Why Design Matters: Lessons from Stripe, Lyft and Airbnb

today on design review we'll be doing something a little bit different I'll be interviewing Katie Dill Stripes 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 strip 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 [Music] 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 leave the design organization and what that means is that we have the product designers uh researchers content designers that work hand inhand with Engineers product managers building the product so for us that's strip 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 and 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 in to 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 lift 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 a stripe it's moving your money with lift you're getting a stranger's car with uh 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 don't know what do you think 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 H 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 ryant 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 I 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 H where it you're 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 cison 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 and 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 weit but I think there's also attributes to moving fast and taking things down in maybe more bit-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 o 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 how well is this solving their problem 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 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 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 we create 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 in foremost which is fascinating given that those are human beings that work in those companies right and like why not bring you know the 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 it's a musthave 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 the product is working overall um and you know bringing a little bit more joy to the 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 uh the checklist is a really great way of making sure you never miss a thing but the other aspect that uh my CFI has taught me is that you should be looking at it as if you know something is wrong with the plane you're just trying

to find it and so that mindset is really helpful because it really requires you to take a different posture of that like there's something here and I'm going to find 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 a 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 what are the details of it that are really nice and just like taking note of that um and then of course you 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 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 are there any other tips that you would have for people that are trying to level up their own design skills

as a founder and that they can bring to their company we can learn a lot from observation pay attention to the products you don't like and why uh pay attention to the products you do like um certainly you know I I recognize sometimes it's a little chicken and egg it's like we want to get great designers but without great design they don't want to be here you know so um I think a big part of that too is you know getting out there in the community and also you know if you're trying to hire great

designers to your team like help them understand what role they can have in the company um if you don't know how design Works don't presume to tell them how it works think about how you can learn from their ideas design often does work differently than uh perhaps an engineering discipline uh and so that is something that you know you as a Founder can learn a little bit about by bringing folks on and maybe even just an advisory role to help you think about how you're going to hire or um maybe even coach maybe a junior

designer that's on your team uh and yes I think just meeting people learning from them and uh seeing their examples as a a really great way of of cultivating that taste can you teach taste I think you can make it better I I think you know to be honest with you in hiring for example I would certainly say that it is easier to teach somebody the tools or the the domain and the you know the space that you work in than it is to teach taste for example if you see somebody's portfolio it's like oh

but like you know we're in the you know fintech space and this person's worked in fintech forever but they don't exemplify great taste I think that's you dangerous because I think it would be not necessarily easy but easier to help them learn your space uh whereas um taste I think it's also like a passion for it you know that also can be difficult to to teach because um you know are is their mindset there is it something that they like think about every day that they you know just want to make things more attractive more

actionable more useful like you you want that like deeply in that individual if that's what they're you know main job is in your company right let's talk about design and and your design process at stripe tell us a little bit about the process and how that works yeah I think first and foremost is actually even thinking about how we're organized and we work together uh we have a highly collaborative environment where uh designers Engineers product managers they work hand in hand so like if you ask any designer on the team like what team are you

on they'd be like well I'm on the connect team and I'm on the design team so you're not like a service or that people just kind of reach out to like an agency to get work done and then kind of go back to your cave yes yeah for a number of reasons so number one you know all those functions that I talked about earlier are all a part of the design or because on purpose we want all those teams working well together because we want the user experience to feel coherent so whether you see us

on the billboard or the website and then into the product that should should feel like one coherent story that's building on itself so that's why we're all in one org but of course we don't want you know the designers to be just like popping in and out of projects and not having the context of the product really the Deep expertise and also not the same goals in mind so they are embedded in the teams they have the same shared goals as PMs and engineers and they're working on these things together start to finish and that

makes a big big difference in how the work gets done and so in terms of process uh you'll not be surprised but we of course always start with like well who's the user and what is their need and that's where you know all these you know kind of ideas for new products and things come from is that we're often hearing from our users and they are very much like engaged in in working with us and vice versa and so we you know potentially learn about uh a need for a product I I just mentioned connect

so this is our product for platform businesses and marketplaces and so it allows them to create essentially a relationship with other businesses so that they can help them grow grow their own business and and even offer uh financial services and so these organizations um that worked with us one of them was lift for early days for example they you know Came Upon This need they wanted to pay out drivers and so they built the product with us um I can talk about another product that I'm super excited to show you which is called workbench similarly

like we worked with slack and notion on you know how to make that product better every day and so we are doing prototyping and iterating and and they are giving us feedback almost on a weekly basis and that real like tight feedback cycle and iteration in the product really helps us kind of stay away from going down faulty assumptions and creating things that just won't work in real life and the spectrum of users that we serve and and this is probably the case for most of your Founders too like you know there's not going to

be one type of user you know that they're going to be interacting with and so to work with a range of users and have that iteration cycle really helps reveal things that you might not otherwise never have thought about and that really could persists straight on into the execution and the shipping and we keep learning and iterating because one thing that I think you know never ceases to surprise us is that you know you could design this perfect little product and you get it out into the world and then what do you know like three

months later it's full of bugs and you know the interaction points with your next new product aren't great and so you really got to stay steadfast into learning about your product and seeing also how it continues and so we actually have this uh part of our process and it's almost like a culture uh that of using the product and doing walk the store exercises where people from you know honestly anywhere in the company but especially you know in the product teams you know Engineers product managers designers um trying the product like a user would in

the journey aspect right not just that moment in time where the product shows up but thinking about it from you know how do I learn about it and an email how do I oh and then I go into the website oh and then I go into the product and how does that feel and what are the moments where it doesn't make sense because you know the day it shipped for the first time it may have been all perfect but over time like it starts to you know potentially erode with the creation of new things so

you got to continue to evolve it too I think every founder has had that experience of trying to nail the product launching it focusing on other things and then coming back and trying your product six months later and being like Oh my God what has happened here how did this happen yeah I mean it's a it's kind of funny one team members had given this analogy it's like when you're working on your house and like you redid the dining room and so you added nice new molding and like little light plates and painted the wall

and now all of a sudden the dining room next to the kitchen looks horrific and you know you have to think about how you know you're continuing to push and pull different parts of your product and uh never lose sight of how it fits across all of them how often do you do that walk the store with all your products I mean I bet you someone is doing it right now um it is it's just a it's a cultural norm um we have a a program where it is like very organized and established it's called

our essential Journeys and so what we did was we identified what are the you know top 17 you know most important user flows that many of our users go through you know daily um and it's not a comprehensive list by any means but we just needed something kind of digestible and so there's 17 and we have dris and team members assigned that every quarter they review that experience they score it they friction log it so that's like kind of writing down your experience as you go and and noting where like well that felt weird and

this is kind of that like check that uh pre-flight thing that I mentioned of like using a checklist to like does this make sense or not and noting that down scoring it we keep it on a scoreboard there's a little social pressure of like let's get these things to green and our scoring mechanism it's nothing fancy it's literally it's just like red orange yellow yellow green and green uh and we pay careful attention to it it's a company goal to get these things to green and keep them at Green and so you know as I

mentioned like regressions can happen so how do you stay steadfast on that improve it quickly get it back out there and so yeah it it's definitely happening a part of that program but I think what's super cool is when you know somebody from the you know um sales team does a walk the store of the you know uh billing product and then sends their friction log to the billing team because those are those great moments of hearing what somebody thinks who's not living in it day after day and like see that like oh that actually

doesn't make as much sense as we thought for somebody who doesn't have the context I love that cultural norm of measuring these things and having effectively like leaderboards and calling it out publicly and making that visible to everybody that's a really great way to emphasize this in the culture yeah absolutely so we have several examples that I'd love to show you and yeah would love to check it out yeah so uh one of the things that I think actually came out of the walk the store exercises that we do um is that you get to

experience the product firsthand and you really get to feel it like a prototype might not always show you how is it going to show up in the real world so using it real world is is very helpful and the other thing I didn't mention is that we have um a bugs at email Alias that anybody can send a bug to in in the company and outside the company because of that we can hear from various people in the company that have tried the product and seen an issue and it's like if you see something say

something which is you know super helpful so one of the things that came out of that was that we have this product called link uh which is our extremely fast way of checking out online uh but what we also provide with it is a way to buy crypto really quickly and so in this website here is nice easy tool where you can quickly buy crypto and what we found is that when you proceed and somebody types in their email address uh what was happening I I I'll tell you what the problem was cuz it's gone

now so I have to tell you but you would type in your email address and before you would stop typing in the email address there would be an alert that it was inv valid was invalid and that I'm sure you know maybe in the figma file was like great we're going to do this and it's going to be fine but what like actually is different when you feel it is just like that's really annoying you're yelling at the person before they even finished and so what we did was just you know we saw that that

was a bug filed and so now as I I type it in it it doesn't yell at me and what's cool is even when I hit a space right the space is not needed but it's just like a natural thing a human does that is not you know on purpose it's not yelling at me now it will yell at me if I give it a second so now it alerts me when it's appropriate right it's just like a little bit delayed and that microc that matters and so I'm I'm super glad that was filed and

taken care of Y another example that I think is going to be used ful as a point of how much design can really impact the bottom line is uh this great one about a email so we had this one email that was trying to communicate to a user what to do with the product after they have signed up and as you could see it's just like there's not a lot of hierarchy it's not a real clear call to action what to do if you read it you know the words just like not super clear it's

kind of a wal text it's easy to delete that and ignore it yes exactly and it's just like what is the role of that versus something else so we redesigned it and we thought about the words of course we thought about what happens after you hit this button is this button clearly communicating what happens uh we certainly added more hierarchy a little bit more visual interest which also communicates better and doing that increased product conversion by 20% from this email which is pretty huge and I can see why there's a clear call to action there's

a headline that you know I can't read the sub paragraph there but I can read that headline from here and it immediately gets my attention yes yes okay so let's talk some product stuff so um so thrilled about this product uh that we launched this year that is called uh workbench and so we were hearing from the developers about the you know some of the challenges they have with working with the Integrations and and continuing to maintain and grow um one of which was you know essentially breaking their flow state so they would be working

in you know the stripe uh dashboard and they would be going back to their code editor and you know a lot of of switching of um what do you call it contact switching um or going to the docs and cont sing lots of tabs Etc and we had a you know we've had a developer area but that was kind of getting like a little too jam-packed in a small space and so we wanted to create a tool that would make it a lot more powerful and easier for developers to use and stay in their Flow

State and so with workbench um it comes in here at the bottom of the product and you can see you could pull it up um you could change the how much of it it takes over this screen and what it provides for you is basically it's both like a microscope and a telescope of what's going on with your integration and so you can debug it you can prototype it you can make changes um and all of that stuff is right there for you so I can give you an example so let's minimize this for a

second and so let's say I'm in the dashboard and maybe somebody in the um company let me know that a user called and the invoice didn't work out and so we got to debug it what Why didn't it why didn't they get charged so we come over here we go into invoices um and I take a look and it's like okay here's the the user uh what what happened here um what are what are the issues and so you see here in workbench it's offering this little information to inspect I could also see whether or

not there were errors related to it but it looks like not right now but if I click on the inspector I can come in here now I can see the background of what is involved in this invoice which is also helping my mental model of how the API is constructed which then you know kind of fuels the developers ability to go further with it and build potentially you know new Innovations in top of that and so let's say Okay I want to learn about the customer what's going on with them what happened in the event

and I can go right into the API explore to then you know if I need to understand what's happening in the API and make changes and so this is almost like a little coach for you to be able to see how this works what's behind all of these various parameters and you know what you would normally be doing today would be going to docs also reading about it and it's just like again contact switch so that information is now here I can make oh okay that's what wrong it's their email is wrong so I'm going

to just get rid of that error let's do that let's run it okay it's updating let's get the code snippet so I can just bring that into my editor it's right there in my language which I could switch out and now if I go back to that spot there and see this user it's already updated right into the dashboard so it's really kind of like lowering that hurdle between the dashboard experience and you know your editor and really being able to like bring the power of the CL right into the dashboard and so we've gotten

great feedback and this is that example I told you about where we were working directly with notion and slack and iterating in real time and hearing from them how to make that better yeah this is great I I don't know that I've ever seen something like this before um and it seems like you came up with this from some first principles thinking it's like a web inspector but specific to stripe and for all the tools that you would need to manage and improve um all of your stripe Integrations that's super cool it's really cool and

thank you for saying that I think the team crushed it on this one and you know one of the other things that I love about this is so check this out so part of this like process of working with users on it was that we created uh this forum this community called insiders and so we can you know continuously hear from developers about their experiences it and learn from it and so even recently the designer on this work back in May posted about it and it's like hey here we did this what do you think

and you get the commentary right on it it's like actually this isn't working and like this is really great and you know no matter what size the company is that regular touch with users is so critical to actually make a product for users I think one of the things that I take away from this conversation is How Deeply integrated the entire company is with your users and you've got Founders talking to users and sharing that with everybody everybody's encouraged to be a user of the product and Report feedback and things that they learn on a

regular basis and uh you've got forums like this that uh help you connect really closely with your users and I I think that probably clearly explains why stripe builds such great well-designed products and so you know kudos to you for leading a lot of that and um the other thing that stands out to me is pride it's very clear that you and the founders and everybody that works at stripe takes a lot of pride in the products that you put out and I think that that shows and you hold that high bar for yourself and

I think that's a lesson that all founders can take away the level of Pride and the level of detail that you go to to make something incredibly great for users so um I've learned a lot about that today so thank you well that is all very very nice to say I appreciate that and yeah honestly I I I do think like the the Cs and brothers did such a fantastic job instilling that in the culture it does move the needle you know design certainly does make you know business sense but even if it didn't they

they would still do it and I think that that that's that X Factor that's the thing that's going to make you know hard decisions along the way possible and certainly worth it awesome well thank you so much for for having us yeah of course thanks for having me [Music]