Embedding Design into the Fiber of Fintech

Welcome to the first article in our Design Impact Series, where we explore inside stories from our portfolio companies. From internal team structure to design philosophy to UX, this series looks at the ways design can lead to greater impact.

How Stripe changed the game

Stripe exists because Patrick and John Collison decided to fix the overly complex process of moving money online. Since its founding in 2010, Stripe has evolved from a developer-focused payments platform to a 14-product suite that facilitates an array of financial interactions online, supporting businesses and entrepreneurs around the globe.

Like any successful start-up, there’s the mythology and then there’s the messy reality. Reality is hard to distill into a sound bite, but it’s what helps founders and designers tackle the challenges and decisions they face in their own companies and lives.

Design has had an impact at Stripe because it is valued, nurtured from the top, and focuses on making a positive impact on people. Success takes being intentional about how design works within the company at every stage of growth. And it takes an unimaginable amount of grit.

In order to share some of the unique characteristics and dynamics at play there, we talked to a few of Stripe’s designers, both past and present: Malthe Sigurdsson, Stripe’s first Head of Design; Everett Katigbak, Executive Producer of Stories; Megan Crabtree, Design Program Manager; and Katie Dill, Stripe's new Head of Design. What we’re sharing here are a few insights and anecdotes that illuminate how design has helped Stripe succeed.

Imagine if we made it the best possible thing?

Way back in the day Stripe was known for making amazing websites and products and people would ask ‘how do you do it?’ We would say we simply spend 20x more time on this than what anyone else would. And refuse to cut corners along the way. Designers aren’t usually given that playing field or power to do that. Malthe Sigurdsson, Head of Design, 2015-2020

One thing that came up again and again in our conversations is Stripe’s obsessive attention to detail and craft. From early on, Stripe was known for beautiful landing pages and insidery easter eggs, and, as a result, developed something of a cult following amongst designers. Designers at Stripe have always pushed for the time to noodle on something until it’s not just good, not just great, but exceptional. They take their work all the way to the outer edges of what's possible or reasonable — which sometimes takes navigating tight deadlines and competing priorities from the business.

Users above all

Stripe isn’t the kind of environment where lone wolves or would-be superstars thrive. It’s a demanding, collaborative culture, and the pursuit of greatness is ultimately for the benefit of users, not simply for creating something “cool” or portfolio-building. Everett explained that this user focus inspires the design team to find the right balance between function, craft, and joy — very unique (and difficult) for a financial product.

Even if your product is for B2B, they’re humans at the end of the day using these products. They have all of the same challenges you’re going to see in consumer spaces and the problems are just as meaty, complex, interesting, and rich. Katie Dill, Head of Design

Megan shared a favorite example — how Stripe's Dashboard and docs experiences work together. If a developer is digging through Stripe's docs to figure out how metadata is handled, for example, they are likely logged into their Stripe account. If so, Stripe can not only serve up the necessary code snippets in their preferred language, but also intelligently insert their unique API key into the snippet to make it work for their integration. This is the sort of thing that developers love Stripe for, and it signals that there's a human being who thought about what they need at that moment and provided it for them.

Team-building the Stripe way

The Stripe team doesn’t stop at demanding greatness on behalf of its customers. Keeping the team engaged and excited is of equal importance. Every year Stripe hosts an internal event called Convergence, a virtual playground for the entire company to look back at the past year, and forward to the next. The intent was to provide an opportunity to connect and learn from each other, communicate strategy across the organization, and get inspired. Last year the constraints of COVID prompted the team to reimagine a virtual event as something uniquely engaging, kind of weird, incredibly well-designed, and purposeful. They called it "Nonvergence," and the lineup featured presentations, fireside chats, and stories from Stripe users themselves.

Also made this injection-molded figurine (which people customized in truly amazing ways) for the same event — from modeling to 3D-printed prototypes. We work on the weirdest stuff sometimes. pic.twitter.com/BXueST96ZK

— Philipp Antoni (@phlntn) August 19, 2021

Play the long game

Notoriety online can have a meaningful impact on the brand overall. Especially the employer brand. It’s signposting to people who are irrationally excited about, say SVGs or animation, then come work for us. Stripe knows how to play the long game and this is part of it. Malthe Sigurdsson, Head of Design, 2015-2020

Stripe’s relentless attention to craft has become their Field of Dreams. Build the most compelling version of a thing, and passionate people will show up. But it takes a lot of trust, time, and investment to build in that way. When done right, it can lead to a huge long-term advantage. Stripe’s quality-driven approach has had obvious implications for recruiting, given Stripe’s reputation with designers and developers. But it also comes into play with some of the more unconventional projects Stripe has taken on.

A technology company that makes books

Stripe Press (“Ideas for Progress”) is one such magnet for people interested in big ideas. Gorgeous printed books are written, edited, and designed for people with a deep interest in economic and technological advancement. Topics are chosen with genuine attention to what stimulates those readers, as opposed to a more cynical content marketing-driven approach. In turn, of course, it has become excellent content marketing.

Stripe Press is not a random endeavor. It reinforces Stripe’s aim of democratizing innovation. By making so many of their insights publicly available through these books and their magazine, Increment, Stripe invites entrepreneurs and innovators to step up and turn their ideas into reality. And then, Stripe Atlas (Stripe’s “startup toolkit”) can help them form a real business structure and raise money, to the tune of some 20,000 businesses founded to date. It creates a positive feedback loop between the interests of Stripe's internal and external audiences and its business interests.

If the books get into the hands of someone who might not have direct access to a lot of the things we have in Silicon Valley, but they’re inspired to do something they’ve been dreaming about, that is exciting. Everett Katigbak, Executive Producer of Stories

Metamorphosis of a design team

What are the foundations of our design team? How do we run it like a business? What are the budget implications? How do we work with cross-functional partners? How might we interface with external vendors? How are we spinning up projects and how should we put different designers on different projects to create a cohesive body of work. Megan Crabtree, Design Program Manager

Despite Stripe’s early investment in design, it didn’t make the design team immune to the challenges of scaling up. The right people at the beginning — big picture, generalist, visual and product-focused — become just one component of an increasingly complex team over time. As their scale demanded more specialists, Designer Fund was able to assist Stripe with hiring more storytellers, design researchers, content strategists, and others.

Read our Guide to Hiring your First Designer here

Losing the thread

But what can go wrong during this transition is fragmentation. Losing the thread and becoming more focused on individual solutions than systemic ones. Or there can just be so many stakeholders that a seemingly small change gets stuck. One example is the login and register experience at Stripe. It sat neglected for years, and the design team kept trying to ship changes, but just couldn’t get it approved. One holdup was because it would mean one extra click for their users. Stripe builds for builders, and speed is paramount.

stripe's login page is an early 2010's relic i absolutely adore pic.twitter.com/XQbHiy5jyd

— @rubynerd (@rubynerd) December 1, 2019

Stripe finally re-did their login page. I’ll go ahead and pour one for @ludwig tonight for the old screen that lasted for almost a decade 🙏 pic.twitter.com/rj2GxzC488

— Jori Lallo (@jorilallo) February 20, 2020

It just lived in this world that looked like a dinosaur for a really long time. I think the past year we finally updated it. We got so many tweets from so many people just being like, when are you going to fix this. For some reason we just couldn’t land on an answer for it. Megan Crabtree, Design Program Manager

Self-examination breeds resilience

To mitigate these kinds of risks, Stripe now has five team members dedicated to design program management — one focused on cohesion across all design disciplines, two focused on product design, and two focused on operations of the UX research team. In tandem with cross-discipline leadership, they now manage over 100 designers to ensure the success of the work and growth of the design team.

The design managers and leadership help keep both the forest and the trees in sharp focus. Weekly stand-ups for the full team surface opportunities for "jam sessions," where smaller groups can hash out problems or connect around a specific topic. For initiatives that reflect where the team collectively needs to excel, there's The Design Collective. Coordinated working groups focus on initiatives that affect the whole team, recently tackling Craft & Quality and Diversity, Equity, and Inclusion. There are also a handful of ways the design team stays connected on a more personal level — from sharing personal hobbies at "Inspiration Station" sessions to quarterly "offsites," fostering togetherness is a priority.

This kind of self-examination is invaluable for design teams. It means setting aside time and eventually hiring for roles that exclusively look at how work gets done, and how to improve it. It goes beyond managing single tasks and putting out fires, instead building more awareness and resilience into the organization.

The ability to evolve and run with changes is huge. If you want to roll something out and revel in it and put it on a pedestal, it’s never going to work here. Megan Crabtree, Design Program Manager

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On the horizon

What’s a way to evolve without just coasting? Malthe

Stripe’s achievements so far are characterized by a lack of fear — starting with the guts to tackle a space with a high bar for success, massive incumbents, and an unsexy reputation. But now they are the massive incumbent. So where do they go from here?

For Megan, Stripe's design team has to “work extra hard to maintain visibility of work being done across our team, across product spaces, and across geo-zones. The bar we've set for ourselves in the past is one we really care about maintaining, but will constantly demand deeper understanding.”

Katie Dill, Stripe's new Head of Design, previously led design at Lyft and Airbnb so she understands better than anyone what it means to scale global, design-forward companies. Now she has the challenge of bringing that experience to a different problem space in a distributed team — no small task. For her, success lies in deepening collaboration with business leads and keeping design thinking at the forefront. And that means strategic hiring for design roles across the organization: "If we aren’t intentional about what is the company strategy, what are our priorities, and do we have team members in the right place, the design team isn’t going to be able to show up as the right partners to the business leads."

Stripe has to continue to ensure designers have the influence and data to make their work strategic, the time and space to excel, and the communication channels and methods to create a cohesive whole. Whatever path they choose, it's unlikely Stripe will pick the easy one.