Scalying New Heights: How Company Culture Impacts Engineering, Reliability, and More at Uber and Airbnb

We often take the culture of a company for granted, and we don’t pause to think about all of the implications a culture can have — not just on the people and day to day work environment, but on the products as well. Donald Sumbry recently joined Airbnb as Head of Reliability Engineering, and he held a similar position at Uber for four years. His organization is responsible for two main things: the overall reliability of the Airbnb platform and running the internal production platform. Sumbry, as he prefers to be called, is also a member of ENG, a peer network of VPEs and CTOs from leading SaaS companies. Reliability Engineering’s customers include both the hosts and guests that use Airbnb, and the technology engineers who operate their services internally. The mandate of the team is to provide a great experience for all of these users.

Sumbry made the switch from Uber to Airbnb early in the global Covid 19 pandemic.  “If I was a fortune teller, and I could go back in time and try and predict what would have happened over the past five months, I don’t think I would have even gotten close. It’s been one heck of an onboarding experience. I started out having the typical things that you’re trying to do when you start: meeting peers, your team, and working on the vision and the mandate for the org.”  Then one month into the process, everyone went home to work and his carefully formulated on-boarding plan had to change completely.  

“I had the challenge of continuing to onboard while also figuring out how to get our team to work while we were all quarantining from home. It’s not quite the same as working remotely, because there’s no daycare for team members, nothing’s open, and maybe your significant other is also working at the same time. So you’re just trying to figure out all of this stuff, while the company’s also figuring it out at the same time.” It was a lot of trial and error, and the strong culture of Airbnb was a big help. It’s very relationship focused, and Sumbry was given the time to learn and integrate before he had to drive change. One of the interesting preferences he developed as he got to know his team, and they got to know him, was around video conferences.

I’m not a fan of using virtual backgrounds. I think by not having it, you welcome people into your home.

This was made more challenging because the products — and the cultures — of Uber and Airbnb are very different. With Uber, the experience is fast. “You’re getting into somebody’s car for a short amount of time. The average transaction is under $20, so you’re in and out fast. Everything is transactional in nature. Whereas on the other side of that, Airbnb is a hospitality company. It’s all about belonging.”  

“When you’re joining a new company, you need to take the time to understand the culture and what makes it different, and not jump in and try to make a bunch of changes right away.” 

This is good advice for anyone making a management change — whether CEO, executive, or manager. I’ve changed jobs and industries several times myself and I always start with a listening tour that include direct reports and peers, top talent, customers, partners and other stakeholders.  My own rule is to try not to make important decisions for at least 30 days, and a quarter is even better. This means people, process and product. Sometimes what seems like a good idea — or vise versa — isn’t once you have more context.

Prior to joining Airbnb, Sumbry spent four years at Uber, including a roller coaster 2017. It was there he learned about leadership. In early 2017 the Susan Fowler blog post went viral. “I realized that I was so knee deep in the work, and there were so many problems to solve, that we attracted people that just jumped into a problem. So it was easy to miss some of the things that were happening around you. And if there’s one big lesson I’ve learned from that, it’s that you’ve got to pay attention to everything, you can’t be super focused on one specific problem. You’ve got to also be paying attention to everything that’s happening across the board.” 

They had a saying at Uber. 

Anyone can drive the ship when the sea is calm. True leaders emerge when the seas are rough.

Everyone worked hard to create positive change across the whole company. “I’m really proud of what we did there over the years. I feel like I’m one of those people that left the company in a better situation than before I started. I’m definitely proud of that.” 

He’s also proud of how they improved global reliability. Uber had thousands of microservices, and measuring and reporting on the availability of all of that infrastructure, in a way that was simple and easy to understand, was a big challenge. The company had tried three times to report on a single global availability metric. “One of our big accomplishments is we got the company to the point where we could report on global availability in a very clean way. It was a cross company effort, and the industry in general is moving towards measuring availability in the same way.”

At the same time, the team changed the way production engineering worked at Uber and moved to a team-based approach where Site Reliability engineers were paired with different parts of the business. It resulted in happier engineers because people were able to do both software development and operational work. Sumbry is proud but not confused about the impact he had at Uber, which he took with him into Airbnb. 

Avoid the savior complex. It takes a team.

Even if you’ve seen the same problems before — like in the transition from a company like Uber to Airbnb — the reality is that each company and culture is unique. “Take the time to learn first and then apply your own unique knowledge and experience on top of that. 

Sumbry sums it up with a lesson from the real world outside of tech.  “I learned to snowboard as an adult, and the first time I tried it, I loved it. But of course I fell a lot. And the reality is, everybody falls. The way that someone learns to snowboard is the same way they approach things in general in life. Some people fall repeatedly, and they’ll get frustrated and blame it on everything except themselves. On the flip side there are people who fall, then look up and see all these other people snowboarding, and they’re like, if those people can do it, there’s no reason why I can’t do it as well. So they watch, learn and push themselves.” 


About the Author

Christine Heckart is CEO of Scalyr, which provides a log analytics SaaS offering and an Event Data Cloud, which delivers analytics as a service for event data and can be integrated with existing dashboards, user interfaces, and custom applications. Scalyr also curates a peer-network of VPEs, CTOs, and top technical executives at leading SaaS companies called ENG (Engage, Network, Grow). To learn more about Scalyr or to join ENG,