Braintree: Solving big problems with little ego

The payment processing leader is staffing up in
San Francisco, with an eye toward product design

Job Portraits
Aug 10, 2015 · 9 min read

This portrait was commissioned by Braintree and produced by Job Portraits, which highlights job openings at Bay Area startups. For the interview below, Job Portraits spoke with Braintree Product Manager Archie Puri, Developer Brent Fitzgerald, and Product Designer Trevor McNaughton at their San Francisco office. Braintree, which started in Chicago, also has offices in Austin, New York, London, San Jose, Sydney, and Singapore. See open positions here.

What does Braintree do, and why does it matter?

Archie: Braintree provides payment processing solutions for anyone who sells something on the web or on mobile. We give merchants the ability to accept different payment types in their checkout experience, across many countries and currencies.

Brent: For example, Uber integrates several of our products, which helps them create an onboarding and payments experience that a lot of people think of as “magical.” We make it simple for any company to provide that experience to their users.

Top: Braintree occupies the top floor of the Townsend Building, near 2nd Street, and is growing rapidly. Bottom: Brent Fitzgerald, Archie Puri, and Trevor McNaughton (left to right). Although Archie is based in SF, she was working from the Chicago office the day we visited.

Tell us about the kinds of projects you guys are working on.

Archie: I head up the product management team in San Francisco, San Jose, and Austin. I also manage the Core Payment Processing products.

Trevor: Brent and I work on the developer experience team. We help developers end-to-end with things like how they integrate with Braintree, how long it takes them, and where they’re hitting barriers. We’re trying to make all that as easy as possible.

One of the most tangible pieces of that is the documentation. We’ve made a huge effort over the past year to improve the product’s content, user experience, and user interface, all with documentation. In doing that, we kind of turned the documentation into a product of its own.

Brent: We created a network of people internally who contribute to the docs, including people in support, product managers, and developers.

Members of the developer experience team meet, pair, and discuss in their open-but-intimate section of the office. The Braintree office is divided into “neighborhoods,” which actually promotes more conversation than an open floor plan, according to Operations Manager Gina Belleci.

What’s a normal day like at Braintree?

Archie: I think there’s no specific way to describe the workday at Braintree. People are so different. Some people have kids — I have a 7-year-old — and some people are super young — one of our team members isn’t 21 yet. I think the great thing about Braintree is that it’s possible to work in a meaningful way without having to compromise on your life choices.

For example, I live about an hour from work. I get to the office pretty early, usually between 7:45 and 8, but that means I leave by 4 so I can pick up my daughter every day. And that is not uncommon. With flexible hours like that, each team keeps in synch by starting the day with a standup.

Braintree has been going through some huge growth. Have things changed?

Archie: When I started at Braintree, everyone did everything. I used to do weekly grocery orders, and we were responsible for turning off the lights and locking the office. Now we have a facilities manager and catered lunches.

“What has not changed is our core culture, the values with which our team builds and approaches products.” –Archie

In those early days, we had just one product being developed in each location; one in Chicago and one on the West Coast. Now sometimes within a span of five weeks, we might release five different things. We keep our marketing teams very busy.

What has not changed is our core culture, the values with which our team builds and approaches products, and the way we think about our merchants.

Top: A mock-up of an ad campaign reiterates the core company values with, “Code is an art form.” Bottom three: The wide range of personalities in the Braintree office seems to manifest in the bottles left on employees’ desks. Pick your poison: wine, water, or….Cholula?

Can you talk more about that culture and how you think about users?

Archie: I’ll give you an example. A big part of our job is to help merchants integrate with a really complex network run by credit card brands, such as Visa or MasterCard. So every time there is an outage where a card system or bank is down, it would be easy for us to say, “That’s not our job.”

However, we prefer to see our role as bigger than that; we are enablers for our merchants’ business. For us, one lost transaction from a bank outage might be a tiny thing, but for some of our merchants, it is real money they lose. Looking at it that way, we understand that downstream outages are a problem we can’t ignore. I think we take that approach with pretty much everything we do.

Another big change has been the acquisition of Braintree by PayPal in late 2013? How have things been since then?

Trevor: Obviously some things had to change, like the HR systems became more corporate. But 95% of what Braintree was before PayPal is still true today. We are still in control of our roadmap and hiring. Our leadership team has done everything they can to make sure that Braintree has stayed intact.

Brent: And it’s not just leadership. I think it’s good that we all feel comfortable pushing back when we think there is something that’s not good for our customers or that goes against our longer-term vision. In a lot of ways Braintree and PayPal are growing together to provide an even better experience for developers.

Lunch is served!: The kitchen lives just to the right of the front desk (top), behind a wall of lightbulbs highlighting companies currently using Braintree products (above). Below: Thursdays are salad days (literally!) with lots of yummy proteins to top them off (don’t worry, vegetarians, there’s tofu just to the left).
Left to right: Executive Assistant Aman Bilon, Chief of Happiness Amina Gass, Sourcer Rebecca Tobin and Software Engineer Evan Hahn.

We hear you are a pair programming shop. What percentage of the time are you pairing?

Brent: It depends on the team, but the default mode is to pair. I had never done pair programming before I came here; I like that it makes the product feel more shared. When you are working on something and you know somebody else might come work on it with you, it removes a little bit of ego. Everything is a collective effort, which is really cool.

I also think pairing contributes to the product culture at Braintree. We always have to think about making things easy for someone to quickly learn and use. That requires this sort of mellow professionalism to get along with your pair. And that extends to the way you work with people in non-programming situations, too.

How does design work when engineering is pairing?

Trevor: Design often mirrors the way engineering works. There are even times when design will actually pair with an engineer. I was recently working with a backend engineer to add a simple toggle switch in our control panel. He had everything ready to go, and I just needed to help hook it up. It was a really quick session, because we both trusted each other and knew exactly what needed to get done.

Interested in open positions at Braintree?

Check out their career page.

Super Smash Brothers holds center stage in the office’s game room with two huge flat screens and a tornado of controllers. But Star Trek pinball and good old ping pong get some love, too.

How is design at Braintree different from a consumer-facing company?

Trevor: To start with, the design team intentionally hires remarkably technical designers. I wouldn’t call myself an engineer, necessarily, but I have a deep technical understanding of the problems we’re solving and the technologies we use.

Brent: There are also a bunch of folks on the developer experience team who don’t consider themselves designers, but who talk about designing an API or designing the auth experience. I remember a situation when I was pairing with a newer developer and he was like, “What should I do here?” It was not a visual question, but it was about how something was supposed to feel. It was still like, “We’re the designers now.” Developers respect the design role at Braintree, but we also know how to make design decisions ourselves when we need to.

Top: Klas Back, GM of International Payment Strategy, chats with CTO and GM Juan Benitez near the office’s personalized lockers (middle). Bottom: PayPal Brand Manager Alice Whitley (left) and Anne Nickel, Senior Manager, Global Brand Strategy for PayPal.

What kind of person would really love working on this team?

Trevor: One of the most exciting things about Braintree is that it’s an extremely complicated system to work on, with multiple properties. Just through the lens of developer experience, there’s the marketing side, documentation, the control panel, and then the API.

For me, thinking about all that as a design problem is really interesting because it isn’t just taking one thing and making it a little better — it’s taking this whole system and making it make sense.

“Anyone who doesn’t feel comfortable taking ownership is probably not going to flourish here.” –Trevor

Brent: If you think you’re a pretty good, well-rounded designer and you want to become a stronger coder, this could be a really cool environment to do that. For engineers, if you’ve built a lot of apps or consumer websites and you’re interested in tackling a super complex tool that’s used by other companies, this is a great place for you.

Is there someone who might not enjoy the work here?

Trevor: Someone who is expecting to be told what to do or someone who is not willing to take the initiative might struggle a bit here. One thing that I love about working here is that I see something that’s not right, I fix it, and then it ships. In that way, it’s still very much like a startup. So anyone who doesn’t feel comfortable taking ownership is probably not going to flourish here.

The week’s Thursday happy hour was sweetened with three kinds of cake and a cherry pie, provided by Veronica Klaus (middle). And what happy hour would be complete without a friendly game (or six)? Including Magic: The Gathering (top), pinball (bottom left), and Centipede (bottom right).

Are there opportunities for people to learn new things here?

Trevor: Most of what I know now, I didn’t know a year ago. That’s mostly because the teams I work with are always helping me learn. Whether it’s the apps we’re building, or really, I’m still learning stuff about Braintree as a company, even two years later, which is actually really exciting.

Brent: We also encourage people to teach themselves new things, and we set aside open dev time for that every other Friday. It’s a good time try new things, to experiment.

Trevor: At the last open dev I wanted to learn more about React, a newer JavaScript framework we are starting to use. Whenever I ran into a problem, I would just ask one of our friendly developers. I would post in the frontend Slack channel and say, “Someone help me!”

Brent: I feel very comfortable hopping into channels where I don’t know who’s in it, and asking a question. I’m not afraid of sounding stupid because everybody is so friendly.

“I’ve never seen someone make a decision based on pride. It’s always because it’s the right thing to do.” –Trevor

Trevor: I think that comes back to something Archie talked about, with ego. I used to work in advertising, which is essentially an industry of ego. When I made the shift into products, especially coming to Braintree, the most striking thing was that no one here has any ego. I’ve never seen someone make a decision based on pride. It’s always because it’s the right thing to do.

Join the team!

Interested in joining the Braintree team? Check out their job openings here, or contact Kyle Barbato,, in San Francisco and Lindsay Verstegen,, in Chicago. In addition to product positions, the Chicago office is looking for underwriters, risk analysts, data analysts, sales reps, account managers, and support staff.

Your moment of zen: Ayaka Nonaka rides one of several office skateboards past Sam Soffes, hard at work in the office’s work/nap pods (both are iOS engineers at Venmo). Cover image: Braintree Product Engineer Elliot Lee, Developer Brent Fitzgerald, and Software Engineer Gary Bramwell chat during their morning standup.

Job Portraits

Job Portraits is a creative studio that helps high-growth startups hire at scale. We are former journalists, founders, developers, and, yes, job seekers, working to improve the hiring experience from both sides of the table.

Thanks to Jackson, Lindsay Verstegen, Kyle Barbato, Katie, Brent Fitzgerald, and Archie Puri.

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Job Portraits

Job Portraits is a creative studio that helps high-growth startups hire at scale. We are former journalists, founders, developers, and, yes, job seekers, working to improve the hiring experience from both sides of the table.