Why Design Matters: Lessons from Stripe, Lyft and Airbnb | Design Review

0:00Today on Design Review, we'll be doing something a little bit different. I'll be interviewing Katie Dill, Stripe's head of design. The gravitational pull is to mediocrity. It's never easy. There is no black and white answer of like, oh, you ship it when it's this or you ship it when it's that. It's best to always come back to like, well, what problem are we trying to solve and who are we trying to solve it for? Katie has led design teams at some of the most successful companies in Silicon Valley, like Lyft, Airbnb, and now Stripe. So I sat down with her to learn about how design played a role in their success and how you can build a culture of high quality design from the earliest days of your startup.

0:41Katie, thank you for having us today. Well, thanks for being here at Stripe and thanks for having me on. So our audience is early founders and I think you and I are very much aligned that we would love to see more great quality design in the world. So I am excited for them all to learn from you today about how to do that, what great design looks like and how to bring that to their startups at the earliest stages. Maybe to start, why don't you tell us a little bit about your role here at Stripe and a little bit how the design team operates here. So I lead the design organization. And what that means is that we have the product designers, researchers, content designers that work hand in hand with engineers, product managers, building the product.

1:22So for us, that's Stripe billing. That's the checkout. That's pulling together all of the various products that show up in our dashboard or in our consumer interfaces. But also a part of the design organization is the brand studio team that works on our advertisements, our events, our branding, the books we design at Stripe Press. And then lastly, the website team, Stripe.com. Everybody watching this will probably be familiar with Stripe and Lyft and Airbnb and a number of other companies that you've worked at. And they're also known for having great design and a great user experience. What is the role that you think design played in the success of those companies?

2:01It's really interesting if you think also like back to their early days, right? So like Airbnb was creating a product that was pretty different at the time, right? Very novel. Like I'm going to stay in somebody else's house. Like I've never done that before. I don't know. And so design was instrumental in making that something that people could identify with and gain confidence in the safety, security, and enjoyment of that experience. And so the founders did an incredible job bringing very thoughtful details to that experience. Like, how is this going to work? How is the money exchanged? How are they communicating?

2:34How do we portray it on the internet? And by doing that and really sweating over every one of those details, I think they made it more approachable for somebody to try something new. And I mean, look at them now. That's just like grown in such wonderful ways and they're continuing to make design such an integral part of it. And that same thing for Stripe. You know, Stripe, you know, the founders, when they were creating, you know, the early days of these products, it is, you know, also something new and different. Like, people were taking payments online, but they had never solved the problem in that way.

3:02And, you know, these founders care a lot about every detail of the user experience. And they put that in to the early days of the work such that people could feel more confidence by seeing how much they cared about the details of, you know, just how the interface is portrayed. that like, oh, maybe then you also are going to take very good care of my money. And you're also going to take care of these other parts. It builds that confidence, builds that trust, and also makes the product more functional and easier to use. Yeah. It's interesting from the outside. I bet a lot of people think of Airbnb as the UI that you interact with, Lyft, the app that you call a car, you know, Stripe, maybe the developer API or, you know, other tools that you have.

3:41And they don't think of the holistic experience of what goes on behind the scenes there. And I think one thing that all of those companies have in common is that you need incredibly high levels of trust, more than like any other type of B2B software. A Stripe, it's moving your money. With Lyft, you're getting a stranger's car. With Airbnb, you're staying at a stranger's house. And if it didn't look trustworthy and the experience was not a well-oiled machine that felt really friendly and approachable and trustworthy, I don't think those businesses would have worked. I don't know. What do you think?

4:14I absolutely agree that there is a huge part to that. I mean, if you just think about the small details, and sometimes it's subconscious, right? It's like you see a typo, and you're like, oh, okay, that's like a little weird. And then maybe something else is just like not really laid out correctly, or that like you closed out that box, and then you lost all your work, and then you're like, oh gosh, I have to start again. You start to question like, well, if they haven't pulled that off right, if they haven't gotten that detail, what other detail aren't they getting right? And I think people also have to consider, You just pointed out that these are companies that are reliant on that trust in that relationship.

4:47But if you think about just competition in general, you are reliant on building that anyway. There's too many options out there. Why would I work with the janky one when I can work with the one that's going to more reliably get it right, both on the surface and underneath? Yep. I'm curious, you know, in building these big companies and having design be so integral to what the companies do, how important is the role of the founder there? And also, have you worked at companies where the founder did not care about design and sweat those details like you're talking about quite as much? Maybe they had another focus or, you know, another thing they're more interested in.

5:24And like, how does that play out in the role of the company too? It definitely is a major component because it is part of the culture. And so I think, hopefully, we can agree that design makes a difference in the value and the effectiveness of the product, right? I mean, it's not hard to look around and see places where that example comes through. And so luckily, I think most would say like, yeah, we want to have a well-designed product. But if they are only thinking about it in terms of, well, it's going to move the numbers, then they're only going to do it when it moves the numbers. And there are plenty of times when you're making a design decision where you're not going to be able to prove it just yet, maybe eventually, but not right off the bat.

6:06What I think the founders that we're talking about here, right, like Brian Chesky and Joe and Nate and then the Collison brothers is that it is so fundamental to how they think about building and that they first and foremost care about who are the users, what do they need, how are they going to do it, and how do we build something with so much intention, like every detail, every part of that experience, how can we make sure that is meticulously thought about and executed on? And having that mindset and then hiring that mindset in every person that enters that company will end up creating this kind of X factor that is very different than the motivation of like, well, how is this thing going to move the numbers?

6:46And so when you encounter one of those difficult decisions of like, is this thing worth it to do it or not, that, you know, you lean on the back of like, well, our pride is telling us that we need to do it. How have you seen some of these companies build that culture from the earliest days to give the space and the permission to actually be able to go that extra mile and delight users and go above and beyond? Yeah. I think it is definitely something that, again, has to kind of come in in the early days in the culture and you have to instill it and you have to exemplify it, is showing that that is important and then, you know, having the courage to make those hard choices.

7:21Like, frankly, unfortunately, you know, the gravitational pull is to mediocrity. You know, there are, you know, I would imagine most companies on this planet want to do great work and they want to say that they will say they want product quality. But what it really comes down to is those like micro decisions every day. And are you making the one that is actually moving the product into a better place? Or are you letting it like slip back down to meh? And that courage is something that the founders can do. And they can show that, right? It's just like, you know what? Actually, we're going to hold on this ship.

7:55We're going to take another spin on it. And we're going to ship it next week because it's important we get it right. And that, I think, is really hard to do. It can hurt the team. But we've been working on it. We want to get it out. She's like, yes, but it's more important that we get it right. And we're going to exemplify that. How do you balance that with the ethos of ship early, ship often, get it in front of users, get their feedback when you know it's not the best version that it could be? Yeah. And I recognize that it's really just to say, just like, stop the ship and wait until it's like, great.

8:27And that is just not a possibility, especially when you're, I absolutely understand the need for urgency at a startup, but also like, you know, even Stripe is much, you know, a larger organization. Our users are dependent on what we are providing. And so like, yeah, we want to get that feature out. So I would say that, you know, it's never easy. There is no like right or, you know, black and white answer of like, oh, you ship it when it's this or you ship it when it's that. But I think it's best to always come back to like, well, what problem are we trying to solve and who are we trying to solve it for?

8:57And if this is going to hinder the user experience, if this is going to leave a mark, right, that like, you know, potentially hinder that first impression that you might make, then that's serious enough that you do want to hold and wait. But I think there's also attributes to moving fast and taking things down in maybe more bite-sized ways. So we really leverage betas as a way of getting something out there and most importantly, getting feedback. Because if you're just like sitting there, like crafting it all day long and taking your sweet time, but never actually learning from folks, then you're not getting the product better.

9:32And certainly you're leaving people waiting. How do you know when you've hit that bar? I mean, it seems like it's kind of a taste thing, but like in your own work, how do you know whether you should wait that extra week and, you know, do the extra stuff to go the extra mile maybe, or whether it's actually hit the bar and you're ready to move on to the next thing? I will say it is one of the hardest parts of the job where, you know, you're just like, am I going to be a stick in the mud on this and ask for another iteration or not? And is it worth it? I think the ways to make that easier, but definitely not easy, is again, going back to users.

10:09What do they think? How well is this solving their problem? Is it actually a net positive or is this not really actually moving the needle or is it maybe even having detrimental costs to it? I think the other piece is that there is a number of things that you should think about, almost like a checklist of things that you look for in product quality. A high-quality product is highly functional. First and foremost, it has to have utility. It has to serve a purpose and solve a problem for the user. Secondly, it has to be usable. You can imagine a chair solves a problem, you can sit in it, but it's extremely uncomfortable.

10:48Well, that's not going to work out for you for very long. So usability is that second most important thing. And then third is craft and beauty. Obviously, craft and beauty is not like a nice to have. It's absolutely material to increasing the utility and usability of a product and also making it far more enjoyable. But there's no reason crafting something nicely if you can't actually sit in it, for example. And so if you use this kind of as a checklist, as I look at this product, it's like, well, first and foremost, solving a problem. You know, if it's not, then you definitely should not let it go forward because what's the point?

11:21You're just adding cost to your maintenance later. And then, you know, the next pieces come along. And it seems like, you know, whether you value and to what level craft and beauty, like it's there. Whether you make the choice to invest in it or not, just sometimes it's not good. Yeah, honestly, I think a big, big, big part of design when we're talking about design is it's just intentionality, right? It's just like, are you being thoughtful about how this thing is going to be perceived or not? And if there's infinite options, why not choose the one that is most appealing and most easy to use and just like sparks a little joy?

11:57We create software for people to run their businesses. And, you know, I think a lot of enterprise software out there doesn't put that first and foremost, which is fascinating given that those are human beings that work at those companies, right? And like, why not bring, you know, the joy to the work for anybody? We do think about craft and beauty as definitely not a nice-to-have. It's a must-have. And thinking about those details, making sure that there is no defects that somebody might start to question whether or not the product is working overall, and bringing a little bit more joy to the utility.

12:34Yeah. Or founders maybe that don't consider themselves to have an eye for design or a design background or something like that. How can they know what great design looks like? Yeah. Yeah. I think part of it is going back to that kind of like a checklist and thinking like knowing what to look for. I'm a pilot. And one of the things that my CFI taught me is that, you know, before you take off, you do what's called a pre-flight. And so you look at all the aspects of the plane, you follow a checklist to make sure that it's airworthy before, you know, you take off into the sky. And the checklist is a really great way of making sure you never miss a thing.

13:08But the other aspect that my CFI has taught me is that you should be looking at it as if you know something is wrong with the plane. You're just trying to find it. And so that mindset is really helpful because it really requires you to take a different posture of that, like, there's something here and I'm going to find it. I'm not just going to take it for granted. And when you do that, when you think through, like, let's say you're about to launch an app for ordering coffee online and you're kind of going through and you yourself as the founder want to see if whether or not the product is any good.

13:38And you start questioning every word, Every pixel, you know, it can be annoying for the team, but it is important that you do because when you start to question it, you wonder like, oh, yeah, it's a little weird that, you know, when I hit this button, I end up here, but I have no context of where I just came from. And like, actually, these words don't really communicate our brand. And actually, that's not really communicating what I'm supposed to do next. And so you start to think a little bit more about each of those details and observe. Like, how is it making you feel? How is it actually helping you along your way?

14:09and is it or is it not? And what are those gaps? And, you know, that might not be taste, but it is certainly, you know, utility. And I think that's like, obviously, again, a super important part. Developing taste, I think, is also, you know, it's one of the harder things to develop, but you can certainly hone it and you can improve it. One of the ways, of course, is to observe and, you know, see what do you like about the companies out there that you enjoy their products in? What seems to be working? You know, what are the details of it that are really nice? and just like taking note of that. And then, of course, you're going to hire well and listen to your people and observe.

14:44And that can certainly cultivate your taste too. It's interesting when you talk about that checklist. I think one thing that technical founders are really good at is like finding the edge cases and finding all the ways that like the product or the code that they've written might fail and not work. And it's really interesting to think about actually just applying that to the design side of things and trying to find those edge cases or the areas that it will break might be like a good way for them to think about it and to be able to level up their own design thinking and paying attention to their own product.

15:18Yeah, absolutely. I think one of the hardest parts for any of us is stepping outside of our own viewpoint. I mean, if you're working on this thing, it's your baby, you think about it night and day, it is really hard to imagine, you know, to just like erase that what you know from your brain and experience it like somebody who doesn't see it every day. So obviously, you know, you can do a lot of the assessment yourself, but bringing users into it is really, really important. And, you know, it's never once. It's not like, oh, we just did it. You know, we did user research in the beginning. It's like ongoing and, you know, work with the user, hear from them, have them talk out loud as they look at your product and recognize that, you know, they are operating with a very different context in mind and a lot less knowledge about the product.

16:00And what do they see? And, you know, what does it make them feel like? What is their impression of who this brand is based on, you know, the colors or the way it's laid out or how it interacts? And is it clear to them what happens next and how do I get there? Yeah. You talked about hiring. And I think one of the ways to get good at hiring is to see lots of candidates to understand what good looks like. And it sounds like what you're saying is that one of the ways to get better at design is to see lots of good design, interact with it, and, like, see what good looks like. and then that can help you level up.

16:32Are there any other tips that you would have for people that are trying to level up their own design skills as a founder and that they can bring to their company? We can learn a lot from observation. Pay attention to the products you don't like and why. Pay attention to the products you do like. Certainly, I recognize sometimes it's a little chicken and egg. It's like, we want to get great designers, but without great design, they don't want to be here. So I think a big part of that too is getting out there in the community and also if you're trying to hire great designers your team, like help them understand what role they can have in the company.

17:03If you don't know how design works, don't presume to tell them how it works. Think about how you can learn from their ideas. Design often does work differently than perhaps an engineering discipline. And so that is something that, you know, you as a founder can learn a little bit about by bringing folks on and maybe even just an advisory role to help you think about how you're going to hire or maybe even coach, maybe a junior designer that's on your team. And yes, I think just meeting people, learning from them and seeing their examples as a really great way of cultivating that taste. Can you teach taste?

17:40I think you can make it better. I think, you know, to be honest with you, in hiring, for example, I would certainly say that it is easier to teach somebody the tools or the domain and the space that you work in than it is to teach taste. For example, if you see somebody's portfolio, it's like, oh, but like, you know, we're in the fintech space and this person's worked in fintech forever, but they don't exemplify great taste. I think that's dangerous because I think it would be not necessarily easy, but easier to help them learn your space. Whereas taste, I think it's also like a passion for it, you know, that also can be difficult to teach because, you know, is there mindset there?

18:22Is it something that they think about every day, that they just want to make things more attractive, more actionable, more useful? You want that deeply in that individual if that's what their main job is in your company. Right. Let's talk about design and your design process at Stripe. Tell us a little bit about the process and how that works. Yeah. I think first and foremost is actually even thinking about how we're organized and we work together. we have a highly collaborative environment where designers, engineers, product managers, they work hand in hand. So if you ask any designer on the team, what team are you on?

19:02They'd be like, well, I'm on the connect team and I'm on the design team. So you're not like a service org that people just kind of reach out to like an agency to get work done and then kind of go back to your cave. Yes. Yeah. For a number of reasons. So number one, And all those functions that I talked about earlier are all a part of the design org because on purpose, we want all those teams working well together because we want the user experience to feel coherent. So whether you see us on the billboard or the website and then into the product, that should feel like one coherent story that's building on itself.

19:31So that's why we're all in one org. But of course, we don't want the designers to be just like popping in and out of projects and not having the context of the product, really the deep expertise, and also not the same goals in mind. So they are embedded in the teams. They have the same shared goals as PMs and engineers, and they're working on these things together start to finish. And that makes a big, big difference in how the work gets done. And so in terms of process, you'll not be surprised, but we, of course, always start with like, well, who's the user and what is their need? And that's where all of these kind of ideas for new products and things come from is that we're often hearing from our users and they are very much engaged in working with us and vice versa.

20:11And so we potentially learn about a need for a product. I just mentioned Connect. So this is our product for platform businesses and marketplaces. And so it allows them to create essentially a relationship with other businesses so that they can help them grow their own business and even offer financial services. And so these organizations that worked with us, one of them was Lyft for early days, for example. They came upon this need. They wanted to pay out drivers. And so they built the product with us. I can talk about another product that I'm super excited to show you, which is called Workbench.

20:45Similarly, we worked with Slack and Notion on how to make that product better every day. And so we are doing prototyping and iterating, and they are giving us feedback almost on a weekly basis. And that real tight feedback cycle and iteration of the product really helps us kind of stay away from going down faulty assumptions and creating things that just won't work in real life. and the spectrum of users that we serve. And this is probably the case for most of your founders too. Like, you know, there's not going to be one type of user, you know, that they're going to be interacting with. And so to work with a range of users and have that iteration cycle really helps reveal things that you might otherwise never have thought about.

21:24And that really could persist straight on into the execution and the shipping. And then we keep learning and iterating. Because one thing that I think, you know, never ceases to surprise us is that, you could design this perfect little product and you get it out into the world. And then what do you know, like three months later, it's full of bugs and the interaction points with your next new product aren't great. And so you really got to stay steadfast into learning about your product and seeing also how it continues. And so we actually have this part of our process, and it's almost like a culture that of using the product and doing walk the store exercises where people from, you know, honestly, anywhere in the company, but especially, you know, in the product teams, you know, engineers, product managers, designers, trying the product like a user would in the journey aspect, right?

22:12Not just that moment in time where the product shows up, but thinking about it from, you know, how do I learn about it in an email? How do I, oh, and then I go into the website. Oh, and then I go into the product. And how does that feel? And what are the moments where it doesn't make sense? Because, you know, the day it shipped for the first time, it may have been all perfect. But over time, it starts to potentially erode with the creation of new things. So you got to continue to evolve it too. I think every founder has had that experience of trying to nail the product, launching it, focusing on other things, and then coming back and trying your product six months later and being like, oh my God, what has happened here?

22:46How did this happen? Yeah. I mean, it's kind of funny. Team members had given this analogy. It's like when you're working on your house and you redid the dining room and so you added nice new molding and like little light plates and painted the walls. And now all of a sudden, the dining room next to the kitchen looks horrific. And you have to think about how you're continuing to push and pull different parts of your product and never lose sight of how it fits across all of them. How often do you do that, walk the store with all your products? I bet you someone is doing it right now. It's a cultural norm.

23:18We have a program where it is like very organized and established. It's called Our Essential Journeys. And so what we did was we identified what are the top 17 most important user flows that many of our users go through daily. And it's not a comprehensive list by any means, but we just needed something kind of digestible. And so there's 17 and we have DRIs and team members assigned that every quarter, they review that experience, they score it, they friction log it. So that's like kind of writing down your experience as you go and noting where like, well, that felt weird. And this is kind of that like that pre-flight thing that I mentioned of like using a checklist to like, does this make sense or not?