Interview with Benjamin de Cock, Early Designer at Stripe

This article is part of a series revealing the stories of early employees from the most successful tech companies of the past few years. You’ll walk away having learned about what these individuals experienced, what they wish they knew, and the advice they’d give to others joining high-growth startups. Key takeaways are at the top and you can find the full interview below. 

This interview is with Benjamin de Cock. Ben is a designer who started working for Stripe in 2012 and spent 8 years there, working on many projects including the Stripe home page and Stripe Checkout. Ben has been a member of the CSS Working Group and is currently a designer at Increase. 

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Key Takeaways

• On Stripe’s focus on design – “Stripe understood the importance of good design and user experience very early and they invested in it at a time where companies were usually taking a different approach. Most startups were embracing a release early, release often type of development, where design was often an afterthought and something that'd be contemplated once product market fit was clearly assessed.”
• On learning from Patrick Collison – “His optimism is also remarkable and contagious. We went through many difficult periods over the years due to exponential growth, reliability concerns, etc. and his tendency to see solutions wherever others see problems is simply wonderful.”
• On what stayed the same in Stripe’s culture – “The users-first culture, alongside shipping surprisingly-great things (as Patrick liked to say) stayed the same the whole time. To me, this is Stripe's most remarkable achievement. Usually, quality tends to degrade over time, especially when a company grows that fast. That really wasn't the case at Stripe.”
• On remaining a individual contributor – “My passion is in the creative process, not in the management business, and I'm pretty certain I'd have done a terrible job at it. Fortunately, Stripe doesn't force you to follow that direction. You can absolutely grow and evolve in the company, take more responsibilities as a senior individual contributor, and keep building ambitious projects without being artificially limited by the path you're taking. I admire Stripe for that.”
• On learning about startup equity & taxes – “I had to learn pretty much everything at once and while it was overwhelming at first, it quickly became intellectually interesting. It also led me to learn more about personal finance, the stock market, and other financial topics. Even though I came to it by accident, I enjoyed the process and I became quite passionate about it — turns out it's a lot less difficult than it seems!”

How did you first hear about Stripe? What made you want to join? 

Ludwig Pettersson (Stripe's first designer) reached out in November 2011. At that time, I was mostly working on Kickoff (a collaboration Mac app) but I was also doing some freelance projects on the side. When Ludwig asked me if I'd be interested in freelancing a little bit for Stripe, I accepted immediately—I admired Ludwig's work and it was clear to me Stripe cared a lot about design, quality, and polish from the start. The "few days of freelancing" turned into eight years.

What were you hired for? What was your first project?

Stripe understood the importance of good design and user experience very early and they invested in it at a time where companies were usually taking a different approach. Most startups were embracing a release early, release often type of development, where design was often an afterthought and something that'd be contemplated once product market fit was clearly assessed. 

Stripe did the opposite and recognized the value of branding and the impact of great user experience from the very beginning. They hired me at a time where it was probably not strictly necessary as my first projects were low-impact (small icons, etc.) but it was part of a longer, broader vision.

What’s a unique tradition that Stripe followed that might seem ordinary but you think had an outsized impact on your team’s success?

I'm not sure it qualifies as a "tradition", but the quest and research for excellence is quite unique at Stripe. A lot of companies claim to care about quality overall, but once they realize the cost and effort it takes to actually reach that level of quality, they're quick to accept compromises. 

Going the extra-mile is often hard to justify and quantify with cold numbers and raw data, but it's clear to me the impact is outstanding, especially over the long run. The spillover effects coming from a culture built on very high standards are often underappreciated. For instance, hiring became easier and easier over time as the brand, the reputation and the culture were highly regarded. Developing that kind of culture takes a lot of time and effort in the beginning, but it really pays off. Stripe's success is essentially due to the exceptional group of people working there.

I’m sure there are many, but who are 2-3 Stripe co-workers that you worked with that still inspire you in your work today? 

I've honestly worked with so many people over the years who are ridiculously good at what they do I wouldn't be able to mention just a few of them. Instead—and he'll hate me for writing this — I'll just pick one, and that's going to be Patrick. It seems cliché, but he's probably the person that inspired me the most in my life, and I genuinely think he's one of the best CEOs of our generation. He's shockingly smart, incredibly nice, extensively resourceful, and many other things exceptional leaders often demonstrate, but the things that really made a difference for me were his humility and optimism. 

Despite his incredible success, his outstanding abilities, and his extensive knowledge and general culture in a wide range of subjects, he's literally the most humble person I've ever met. It is real, genuine humility — he's just smart enough to realize all the things he doesn't know, and he values other people's opinions so much he'll always question his ideas and assumptions in light of new context provided to him. 

His optimism is also remarkable and contagious. We went through many difficult periods over the years due to exponential growth, reliability concerns, etc. and his tendency to see solutions wherever others see problems is simply wonderful.

What about the culture changed most from when you joined Stripe in 2012 to when you left in 2020? What stayed the same? 

The users-first culture, alongside shipping surprisingly-great things (as Patrick liked to say) stayed the same the whole time. To me, this is Stripe's most remarkable achievement. Usually, quality tends to degrade over time, especially when a company grows that fast. That really wasn't the case at Stripe. 

The environment and the dynamics did change quite a bit though, but that's inevitable and necessary — you just can't keep the same “yolo”-type of development when you go from 10 to 1,000 employees. You gain a lot of benefits by having a less chaotic startup environment: stability, better planning, better work-life balance, etc. but you obviously lose some speed and flexibility. Trying to retain those startup vibes as you grow is a challenge.

Were you ever scared that Stripe was going to fail? 

"We haven't won yet" is literally one of Stripe's mottos, so I think the very possibility the company might fail is ingrained in every employee, in a good way. The last thing you want is to become complacent. We rarely looked at the competition as we thought the responsibility and the cause for success or failure was almost exclusively in our hands.

What are you most proud to have built in your time at Stripe?

I think the home page is probably the most impactful project I worked on, as it was defining the identity and the brand as a whole. The two home pages I designed had different challenges and benefits over their previous versions.

The first one I made that shipped in 2016 really helped defining a brand image and a unique Stripe-y look and feel, with the slanted backgrounds, the stripes (obviously), the purple, the simplified illustration style etc. creating a strong and distinct identity that we were missing until then.

The goal for the second one was essentially to address productivity, consistency, and scaling issues. The site became really big, and it was becoming increasingly difficult to design every single page from scratch without a solid design system in place. We needed reusable components, icons, and page skeletons that we could rely on to create new pages quickly while retaining an interesting visual language, and a site that doesn't look like a fully automated CMS. This second version was also a major improvement internally as it was a much more collaborative project than we used to have, and everyone in the team contributed to it and made it better. I'm very proud of the work we did together!

What advice would you give to someone joining as an early designer at a technology startup?

Treat the startup as your own company (it probably is, to some extent) and expand your horizon and responsibilities. The biggest, most significant thing startups will teach you is to make decisions by yourself, and get out of your comfort zone. Startups have pretty much nothing figured out, so no one will give you a definitive answer or handle some parts of the problem for you; it's your responsibility to figure out things by yourself that aren't supposed to be your area of expertise. You'll grow tremendously, not only as a designer, but also and more importantly as an owner and an entrepreneur. It's a rocky path, but it's well worth the effort!

How did design as a function work when you only had a few people covering marketing, website, and product design?

We had the chance to have a design team full of very independent people who have built products and companies before Stripe, and shared the same entrepreneur kind of mindset. Therefore, most designers would go far beyond their primary roles and tasks to do whatever is necessary for the company. No task is "out of scope" when you're a small team, you just do what's required to reach your goal, even when the task is unglamorous. You need a certain type of people to feel comfortable in this kind of environment but again, that's where Stripe really succeeded in my opinion.

How did the design team determine if something was good enough to ship? How can other teams think about where to set the quality bar?

Hiring. Hiring is the answer to most of those questions and issues — I just can't stress it enough. We were about five designers for a fairly long time, and literally all of them were better than I am. Hiring people better than you is all the quality insurance you'll ever need, not only because they're inherently great at what they do, but because it creates de-facto a culture where you want to be at the same level as your coworkers. It's contagious.

How did the design team interface with engineering and product early on? What was the role of the designer when Stripe had no product managers?

All the first designers were very technical. Ludwig implemented most of the original dashboard by himself. I implemented the home page by myself. Philipp Antoni is more comfortable with WebGL shaders than most Stripe engineers. The list goes on. We were just handling a lot by ourselves. Of course, it didn't scale forever, but it bought us a lot of time in the beginning.

Startup equity isn’t something that most people know about until they’ve joined a startup (often too late). How did you first learn about stock options, exercising equity, and the tax implications of it all?

Honestly, I didn't think about it for a very long time — it simply wasn't my priority. I've been forced to think about it when I considered moving to California as it had some pretty serious tax implications. I had to learn pretty much everything at once and while it was overwhelming at first, it quickly became intellectually interesting. It also led me to learn more about personal finance, the stock market, and other financial topics. Even though I came to it by accident, I enjoyed the process and I became quite passionate about it — turns out it's a lot less difficult than it seems!

How did you think about being an individual contributor vs a manager?

I thought about it several times over my career at Stripe, mostly because the industry as a whole makes us think it's the only possible evolution, and the logical next step as you grow in a company. The more I thought and learned about it, the clearer it became it wasn't for me. My passion is in the creative process, not in the management business, and I'm pretty certain I'd have done a terrible job at it. 

Fortunately, Stripe doesn't force you to follow that direction. You can absolutely grow and evolve in the company, take more responsibilities as a senior individual contributor, and keep building ambitious projects without being artificially limited by the path you're taking. I admire Stripe for that.