Katie Dill - The new era of design at Stripe

We talk a lot about how the landscape of design is changing, but how does that affect a company like Stripe?

>> There's no more of the oh, you know what would be great if and like what about like I got to go like find, you know, some couple of people. I'm going to have to convince them of 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?

out. What do you think?

>> What traits are they looking for in new hires? And what does it take to thrive

hires? And what does it take to thrive there as a designer? the part you get to play in product development, you know, opportunity identification, product

shaping, all the way down to like like to building something. 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 [clears throat] they want to like, you

know, get up and go.

>> Welcome to Dive Club. My name is Rid and this is where designers never stop learning. Today's episode is a deep dive

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 to consistently push past [music] the status quo. And I love how this episode starts because Katie walks us through all of the little design decisions in the allnew Stripe.com. you

want to do something that's [music] 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 5 years we have designed millions of waves uh and that that's great like I mean I it's one of my favorite parts of

the job that we get to really just explore the kind of the boundaries of what you know one can do in code with, you know, with color, with light, with

form, there's infinite possibilities and we've, you know, 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, you know, impact when you first come and you open up the the website. Uh, but also it can, you

the website. Uh, but also it can, you know, play a role in here that you're going to see, you know, again and again.

as we kind of go through some of the elements of uh the exploration. Uh 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 you know they relate for sure. You know I you know we have plenty

sure. You know I you know we have plenty of businesses that work with us and they you know use a number of our products and so they might use us for usage based billing. They also use us for payments.

billing. They also use us for payments.

They also use us for agentic commerce.

they also use this for issuing etc. you know that you can kind of work with all of these things together, but also they can work in part. Uh, 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

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 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.

>> 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

want. Like I'm I'm going to copy this. I

know a bunch of other people are going to as well.

>> 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

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

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 crit a few critical things in the hierarchy. Like one, we want to show

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,

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

website, right? Like I'm scrolling pretty fast and I'm kind of getting gists. So, we're searching for imagery

gists. So, we're searching for imagery that like kind of gives you that sense of like what is that talking about without having to read any of the words

and then, you know, as quick, concise, salient as we possibly can be about what this thing is. And one of the things that I think is like a very stripism

thing that I'm very glad for is we try really hard to just be very straightforward with our speaking in in the context of the website or anywhere, right? Like trying to remove marketing

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 say directly what the thing does and who it does it for?

And not easy. It is definitely I mean I can't even tell you how many iterations in the words that we've probably done here trying to get that right.

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Okay, now on to the episode. Can we

double click on that for a second? Cuz

there's something that you do that I haven't seen before, which is that very top H1 in the hero section. And I think there's like this almost meme at this point where as a company scales, the H1 becomes more and more generic, right? It

starts off super pointed and by the end it's like delivering actionable insights kind of thing and it doesn't even mean anything where you're doing so many things. If you were trying to fit into a

things. If you were trying to fit into a traditional H1, it would have to be generic. Like there's just too much to

generic. Like there's just too much to fit into something that is like seven or eight words. And so I haven't seen this

eight words. And so I haven't seen this pattern before where you basically wrote a sentence as your heading. Was like how quickly did you get to that? I'm curious

how wide the spectrum of exploration was for that piece of copy specifically.

>> 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 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 [laughter] that right so like let's not hide the fact that like that's not enough like there 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, you know, 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 skimable, but like the reality is that like that's just not what's being said here. Like there's

there's more to say.

>> Are there other details on this site that you're particularly proud of where they landed?

>> Yeah, I mean, let's see what else to take through. There's so much. I mean, I

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 I think this area, we call

magic. Like I 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, why would the team, you know, take time with this?

Like the visual doesn't actually say anything. And well to us like the visual

anything. And well to us like the visual says a lot. The v like number one you know beauty for the sake of beauty is a wonderful thing. And you know there

wonderful thing. And you know there there quite literally is utility in that. It it brings joy. It makes

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

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 you know like a a gist that we are trying to give to you in these visuals. The other thing it communicates is you know the the love and the care and the you know the technical ability and again that is an

important message in the front page of our website. I mean we move people's

our website. I mean we move people's money. We are uh a part of the creation

money. We are uh a part of the creation of millions of businesses. They are

relying on us. So to communicate that like we care about the details and we are going to like painstakingly work on this animation so it moves just the

right way. Um is probably an important

right way. Um is probably an important thing for them to know. Um and so yeah, a lot goes into that. Uh this is just like a fun thing. It's like you know again a moment of joy, a moment of

surprise. And the kind of the cool

surprise. And the kind of the cool behind the scenes story is that the visuals here, the imagery, um are photographs from one of the lead designers on this, Tatiana, uh from her

trips hiking in the mountains. Uh no

way. And so these are like actual like this is the color of the sun when she was hiking uh that went behind this.

>> That's so cool. 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 Stripe's 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 you know, change the cost depending on the inference rate

at the time. Like these are very helpful things to understand and then like it makes a bit more sense about what the 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 these are just like these kind of fun images that we're doing that are also a part of a a campaign that we 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

the image. Wait till you see them animated. They are. We have animated

animated. They are. We have animated versions that we'll we'll put up soon.

Um 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 and this or other organizations. So we want the other

organizations. So we want the other organizations 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 the 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 oneshot it. You're like, "Yeah, look at

oneshot it. You're like, "Yeah, look at that. How amazing it is." But like very

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 I wish I had the example of what like what actually happened in Crit because the image when I saw it go 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

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. Um so it's a a kind of interesting to imagine like all those details and you when you think about like when does that detail matter

that much like what if we didn't fix the lighting there. Uh, I think the reality

lighting there. Uh, 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

other details. So, that's kind of where it ends up becoming an arduous but worthwhile effort.

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? We've been thinking

about what are, you know, those little moments of detail or magic of or of beauty that, you know, can kind of enhance an experience but not get in the way, you know, and and Patrick Collison

has asked about it is like, 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 whites space and clean it up. Like there's

there's definitely some good in that for sure. You know, I am very interested in

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

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

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 our little stamp. It's just

like fun little details that give it an extra touch of care.

>> Can you tell me a little bit about the call for a new aesthetic? And you I feel like a lot of people saw the post on Twitter. What's the backstory there? I'm

Twitter. What's the backstory there? I'm

kind of curious how this influences the design or at Stripe, too.

>> Yes. Yeah. So, what you're talking about over the holidays, uh, Patrick Collison and Tyler Cohen, uh, tweeted that they were putting out a call for proposals

that were exploring ideas of new aesthetics and so that they would offer grants to people that are exploring these things. And the the thinking

these things. And the the thinking behind it as they describe in this kind of like very brief one-pager is you know that there's an opportunity to think about what are you know 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 and this is my words not theirs but like you know

we've certainly kind of gotten into a bit of a rut where you know we certainly have taken you know some of what I I would consider absolutely exceptional

beautiful styles from you know bow house and international architecture and beautiful forms that over time I think people have kind of halfassed 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. Uh, 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 you know, at at best they're clean, at worst they're stark or sterile. And

so we've heard a lot, you know, in in working with Patrick, like he certainly has talked about this and it's something that comes up in the work all the time, which is just like, you know, 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 very important part of product quality and like what we strive for. And I appreciate that, you

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 at Stripe is like what are we doing to help

shape the new aesthetic. It reminds me of this video that I watched recently.

It's by a game guy named the cultural tutor.

>> Oh, yes. Yes, yes, yes.

>> Did you see this? I was like I was like, you have to watch it if you haven't yet cuz it's right up your alley. And

>> for people who are not familiar, a big part of this video is >> juxtaposing the types of lamp posts in London >> and how they used to be incredibly

detailed. And they talk about like

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

that. It just feels good to be there even if you don't necessarily notice the lamp post. And now everything is just

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 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

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.

>> 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 the seven 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, the new business tool.

Atlantic. Beauty, the new business tool.

This is from 1927 in the Atlantic. Oh,

wow. And so what the author is talking about is like off the heels of the second industrial revolution where you know things were being mass-produced and like machine-made and it's like

and the author was 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

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 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 um

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 at the way things used to be made and you know the like the love and care that like people labored over. Um

another good example on that is like he shows like sewage plants right like sewage plants you [laughter] know that were like so loved um and just >> it looks like a museum. [laughter]

>> Exactly. Versus like things that are just like mehay. And you know, people will talk about it's like, well, it's about cost and it's about scale. And I

think sometimes, you know, that's reasonable. Like I can get how some

reasonable. Like I can get how some things are like, yeah, it's probably cost prohibitive to make every lamp post, you know, a gem. However,

not I think sometimes it's laziness. I

think we've like allowed oursel that excuse. And I think you are totally

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 uh into things now. So hopefully we'll see a

things now. So hopefully we'll see a part of this like new revolution like a greater commitment to loveare and beauty in the works.

>> 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?

>> I do think everything around us is evolving rapidly and Stripe's positioning is particularly interesting, I think, because of what we do. So, we

are we're building tools for millions of businesses. These businesses are

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

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.

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

responsive. And then thirdly, we can use AI for the way we work and like how do we, you know, accelerate product development, expand the creative exploration, like all of these things.

So like there's like a three-fold way that things are different now. And so

yes, I would say it does change the way, you know, design operates. You know,

we've been doing a series of reviews this week for, you know, some big upcoming ships we have at, you know, our event coming up in the spring. And, you

know, most of the work that we're seeing are are prototypes. uh we uh built a internal tool uh we call protodash 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 like playground and you can evolve it from a starting

point and so it like speeds things up quite a bit 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

going to feel so putting it in context is extreme 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, you

know, 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 well one you know there's like you know the saying like you could just build things now. So I I feel like there's no more of the oh you

know what would be great if and like what about like I got to go like find you know some couple of people I'm going to 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 exciting 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 we can be a bit more you know kind of exploratory and you know kind of It does 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 I think I think if you ask them uh the designer ers would say

they're just more empowered to be proactive with with big ideas, which is a good thing.

>> When the practice of design changes that much, how much does it evolve like the process or 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.

>> Please don't present. Please don't pitch your ideas. Please don't take a week

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 it.

[laughter] 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 inensive and costly to put those ideas together. You know, as much as I said

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 that, you know, ended up being a lot of 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 and provide

like more thoughts at the earlier stages product development and and drive strategy faster with that kind of method for visualization. So at Stripe for

for visualization. So at Stripe for example we were a part of an evolution as like design changed over time. when

you know Stripe first was you know building products it 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 in a UI and dashboard board.

So designers have evolved from being really focused on the surface level to being you 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 the project and you know 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.

I really like that because I think that there's a narrative that I see frequently and 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, 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

showing. Being able to hold both of those in balance is it's indicative of the type of practice that I want to have moving forward. We certainly see more

moving forward. We certainly see more designers doing more you know kind of like product think like what has traditionally be PM like product thinking and product shaping and problem

development or problem identification and then we definitely are seeing you know PMs 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 you know like creative ideas can we look at that but before we were just kind of like minimizing because we just didn't have you know 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.

>> It sounds like there's quite a bit of bottoms up innovation happening. When we

last talked, you mentioned something kind of off-hand to me about how, you know, it's like a new year kind of new opportunities thing. So maybe I could

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 or 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 or I'm proud of how we've evolved with the times. I'm proud of

where we got to." 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

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 rapidly 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 dropdown for the date picker, you know, every time they do one. Like that seems like a basic like

one. Like that seems like a 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 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 finan 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 and the money would come into

Stripe 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 take bring the money in and then they have all these superpowers with it like right in Stripe. They can pay out to anybody just

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

things. But when the team was doing the design work for this thing, they of course they use the system and it looked like you know the usual way our the system does in the dashboard. And I

remember the review and we're we're all meeting together and uh Will our our head of product and business is like you know 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 were doing was you know we were just using very basic form fields and basic you know kind of drawer interactions from 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 ers 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 this is like oh I have I

have this bucket of money this is in USD this is in uh 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 subop optimal and so that's an opportunity where I want to see the

creativity and I 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 what will really you

know help to answer their needs and kind of like deliver on the promise of what we have there kind of 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 ity and kind of like push the way that we're doing things to maybe create you know new patterns, new paradigms or you know

new aesthetics that like you know 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.

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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 or whatever that looks like.

It's exciting.

>> Yes. I love that. And that is such a good way of putting it like the seven out of 10 experiences for eight. Yes. So

like [laughter] now how do we make some like 15 out of 10 experiences?

>> 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 does that look like in practice whether it's crit or async can we just kind of shine a flashlight on collaboration at Stripe?

>> 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

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

and we are not okay with mediocre. You

know, I've had a lot of conversations with Patrick Collison 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. [laughter] Um, and we've talked about like how that's a

good thing, you know, because a lot of companies don't do that. 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 forward, right? Like how many times like that's happened, right?

>> Totally. And I really really appreciate that you know what 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 it might have in 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. 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. And there's

right? No, absolutely not. And 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 a 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

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

not? And so, doing those two things can be hard. And it's definitely something

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? [laughter]

How do we make it like e, you know, warm and accepting and a place where we can like try and fail and and and take risks but also continue to hold those high standards. So, I don't know if you know

standards. So, I don't know if you know what the answer is, definitely let me know. You know, a pursuit [laughter]

know. You know, a pursuit [laughter] um 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 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

to 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

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 and not everything is perfect right off the bat. 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 and the good conversation can come from that.

>> 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

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 a lot

candidates. You've obviously hired a lot of people and been in a lot of these conversations over the course of 5 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 or build around for the rest of this vision? I think that there's still some of the same themes, but I

think they've it's been adapted in like the certainly the way that I look for it and 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 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

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. Um,

it's intimidating. It's overwhelming.

You know, everything like you think you're on top of it one day and then tomorrow there's a new model and a new tool and a new possibility. I don't

expect, you know, every person we meet to have it figured out, right? Because

again, they would be at a 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

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-determined product. You

have to think about like how can you, you know, embrace ambiguity in a whole new level and think about it as, you know, an 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

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 then the opportunity to that they are genuinely interested, genuinely trying, genuinely 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 is like tasks evolve, roles are evolving, uh 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 um you know I've been oh I you know 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 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 that

like stories of being on the frontier, but like you want those people that are um they don't know what where we're going. They don't know what the answer

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.

>> Let's imagine this hypothetical candidate, right? They have the

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

person. I'm curious, what are some of the best behaviors or traits that you see in the IC's 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?

>> 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 um 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 a week. I don't you know all sort

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 on our team Chris who's like you know what the way that our like we we serve platforms and you know there

these behemoths of businesses that are ra you know can be quite complex you know so if you think about like the Shopify is the world, right? Like they

have um 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, sole solely one entity. And so, you know, he and the

entity. And so, you know, he and the team recognized 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 like it didn't feel like

the work. and like it didn't feel like it was centered around their experience um and that like the experience was built for a a 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 you think about like how do I make this problem better longer term um

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 of folks around

you with new ideas for what would be a better solution >> can I point the question at you Now, I guess I'm curious given all of the change and the fact that you know 5

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?

>> Well, 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 um 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 the right person to make the great work happen it's more of

the actually crafting the community that does that and and the way that we do that. I think the opportunity I have is

that. I think the opportunity I have is like while trying to shift to that other way of work where you know I I focus on

uh building the system that does the great things and you know that includes the team is not losing touch with what are we making and what are our users

needing. uh we actually have a pretty

needing. uh we actually have a pretty intense culture of commitment to uh this idea of walking the store, spending time with users. You know, it's something

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 cases like I will never be a CFO of a Fortune50, I will never be on the you

know the payments team or running a platform. like I won't know as

platform. like I won't know as intimately 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 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 um better, you know, mimicking the product experience and better understanding what it would feel like to be uh running a large enterprise and seeing my business evolve over time

and how that's going to shape my Stripe experience. I like that that's your

experience. 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.

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 the designers that are thinking and doing that all day but 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,

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 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 am in touch with what you know today feels like.

>> Yeah. I mean cuz most people that get to where you are 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 >> I still probably open Photoshop up more

than people on my team do. [laughter]

>> I know this tool so well.

>> I respect it. I respect it. Uh well,

Katie, thanks for coming on. Just a big fan of everything that you all do and who you are as a 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. [music]

>> Absolutely.

>> Before I let you go, I want to take just one minute to run you through my favorite products because I'm constantly asked [music] what's in my stack. Framer

is how I build websites. Genway is how I do research. Granola is how I take

do research. Granola is how I take [music] 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.

[music] 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.

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