today on design review we'll be doing something a little bit different. I'll be interviewing Katie Dill, Stripe's head of design.

The gravitational pull is to mediocrity. It's never easy. There is no black and white answer of like, oh, you ship it when it's this or you ship it when it's that.

It's best always come back to like, well, what problem are we trying to solve and who are we trying to solve it for.

Katie has led design teams at some of the most successful companies in Silicon Valley like Lyft, Airbnb, and now Stripe. So I sat down with her to learn about how design played a role in their success and how you can build a culture of high quality design from the earliest days of your startup.

Katie, thank you for for having us today. Well, thanks for being here at Stripe and thanks for having me on. So our audience is early founders and I think you and I are very much aligned that we would love to see more great quality design in the world.

Yes, so I am excited for them all to learn from you today about how to do that, what great design looks like, and how to bring that to their startups at the earliest stages.

Maybe to start, why don't you tell us a little bit about um your role here at Stripe and and a little bit how uh the design team operates here.

So I lead the design organization and what that means is that we have the product designers, uh researchers, content designers that work hand in hand with engineers, product managers building the product.

So for us that's Stripe billing, that's the checkout, that's pulling together all of the various products that show up in our dashboard or in our consumer interfaces, but also a part of the design organization is the brand Studio team that works on our advertisements, our events, our branding, the books we design at Stripe Press, and then lastly the website team.

stripe.com. Everybody watching this will probably be familiar with Stripe and Lyft and Airbnb and you know a number of other companies that you've worked at.

Um, and they're also known for having great design and a great user experience. What is the role that you think design played in the success of those companies?

It's really interesting if you think also like back to their early days, right? So like Airbnb was creating a product that was, you know, pretty different at the time, right?

Very novel. Like, I'm going to stay in somebody else's house. Like, I've never done that before, I don't know.

And so design was instrumental in making that something that people could identify with and gain confidence in, you know, the safety, security, and enjoyment of that experience.

And so the founders did an incredible job bringing very thoughtful details to that experience, like how is this going to work?

How is the money exchange? How are they communicating? How do we portray it on the internet? And by doing that and and really sweating over every one of those details, I think they made it more uh approachable for somebody to try something new.

And I mean, you know, look at them now. That's just like, you know, grown in in such wonderful ways and they're continuing to make design such an integral part of it.

Um, and that same thing for Stripe, you know, Stripe, you know, the founders when they were creating, you know, the early days of these products, it is, you know, also something new and different.

Like no people were taking payments online, but they had never solved the problem in that way.

And you know, these founders care a lot about every detail of the user experience and they put that into the early days of the work such that people could feel more confidence by seeing that how much they cared about the details of, you know, just how the interface is portrayed, that like, oh, maybe then you also are going to take very good care of my money and you're also going to take care of these other parts.

It builds that confidence, builds that trust, and also makes the product more functional and easier to use. Yeah.

It's interesting, from the outside, I bet a lot of people think of Airbnb as the UI that you interact with, Lyft, the app that you call a car, you know, Stripe, maybe the developer API, or, you know, other tools that you have, and they don't think of the holistic experience of what goes on behind the scenes there.

And I think one thing that all of those companies have in common is that you need incredibly high levels of trust, more than like any other type of B2B software.

At Stripe, it's moving your money. With Lyft, you're getting a stranger's car.

With Airbnb, staying at a stranger's house. And if it didn't look trustworthy and the experience was not a well-oiled machine that felt really friendly and approachable and trustworthy, I don't think those businesses would have worked.

I I absolutely agree that there is a huge part to that. I mean, if you just think about the small details and sometimes it's subconscious, right?

Is it like you see a typo and you're like, huh, okay, that's like a little weird.

And then, you know, maybe, you know, something else is just like not really laid out correctly or that like you closed out that box and then you lost all your work and then you're like, oh gosh, I have to start again.

You start to question like, well, if they haven't pulled that off, right?

If they haven't gotten that detail, what other detail aren't they getting right? And I think people also have to consider, you know, you just pointed out that like these are companies that are reliant on that trust in that relationship, but if you think about just like competition in general, you are relying on building that anyway, right?

Like, there's too many options out there. Like, why, why would I work with the janky one when I can work with the one that's going to, you know, more reliably get it right both on the surface and and underneath.

Yep. I I'm curious, you know, in building these big companies and having uh design be so integral to what the companies do, how important is the role of the founder there?

And also, um, have you worked at companies where the founder did not care about design and sweat those details like you're talking about quite as much?

Maybe they had another focus or, you know, another thing they're more interested in and like how does that play out in in the role of the company too? It definitely is a major comp because it is part of the culture.

And so I I think hopefully we can agree that, you know, design makes a difference in you know, the value and the effectiveness of the product, right?

I mean, you it's not hard to look around and see places where that example comes through.

Uh, and so they I luckily I think most would say like, yeah, we want to have a well-designed product, but if they are only thinking about it in terms of like, well, it's going to move the numbers, then they're only going to do it when it moves the numbers, and there are plenty of times when you're making a design decision where you're not going to be able to prove it just yet.

Maybe eventually, but not right off the bat. What I think the, you know, founders that we're talking about here, right, like, you know, Brian Chesky and Joe and Nate, and then, you know, the Collison brothers, is that it is so fundamental to how they think about building and that they first and foremost care about who are the users, what do they need, how are they going to do it, and how do we build something with so much intention, like every detail, every part of that experience, how can we make sure that is meticulously thought about and executed on, and having that mindset and then hiring that mindset in every person that enters that company will end up creating this kind of X factor that is very different than the motivation of, like, well, how is this thing going to move the numbers?

And so when you encounter one of those difficult decisions of, like, is this thing worth it to do it or not, that, you know, you lean on the back of, like, well, our pride is telling us that we need to do it.

How have you seen some of these companies build that culture from the earliest days to give the space and the permission to actually be able to go that extra mile and delight users and go above and beyond?

Yeah, I think it is definitely something that again has to kind of come in in the early days in the culture and you have to instill it.

You have to exemplify it, is showing that that is important.

And then, you know, having the courage to make those hard choices, like, frankly, unfortunately, you know, the gravitational pull is to mediocrity.

Uh, you know, there are, you know, I would imagine most companies on this planet want to do great work, and they want to say that they they will say they want product quality, but what it really comes down to is those like micro decisions every day, and are you making the one that is, you know, actually moving the product into a better place, or are you letting it like slip back down to me?

And that courage, you know, is something that the founders can do and they can show that, right? It's just like, you know what, actually, we're going to hold on this ship, we're going to take another spin on it, and we're going to ship it next week because it's important we get it right.

Um, and that I think is really hard to do. It can hurt the team, like, but we've been working on it, you know, like we want to get it out, just like, yes, but it's more important that we get it right, and we're going to, you know, exemplify that.

How do you balance that with the ethos of ship early, ship often, you know, get it in front of users, get their feedback when you know it's not the best version that it could be?

Yeah, and I I recognize that, you know, it's really to say just like stop the ship and wait until it's like great, and that is just not a possibility, um, especially, you know, when you're I you know, absolutely understand that the the need for urgency in a startup, but also like, you know, even Stripe is much, you know, larger organization, our users are dependent on what we are providing.

And so, like, yeah, we want to get that feature out.

Uh, so I would say that, you know, it it's never easy. There is no like right or, you know, black and white answer of like, oh, you ship it when it's this or you ship it when it's that, but I think it's best always come back to like, well, what problem are we trying to solve and who are we trying to solve it for?

And if this is going to hinder the user experience, if this is going to leave a mark, right, that like, you know, potentially hinder that first impression that you might make, then that's serious enough that you do want to hold and wait.

But I think there's also attributes to moving fast and taking things down in maybe more bite-sized ways.

So we really leverage betas as a way of getting something out there and most importantly, getting feedback because if you're just like sitting there, like crafting it all day long and taking their sweet time but never actually learning from folks, then you're you're not getting the product better.

Um, and certainly you're leaving people waiting. How do you know when you've hit that bar? I mean, it seems like it's kind of a taste thing, but like in your own work, how do you know whether you should wait that extra week and you know, do the extra stuff to go the extra mile maybe, or whether it's actually hit the bar and you're ready to move on to the next thing?

I will say it is one of the hardest parts of the job where you know, you're just like, oh, am I going to you know, be a stick in the mud on this and ask for another iteration or not and is it worth it?

I think the ways to make that easier, but definitely not easy, um, is again, you know, going back to the users, like, you know, what do what do they think?

You know, is it actually a net positive or you know, is this not really actually moving the needle or is it maybe even, you know, having detrimental costs to it.

Uh, I think the other piece is that there is, you know, a number of things that you should think about, like almost like a checklist of things that you look for in product quality.

Like a high quality product is highly functional, right? First and foremost, it has to have utility, it has to serve a purpose and solve a problem for the user.

Secondly, it has to be usable, right? So, um, so you can imagine a chair, like, solves a problem, you can sit in it, but it's like extremely uncomfortable.

Well, you know, that's not going to work out for you for very long.

So usability is that second most important thing. And then third is craft and beauty. Obviously, craft and beauty is not, like, you know, nice to have.

It's absolutely material to increasing the utility and usability of a product and also making it far more enjoyable.

But there's no reason, you know, crafting something nicely if, like, you can't actually sit in it, for example. And so if you use this kind of as a checklist as I look at this product as, like, well, it first and foremost solving a problem, you know, if it's not, then you definitely should not let it go forward because what's the point?

You're just adding cost to your maintenance later.

Um, and then, you know, the next pieces come along and it seems like, you know, whether you value and to what level craft and beauty, like, it's there whether you make the choice to invest in it or not.

Just sometimes it's not good. Yeah, I I honestly, I think a big, big, big part of, you know, design when we're talking about design is it's just intentionality, right?

it's just like, are you being thoughtful about how this thing is going to be perceived or not? And if there's infinite options, why not choose the one that is most appealing and most easy to use and, you know, just like sparks a little joy?

Uh, you know, we, you know, software for people to run their businesses and, you know, I think a lot of enterprise software out there doesn't put that first and foremost, which is fascinating given that those are human beings that work in those companies, right?

And like, why not bring, you know, the joy to the work, um, for anybody?

We, we do think about craft and beauty is definitely not a nice to have, it's a must-have. Uh, and, you know, thinking about those details, making sure that there is no defects that somebody might start to question whether or not the product is working overall.

Um, and you know, bringing a little bit more joy to the utility.

Yeah, for founders maybe that don't consider themselves to have an eye for design or a design background or something like, how can they know what great design looks like?

Yeah, I think part of it is going back to that kind of like checklist and thinking, like, knowing what to look for.

Yeah, I'm a pilot and one of the things that my CFI taught me is that, you know, before you take off, you do what's called a pre-flight.

And so you look at all the aspects of the plane, you follow a checklist, um, to make sure that it's air worthy before, you know, you take off into the sky.

And the checklist is a really great way of making sure you never miss a thing, but the other aspect that my CFI has is that you know before you take off you do what's called a pre-flight and so you look at all the aspects of the plane you taught me is that you should be looking at it as if you know something is wrong with the plane, you're just trying to find it.

And so that mindset is really helpful because it really requires you to take a different posture of that, like there's something here and I'm going to find.

I'm not just going to take it for granted. And when you do that, when you think through, like, let's say you're about to launch, um, an app for ordering coffee online and you're kind of going through and you're, you know, you yourself want as the founder want to see if whether or not the product is any good and you start questioning every word, every pixel, you know, it can be annoying for the team, but it is important that you do because when you start to question it, you wonder like, oh yeah, it's a little weird that, you know, when I hit this button, I end up here, but I have no context of where I just came from.

Um, and like, actually these words don't really communicate our brand and actually that's not really uh communicating what I'm supposed to do next.

And so you start to think a little bit more about each of those details and and and observe like how is it making you feel?

Is how is it actually helping you along your way? And is it or is it not? And what are those gaps?

Um, and you know, that might not be taste, but it is certainly, you know, utility and I think that's like obviously again, a super important part.

Developing taste, I think, is also, you know, what one of the harder things to develop, um, but you can certainly hone it and you can improve it.

Um, one of the ways, of course, is to observe and, you know, what do you like about the companies out there that you enjoy their products in what seems to be working, you know, what are the details of it that are really nice and just like taking note of that.

Um, and then of course you're going to hire well and, you know, listen to your people and and and, you know, observe.

Um, and and that can certainly cultivate your taste too. It's interesting when you talk about that checklist.

You know, I think one thing that, um, technical founders are really good at is like finding the edge cases and, um, you know, finding all the ways that like the product or the code that they've written might fail and not work.

And it's really interesting to think about actually just applying that to the design side of things and trying to find those edge cases or the areas that it will break might be like a good way for them to think about it and to be able to level up their own design thinking and and paying attention to their own product.

Yeah, absolutely. I I think one of the hardest parts for any of us is stepping outside of our own Viewpoint.

I mean if you're working on this thing, it's your baby.

You think about it night and day. It is really hard to imagine, you know, to just like erase that what you know from your brain and experience it like somebody who doesn't see it every day.

Um, so obviously, you know, we you can do a lot of the assessment yourself, but bringing users into it is really, really important.

And, you know, it's never once it's not like, oh, we just did it at the you know, we did user research in the beginning.

It's like ongoing and, you know, work with the user, hear from them, have them talk out loud as they look at your product and recognize that, you know, they are operating with a very different context in mind and a lot less knowledge.

about the product and what do they see and you know what does it make them feel like, um, what is their impression of who this brand is based on, you know, the colors, the way it's laid out, or how it interacts, and is it clear to them what what happens next and and how do I get there?

Yeah, you talked about hiring and I think one of the ways to get good at hiring is to see lots of candidates to to understand what good looks like.

Um, and it sounds like what you're saying is that one of the ways to get better at design is to see lots of good design, interact with it, and like see what good looks like and then that can help you um level up.

Mastering Product Design With Katie Dill: Lessons from Stripe, Airbnb and Lyft

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Design played a crucial role in the success of companies like Airbnb, Lyft, and Stripe by building user confidence and trust through meticulous attention to detail and a focus on solving user problems.

Founders should prioritize understanding user needs and building products with intention, instilling a culture of high-quality design that values both functionality and aesthetics.

Companies should foster a culture of continuous user feedback, internal product testing, and a commitment to addressing issues, ensuring the product remains user-friendly and effective over time.

🌟 The Importance of Design in Early-Stage Startups

Katie Dill, Stripe's head of design, emphasizes the critical role of high-quality design in startups. Great design, she notes, should be a priority from the earliest stages. **This focus can significantly contribute to a company's long-term success**.

🤝 Founder Involvement and Design Culture

The involvement of founders in design is crucial for building a design-centric culture. Founders who deeply care about the user experience and meticulously consider every detail are more likely to foster a culture of high-quality design. **This mindset permeates the entire company and leads to exceptional products**.

Dill highlights that founders who prioritize user needs and build with intention create an "X factor" that differentiates them from those solely focused on metrics. **This dedication to quality, driven by pride, is a key takeaway for founders**.

While shipping early and often is important, Dill cautions against sacrificing quality. **The key is to balance urgency with the need to create a positive user experience**. This often involves making tough decisions about when to hold back a release to ensure it meets a high standard.

Using beta programs to gather user feedback is a great way to release product features, but without releasing the full product. **This allows for real-world testing and iteration, ensuring the final product meets user needs**.

✅ The Design Checklist: Functionality, Usability, and Craft

Dill outlines a checklist for evaluating product quality. First, the product must be highly functional, serving a clear purpose and solving a problem. Second, it must be usable and comfortable. Finally, craft and beauty are essential for increasing utility and enjoyment. **Intentionality in design is crucial**.

According to Dill, software should bring joy to the user. **This means paying attention to details, eliminating defects, and ensuring the product is both useful and delightful**.

Founders can improve their design skills by observing and analyzing both good and bad designs. **Questioning every aspect of the product, from the wording to the layout, is essential**.

Bringing in users for feedback is also critical, Dill says. It is not enough to do user research in the beginning; it should be ongoing. **User insights provide valuable context and help identify areas for improvement**.

Stripe fosters a highly collaborative environment where designers, engineers, and product managers work closely together. **Designers are embedded within product teams, sharing goals and working on projects from start to finish**.

A key part of Stripe's design process is "walk the store" exercises, where team members try the product as a user would, identifying pain points and areas for improvement. **This helps the company stay user-focused and avoid regressions**.

Stripe also utilizes a program called "Essential Journeys," where key user flows are reviewed and scored quarterly. **This ensures that the most important user experiences remain high-quality**.

✉️ Real-World Examples: Link and Email Redesign

One example of Stripe's design process in action is the improvement of their Link product. **A bug was filed when the product yelled at the user before they finished typing their email address, so the team quickly addressed it**.

Another example is the redesign of a signup email. **By improving the hierarchy, call to action, and visual interest, Stripe increased product conversion by 20%**.

🛠️ Introducing Workbench: Empowering Developers

Stripe's Workbench is a tool designed to help developers stay in their flow state by providing a microscope and telescope into their integration. **It allows them to debug, prototype, and make changes without constant context switching**.

Dill notes that the creation of a community forum allows developers to share their experiences and provide feedback. **This continuous engagement ensures that the product remains user-centric and effective**.

Introduction to Katie Dill and the Design Review

Katie Dill, Stripe's head of design, is interviewed about product design.

Katie's experience at Lyft, Airbnb, and Stripe will be discussed.

Katie Dill's Role at Stripe and Design Team Operations

Katie leads the design organization, including product designers, researchers, and content designers.

The design organization includes the Brand Studio team and the website team.

The Role of Design in the Success of Companies Like Airbnb and Stripe

Design was key in making new concepts like Airbnb approachable and trustworthy.

Paying attention to design details builds confidence and trust in the product.

The Importance of Trust and Holistic Experience in Design

High levels of trust are crucial for companies like Stripe, Lyft, and Airbnb.

Good design builds trust and is essential for competition.

The Founder's Role in Building a Design-Focused Culture

The founder's attitude towards design is a major component of the company culture.

Founders who prioritize user needs and meticulous design create a unique 'X factor'.

Building a Culture of High-Quality Design

A design-focused culture must be instilled early and exemplified by leadership.

Companies should prioritize product quality over mediocrity by making better micro decisions daily.

Balancing Speed of Delivery with Design Quality

Prioritize solving the user's problem, but hold back if the user experience will be hindered.

Use betas to get feedback and improve the product iteratively.

Determining When a Product Has Hit the Design Bar

Assess the product based on user feedback and how well it solves their problem.

Use a checklist to assess product quality, focusing on functionality, usability, and craft/beauty.

Use a checklist and adopt a mindset of looking for potential problems in the design.

Observe and learn from well-designed products and hire talented designers.

The Importance of User Feedback and Testing

It's difficult to evaluate a product objectively after working on it for a long time.

Ongoing user research is essential to understand how users perceive and interact with the product.

Tips for Founders to Improve Their Design Skills

Pay attention to both good and bad design and understand why you like or dislike certain products.

Don't presume to know how design works; instead, learn from designers' ideas and potentially hire advisors.

It's easier to teach domain knowledge than to teach taste.

Look for designers with a passion for making things attractive, actionable, and useful.

Stripe's Design Process and Collaborative Environment

Stripe fosters a collaborative environment where designers, engineers, and product managers work together.

All design functions are in one organization to ensure a coherent user experience across all touchpoints.

Starting with User Needs and Iterative Prototyping

Stripe's process starts with understanding user needs, often through direct engagement.

Prototyping and iterating with user feedback helps avoid faulty assumptions and ensures the product works in real life.

Continuous Learning and 'Walk the Store' Exercises

Stripe emphasizes continuous learning and iteration to address bugs and improve product interactions.

'Walk the store' exercises involve team members using the product like a user to identify pain points.

Essential Journeys Program for Monitoring User Flows

Stripe has a program called 'Essential Journeys' to review and score the most important user flows quarterly.

The goal is to get these flows to 'green' and maintain them, with a company-wide focus on improvement.

Examples of Design Improvements at Stripe

Experiencing the product firsthand helps identify issues that prototypes might miss.

A 'bugs at' email alias allows anyone in the company to report issues.

An invalid email alert was showing up before users finished typing, which was annoying.

Redesigning an email with clear hierarchy and a call to action increased product conversion by 20%.

Workbench: A Tool for Developers to Improve Integration

Workbench was created to address challenges developers face with integrations and context switching.

Workbench acts as a microscope and telescope, allowing developers to debug, prototype, and make changes within the Stripe dashboard.

The Importance of Community and User Feedback

Stripe uses a community forum called 'Insiders' to gather feedback from developers.

Regular touch with users is critical for creating products that meet their needs.

Pride and Attention to Detail as Key Factors

The pride that Stripe and its founders take in their products is evident and sets a high bar for quality.

The founders' commitment to design, even if it didn't directly impact business metrics, is an 'X factor' that drives success.

Mastering Product Design With Katie Dill: Lessons from Stripe, Airbnb and Lyft

Mastering Product Design With Katie Dill: Lessons from Stripe, Airbnb and Lyft

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