Why Stripe's Culture Wins

What about Stripe's culture makes the company consistently produce incredible services, with best-in-class quality, at breakneck speed?

I wanted to know. I went on a deep dive into what makes Stripe's culture unique. Here is what I found.

First, if you do not know, Stripe ↗ offers a suite of payment APIs that powers commerce for online businesses of all sizes. Also, as of this writing, Stripe is the most valuable U.S.-based startup. In 2020, Stripe was valued at $36 billion. One year later, as of March 2021, Stripe was valued at $95 billion ↗ and still growing rapidly.

Stripe's mission is to increase the GDP of the internet, and wow are they doing that. Their market is basically anything that involves money on the internet. Their team is world-class, and their product list is growing. In fact, if you have ever purchased from a Shopify store or paid for a Lyft, you have inadvertently used their platform.

Back to the question: what is so special about Stripe's culture?

Short answer: a lot.

Here are a few key ingredients.

Customer Obsessed

Everything Stripe does focuses on creating the best possible user experience.

The question is not, "How can we stay competitive?" or "Does the industry do this?" The persistent question is, "How should this ideally work for the user?" and "How can we make this easier and faster for the user?"

This is reflected not only in how easy Stripe's products are to integrate into online stores, but also in other details. For example, Stripe's CEO Patrick Collison gave the annual keynote speech in 2021 via video. You could watch the video, or, if pressed for time, read the summary ↗. Same with the other Stripe conference talks.

Another example: engineers still meet and speak directly with customers. Everyone, not just customer support, has a chance and is encouraged to interact with and better understand customers.

Fun fact: Stripe was originally a payments services company targeting developers as its primary customers. Back then, around 2010, Stripe's company name was /dev/payments.

Rigorously Thoughtful

Organizations often accidentally, and sometimes deliberately, choose cohesion over correctness. Stripe demands that team members be both open and rigorous. That way, new ideas can be fleshed out, refined, and built.

To that end, the default method of sharing knowledge is writing. Not slide decks. Not videos. Writing.

For example, if you have an idea for a new product, you do not just bring up the idea in a meeting to brainstorm. You write a clear, succinct memo and share it with the relevant stakeholders to read and refine. This approach is just one example of the Stripe cultural processes that consistently lead to better outcomes.

Fun fact: Patrick Collison used to structure his emails like research papers and include footnotes at the bottom so he could provide supporting documentation while keeping the main message the main message.

Rigorously Futuristic

The internet is colossal and only getting bigger. Recall that Stripe's mission is to increase the GDP of the internet. To achieve that mission, Stripe's executive team thinks with a multi-decade strategy.

That strategy includes services such as:

• Tax
• Identity verification
• Card issuing in the U.S. and the E.U.
• Treasury
• Climate
• Payments optimization
• Billing
• Invoicing
• Terminal

The above list does not capture all of Stripe's services. Here is what is most impressive to me: the company is building payments infrastructure for dozens of countries around the world. Stripe is effectively building the financial infrastructure layer for earth.

No joke.

Fun fact: an interesting example of Stripe thinking long term is its investment in Fast.co ↗. Fast.co was a tech company building one-click checkout as a service. Believe it or not, Fast.co was a Stripe competitor. Stripe had one-click payment. But because Fast.co succeeding meant online merchants succeeding, which meant expanding the size of Stripe's market, Stripe led a $20 million financing round into Fast ↗.

Increasing the GDP of the internet indeed.

Ever Evolving

The executive team understands that once a culture has been created, it is not above continued improvement and iteration.

Patrick Collison is specifically clear that culture is required to adapt and evolve as a company grows.

Fun fact: Patrick and John Collison, the brothers and co-founders of Stripe, were only 21 and 19, respectively, when they created the company.

Urgent

Stripe is dedicated to moving very, very fast.

You can see this urgency everywhere. Tripling valuation in one year to $95 billion is urgent. Another example is headcount. Stripe started in 2009 with two people; by 2021 it had 4,000 people working to increase the GDP of the internet.

Fun fact: Patrick Collison has a page on his website ↗ devoted to fast achievements, sharing ambitious projects from history that were done quickly. For example, it took the U.S. government 134 days from decision day to launch and land Apollo 8 on the moon.

Low Entitlement

Put differently, part of what Stripe looks for in potential hires is kindness.

Patrick and John Collison consistently emphasize the importance of hiring people who are smart, interested in long-term difficult projects, and nice. More specifically, Stripe looks for people with interpersonal warmth and a desire to make others around them better, along with technical aptitude that fits the job description.

Radically Transparent

In the early days, Stripe staff BCC'd all other Stripe staff on email ↗. This resulted in everyone having more context, fewer meetings, and ultimately more productivity.

As the company grew, email moved to lists that went to the entire company or a particular team. In practice, this means the company grants a high level of trust and access to employees.

Fun fact: in 2012, Stripe used to employ a concept called FUD at the end of company all-hands meetings: fear, uncertainty, and doubt. Basically, anyone could raise objections that were creating fear, uncertainty, or doubt.

Hungry to Educate, and to Be Educated

Stripe has its own publishing arm, Stripe Press ↗, with great books like Richard Hamming's The Art of Doing Science and Engineering and Jordan Mechner's The Making of Prince of Persia: Journals 1985-1993.

I actually have every book Stripe Press has published. They are genuinely that good.

Stripe Press also publishes a quarterly software engineering magazine, Increment ↗.

Final Thoughts

Stripe's headcount currently sits around 4,000. Throughout my research and reading interviews with dozens of former and current employees, there was a consistent theme: the clarity and depth of thought exemplified by Patrick and John Collison.

Patrick, particularly, has been public with his reading lists, thought processes, and ideas. Both brothers have attracted a genuinely world-class executive team, which in turn has attracted outstanding managers and individual contributors.

My greatest takeaway: long-form writing is a superpower.

Writing spreads ideas. Writing aligns disparate teams. Writing creates clarity across organizations. Writing gets people rigorously into the deepest details of a project.

Wield accordingly.

Be right back. I am off to attach footnotes to my next email.