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- [00:00]
Rid
We talk a lot about how the landscape of design is changing, but how does that affect a company like Stripe?
- [00:07]
Katie Dill
There's no more of the, oh, you know what would be great if. And, like, what about, like, I gotta go, like, find, you know, a couple of people. I'm gonna have to convince them to this so they can build the prototype. And it's just, like, I had an idea for this thing. So here it is. Like, here's the link. Go check it out. What do you think?
- [00:22]
Rid
What traits are they looking for in new hires? And what does it take to thrive there as a designer?
- [00:28]
Katie Dill
The part you get to play in product development, you, opportunity identification, product shaping, all the way down to, like, to building something you want. Those people that are. They don't know where we're going. They don't know what the answer is, but they know that it's, like, somewhere out there and they want to, like, you know, get up and go.
- [00:47]
Rid
Welcome to Dive Club. My name is Rid. And this is where designers never stop learning. Today's episode is a deep dive into design at Stripe. With their head of design, Katie Dill. We're going to talk about how the practice of design is evolving and all of the little things that they do do to consistently push past the status quo. And I love how this episode starts because Katie walks us through all of the little design decisions in the all new stripe.com.
- [01:15]
Katie Dill
you want to do something that's, like, fresh and novel, but, like, also is going to have lasting power, is not easy. And there were definitely many iterations. Like, I can't even tell you how many different waves we've looked at. You know, at Stripe in general, I've been here about five years. We have designed millions of waves. And that's great. Like, I mean, it's one of my favorite parts of the job that we get to really explore the kind of the boundaries of what one can do in code with, you know, with color, with light, with form. There's infinite possibilities, and we've certainly explored a large share of them already. But, you know, you want to find something that, you know, you're not going to get sick of that. Like, it has impact when you first come and you open up the website, but also it can play a role in here that you're going to see again and again as we kind of go through some of the elements of the exploration. The part I was saying about the storytelling was, like, this was the unlock for that because we have a number of things that we provide and they relate for sure. We have plenty of businesses that work with us and they use a number of our products. They might use us for usage based billing, they also use us for payments, they also use us for agentic commerce, they also use us for issuing, et cetera. That you can work with all of these things, things together, but also they can work in part. And you know, plenty of organizations are only using us for certain parts of this, you know, kind of overall product ecosystem. And so we wanted to make it clear that kind of large gamut of things that we do, but also make it easy to traverse, you know, the scale of it. Because for a lot of organizations, you know, they may not have known that we have, you know, built these products since they first got to know us. A critical part, of course the experience too is like, as you traverse this and you know, get to know it a little, little bit, like, how do we keep you centered here without, you know, completely distracting you to then learn a little bit more? So that's what this like page overlay thing is for.
- [03:21]
Rid
I think this is what's going to get copied the most. For what it's worth, like we're going to copy the heck out of this website over the next few years. I think this pattern where you have the bento grid and you're able to keep it really, really simple in the grid itself. Like too many bento grids have all of the text and you're forcing three lines of subtext for each individual item and how you had like a very clean entry point with as much information as you want. Like, I'm, I'm going to copy this. I know a bunch of other people are going to as well.
- [03:46]
Katie Dill
And I feel like every designer can relate to the challenge of wanting to layer in so much, right? Like, oh, well, let's also put the value proposition here and let's give more detail and why don't you list out each of the related products. And it was certainly, you know, kind of a negotiation in that. And of course, like, we've mocked up a million different versions where we've looked at different things, but also having to stay with the priority on the user's experience. And you know, Nobody can read 19 things at once. And so what we're trying to do here is like kind of a few critical things in the hierarchy, like one we want to show rather than tell. So like, how can somebody, like, if you imagine you're coming to a website and you read only 10% of the words on the page, do you get a sense, like, I don't know about you, but that's what I do when I go to a website, right? Like I'm scrolling pretty fast and I'm kind of getting gist. So we're searching for imagery that kind of gives you that sense of what is that talking about without having to read any of the words. And then as quick, concise, salient as we possibly can be about what this thing is. And one of the things that I think is a very stripeism thing that I'm very glad for is we try really hard to just be very straightforward with our speaking in the context of the website or anywhere, right? Like trying to remove marketing speak and like fluffy language that just, you know, you can kind of see in a lot of different sites and it just like, it makes you kind of roll your eyes. Like how do we just like don't say directly what the thing does and who it does it for and not easy. There's definitely. I mean, I can't even tell you how many iterations of the words that we've probably done here trying to get that right.
- [05:24]
Rid
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- [07:07]
Katie Dill
Yeah, well, it's a great call out and it definitely was a debate. And I remember when the team showed me like a couple of different options and one of them, of course, was, you know, financial infrastructure grow. Your revenue was like. Or maybe it was even just financial infrastructure like our previous site. It was just like, that was large and everything else was smaller. And I was like gravitating towards that. I'm like, I think that's going to be more readable because it's just like, you know, a couple of words that I have to digest at once. But the team felt strongly like, but this feels like it's more of the. Like, we're trying to set the pace for what you are going to experience. And, you know, we're not trying to be shy about. Like, we've got a, you know, pretty big hefty product system to tell you about here. And, you know, honestly, I think they're right. Like, financial infrastructure grow your revenue. Can't say that a ton of people know exactly what that means just by reading that. Right. So, like, let's not hide the fact that, like, that's not enough. Like, there's more words that we have to share with you to give you a sense of what this is. And if we're like, you know, kind of asking you to take a pause and read the paragraph, like, I. That sometimes it irks me a little bit because most of the time when we're trying to design something for the user, we want to make it quick and easy and skimmable. But, like, the reality is that, like, that's just not what's being said here. Like, there's. There's more to say.
- [08:27]
Rid
Are there other details on this site that you're particularly proud of? Where they landed?
- [08:31]
Katie Dill
Yeah, I mean, let's see what else to take through. There's so much. I mean, I just, I'm really proud of the work that went into this. The team was so thoughtful and so dedicated and worked so hard to try to just find moments of magic. Like I think this area, we call it the data viz. Obviously this is not an actual data visualization, it's more of an accompaniment to it. And it was interesting to see people's response. You know, it's like, oh well, why would the team take time with this? Like, the visual doesn't actually say anything. And to us, like the visual says a lot. Like number one, you know, beauty for the sake of beauty is a wonderful thing. And you know, there quite literally is utility in that. It, it brings joy, it makes something more compelling. It like, you know, as you think about, like imagine this page without that, right? Like you would probably just like skim right by, but it makes you, you know, take a beat for a second and want to see what this is about. And again, like out of the corner of your eye, is it communicating something like. Yeah, this is communicating global scale. Like you, you do get that read from that. You know, you do get the, the sense that there is something to have been a gist that we are trying to give to you in these visuals. The other thing it communicates is the love and the care and the technical ability. And again, that is an important message in the front page of our website. I mean, we move people's money. We are a part of the creation of millions of businesses. They are reliant on us. So to communicate that we care about the details and we are going to painstakingly work on this animation so it moves just the right way is probably an important thing for them to know. And so, yeah, a lot goes into that. This is just like a fun thing. It's like again, a moment of joy, a moment of surprise. And kind of the cool behind the scenes story is that the visuals here, the imagery are photographs from one of the lead designers on this, Tatiana, from her trips hiking in the mountains.
- [10:36]
Rid
No way.
- [10:37]
Katie Dill
So these are like actual, like this is the color of the sun when she was hiking that went behind this.
- [10:43]
Rid
That's so cool.
- [10:44]
Katie Dill
I'm very excited about this area because of course, like a lot of the, you know, importance of what we're kind of communicating is the impact of what stripes doing and you know, who we do it with and how, you know, we help businesses grow and help them accomplish their goals. Like that's what brings to life these products, right? Like when I tell you like we do subscriptions, you're like, sweet. I don't know what that means, but it's like, well, we, you know, help lovable. So that they can build an AI business so that they can change the cost depending on the inference rate at the time. These are very helpful things to understand and then it makes a bit more sense about what these products do. So we're excited to get user stories in there. There's actually like several places where user stories show up, as you can see. But these are just like these kind of fun images that we're doing that are also a part of a campaign that we've run where we have billboards around that have kind of like the similar idea where the stripe parallelogram becomes part of the image. Wait till you see them animated. We have animated versions that we'll put up soon. They are delightful. Just like little moments of magic. But yeah, this is just such an interesting thing because, you know, as we were kind of creating the brief on this and it's like, okay, we're going to, you know, it's. It's about the partnership with us in this other organization. So we want the other organization's brand to kind of come through, but we also want to have like, you know, the strike, you know, kind of magic as a part of it. So the parallelogram taking place in the kind of the business's kind of context, I cannot even tell you the blood, sweat and tears behind these scenes on these things, because AI is magical and it does a lot of things that feel really good. Especially like, you know, you can one shot it, you're like, yeah, look at that, how amazing it is. But like, very rarely, you know, are we at the point now yet gets better every day. But like, okay, it's ship ready. And so like, actually this imagery I'm showing you today, I wish I had the example of what, like at what actually happened in crit, because the image, when I saw it come through crit is that they had like little notes, like almost like every inch on here of like the lighting is off right here. And this shadow isn't exactly right. And so it is AI plus a lot of manual figuring it out in Photoshop 3D control and like reworking it to get, you know, the image and get the, the realism correct. And of course when we animate them, like even more so. So it's a kind of interesting to imagine like all those details and you, and you think about like, when does that detail matter that much? Like, what if we didn't fix the lighting there? I think the reality is like subconsciously, you know, you would feel that something's off and then, you know, what does that then do to your feelings of, like, the realism and, you know, the care behind all the other details. So that's kind of where it ends up becoming an arduous but worthwhile effort.
- [13:38]
Rid
I think my personal favorite detail on this site that totally does not have to exist, but it's amazing, is the interactivity on the little dividing lines where they kind of, like, twist and swirl. Unbelievable. I don't know how, like, how does that even happen? Like, how does a giant company like Stripe even ship something like that?
- [13:57]
Katie Dill
We've been thinking about what are, you know, those little moments of detail or magic or of beauty that, you know, can kind of enhance an experience but not get in the way, you know, and Patrick Collison has asked about it is, you know, the way he's kind of put it to the team is just like, what are the things that modernism left behind, you know, when we've evolved to this, like, ultra clean, sometimes sterile look and feel in modern architecture and in a modern product design, you know, and it's all about, like, focus and clarity and white space and clean it up. Like, there's definitely some good in that for sure. You know, I am very interested in allowing a user to fully understand what's going on and know where to focus and know where to move on, and they don't want to clutter their experience or get in the way. But, like, have we taken it too far and have we gotten into a place where some of the product experiences today can feel a bit disconnected, bit sterile, a bit, you know, not inhumane. That's the wrong word. But lacking of humanity. And so, yeah, we, like, searched for and thought about, like, well, where. Where do we bring that in in a way that doesn't get in the way? So, like, that's, of course, one of them. And so it's just like, it's a little detail. Most people might not even see it, but if you do, you know, maybe gives you a smile, you know, something like this, where it's like our little stamp. It's just like, fun little details that give it an extra touch of care.
- [15:25]
Rid
Can you tell me a little bit about the call for a new aesthetic? And, you know, I feel like a lot of people saw the post on Twitter. What's the backstory there? I'm kind of curious how this influences the design. Orchid stripe, too?
- [15:38]
Katie Dill
Yes. Yeah. So what you're talking about. Over the holidays, Patrick Collison and Tyler Cohen tweeted that they were putting out a call for proposals that were exploring ideas of new aesthetics so that they would offer grants to people that are exploring these things. And the thinking behind it, as they described in this kind of like very brief one pager, is that there's an opportunity to think about what are the new aesthetics of this modern era. Because what we're living in today does feel like it is a continuation of many of the things that we've seen. And this is my words, not theirs. But we've certainly gotten into a bit of a rut where we certainly have taken some of what I would consider absolutely exceptional, beautiful styles from Bauhaus and International architecture and beautiful forms that over time I think people have kind of half assed the interpretation of and you know, you get these almost like lifeless, simple manifestations of like gray concrete blocks and you know, window walls without, without love and care that they don't age well, they don't demonstrate, you know, a care for humanity and a love for beauty or for detail. And so there's opportunity to explore that certainly also in product design, digital product design or what have you, is that you see a lot of the same forms again and again and at best they're clean, at worst they're stark or sterile. And so we've heard a lot in working with Patrick, he certainly has talked about this. And it's something that comes up in the work all the time, which is just like what are ways that we can demonstrate care for our users through our work. And part of that is certainly making products that are extremely powerful and can do a lot and solve our users problems. That's like number one. But number two, does the product serve them? Does it fit their mental model? Is it really usable? And number three, does it bring delight to their experience? Is it beautiful? Do they enjoy using it? And like all three of those things are a very important part of product quality and like what we strive for. And I appreciate that. You know, he's of course Patrick has, you know, talked about this in terms of our own team and we think about that at Stripe is like what are we doing to help shape the new aesthetic?
- [18:14]
Rid
It reminds me of this video that I watched recently. It's by a game guy named the Cultural Tutor.
- [18:20]
Katie Dill
Oh yes, yes, yes, yes.
- [18:21]
Rid
Did you see this? I was like, I was like, you have to watch it if you haven't yet because it's right up your alley. And for people who are not familiar, a big part of this video is, is juxtaposing the types of lamp posts in London and how they used to be incredibly detailed. And they talk about like tourist spots, often having These lamp posts. And there's like, a reason for that. It just feels good to be there, even if you don't necessarily notice the lamp post. And now everything is just very, you know, modern and minimal. And, man, my hope is that with all of the efficiency gains that we are getting with AI, that it buys us time to not necessarily do more in terms of the breadth, but it gives us time to make the finely detailed and artistically chiseled lamp posts. And what does that look like in product design? That was what I came out of that video. Being inspired to do is like, just not necessarily to try to go faster. You know, let's see how many agents I can spin up and how many work trees I can be working on simultaneously. And it's like, what if I just slow down a little bit and put a little bit extra care and try to push past what I get almost out of the box.
- [19:33]
Katie Dill
That is so well said. And I do think as things get easier to make, people are aware that it is easier to make things that are, you know, the 7 out of 10, the baseline experience that, you know, I think there'll be even a stronger call, a stronger want for those things that demonstrate a little bit more love and care. And actually there's a great article from the Atlantic. Beauty is the New Business tool. This is from 1927 in the Atlantic. And so what the author is talking about is like, like off the heels of the second industrial revolution where, you know, things were being mass produced and like a machine made, and they're just like. And the author is talking about how people were yearning for things that showed a bit more love and care and the care of the maker. Because, like, you know, you think about like a Zara versus a Hermes, right? You know, you're just like, yes, like this thing that was labored over and cared for, like, that's why it, like, achieves a price point versus a thing that was kind of like mass produced production, anybody can have it kind of thing. And I think when we look at what AI will allow us to do, it can kind of like create a design factory and enable, like, the creation of a lot of, you know, decent baseline things. But what are, you know, the things that are going to, like, really set themselves apart are going to be the things that kind of demonstrate that extra love and care beyond that. And I agree with you, like, that video is so phenomenal. I strongly recommend people give it a watch because, like, yeah, when you look back, back at the way things used to be made and, you know, the, like, the love and care that, like, people labored over. Another good example in that is, like, he shows, like, sewage plants, right? Like, sewage plants, you know, that were, like, so loved and just looks like a museum. Exactly. Versus, like, things that are just like, me. And, you know, people will talk about. It's like, well, it's about cost and it's about. About scale. And I think sometimes, you know, that's reasonable. Like, I can get how some things are, like, yeah, it's probably cost prohibitive to make every lamppost, you know, a gem. However, I think sometimes it's laziness. I think we've, like, allowed ourselves that excuse, and I think you are totally right that the tools have taken that excuse away, because it is easier to put more care and attention and detail and beauty for the sake of beauty into things now. So hopefully we'll see a part of this, like, new revolution, like, a greater commitment to love, care, and beauty in the work.
- [22:15]
Rid
I think a big part of this conversation that I'm really interested in digging into is, like, how are things changing? How's the practice of design at Stripe changing?
- [22:24]
Katie Dill
I do think everything around us is evolving rapidly. And Stripe's position is particularly interesting, I think, because of what we do. So we are. We're building tools for millions of businesses. These businesses are evolving and changing, right? Like, they are using AI, and the way that people are building businesses and getting going is obviously different. So anyway, there's, like, pressure for us to figure out how do we partner really well and evolve quickly and evolve our products with them. That's, like, one opportunity. Secondly, we can use AI to make our products more interesting, better, more personalized, more valuable, more responsive. And then thirdly, we can use AI for the way we work, and how do we accelerate product development, expand the creative exploration, all of these things. So there's a threefold way that things are different now. And so, yes, I would say it does change the way design operates. We've been doing a series of reviews this week for some big upcoming ships. We have our event coming up in the spring, and most of the work that we're seeing are prototypes. We built a internal tool we call Proto Dash, where we can create AI prototypes extremely rapidly that look and feel like the Stripe dashboard. And so you can kind of, like, build it in this playground, and you can evolve it from a starting point. And so it speeds things up quite a bit because. Because one, it's, like, already in the context. And of course, like, whenever we're doing work, we're trying as quickly as possible to understand, like, well, what is the user gonna feel? So putting it in context is extremely helpful. There's never, you know, no product is like, ever felt by your user in isolation. It's like they usually got there from something else or they're like bouncing off to something next. So, like, how to see it in that? And so the fact that now designers or engineers or PMs can mock up these different ideas pretty quickly in that, like, looks like, feels like, works like thing is awesome. What that means for, like, how a designer changes is that one, you know, there's like, you know the saying, like, you could just build things now. So I feel like there's no more of the, oh, you know what would be great if. And like, what about, like, I gotta go, like, find, you know, some couple of people, I'm gonna have to convince them to this so they can build the prototype. And it's just like, I had an idea for this thing. So here it is, like, here's the link. Go check it out. What do you think? And that's like super exc. And, you know, we can look at a number of links like, well, here's what it's going to look like in a year, here's what it's going to look like in six months. And so it can be a bit more, you know, kind of exploratory and, you know, kind of like it says not everything doesn't feel so precious and costly like it used to be to do vision work. It's like, okay, are we really going to take, you know, people off other work for two months to go explore a thing and then maybe not get built? Like, now we can do that without, you know, such a great cost to everything else that I think, like, we get, we see more exploratory, you know, more ideas being thought about, more ideas being tried, more ideas put in front of users. So I think that, like, means that. I think, I think if you ask them, the designers would say they're just more empowered to be proactive with, with big ideas, which is a good thing.
- [25:51]
Rid
When the practice of design changes that much, how much does it evolve? Like the process or rituals, collaboration? Like, how is that changing given the fact that, I mean, even down to the tooling, it sounds like you guys have invested pretty heavily in what you're handing over to designers as a playground to explore these ideas.
- [26:11]
Katie Dill
Please don't present, please don't pitch your ideas, please don't take a week making a deck to talk about the thing. Like, I Don't want that for you. I don't want you to waste that time. And honestly, I also don't want to hear any kind of like, let's just get into the work. Like, I just want to see it like a user. I think we've often said that. Like, I've probably been saying that, you know, all my years of design leadership, but like, I feel like we're there now. It's just a lot easier for people, you know, now to get to that prototype stage. And so, yeah, I feel like a lot of these reviews, for example, that I've been doing this week, it's, you know, one sentence is set up and then it's like, okay, let's go into it and let's click around and let's see what it would feel like and work like. I think the, the other part is, you know, the dynamic that can happen in a team. Designers have always had superpowers of like, well, you can visualize the ideas and that's a, you know, it's far better to show people rather than tell people. But I think it was still pretty time intensive and costly to put those ideas together. You know, as much as I said, like, no, no, no, just like, you know, tonight when you know, after work, just like mock it up and then you'll show it to the team tomorrow and you get them excited. Like, that's a lot, you know, ended up being a lot work. Now you can literally just like prompt your way to those ideas. And so I think it is easier and faster for folks to communicate and provide like, more thoughts at the earlier stages, product development and drive strategy faster with that kind of method for visualization. So at Stripe, for example, we were part of an evolution as, like, design changed over time. When, you know, Stripe first was, you know, building products that was very API focused and design therefore could be a bit more surface level. Like, how do we, you know, what does the marketing website look like? How does one encounter the API? And then kind of like the design was less involved over time. Our products are far more like numbered, far more complex, and they like, have a bigger role in an interface and a UI and dashboard. So designers have evolved from being really focused on the surface level to being deep participants in the development of the deep experience. And now I think that transition continues as well. Now also with the powers of AI, we can much more rapidly develop early stage ideas, contribute in even earlier stages of the project, and kind of like lower the barrier to entry to put new ideas on the table. So I think it's a net positive for the org and a net positive for the partnership.
- [28:56]
Rid
I really like that because I think that there's a narrative that I see frequently, just even in different parts of the Internet, different design communities, where by playing more in code, we're actually almost narrowing our exploration space and capping creativity in a way. But you're simultaneously talking on both fronts where it's like, no, no, no. We are making things that are functional and real and yet deeply creative, as evidenced by all of the different things that you are showing, being able to hold both of those imbalances. It's indicative of the type of practice that I want to have moving forward.
- [29:29]
Katie Dill
We certainly see more designers doing more, you know, kind of like, product think, like what has traditionally been pm, like product thinking and product shaping and problem development or problem identification. And then definitely are seeing, you know, PM like, you know, I've got an idea, let's mock it up and like, let's prompt our way there. And like, I'm glad for that. Glad for, you know, engineers to be able to more rapidly create ideas. So, like, we're just like, easing the interchange moments that existed between disciplines. But it also means then, like, with that, like, what, you know, what, what now can we do? Like, how many more, like, creative ideas can we look at that before, we were just kind of like, minimizing because we just didn't have enough time or like, you know, it was, it was a lot more costly to make three prototypes than it was to make, you know, one. And now, I mean, you can make 30.
- [30:20]
Rid
It sounds like there's quite a bit of bottoms up innovation happening. When we last talked, you mentioned something kind of offhanded to me about how, you know, it's like a new year kind of new opportunities thing. So maybe I could toss a hypothetical your way, which is, let's say it's the end of 2026 and you're reflecting back on this year and the Design Org at Stripe. What would you hope to see that would make you be like, yeah, this, this year was a good year for the design work. I'm proud of how we've evolved with the times. I'm proud of where we got to.
- [30:53]
Katie Dill
Well, I think with a lot of the design community, you know, I think we're all talking about, like, awesome that these tools are kind of raising the floor. We can build, you know, more generally good things quickly. Awesome. What we also need to do is raise the ceiling. How, you know, can our taste and ability go further? How when we're not so busy doing basic stuff. Can we take advantage of that time to do something, you know, extra special like that is. Those things are definitely on my mind. So for example, you know, as we scale and as we use these tools and as we rapidly prototype and we reactively create, how do we, you know, only further leverage our systems? Like, I don't need people to reinvent the wheel when things are working really well and you want to be able to provide good coherency and consistency for the user. So for example, like I don't need people to reinvent the drop down for the date picker. You know, every time they do one like that seems like basic. Like, however, I do want people to think about when is the status quo holding you back and when is there an opportunity to do something even better for the user. And so like thinking from like first principles, like, is this genuinely the best way to do this or does this require something better? And that could be, you know, purely aesthetics and like, is it just about, like, is there opportunity to do something more beautiful here or is there's like this just like pattern is not a good interaction. It is limiting and it does not allow us to do a thing, you know. So I'll give you like more of a tactical example. Last year we launched financial accounts at Stripe. And this is like an awesome unlock for users because before what was happening is people were using Stripe to, you know, sell their goods online or in person and take money, money and the money would come into stripes and they would move it out to a bank account, maybe move it, you know, to you know, another thing or another country or whatever. And it's like cost and time. Like that's what was involved in all those steps and it was painful. Now they can like bring the money in and then they have all these superpowers with it. Like right in Stripe they can pay out to anybody just with an email. They can put it in the credit card and use it for payouts. Like, it just like becomes this like much easier, faster, useful way of doing things. But when the team was doing the design work for this thing, they of course they used the system and it looked like, you know, the usual way our system does in the dashboard. And I remember the review and we're all meeting together and will our head of product and business is like, you know, it's kind of commenting on like this doesn't feel like as magical as this product actually is. And you know, he was totally right. Like what we weren't were doing was, you know, we were Just using very basic form fields and basic, you know, kind of drawer interactions. When you go through one step and then you answer a question, you go to another one. But like, what the magic actually is is that like you have these like, you know, kind of containers that you can like really fluidly move things through. And you know, we can, with direct manipulation, we can make that happen as fluidly in the UI and we can present it in a way that's very clarifying. It's just like, oh, I have this bucket of money. This is in USD, this is in pounds. Like I can, I can shift it over to here, I can put it towards the credit card over there. The UI was not fit to purpose and the UI was leveraging the status quo, which was suboptimal. And so that's an opportunity where I want to see the creativity and want to see, you know, us to think about, like, what is the most best way of doing this for our users? Like, what will, what will really, you know, help to answer their needs and kind of like deliver on the promise of what we have there. Where I'm going with this is that I want us to be in a better position where it's a lot easier for people to kind of like pick these battles and see these opportunities to really push their creativity and kind of like push the way that we're doing things to maybe create new patterns, new paradigms or new aesthetics that bring interest to the experience. And I think we're unlocking that by making tools more powerful, better, leveraging the systems that exist. So again, you're not reinventing the wheel where it's unnecessary to, and kind of making it so that like people can just build things. You can, you can build these ideas, you can get them across and test them out. So in the end of 2026, I would imagine I'd have a lot more stories for you about where that's happened and where, you know, people at any part of the team that like had an idea for a thing, mocked it up, you know, maybe showed it to some users, showed it to some people, got people excited and that like we could just kind of like streamline the path to getting it out there, to building it and you know, getting it live so that we can learn from it and keep pushing it.
- [35:55]
Rid
Hey, really quickly let me tell you about the all new Dive Talent network. I've hand assembled over a hundred of the most talented designers and builders that I know so I can recommend them to my favorite companies. So if you're listening to this and you're open to new opportunities. The talent network is anonymous and super low pressure. It's just an easy way to see what's out there without having to post on social media. So if you're interested in joining or maybe you're looking for your next hire, head to Dive Club talent. Especially as AI continues to raise the floor. The cost of the 7 out of 10 experience is going to be borderline free, you know, in the long run. And to me, the most exciting part of that is this concentration of effort and, like, really thinking strategically about, like you said, like, hey, this part of the product is magical. Like, what if we just took five times the amount of resources and time and creativity and just pointed it directly at the way that these panels move or whatever. That looks like. Like it's exciting.
- [36:54]
Katie Dill
Yes. I love that. And that is such a good way of putting it. Like, the seven out of the ten experience is free. Yes. So, like, now how do we make some, like, 15 out of 10 experiences?
- [37:04]
Rid
Yeah, let's dig into the 15 out of 10 then. Because listening to you talk, like, multiple times, you've pointed at the fact that there's a good feedback culture happening. Like, people are really pushing each other. So can you just go a little bit deeper into what is. Does that look like in practice? Whether it's Crit or Async, can we just kind of shine a flashlight on collaboration at Stripe?
- [37:25]
Katie Dill
Yeah, I think it's one of the things that we have, you know, continued to work on in my time there because we aim to have high standards. We, you know, we want to be a place where the best people are doing the best work of their lives and that we are not okay with good enough enough, and we are not okay with mediocre. You know, I've had a lot of conversations with Patrick Austin about this too, of just, like, you know, there have been times where, you know, he or I or we have, you know, pulled the plug on something last minute. I mean, he has asked us to make changes to billboards that were already up and we've talked about, like, how that's a good thing, you know, because a lot of companies don't do that.
- [38:11]
Rid
That.
- [38:11]
Katie Dill
I think a lot of us have probably been in companies where, you know, you've had that moment of, like, it's not great, but, you know, we got to get it out. And I mean, we've earned, like, we put so much time into it. The team will be crushed if we do, if we don't go for it. Right. Like, how many times like, that's happened, right?
- [38:28]
Rid
Totally.
- [38:29]
Katie Dill
And I really, really appreciate that, you know, when we're faced with that decision and it's like, oh, the team will be crushed, or we let it go and we know it's mediocre, is like, I would. Every time I would rather have that hard conversation and, you know, take the moment there to think about whether or not this is actually great and if it's not, fix it. And I think the team, you know, in the end, while that might have been the hard conversation of, like, okay, we decided to stop this project, or, you know, we decided to take it down after it was already up or whatever, whatever, I think they would, you know, in the end. Absolutely. You know, certainly, the type of people that we're hiring that want to, like, take pride in their work and do great things and put a positive dent in the universe, you know, in the end, are going to be glad to be creating things that they're proud of, rather than put something out that is mediocre, like, hold that high standard. So, anyway, I think that, like, that's a part of it. That's what we strive for. Do we always get it right? No, absolutely not. There's definitely the things that we've shipped that, like, maybe that wasn't the right call, but we strive for it. And then in the feedback culture, I think, you know, this is also tough. Right, Because I want it to be a place where designers feel like they can take risks, that there isn't, like, a fear of failure, that they can try things, wild and crazy things. And, you know, also just, like, take a little bit of, like, the heat off of, like, when they're going to go into a review or whatever. I don't want people to be, like, you know, on edge, that, like, how is it going to go well or not. And at the same time, we're pairing that with, like, well, we're. We're going to, like, beat this thing up, and we're going to look at it tightly, and we're going to ask ourselves, like, is this thing great or not? And so doing those two things can be hard. And it's definitely something we've, I think, been talking about, you know, in my time there, of just, like, how do we get. How do we do both? How do we make it, like, you know, warm and accepting and a place where we can, like, try and fail and take risks, but also continue to hold those high standards. So I. If you know what the answer is, definitely let me know. You know, pursuit that we have. I Think our best shot is just, like, literally calling that out and just being like, we're. We do some serious stuff here. Like, for example, if there are bugs in our product or, you know, we have a typo, like, that is a big deal because we move people's money and our partners rely on us to, like, do the work well. And our surface level all the way down to our infrastructure is a part of what they are trusting us in us. If we allow things that, you know, erode trust to exist, then, you know, that can put all things in question. And so we want to demonstrate the kind of, like, commitment, the quality that we have at every level of the stack and that this, like, starts, of course, with, like, that surface level experience. So, yeah, we. We do some serious work. And that means that, you know, we certainly should take a lot of responsibility for what we ship, but in the process, would love for it to be, you know, also a place where people can, you know, experiment. Not everything is perfect right off the bat. And so I think that's, like, where we do that is the nature of the conversation and just, like, being real with each other. And like, just so you know, what you're about to see here, this part is not figured out yet, and the good conversation can come from that.
- [41:50]
Rid
Okay, so we've been talking a lot about how the role of the designer has evolved at Stripe. It kind of makes me want to talk a little bit about hiring and what you're looking for in different candidates. You've obviously hired, hired a lot of people and been in a lot of these conversations over the course of five years or however long you've been there. What I'd love to know is when you think about the main signals that you were looking for in people when you first joined Stripe, what are some of the biggest changes now as you're thinking about the types of people that you want to loop into this org and build around for the rest of this vision?
- [42:25]
Katie Dill
I think that there's still some of the same themes, but I think they. They've. It's been adapted and, like, certainly the way that I look for it, but, like, specifics, but, like, curiosity always would have been something that I would probably have shared with you on, like, my top list. You know, I just, like, certainly I'm looking for people that are, you know, humble, have exquisite talent, and that they are curious and that they're going to, like, you know, really just, like, constantly be looking to grow and constantly better understand the circumstances of the work that they're doing. And their users experience or you know, know their collaborators. Like I think that just like generally makes people better within a team. What does that curiosity look like today has evolved? You know, I think the, you know, certainly critical piece is like is this person kind of leaning in to this evolution or this revolution that we are a part of with, you know, AI it's intimidating, it's overwhelming. You know, everything. Like you think you're on top of it one day day and then tomorrow there's a new model and a new tool and new possibility. I don't expect, you know, every person we meet to have it figured out, right? Because again they would be out of date as soon as they, you know, thought they were on top of it all. But that like they demonstrate a genuine interest and curiosity because again, like kind of going back to what I said earlier, I think, you know, in the stripe work it is so much more complex to the levels because it's about what our users are experiencing and how they're using the technology and how it's shaping their business, how we're providing for them and then also how we're building those tools. And so somebody that takes great interest in this technology also means that they're probably more interested in what our users are going through and they're going to be more likely to be able to shape these things. I mean AI product thinking is different, right? It's like a non determinant product. You have to think about like how can you embrace ambiguity in a whole new level and think about it as, as, you know, a great opportunity and a great input to not only shape your own work but shape your output. We need to see that. Certainly we're seeing more of AI experience in somebody's work. But yeah, I don't think like we're going to encounter that many people that have had like I've been doing AI for 10 years, like that doesn't happen. But like do they demonstrate that, you know, despite, you know, the years that they, they've led, that they've in the most recent years and then the opportunity too that they are genuinely interested, genuine trying, generally experimenting and are ready for that. And then the last thing I would say is agency. I think that's another piece that has always been important but has a new role and that is that because what we were talking about earlier as like tasks evolve, roles are evolving. The part you get to play in product development, you know, opportunity identification, product shaping, all the way down to like the, like to building something. The fact that you can just build now is so exciting and so empowering. And does that person demonstrate agency? It's the other side of curiosity. It's like, you know, doing something with it, essentially. And, you know, I certainly look for that. You know, sometimes you see that in, you know, outside of the person's work. Like, you know, oh, yeah, like my hobby. I do this thing and, you know, I've been. I made my husband this website to, like, help on this other thing. Like, it doesn't necessarily even have to be in their work, but you can kind of see, see, like, who are these people that just, like, have a fire under their belly and they just, like, they want to go and do, like. I don't know, there definitely feels like, like, stories of being on the frontier. But, like, you want those people that are. They don't know what. Where we're going. They don't know what the answer is, but they know that it's like, somewhere out there and they're. They want to, like, you know, get up and go.
- [46:11]
Rid
Let's imagine this hypothetical candidate, right? They have the intangibles of Curiosity Agency. They show up ready to go. Maybe we can fast forward again to this end of year reflection question only pointed at this person. I'm curious. What are some of the best behaviors or traits that you see in the ICs at stripe that are really thriving that you would then hope, kind of rub off and shape this new candidate over the course of the remaining 10 months this year?
- [46:41]
Katie Dill
Yeah, well, like, you know, I was talking about this thing, Proto Dash, that we have. Like, that was one guy's baby, like, his idea, you know, and he. Owen, recognized that we had, like, a barrier to entry. Like, okay, AI can help us make things faster. But the hard part is, you know, everybody's got to get acquainted with the tools and, like, people have different knowledge, and then they have to, like, start from scratch every time. And so he's like, I can fix this. And, you know, when he fixed it, I don't. It was probably nights and weekends. I don't. You know, it's a combination of things. But he was like, hey, I made this thing. What do you. What do you think? And, you know, like, oh, this is really useful. And. And he's, like, continued to, like, evolve it and make new versions of it. And so he's like. He is pulling us ahead. And then, you know, another example of there's a content designer, our team, Chris, who's like, you know what? The way that our, like, we. We serve platforms and, you know, there are these Behemoths of businesses that are rather, you know, can be quite complex. Complex, you know, so if you think about like the Shopify is of the world, right? Like they have businesses within businesses and we provide tools to help, you know, those businesses grow their needs from stripe can be different than a business that is, you know, sold solely one entity. And so, you know, he and the team recognize that, like, there are a number of places across our product where we're making it harder on them to find their information and to organize the work. And it didn't feel like it was centered around their experience. And that like, the experience was built for a singular entity. And so, like, they put together a strategy and a new idea and prototype things and, and put that forth. And so you are totally right when you said, like, you know, it can be bottoms up. Good ideas can come from anywhere. I think the critical piece is that like, you know, you've got a good idea, you see a problem, you see a piece of trash on the floor, you pick it up and like, you like, how do I make this problem better, longer term, for more for everybody, for, you know, and, and how, how might I, you know, kind of inspire action to that? And so, yes, at the end of 2026, I think we are all better equipped to be able to, you know, see a thing and do it, do something about it and proactively elevate the ambition of folks around you with new ideas for what would be a big better solution.
- [49:05]
Rid
Can I point the question at you now? I guess I'm curious, given all of the change and the fact that, you know, five years is a long time. Like, you've, you've seen a lot of even market shifts and obviously tooling shifts. So what are some of the ways that this is shaping how you show up as a leader or where you think about the ways to evolve your own practice?
- [49:28]
Katie Dill
My role has definitely evolved over the five years that I've been here. You know, our team has grown, our company has grown. I've learned a lot of things that, you know, I could do better and thought about where, you know, where is my time most valuable. You know, certainly every little project we do, every big project we do, I don't need to be, you know, intimately involved. And in fact, that might be a failure state. And it's more about how do I help put the conditions in place where this is an organization where great work gets done. I am not often the right person to make the great work happen. It's more of the actually crafting the Community that does that. That and the way that we do that, I think the opportunity I have is, like, while trying to shift to that other way of work where I focus on building the system that does the great things, and that includes the team, is not losing touch with what are we making and what are our users needing. We actually have a pretty intense, intense culture of commitment to this idea of walking the store, spending time with users. You know, it's something that I think every company needs to do. And I think as companies grow larger or your products get more complex, or in our case, it's like, I will never be a CFO of a Fortune 50. I will never be in the, you know, the payments team or running a platform. So, like, I won't know as intimately, ultimately what our users experience as I might, you know, when I worked at Lyft and I could take a lift to, you know, to the office that day. And so spending time with users, getting into the product and actually trying it and then putting yourself in their shoes is so important. So I do think about, like, how do I just actually increase my participation in that? And sometimes these tools are a really great way of better mimicking the product experience and better understanding what it would feel like to be running a large enterprise and seeing my business evolve over time and how that's going to shape my stripe experience.
- [51:39]
Rid
I like that that's your answer, because every time I talk to a leader that's in your position, there's some pressure to help this team cross the bridge onto, honestly, a completely different way of working, totally different types of tools and abilities, and it's very easy to kind of narrow in on that as the objective when that is very much so just the means to the end.
- [52:02]
Katie Dill
Well, and I think the other part is it's really easy to just be busy and, you know, talk about how important these tools are, but, like, be out of touch. I am also using Proto Dash to, you know, make versions of the product. And, you know, are mine going to be better than, you know, the designers that are thinking and doing that all day? No, definitely not. But, like, will I have a lot better understanding of, like, what they're going through and what it takes to, like, make something. It's vital that I, you know, get to know these tools firsthand. And, you know, absolutely. I'm like, you know, making my own, you know, vibe, coding my own websites on the weekend so that, like, I, you know, know what that's like. It is definitely hard to take the time to, you know, play and make and, and lead and check all the emails and all the slacks. For sure, for sure. But I do think that that is an important part of knowing the reality of work these days and will make, you know, me a better leader if I'm in touch with what, you know, today feels like. Yeah.
- [53:02]
Rid
I mean, because most people that get to where you're at do so on the back of being in the trenches and using the tools that we're all familiar with. And yet now everything has kind of changed. Like you don't have that track record with these tools to draw from, you know, and obviously there's like the high level principles that are the same, but
- [53:18]
Katie Dill
I still probably open Photoshop up more than people on my team do school so. Well,
- [53:27]
Rid
I respect it. I respect it. Well, Katie, thanks for coming on. Just a big fan of everything that you all do and who you are as a leader and someone just contributing and shaping the design community as a whole. So I appreciate you taking the time and giving us a little tour of all the work today and what's happening at Stripe.
- [53:47]
Katie Dill
Absolutely.
- [53:48]
Rid
Before I let you go, I wanted to take just one minute to run you through my favorite products because I'm constantly asked what's in my stack. Framer is how I build websites. Genway is how I do research. Granola is how I take notes during crit. Jitter is how I animate my designs. Lovable is how I build my ideas in code. Mobin is how I find design inspiration. Paper is how I design like a creative. And Raycast is my shortcut every step of the way. Now, I've hand selected these companies so that I can do these episodes full time. So by far the number one way to support the show is to check them out. You can find the full list at Dive Club Partners.