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The Organizational Structure of Uber: Beyond the Bubble with Chris Weber

Written by Ben Dietderich

Hello, and welcome to this edition of Beyond the Bubble. I’m your host, Ben Dietrich. On behalf of Career Services, I’d like to welcome you tonight. We’re here with Hillsdale alum Chris Weber. He’s a graduate of the class of 2007. Chris, thanks for joining us tonight.

CHRIS WEBER: Absolutely.

BEN DIETDERICH: So Chris works at Uber, where he is the Global Head of Kitchen Collectives. And we’re going to talk about tonight the organizational culture at Uber and, moreover, relate that to all of our alumni out there. So first, I want to ask you, Chris, how did you get from being a Hillsdale graduate to where you are now?

CHRIS WEBER: Yeah. So a bit of an untraditional path. After leaving Hillsdale, I went to law school at Vanderbilt University. I got to law school, and pretty early on in my stop there realized that I wasn’t really going to be a lawyer. I didn’t really enjoy the coursework—particularly memorable moments in legal writing in my first year, where I knew that this wasn’t the path I wanted to pursue.

That said, I was fortunate to be there on a partial scholarship and decided that I would stick it out, because more education is always better than less. I altered my coursework there to be more focused on the business side of the equation and tried my best to make it a bit of a mini MBA, if you will.

I graduated from Hillsdale and ended up on a pretty large-scale doc review project, which is basically what unemployed lawyers do. And while I was on that project, I was transitioned from actually reviewing documents to more of a project management role, where I was responsible on a daily basis for allocating work to five hundred attorneys across that. And I fell in love with that kind of operational role, that project management or consultant-like role.

So I stayed in that for about nine more months, and then my wife and I decided we wanted to move back to the Midwest, where I have roots. I’m from the Detroit area. She has some roots in northern Indiana. So we moved from Orange County to Chicago. And I started interviewing at a bunch of different consulting firms, probably all the ones you’ve heard of and a bunch you haven’t.

I found myself taking Uber cabs to and from these interviews. And it was back when there was only UberTAXI and UberBLACK. I was taking UberTAXI. And I just found myself talking to these cab drivers, asking them how this new app had improved their livelihoods, improved the way they moved around the city.

Before I knew it, I had fallen in love with this app. And one night I just went to their website to see if they had any jobs that might be appropriate for someone with my skill set—or what I probably foolishly thought my skill set was—and applied. Seven weeks later, a bunch of interviews later, I got a role as a driver operations manager in Chicago. And the rest is history.

BEN DIETDERICH: Wow. Very cool that you found it that way. Since you started there, how do you think the culture has changed?

CHRIS WEBER: Well, to frame the context appropriately, when I started, I was employee 291. There are about 21,000 employees now. So over the last five and a half years, the company has grown by a couple orders of magnitude.

And so the culture, when I started, was very loose. If you needed something, you knew exactly who you needed to go talk to to track that down. And so when you have a culture like that, it’s very informal. Meetings were referred to as jam sessions. That’s something that’s not a secret. Unfortunately, our culture was pretty publicized for a couple of years there.

I think one of the pieces about our culture and that informal nature that has changed dramatically, unfortunately, came about because there were some pretty glaring problems with the company that surfaced in 2016, 2017. And I think those problems were caused because we did grow so quickly. All signs—dollars and cents, rides per month, monthly active users—all of those numbers were up and to the right. The business was great, and that served as a means of covering up some deficiencies in how we ran the business, how people were treated in the business.

And so, unfortunately, it took some stumbles to get us fully back on track, which—of late, I think we’re doing incredibly well on the cultural side. But we had to slow down a bit, quite honestly. I think that was a huge catalyst for some of the more recent success—is just saying, hey, not everything needs to be done tomorrow. Not everything needs to be done at a breakneck pace. Let’s slow down. Let’s put some more formal guidance around this.

We can still be aggressive. We can still be innovative. We can still do a lot of the things—challenge a lot of the assumptions that we needed to challenge to grow this business in the first place— but we can do it in a way that is respectful, rather than rude.

We can do it in a way that is aggressive but not overly so. We can do it in a way that is collaborative rather than disruptive, which has become a bit of a buzzword. When your product’s disruptive, it’s really good. When your behavior is disruptive, it’s not as much.

BEN DIETDERICH: Thinking generally, do you think the benefits of working at a startup outweigh the negative consequences, on a more general front, thinking of what you know from your own experience and what you’ve heard from other startups that are in a similar boat as you, or maybe have grown to a bigger size now?

CHRIS WEBER: Yeah, I would say they only do if you’re willing to be a bit introspective and learn from them. Unfortunately, there are a number of my peers who, I think, looked around and said, oh, we’ve got a target on our back because we are Uber, and we’ve grown so much, and people want to pick on us.

And to a lot of those people, I either would say, or actually did say, no, you have to understand; there are some bad things going on here. This isn’t the media picking on us. There are actually things that need to change. And so working at a startup and going through the highs and lows, it’s not different than working at a Big Four consulting firm.

You’re only going to benefit as much as you’re willing to take a step back every once in a while and go, hey, all this stuff that’s being written about us, that negative comment that I just heard in a meeting—is that how I want to manage? Is that how I want to lead, either while I stay here or at my next company? And if you can step back, and you can look at that, that’s where, even through the worst of times, it’s going to be worth it to be at a place going through some darker times.

BEN DIETRICH: Right. So tell me, for your company and for companies like Uber and other startups, how does one start in a lower-end position, coming fresh out of college, but work your way up the ladder? Because I believe a lot of people think it might be different, because of the culture you have at a younger company that’s more fast-paced, than trying to move up in a more typical, traditional company.

CHRIS WEBER: Yeah, when I started, this was certainly the case. It can still be the case at Uber if you want it to. But there was not a traditional career path at Uber. If you’re a consultant, you start as a junior associate. And then, after two and a half to three years, if you are an average to above-average performer, you become an associate. Then another two to three years, and you’re a senior associate. Then you become a junior manager or a manager. And there’s a path. And in some HR person’s office, there is literally that path printed out, and the progression is known. My wife’s an attorney. She knows that, at the end of her sixth year, she’s going to be a seventh-year associate. At the end of her seventh year, she’s going to be an eighth-year associate, et cetera.

That wasn’t the case at Uber when I started. So, for me, it was a lot more about communicating what I wanted out of my next role to my managers, trusting in them that they would listen, and then just busting my ass. The best thing you can do is communicate what you want, communicate what you’re looking for. Then just make sure that there is no doubt in the mind of your manager that, when that position becomes available—when the next challenge starts to present itself, don’t leave a shred of doubt in your manager’s mind that you’re ready for it, because when you communicate it, of the ready, willing, and able checklists, you’ve checked willing.

By busting your ass, you’re going to show them the able part of this. And then, when it presents itself, that’s when ready matters as well. If you just set to doing your work as best you can do it, and you have a good manager—and I’ve been really fortunate to have many of those in my time here—you’re going to move up, regardless of where you are in any culture.

BEN DIETDERICH: One last question. Is there any type of person, or characteristic in a person, that perhaps would not fit so well in a fast-paced company like the one you work in? Or specific characteristics that you would look for if you were hiring?

CHRIS WEBER: I think the people who thrive here are the ones who are very comfortable with that lack of clarity about where their next role might be or what the progression looks like if they do perform well. They’re the ones who thrive in uncertainty of next steps, but certainty that they’ll be rewarded.

Listen, the person who wouldn’t do well—and I’ll pick on her because I’m married to her—is someone like my wife, who’s a little more risk-averse. She likes the comfort of knowing that, after her first year at her law firm, she’s going to get a little bit of a raise, and she’s going to become a second-year associate. And that’s fine. But what she gives up in that is, if she is a rock star—which she is—she can’t all of a sudden become a third-year after her first year; whereas if you’re a rock star at a company like Uber or at a company that doesn’t have that lock-step, you can jump from first to third and third to seventh much faster than you’d be able to at a more traditional company that doesn’t give you some of that leeway.

BEN DIETDERICH: Very well put. Chris, thank you so much for joining us tonight.

CHRIS WEBER: Yeah, absolutely.

BEN DIETDERICH: That was Chris Weber. We were just discussing organizational culture. He works at Uber. He’s also a graduate of the class of 2007. You’ve been watching Beyond the Bubble, where we talk to Hillsdale alumni and other friends of the college as they give advice to people who are breaking out—or alumni or students who are breaking out into the real world, looking for work. Thank you so much again, and we hope you have a great night.

Benjamin DietderichBenjamin Dietderich grew up in Vienna, Austria. He is currently a junior studying political economy and journalism. Originally from Seattle, Washington, he is an Eagle Scout, former White House intern and radio host at Radio Free Hillsdale. His interviews have been nominated for two IBS awards and have included prominent guests such as Ben Shapiro, Gov. Gary Johnson and John Bolton. Follow Ben on Twitter @ben_dietd.

Published in February 2019.