Chatting with Benjamin De Cock: Design Lead at Stripe
We are Central, a Brussels-based team specialized in designing digital products. Every month, we organize Umami Talks: live interviews with people who create digital products for a living. So far, we’ve interviewed CEOs, CTOs, start-up founders, product managers, developers and designers.
This article is a slightly edited version of the chat we had with Benjamin.
Benjamin is Design Lead at Stripe. The company was officially launched in 2011 and has since grown into a 900-people company. Their main aim is to allow individuals and companies to easily set up payments for their online shops. Aside from working for Stripe, Benjamin is a member of the CSS Working Group.
Hi Benjamin, thanks for being here. Can you tell us a bit more about what you do at Stripe?
I’m the Design Lead of the communication team. In practice we design and build the site for Stripe. We try to explain what Stripe offers in a nice and easy way by making the information obvious and natural to navigate. We also work on the brand and the identity so that people can easily identify and trust the brand.
Stripe is based in San Francisco and you work here in Belgium. What methods do you use to make that work?
There are a few things in place that make collaboration with remotes easier. For example, we strongly promote Slack, email and sharable documents over verbal decisions. To be clear, that’s not only useful for remotes, it’s also an easy way to document every decision we make without introducing too much friction. We also have quite a lot of conference calls using a service called BlueJeans, which works really well. All the meeting rooms are equipped with all the hardware needed to make that possible. I also travel quite a lot to mitigate the time difference because, honestly, no matter what you do a 9-hour time difference is a very hard problem to solve. So, overall it’s just a big pile of hacks but it’s been working surprisingly well so far.
Do you prototype your designs before you implement them?
Yes, we do. For the dashboard, the interactions can be quite complex, the navigation can be very deep and we have a lot of edge cases. So usually, our UX people build pretty comprehensive prototypes so you can really feel if the solutions might work or not. For the site, we don’t prototype as much. We usually just build the real thing and iterate on that. It’s mostly because our designers are pretty technical and it’s usually faster and more productive to jump right into the real thing.
A few years ago, Stripe did not have a design style guide. What are the pros and cons of that?
You know what developers like to say about premature optimization being evil? I think that also applies to design. Building a solid style guide is quite a big undertaking and honestly a relatively big distraction for a small team. Now that our design team is much larger, it definitely makes sense to invest in documenting our visual language in a style guide. But we tend to keep our style guide rather light. We have a lot of shared styles, a lot of rules about typography and button treatment, a very detailed color palette and stuff like that. But we only specify the things that deeply contribute to creating a consistent look and feel without locking ourselves into a rigid template.
I think that the danger and the risk with style guides is that many designers end up creating a very strict set of rules and they end up with a site that looks like a big CMS. That’s obviously not what you want. You want to have the freedom to experiment on every new page and get the chance to refresh your style with every release. So, I think a minimal set of rules is crucial, but doing more than that is counter-productive.
Why did you decide to work for Stripe?
It’s hard to pin-point one specific reason. It’s a mix of a fascinating culture, working on a product that solves a real problem, the fact that I joined early enough that I could still make a big difference as opposed to joining large companies like Facebook for example. The founders are also the smartest people I’ve ever met. But if I had to pick just one thing, I would probably go for the culture. I remember being really impressed since day one about their craftsmanship and the level of excellence they were looking for in every single aspect of the company. For example, I remember many discussions in which everyone was trying to ignore all the technical problems and challenging assumptions… That passion for doing the right thing really resonates with me. I think that’s the main reason I joined Stripe. It’s not because I’m a huge sucker for online payments.
At Stripe, everyone goes the extra mile, tries to polish the product, wants to do what’s best for the user, to reduce the friction in every single step. We want people to be able to start accepting payments in literally 5 minutes. That’s our goal. I like it when companies try to kill all the crap and try to make things nice for the end-user.
Is there a specific person you’ve learned a lot from professionally? What did you learn from him/her?
In terms of user interface (UI) design, I think I learned a lot from Apple. I realize it sounds very cliché to say that, but 10 years ago UI design, as a specialization, was not really a thing yet. I think back then, macOS was a masterpiece of consistency, visual polish, clever interactions, making interactions super obvious for the vast majority of users while allowing power-users to still feel at home. I think that some of the things they did after that were questionable, but back then I was really inspired by the kind of system they created and I really tried to apply these best practices to the web where we have zero consistency in rules and guidelines.
These days, I honestly mostly learn from my co-workers who are all better than me in every possible way. Some of these people have a lot of experience in different companies like Facebook, Pinterest, Apple, etc. They tend to bring a lot of setup and workflow around our work and that’s fascinating. Then, in terms of execution and visual polish I think that some of the things they do are just incredible. I definitely learn a lot just by looking at their work.
You’re part of the CSS Working Group. Can you tell us what that is?
The CSS Working Group is responsible for creating, developing and fixing CSS (a coding language). This group is part of the World Wide Web Consortium (W3C). The goal is to create standard specifications that all major browsers agree on. Most of the members are employees from Google, Microsoft, Apple and Mozilla. The main benefit for the end-user is that no matter what device or browser is being used, the end result will be the same.
What are the hottest topics being discussed in the CSS Working Group right now?
Most of the topics we discuss are far from being exciting to be honest. It’s pretty unusual for us to contemplate potential new features. It obviously does happen; a few weeks ago we introduced a new gap property which is roughly the same as the grid gap property that you have in CSS grid and would apply to Flexbox and multi-column. Right now, I’m also trying to introduce a new border property but it’s pretty hard to convince other people, so we’ll see. We have to come up with examples and use-cases to show that the suggestions brought forward are necessary.
But honestly, most of the discussions we have are about fixing bugs in the specs or discussing what to do when we don’t have interoperability. What does that mean? We often see edge cases looking different in different browsers and that might be because the spec was not perfectly clear or because there was an implementation bug in the browser. But even in that case, we often end up changing the spec based on the behavior of the browsers instead of requiring the browsers to change the behavior because that may break a lot of sites. So most of the work is not very glamorous, but the group is very thoughtful about what goes in the specs or not and it sets the right priorities, in my opinion.
Your Dribbble account includes icons, detailed illustrations and page views. How did you become so proficient in such a wide array of skills?
I guess I just like all things design. I’m just as fascinated by industrial design, photography and architecture as I am by digital design. The other thing is that, early in my career, I started working on my own app with a friend. It turns out building an app requires a lot of different skills. So I had to learn how to design an icon, how to code, how to draw big illustrations for the announcement blog post, etc. It led me towards various areas that I would probably not have dealt with otherwise. Building that app really taught me a lot. My first icons were absolutely horrible…
You’ve said somewhere on the web that you suffer from imposter syndrome. Is that still the case? If so, how do you deal with it?
Yes, I absolutely still have that. It makes my life harder in the sense that every time I start a new project I’m kind of paralyzed by the idea that I won’t succeed. Every other month, I feel like I’m going to get fired because I’m not good enough. It’s mentally taxing. That being said, I now realize that it does help me a little because I still need to prove that I’m capable of designing and building decent web products. It pushes me out of my comfort zone and it’s a nice way for me to keep learning. So I would say it’s both the worst and the best thing to have.
Where do you find your drive?
The thing we just said about imposter syndrome really pushes me to go the extra mile. As I mentioned earlier, I get to work with extremely talented people and that helps me grow. I really want to be on the same level as my co-workers so it’s a big motivating factor for me. Another thing is that I still truly love the web. I think the technologies we have now are absolutely fantastic and it makes me a little sad to see all the crap that you can find online. I want to fight mediocrity and create rich, fast, playful and easy-to-use interfaces. The internet still fascinates me and I want to treat it well.
