What Stripe Gets Right


I recently made the decision to leave Stripe and join Macro Oceans full time. This was a difficult decision and was more about not wanting to miss the opportunity to build Macro Oceans rather than quitting Stripe.

While I was working at YouTube, I began doing something that really helped me: team and company cultures the way I would about a friend. They have a lot of good qualities and some faults. [0]

But when you’re working somewhere everyday, even little faults can be really grating, the way that you might have a friend you really enjoy who you can’t stand after two weeks traveling together.

Part of my breakthrough was to spend more time focusing on the virtues rather than the faults. I also began to accept that the faults developed over time and would take time to change. This made it easier for me to navigate through the things that drove me a little crazy: it was part of what made the place what it was.

With this context, I want to reflect a little bit about what Stripe gets right, if only so I can remember it. These aren’t the only things about Stripe or a balanced picture of what it’s like to work there, but the things I want to remember and to emulate. [1]

  • Ambition: Stripe is a place where you are asked to do work that changes the world. Even if you’re starting small, you’re looking towards the bigger picture and asking how you can do more, faster. This can be uncomfortable, but having worked places where this wasn’t a part of the DNA, I really appreciate it.
  • Brand building: Stripe has mastered the art of elevating their work through story telling and myth making. This is truly cultural. I spent more effort polishing a demo for an all hands than I did for external communications at prior companies.
  • Talent: Somewhat related to the brand building, the level of talent at Stripe is the highest of any place I’ve worked. [2] The conversations within my team happened at an incredibly high level, which is infectious. It’s fun to work somewhere where you are pushed to do your best work just to keep up with others. Somewhat related, I have so many people I’m going to miss working with.
  • Engineering culture: The craftsmanship of the engineering teams in particular will always stick with me. Stripe is not a place where the user experience is pushed off onto Product Managers and Designers. This is modeled by senior leaders — engineers are expected to care about making something awesome. As a product manager, this makes my job so much easier. I still have to make the case for priority (should we solve this problem next) or return on investment (is this worth the time we’ll spend on it), but never for quality as a principle.
  • Responsiveness: Individual Stripes react quickly to problems. You see this on Twitter where posts about problems lead directly to responses. Stripe as an organization reacts to changes, be they market conditions or other strategic factors. New information is put to use quickly.
  • Ideas: Stripe is a very philosophical place. One of my favorite parts of working at Stripe is a slack channel that is devoted to strategy, but the art of doing great work, building a great company, and where progress comes from. Whenever I was in the midst of a particularly fast paced project or under a deadline, this slack channel kept the creative aspect of the work in my mind.

0: At every company where I’ve worked as an adult, with one possible exception, the good qualities outweighed the faults pretty significantly.

1: I enjoyed my time at Stripe and on some level wish it had been longer. If you’re considering a job at Stripe and want more detail about my experience, feel free to reach out: jdillaxyz@gmail.com.

2: The possible exception here is Bain. The difference that at Stripe the talent level is high and distributed across functions whereas Bain everyone basically did the same thing — corporate strategy.

Liftoff by Eric Berger


I’m late to link to this, but here are my Book Thoughts on Liftoff by Eric Berger, which is about the early years of SpaceX:

I picked up this book to better understand how big leaps forward in hard tech innovation happen, but as I got to the end, including the annecdote above, all I could think about is whether or not history is contingent.

I didn’t put this in the Book Thoughts post because it somehow felt out of place, but here are the factors that seemed most essential to SpaceX’s success (not necessarily in order):

  • Have a big mission. This helps to pull in talent in a way that smaller projects don’t

  • Be as iterative as possible in taking on technical challenges. Your speed of failure is inversely correlated to your speed of learning. In a way, the culture of tight deadlines at SpaceX helped with this because it forced the organization to learn from reality rather than debate.

  • Either buy things off the shelf or make them yourself. If you try and find a middle ground between off the shelf and fully customized, you risk getting neither of the benefits.

  • Early customers are in many ways investors. They need to be treated as such, since they’re likely to not get the full benefit of your company existing.

What Google gets right


It’s somewhat popular now to throw shade at Google1, particularly as a place to work: it’s big and bureaucratic, it’s not a good place to start your career and so on. I understand this impulse, but I disagree with it. Particularly for its size, I think Google is really effective company and rather than bagging on it, people should think about what has allowed it to stay as effective as it has despite being as big as it is.

I think people typically misunderstand Google in two key ways that then causes them to misjudge it:

Google isn’t a start up. It is one of the largest companies in the world, with more than 150,00 employees and about as many contractors. Its peer companies, in terms of number of people, are General Motors, Darden Restaurants, and Aeon, to name a few. Just to try and put this into context, my entire current company (Stripe) is smaller than my product area at Google (YouTube).

Because many people still remember Google as a younger, smaller company, they judge Google’s agility against much younger and smaller companies instead of against its peer set. Certainly it’s less agile than it once was, but on a size adjusted basis it’s one of the most agile companies in the world.

Google is much more decentralized than a typical company. I joke that the best way to think about Google is a university attached to a money printing machine. Like a university, Google has many different departments that really aren’t trying to coordinate with each other. This is by design. You may not agree that this is the right strategy, but I think you have to understand it to effectively evaluate the company.

So what does Google get right? Here are four things that come immediately to mind for me.

  • Product focus: an incredible amount of attention is paid at all levels of the company to the specifics of the product — what it actually does for the user. As a typical YouTube product manager, I regularly had to review product details with head of product, head of engineering, and other very senior leaders. These leaders, several levels up from me, were more well versed in the specifics of my product area than my manager or my head of product was at much smaller companies. This product focus isn’t top down, but cultural, which makes it much more powerful. People at Google encourage other people at Google to use their products and have opinions about how they should work.

  • Distributed decision making: For me, this is where the misunderstandings about Google begin to really show up. Google is incredibly effective at decision making for a company of its size. An incredible amount of relatively high stakes decisions can be made at Google very quickly. As an example, if my team made a product change that positively impacted our key metrics, I could have that launched globally to billions of people in two 15 minute meetings.

    Additionally, Amazon gets a lot of mileage out of the Bezos API mandate, but it’s pretty common at Google as well to have some internal help text and an API be all that is needed for different orgs to collaborate. Additionally, as long as team incentives are aligned, it’s pretty easy for individual teams in different orgs to collaborate without any formal sign off from their Product Area Leads.

    Where things do get complicated at Google is major collaborations across product areas where there is a lot of ambiguity. So for instance, if I wanted to get a couple of teams from Google Maps and a couple of teams from YouTube to collaborate on a set of features with high but uncertain potential, I knew that this was going to be a difficult and challenging path. And yet, as difficult and challenging as this would be, on a per person basis, it was much easier to get collaborations like this to happen than at <1,000 employee companies that I’ve worked at.

  • Talent friendliness and talent development. The slides and free lunches are really easy to make fun of, but Google legitimately tries to be a good place to work. The default policies are sensible and friendly to employees. When they make a change, they try to make sure to not punish their people along the way. It isn’t perfect, but especially for its size it’s really good.

    Beyond its policies, Google is a great place to develop your career if you’re thoughtful about it. As long as you’re keeping up with your day-to-day work, you can get exposure to almost any career path as a twenty percenter (once again, think of a university rather than a traditional company). Here the breadth of Google’s product offerings is a real asset; you can get exposure to almost any discipline or industry without changing companies.

Caveats: I worked at Google for about two and a half years, entirely at YouTube and mostly in the Zürich office. Google is a big place that varies a lot by team, so it’s entirely possible that my experience is an outlier. There are also many legitimate criticisms of the company that I’m not the best person to articulate.

Notes: 1: Alphabet