Design, Process, and Collaboration at Stripe

Hi Ludwig. When deciding where to take your talents, what attracted you to Stripe?

I joined Stripe about five years ago, when it was a tiny company in a tiny office in Palo Alto and I was the first designer. There were a handful of engineers just trying to build this crazy thing, and what drew me to Stripe was two things:

First, the product we’re building is a service that I strongly felt needed to exist. Before joining Stripe I’d been building things myself. I’ve always had side projects, and there was one in particular that I’d been working on for a couple of months, and I started thinking: “Maybe I can turn this into a side business and live off of it.” I remember looking into how to charge for it, and it was really difficult. There was all this arcane technology and APIs that were really bad, and I remember thinking, “I’ll figure this out in six months.” But I just stopped working on it before then. And so, working on something like Stripe that removes those hurdles — that was a big part of it. There should be nothing standing in the way of starting a business or selling something online and charging for it. I liked seeing that someone was fixing it.

Second, joining early was a big creative opportunity. Having the ability to set the direction and visual style was exciting, and definitely a big part of why I joined.

How does design fit in with Stripe’s organizational culture?

Very early on we all saw the value of design. I tend to think of design as something that amplifies things that already exist — it can hit the turbo-boost button on a product, a launch, or whatever it might be. It can make something get more attention or be better-received, and will just be an objectively better thing that you create.

Companies saying that they value design has become a platitude in the past several years — it’s the cool thing to say, because you can’t not say it — but I don’t necessarily think that was obvious a couple of year ago. I think it’s true that most companies in tech today value design, but when we got started that wasn’t obvious.

What we got right, or lucked into, was investing a lot of energy into design very early, and when we launched, everyone at the company got to experience why it’s worth investing in design. One of the worst things is coming into a company that doesn’t inherently value design — not having that trust. I think you should always be able to defend your reason for being at the table, but having the trust of the people around you goes a long way. Not having that trust would break my heart, basically.

Being able to prove the value of design very early on has meant that everyone has bought into it and sees why we should continuously invest in it. You want to have that as a reason — to be able to point back and say, “Oh right, that’s why we care about it.” Otherwise, when you’re hitting up against a deadline and things aren’t as good as you want them to be, you’ll start bending all those principles.

Having proved it very early has done us very well in keeping design as a core part of everything we do. It is very important at Stripe, and everybody sees the value of it.

Expanding on that, how has the design team influenced the direction of the company?

The fact that design is core to everything we do — we’re always there, always working — is important for a couple of reasons.

Say you’re working on a product, or whatever it might be. The magical touches that make something really good don’t tend to happen at a meeting with Post-It’s or with everyone brainstorming ideas, but rather tend to happen when you’ve got an engineer or a designer or someone who’s been tirelessly working away and testing their ideas in their own time and their own space. Having designers positioned so early on in everything, we’ve been able to have a lot of impact on everything we’ve built because we’re there working on the products from Day One. If you don’t have that early on, it’s hard to have any impact.

Developer tools tend not to get much design love. Being able to invest in design in an industry where it’s considered an afterthought has propelled our products further ahead, and that has come from designers in their work. Say we’re bouncing around ideas of what to build next, or what the next version of something should be. Having that product design perspective is key, because otherwise — if you think of setting the direction as an isolated process and then it gets sent out to all the teams designing it and implementing it, you lose the magic that is iterating and having the freedom to test things. That’s where all the really good things come out — not from the initial meetings. The actual implementation is where it matters, and I think that us having designers very early in there has made all the products we’ve built so much better.

How does Stripe’s design team collaborate?

We tend to be fairly loose in terms of structure. We try to show each other as much work as possible and keep everyone involved. I think that having completely isolated designers is bad for everyone on the team, because then you have these small islands of interesting things happening, and you miss out.

For example, on a small team, everyone talks all the time. As it grows, the default ends up being that people don’t share all that much. We tend to work very independently on many projects and have a lot of space to experiment and try new things and push things forward, but then we always try to pull it back to what the team wants and the direction we see ourselves going in. We give everyone individual freedom, so then you have to make sure everyone stays up-to-date in everything and everyone’s able to follow along and at the right times give feedback and input.

I’d sum it up with: a designer winds up owning a very large part of something and they can have ownership over it and make the decisions that they think are best, but they still have the support of the team when they need it. You don’t want an overly centralized way of working that smothers creativity, but the extreme opposite end is the design going in ten different directions. Finding the balance there is not always easy, but we err more on the side of trusting each other and giving each other the independence and spacing and then being there when an individual designer wants and needs the support of the team around them.

Is your whole team in-office, or are there remote workers as well?

Most of us are here in San Francisco, and then we have some remote designers. That ends up working out great. We just talk a lot on Slack, and it’s wound up working really well.

What does your team do differently today than it did a year ago?

We’ve started to figure out where to add some minor process. For example, we tried to add a tiny bit of process in places where things used to happen very naturally, and as we’ve grown end up not happening anymore by default. An example there is making sure that — say you’re two designers working together. You’re talking constantly, right? Sending things back and forth. If you’re three designers, everyone starts sharing within the group. Four five six, not everyone is talking to everyone. I think that’s an example of a place where we’ve tried to add a very little amount of process to make sure that everyone gets to share their work, everyone gets to prompt others for feedback, and to make sure that all the things that naturally happen when you’re smaller continue to happen as the team grows.

It’s human nature to want to over-engineer everything. You go into a room and want to come up with a perfect plan for this perfect machine of how design or anything should work, and you plan it all out and you leave and you start up this machine and you can just kind of relax. But that never works, and you wind up with a super complex system that’s hard to change or understand. What we try to do is introduce a little bit of process and recognize “Here’s something that’s missing that we used to do all the time that we now really miss.” An example would be regularly scheduled critiques so people get to share their work and get everyone to look at it and get the thoughts and feedback and comments they want. With everyone having a lot of freedom and a lot of space, if you don’t look out for it it can easily become too independent with people feeling like they’re not getting the support they need. What we try to do is that, any time we start feeling like something isn’t working as well as it did six months ago, we try to figure out the smallest tweak we can make to get back to there.

Do you use a design collaboration tool, like Wake?

We started using Wake a couple of months ago, and it’s working out really well in terms of getting that constant feed of everything going on. That’s a perfect example of something that everyone used to do. In a small team, everyone sends screenshots back and forth constantly, but then if you have these independent channels, or have the main channel for the team, you can very easily start losing out on that because people might feel like they have to post very polished things, or just forget because they’ve already sent it to two people and forget that three others haven’t seen it yet. It’s worked out really well as a default feed of everything that’s going on, which we’re really liking.

That gets people away from the Dribbble mentality of only being able to show polished work.

Right. And then also it’s wound up being a safe space for the team to show whatever they’ve been working on in whatever state it is, so you don’t wind up with just final polished things. You want people involved way earlier than that.

What do you think is the biggest challenge facing the design world today?

This is very individual and very subjective, but something I’m worried about — especially in digital design — is getting stuck in an even bigger echo chamber than we’re already in. If everyone just gets inspired by each other, the field will keep narrowing and narrowing. You want to keep borrowing ideas from neighboring design fields. I think that goes in cycles, where, for example, mobile app design keeps getting narrower and things start looking the same, and then someone or some company mixes it up a bit, and then people are back to having more original ideas again. That is less so something I’m worried about happening, but it is something that happens, and getting stuck there would be unfortunate.

More broadly, in terms of how design gets applied at companies, if it gets channeled and focused on the wrong things… a lot of design works as an amplifier, but you can’t rely entirely on it. You need to back up really good design with really good fundamentals — is the product you’re working on what people want? Is it something people care about? Is it solving the problem it’s supposed to solve, rather than just looking really beautiful but not doing much? That requires asking hard questions about what you’re working on, and that’s never super comfortable. When people rely on design too much by itself rather than relying on fundamentals… that’s not a good thing.