Head of Operations at Upwave, Katie Harper, sat down to chat with Scott Gorlick about his time at Uber, how to break into startups, and what’s got him excited about the future. Gorlick joined Uber in 2012 as one of the first 100 employees and spent six years scaling the company’s operations. After two years helping to run the Atlanta business, he moved to San Francisco to serve in a variety of business operations leadership roles. During his time at Uber, the ridesharing firm went from 10 cities to more than 500+ cities in over 70 countries. Since leaving Uber, Gorlick has moved back to his home state of Florida and is focused on investing in the next generation of startups.

Katie Harper: What led you to Uber?
Scott Gorlick: As a senior in college, I said my dream job would be at the intersection of business and public policy. After graduating, I started consulting for Deloitte, where I was focused on strategy and operations. One rainy night in Chicago, we were running late for a client dinner and couldn’t find a taxi anywhere. I had just read about Uber, so I downloaded the app, pressed a button, and a black car showed up to take us to dinner. And it was fifteen dollars. I was hooked and instantly knew that I wanted to be a part of this company. Very late that night, I shot over a cold email.
After going through a couple rounds of interviews, I flew out to San Francisco to meet with the team. When I got there, I think they were all a little surprised by how young I was. Barely twenty-three at the time, I blurted out, “I’m old enough.” One thing led to another, and I got the chance to join Uber and help start the business in Atlanta. So, in a circuitous and weird way, I ended up right at the intersection of business and public policy just as I had wanted.
What prepared you for the role?
Nothing I had done up until that point could have truly prepared me for Uber, but I do think there were a couple of things that I learned at Deloitte that were incredibly valuable. First, learning project management and how to structure my thoughts logically helped me move faster at Uber. I fully believe that when you’re organized, you can do three times more work. Second, I was also on the road for the vast majority of that year, and I learned to get comfortable being uncomfortable. It sounds crazy, but not knowing where I would be traveling that week, plus the last-minute booking of flights, hotels, and then changing everything all over again, left me oddly prepared me for rolling with the punches at a fast-growing startup.
How did your role at Uber evolve over time?
When I joined, I started and helped run the Atlanta market. Very few of my friends had any idea what Uber was at the time, and we heard over and over again that Atlanta was “too spread out” and a “driving city.” Our first goal was to make sure that riders could get a car whenever they needed one. It was an intense, operations-heavy role, but I loved every single second of it. We stayed incredibly busy hiring a team, pitching drivers to try out our platform, making sure we had enough cars out 24/7, running analyses to see where we could get better, and answering every driver question. In about 2 years, we had scaled Atlanta up to a very significant business.
In mid 2014, I moved to San Francisco to take what I had learned in Atlanta and use it to help scale our global teams. We found that 95% of cities were the same across the board, but that last 5% was very localized. To succeed in those markets, we needed to get there early and have a presence on the ground. That kept me occupied for a while, and then I led teams that worked on special projects, include pricing, operational efficiency, strategy, and expansion. I loved that role because we had a great team and were always working on ten different things at the same time.
When did you know you had joined a rocket ship?
I don’t remember if it was a single point in time, but there were definitely moments. From the early days, Uber was a product people loved. Every time someone tried to shut us down, our riders and drivers stood up in a way that inspired us to keep pushing. When UberX got better, faster and cheaper than a taxi, I knew that the market for our product was huge.
Which parts of the growth were most painful?
In the early days when we were just starting out, everything was scrappy. We had a hundred people at the company, and we were constantly outgrowing the processes we had built the week before. Fortunately, Ops and Engineering at Uber worked well together, and we were able to partner to build some amazing tools that made it easier to grow the business.
2017 was also incredibly painful for the company. Up until that point, Uber had grown quickly, but we were an 8-year-old company in a 60-year-old company’s body. We had optimized for growth and scale at the expense of our culture. A lot of things were broken, and it was a really tough year. While it was a rough time for us, I’ve seen a lot of change at Uber and I’m encouraged by the progress. We’ve still got ways to go, but the team is incredibly resilient. I think Dara and the team are doing a really great job moving Uber forward and are ultimately going to take the company to the next level.
If you were put in a similar position at a similar company now, what you would want to tackle first?
If I was starting at a company like Uber now that is focused on a particular marketplace with supply and demand, I would figure out which side is harder first and focus first on that. For Uber, our business does not exist without our driver partners. When we started in Atlanta, there were maybe a thousand limo drivers in the entire city. We were going to get a lot more riders than that, so for us to be able to scale, we needed some way to grow the number of limo drivers in the city. When you build any marketplace, you have to be creative about how you grow the business.
What advice do you have for someone trying to break into operations?
Read up and see what companies are interesting to you. [Here’s Scott’s recommended reading list.] When you find a company you like, you need to get your foot in the door. Odds are good that the founder’s email address is (first name)@company.com. Hit them up over email, Facebook, or Twitter and try to start a conversation there. These people are spending hundreds of hours building brands, so they truly want to hear from fans. If you like the company, you shouldn’t be afraid to show it.
Next, realize that the role that you want may not exist yet. You might have to create it. When you’re talking to founders of companies that are really small, your skillset might not match a job that’s posted; they’ll need engineers but not operations people. Find a way to be helpful. We had people drive for Uber who provided feedback on the experience. If you’re looking at a consumer product company, try their product. Showing that you’re willing to put that effort and sweat on the table goes a long way. Ultimately, what it comes down to is hustle.
Since leaving Uber this year, you mentioned here that investing is next for you. Why do you want to be an angel investor?
I like venture for a couple of reasons. First, I like solving interesting problems. I think the world fifteen years from now is going to look a lot different than it does today. A lot of that progress is going to be driven by the hard-charging entrepreneurs that create companies in the next several years. As an angel investor, I can invest in and advise companies that I think are going after some of the biggest opportunities. Second, I like helping people build companies. Working side by side with people to scale their businesses has always been fun for me. I think that a lot of the things we learned scaling Uber are applicable to other companies starting out. Third, working at Uber was a life changing experience and all it took was a few people taking a bet on me. And that’s what angel investing is. There are a lot of amazing founders out there and all it really takes is for someone to believe in them.
How’s that change going for you so far?
I’ve invested in several companies I’m very excited about already, and we’ll see how it goes. Venture is a long game, and it can take years to know if an investment will be successful. I’m most interested in companies that are in the marketplace, direct to consumer, eSports space, or operating out of Florida. I strongly believe that not all great tech companies have to be built in Silicon Valley, so I joined Florida Funders as an Operating Partner and will be a part of First Round Capital’s Angel Track this fall. If you’re working on a company in any of these spaces, would love to chat!