was awesome. It was a great, you know, kind of model and a great organization to be a part of. But it didn't scratch that itch of getting closer and being there to, like, see things through.

Actually owning the product development.

Yeah, yeah, yeah. And so that's where I was like, okay, I want to go in-house. What are those roles like? And, you know, I heard, I heard about you and I heard about all the, you know, cool things that you've done and was such a huge fan of the Dropbox team and what you built there. Yeah, the way I ended up at Airbnb is actually kind of interesting as well. I was asked to speak at an event. Finn Barnes reached out to me and he was like, I'm doing this event. I think, I forget what it was called, but he was like, we're, you know, I'd love for you to talk about, you know, do a presentation on design critique or something like this. And I was like, okay, about ready. And then he told me like, you know, like, well, Elle Luna's speaking. I'm like, oh man, I've seen Elle Luna speak. She speaks really well. I don't know if I should go. And I was really ready to say no. And then there was this like voice inside me. It's just like, you don't wanna do this. You're nervous to do this. That's why you gotta do it. You know, like, don't wimp out on this. Like, this is like, you know, maybe the reason why you're nervous is because this matters. And that's a great thing. And so I, you know, talked myself into it, said yes. And like, I look back at that so often, it's like, thank gosh I did. And you know, what other examples of, you know, things I'm afraid of today that I should be saying yes to?

Isn't it wild? Like those little pivot points where like you, it could, it could have been a coin toss, right?

Yeah. Because if I didn't, uh, or actually, well, I'll tell you what happened. So I, I spoke, Joe Gebbia was in the audience. Mm-hmm. And then afterwards he's like, I want you to interview for this role. And so I interviewed for the role and they hired me as their head of experience design. And then I was at Airbnb for, you know, the next very meaningful part of my life.

But I wanna stop for a second because you said something that I think is really important. There was that voice in your head. That told you, you need to go on that stage and confront your fear. And so I, I, I wanna get your perspective or your advice on like, how do we help designers and creatives hear and honor that voice?

It is a great question. And I, I, I do wish I knew exactly how that is done so that I can, you know, help people on my team or like the kids I'm raising. In terms of showing support so that somebody can increase their courage. There's just one example of when I was flying with my instructor, I was getting ready to be able to land the plane by myself. And my instructor, you know, for many of like our, you know, coming around, coming around, he would be there, you know, he is like, I'm on the controls if you need help. Right? He's right there. He's got his feet on the rudder just in case like anything goes wrong. And so like, that makes me feel like good and safe, like he's right there. And then one time we're coming around and he reaches down and he adjusts his chair. He pushed his chair so far back that he could, like, barely grab the yoke or touch the rudder pedals if he needed to. And that has stuck out with me as just, like, this really visceral moment of just, like, he just showed me he trusted that I got it. And it felt so cool because it was just like, oh my, like, he's still in the plane. Like, if something really goes bad, he's going to just, like, lean in and be able to grab it. But it was just like he didn't have to say any words. He just, like, you know, pulled the thing and moved it back. That was very clearly saying, like, you got this.

And without saying it, right? The thing that's really artful about it, he's not sort of declaring, now you're in control, right? Yeah. It's much more like, let you perceive what's happening and recognize what it means. And that's so different, right?

Yeah. It was a really clarifying way. And I always think about, like, how can I do that for people, you know, in my team, right? It's just like, you know, that person's taken over that project. Like, you know, I'm out of it. And like, you, you know, you go ship that. Something great and I can't wait to see it. But what does that look like? What is my pull back my chair moment?

So I think that's a beautiful segue for talking a little bit about these three distinct design cultures that you came to helm. And the thing that I probably admire most about you, having like worked in a similar role, is that exercise of both adapting to the native tongue, to the native way of doing things, but also advancing, you know, your way. Your philosophy, your approach to design that both like sits naturally within that environment, but is also like true to you? It's the reason why you got hired, like the reason why they, they, they called you up and asked you to lead the team.

Yeah, good question. 'Cause, uh, the truth is at first I really screwed it up. When I first joined Airbnb, they were, you know, during the interview process actually, I was talking to, you know, the, the leaders of the team and the individuals in the team and the PMs and the engineers, et cetera. And I got a sense of what was working and what wasn't. And so Airbnb is known for, like, it has like a really strong culture. It's like a great energy and it's, you know, very much like driven to do great design. But I also learned about some of the tensions. There wasn't really great dynamics between product management and design coming together, engineering and design. And there were, you know, a couple of things that I just understood as opportunities for growth in the team. And so when I got in there, I'm like, I'm ready. I'm gonna like, let's change this. Let's make this better. Cool. And so, you know, just set to work right away to try to like start to impart these changes. Well, you probably know where this story is gonna go. About a month into my time there, I got a meeting invite on my calendar for like an hour and a half with 5 people from the design team. And keep in mind, the design team was 10 people at that time. I had taken over from, they were reporting directly to one of the founders. And then, so they had been reporting to me. So 5 of those 10 people and somebody from HR on my calendar. What? Yeah. So Wednesday morning I go into the office and I go into this room and it was like, first of all, Airbnb, every room is awesome. They're so beautiful. They're all like different scenes from Airbnbs around the world. This is the one room that's gray and has no window. Oh no. So it's like a totally gray room.

The scene is set.

Oh yes. Oh yes. And it's just like this oval table and then the 5 people people are sitting there, it's like stack of paper in front of them, and then they just take turns reading from the stack of paper telling me all the things they do not like about my leadership and like about me. And whoa, I mean, it was, it was, it was not my favorite moment.

That's trauma. Oh my gosh.

But like, all right, this— the only way I get through life about like anything I mess up is like the silver lining is what do we learn from that? Yeah. But like, I, you know, I was sitting there listening to this and I mean, there were definitely moments where I wanted to be like, but that's not how it was or whatever. But I had the sense to not push back and just take it all in. And as I was hearing this and thinking about my thoughts on the subject, and I realized like, oh, there, yeah, there's truth here. And the truth is I did not earn their trust at all. They had no reason to trust in what I was doing. They had no reason to trust that I knew who they were or what they were trying to do or what they were great at or what struggles they had. They had no reason to believe that I was there trying to help the situation or help them. It was a month into my time there and I was already making changes without transparency and context to them and that they hadn't seen me or felt me really try to understand them. And so that was an incredible learning. I mean, and whether or not the changes were the right ones, it was more about the how I was going about it. And so, yeah, from there I just had to correct the way I was working. And the good news is that it definitely taught me quite a bit that I could implement right away and I could spend time with the individuals on the team and really understand them and be more transparent about what I was understanding about the situation and why I was making changes that I was making and make them with them, not to them. And, you know, interestingly enough, we had the worst engagement scores in the company before this happened. And then we had the best after, like, just a few months after this. And yeah, we started to reshape the team. My time there, you know, I grew the team from 10 to 100. I can tell you the room that I interviewed every single one of those designers in.

And you hired exceptional people. I mean, folks that have gone on to do extraordinary things, you know. Kind of in some respects got their start in that franchise. I love that you, you took this extremely difficult bloodletting experience and like folded it into, into something better and maybe a different approach to thinking about trust. Has that translated over to how you think about building trust with end users or just building more trustworthy products? How has like your experience at Airbnb then sort of like folded into your time at Lyft and your time here at Stripe? Help me understand, like, what, what are some of the cascading lessons that have come from entering a role in design leadership?

Well, to your point of like what that lesson has taught me, where it's taken me, like I, I do wanna answer that in two ways. One of which is like after Airbnb, I went to Lyft to lead the design organization there, and it was an awesome chance to like, you know, come into a new org or come into an org that already exists. And, you know, knowing what I now know about like, okay, how do I come in here and demonstrate my learning before I start kind of trying to implement change. But one of the really interesting things about the Lyft team is when I came there, the design organization sat in a room, a beautiful room, all white and perfect. It looked like an Apple Store with locked doors separated from the rest of the organization.

This is an actual ivory tower. Yeah. I've always used that metaphor for companies.

Literally, it was a white ivory tower. It was a beautiful room. But yeah, you had to badge in and only the designers could go into this room. Wow. Yeah. And so like, you know, when we talk about like collaboration between engine design and, you know, the importance there, like clearly that was not, you know, the epitome of collaboration. Yeah. Um, you know, it was like you had to like schedule time with someone to get them out of the room or like, you know, get permission to get in there. And so it was very clear once again, like during the interview process, what some of these gaps were and some of the problems, the things to fix. But thank goodness, you know, with the, now learning of, okay, let's— let me spend time with folks to truly, you know, understand where they're coming from and help them understand the situation themselves so that we can like, you know, design the solution together. Eventually, when we kind of like broke down the walls and opened the doors, it was like a group effort. But I wouldn't say it was— they wanted that at first, right? Like, designers liked their beautiful spot. Yeah. Like, it was hard to say like, okay, we're going to open this up. But I think it was a process of which we kind of all saw like, well, what are the benefits of doing that? Are we going to have more say in the work because we're actually there during those conversations and we're working hand in hand and we share goals with our teammates in product and eng? And so now we are on the same page when we're trying to kind of go after change there. A great piece of advice I once got is that speak into their listening. And so what it really means is like, think about what that individual cares about. Really try to understand that. And so for the folks in the design organization, they liked where they were because it was their creative space. We talked about courage before and new ideas are fragile, right? And just like creative concepting and putting yourself onto the page and it's like an empty page and like, what is this idea? That takes a lot of courage and it's scary. And so to be surrounded by other designers that are like kind of contributing to that versus what they were afraid of was like, well, if the PMs and engineers are around, they're gonna like tear down my ideas right away. And it's just doesn't feel safe to creatively concept. And then the other piece was that they kind of worried about whether or not they could have a say in the work that they did and that they could really shape the direction that the company was going, the strategy, the product direction. And so it's like if you piece these things together, the things that they wanted, and then think about like, okay, well, this is what you want, how do we get that for you? And if we think about like, well, where are the PMs and the engineers? When are they making the decisions? Why aren't you able to make that decision with them? And then, you know, it kind of like all comes together. And so it's not so much me saying like, this is what we're going to do. And it's like they're saying, you know what we should do? We should open up the door. And, you know, like, sure enough, like, people can, you know, get more of what they wanted from that. But like, we had to like see that first. But I do think like your point there as well as like vision of like, well, what are we trying to get to? Like, where are we today? But like really, where do we want to be? And then what are the steps to get there? I think is an important thing to have as an open dialogue with people.

I look back on my career as an investor and you look at the whole trajectory of mistakes and it's like, oh my gosh, I was so naive. Or like, ah, like I would have crushed that situation knowing what I know now. And it's not like I'm that fundamentally different, but it's mostly knowledge, hard-earned knowledge. When you look on your own career path and you look at people who are early in their design executive path, what are the things that you find yourself gravitating back to as like tried and true lessons that you feel like, okay, this is the thing that I wish I can just sort of like punt back into my, you know, 2015 version of myself or 2018 version of myself. This is the thing I wish somebody had said to me when I was in that situation and that you find yourself saying to your reports today. Yeah.

When I was at Art Center, I had a teacher named Norm Sherman, and he used to say to me multiple times that it's all about mileage. And what he meant was that I had to essentially do the time to put in the, like, the effort to learn and get better and better by doing. And I didn't want to hear that because I wanted to just like, rush ahead. I was a student in design school thinking I wanted to get into strategy and I want to be a leader. And his point was, you have to build the hard skills to be somebody that one, people are going to listen to and to know kind of the materiality of what you're talking about. Because actually knowing what it takes to make great things, knowing what that process is like, knowing what it how important it is to get a sense of flow and a time of focus, knowing how important it is to try a lot of bad ideas to find a good one, knowing what it's like to kind of develop that taste and know how hard the tools can be a part of the process definitely made me a better leader. And so I had heard that voice of Norm in my head of just like, yeah, it is all about the mileage. I wish I had put that time in then. And so a lot of times folks will reach out, they're like, I'm about to graduate and I, you know, I really want to get into strategy. I'm like, no, like, you know, take the time to, you know, just like get in there with the work and, you know, and spend some time in the, in the pixels and, you know, with your hand skills and like really, you know, get close to the craft, um, before you start to try to like have opinions about other people's craft.

That resonates. And in particular, I think one of the things that you had said earlier was recognizing that sometimes the troubleshooting, the problem solving doesn't just lie within your team. Yeah. It lies along the seams between your team and the rest of the organization. Yeah. If, if I were to go back in time and just like direct energy to my prior self working at Dropbox, I would've said like, spend half as, half of your time on things outside of design. Hmm. That's cool. Right? That like so much of it was like, you know, this is my team, this is what I'm responsible for. So this is the scope of my influence and that ended up just becoming a set of blinders to like how design sort of like, uh, interfaced with the broader organization as it scaled. Because early on it was easy, you sort of, it was tractable. Yeah. You had engineering over here, you had, you know, marketing over there, um, you had product. But as the team grows and scales, like the number of relationships, the number of edges also scales non-linearly. And all of a sudden it's a lot of mouths to feed. And I don't think I had fully kind of prepared for how much our reputation really rode on our ability to interface well with the broader organization. Yes. It's not just how we operated internally, how people felt on the team itself.

Yeah. Yeah. I mean, as we all know, you know, nobody wants when you move the cheese, right? Like you change the product out from underneath them and, you know, it can be jilting, right? And, you know, at Stripe, we're, you know, building products for, you know, millions of businesses around the globe. It could be like a single entrepreneur, it could be a large enterprise. And what we do in the product matters a lot, right? Like they're running their business on this product. Like if we change something or we screw something up, like that could mean that they're not gonna be able to make payroll that week, right? So we have to take these things very, very seriously. And I do think trust is a big part of it. So I think there's one, it's just like as you're imparting change or you're trying to drive a behavior in the product, like how do you build that trust? And I think that learning that you're bringing up is like, well, How about transparency? Like, what can we show? Why are we recommending this? But I think the other piece about trust is like actually the risk of like not having it and, you know, what the role of quality and beauty plays in it. So, you know, we do care a lot about the utility of a product. Like, how is it, like, is it powerful? Is it going to solve real problems and make a difference for our user? Huge, paramount matters first and foremost.. But secondly is like, is it well crafted? Can I access that power? Is it easy to use? Is it intuitive? Otherwise the power is kind of no use, right? If I can't actually access it. But then third, is it beautiful? And that matters. That's a part of what defines quality because the beauty part, one, it certainly helps the thing be more usable. It actually means like I want to use it. So I want to like give it my time and engage with it. But it's also that trust piece. By showing the love and care at the surface, you're actually showing the love and care underneath the surface as well. And I mean, I'll give like the opposite fact, right? It's just like if there is a bug in the system, like a typo or the design system is erratic and it doesn't actually, it's not consistent. And I'm like, why is this new typeface over here? Or why is this not lined up neatly? You start to lose faith that the rest is actually thought about. And we're kind of, playing a big role in an organization's money movement and, you know, their, uh, personal information and, uh, and the what they're doing for their users, like that matters most to them. And so if like it looks buggy on the surface, like that has a huge impact. So I, I do think about like the way we build trust in all levels of how we're building a product and all levels of quality in all of those different dimensions.

Mm-hmm. And I, I appreciate it in particular this idea that like it's If it's an object that can cause you harm or cause you doubt, the trust that kind of evaporates immediately. Yeah. It, it's like it changes your relationship to the, to the object, even if it carries on and does everything else perfectly going forward. You still sort of like reset the relationship with the product. And, and, and when it comes to financial matters, that's, that's where like, that's your bread and butter. You wanna make sure that anything affiliated with that screen, that surface, that product carries its own weight in gold. It, it, it is as reliable as any other entity on the planet because in so many respects for so many people, it's their lifeblood. It's like how they feed themselves and their families and, and the families of their employees. Yeah. You know, maybe we should go back to the airplane example for a minute. Um, you know, what has flying taught you about trust in, in, in a life or death kind of context, right? Yeah.

Uh, Well, you know what's really interesting about, like, what I didn't know about flying for sure beforehand was just like the, the history and the systems and, you know, kind of like the simplicity and the beauty of some of these things. So for example, I fly a Cessna 172. It's probably from the '70s. The number of things that are analog in this thing would like surprise you. So one, like when I, you know, pull back on the yoke, It is pulling a cable that is then adjusting the elevator on the, on the tail. It's a cable. I was like really surprised when I saw that. It just, and I don't know why I had, you know, like less trust in a cable than, you know, in maybe a digital experience. But like, actually, you know, that, that is simple, true, you know when it's not working. And in fact, like I've come to feel a great amount of confidence in these very analog systems. The gauges that I use, they're literally nicknamed steam gauges, and they have worked for many, many decades. And so I think the takeaway that I've had from just seeing these really thoughtful systems, it's like when you understand something so well and you can kind of boil it down to these simple parts is really powerful and long-lasting. And just to know that, like, how long that has been the case and that I can, you know, trust in these systems that have worked for many years. And I have my POH or the, the pilot's operating handbook that'll tell me, you know, how many feet of the runway I will need based on the weather at the time and based on how much fuel I have and all these things. That is awesome. Like that, that history there. So it gives me just like a hell of a lot of esteem for one, just like the, the thought that goes behind it. It makes me think about How, like, how can we know our work better? You know, when we set out to do something, like if we're going to, let's say, you know, create a checkout product, right? Like, and so Stripe builds checkouts that can help any business be able to take funds online or in person. What is the best checkout in the world? Thinking about like the user, the, you know, the customer at the end of the day or the business, like what is the best in the world? And actually start with that as the question because if you're just like, all right, let's make a checkout.

Yeah. Just finish the thing, move on to the next thing.

It's a different thing. Yeah. But you're like, no, let's make the best one in the world. It begs you to ask and understand the use case and the people that are using it and the circumstances they use, the 360 degrees of context so deeply that you can come up with what could be the best long withstanding and a simple right answer for the question. And I think another kind of key piece of that though is also just like always progressing. Like, how do you keep making it better? And so like, for example, like we, like the checkout products that we have, you know, we've had for many years, we've never stopped working on it. It's not like, oh, we got the form and now it's the best one ever. It's like, well, it was the best one at the time, but we know more now. Users' needs have changed. Circumstances have changed. Uh, GenTech Commerce, how do you—

We'll have new payment methods.

Yeah, exactly. It's like we continue to iterate on it and like think about it, you know, from soups to nuts, like both like, you know, how do the pixels, like how do we perfect the pixels, but also, you know, how, how is it working? How is it like, how fast is it? How reliable is it? How can we enhance those things? And like today our checkout experience actually can create 11.9% more revenue for our users based on it being a better version than it was in the past. Yeah. Just by like keep Dedicated to that mission of improving it. I don't know, that feels like gratifying, I would say, from like design's job is never done, but also like being aware that things are changing around us. And so like take that into the work and continue to, to make it better.

Well, Katie, I always learn something new when I talk to you. Thank you so much for hosting me here and, um, thank you for leading the way. I, I really do mean it. I admire like what you've been able to accomplish and the impact you've had on so many. Careers and companies that I just profoundly, profoundly respect.

Thanks, Leo. So nice to be here with you.

Appreciate you. Thank you. This is First of Kind, a new series about design and tech told by its pioneers, sponsored by Framer, Cursor, Vercel, and Profound. Follow us on X, YouTube, Threads, Spotify, and Apple Podcasts. The future belongs to designers who build.