Alumni @ RopesTalk: Conversation with Sabrina Ross, Uber

In the second installment of Ropes & Gray’s alumni podcast series, Alumni @ RopesTalk, strategic transactions partner Megan Baca is joined by Ropes & Gray alum Sabrina Ross for a wide-ranging conversation about Sabrina’s journey from Ropes & Gray associate to global head of policy for Uber’s ridesharing marketplace. This candid and engaging conversation touches upon the myriad challenges—and opportunities—involved with transitioning from big law into an in-house position.

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Transcript:

Megan Baca: Thank you for joining us for the second installment of Ropes & Gray’s alumni podcast. My name is Megan Baca. I am a partner in our strategic transactions group here at Ropes & Gray. I reside in our Silicon Valley office in California. And I am delighted to have Sabrina Ross here today – she's a friend and Ropes & Gray alum from our IP transactions practice. I feel so lucky that we stayed in touch since Sabrina left Ropes & Gray, and I've been so excited to watch her incredibly interesting career path unfold since leaving Ropes.

Sabrina is currently the global head of policy for ridesharing at Uber. And on this podcast today, we're going to hear about Sabrina's career path, her current role at Uber, pros and cons and challenges of being in-house and changes from her former big law life, as well as hearing about some favorite memories at Ropes & Gray. Sabrina, I'd love if you could introduce yourself. In particular, tell us about your steps since leaving Ropes, and your path to your current role here today.

Sabrina Ross: Well, first of all, Megan, thanks for having me. It's such a joy to be here, and to see your face, as always. I would start by saying that leaving Ropes was one of the more agonizing moments of my career. I had spent five years thinking about whether it made sense to go in-house for my field of privacy law. I felt like there were some really interesting opportunities of practicing that in-house. So when Apple called and offered me my dream role in-house, I thought, “I can't say no to this,” but I was also really sad to leave. So I went over to Apple's privacy legal team. And then when Uber called a little more than a year after that to offer me a chance to build out their nascent privacy team, as well as a marketing and advertising legal team, and a regulatory investigations team, I couldn't say no. So I went over to Uber. I guess that would've been 2015, and I basically have spent four plus years there. Although, as you know, after I had my first baby I did take about a year away and did my own privacy consulting, but went back to Uber almost a year ago now.

Megan Baca: So let's pause there on that one-year interim – basically hanging out your own shingle in some ways. What are some of the pros and cons about that year?

Sabrina Ross: First of all, I did it as I was also becoming a new mom, so it was just a whirlwind year. And I chose my timing well, because it was right as GDPR was about to go into effect, so literally companies could not find privacy counsel fast enough. It was incredibly empowering – and it was easy. I didn't do a lot of marketing – I just told a few friends I was doing it. And work came in, and that was really interesting to see how it worked. Lots of people, particularly women, who had had their own shingle for a while, were really generous with their time, of telling me how to set up, and some of the logistics of it. So that was great.

Megan Baca: Malpractice insurance? Don't you have to carry that all that yourself?

Sabrina Ross: Yes, absolutely. You remember – I didn’t know anything about entity formation, so I was learning a lot on the fly, which I liked. So favorite things – it was empowering. I loved picking my clients, liked choosing whom I worked with, and saying “yes” to projects I thought were more fun. Downsides? Two. It was a little lonely. I love being part of a team, so I missed having a real team with me. And at the same time, I didn't feel ready to be growing a full team. I just didn't want that much overhead. And I didn't love some of the business aspects, like learning how to do billing on my own. I thought, "Ropes, come teach me how to do this."

Megan Baca: So did Uber call you back? You joined them again after that stint?

Sabrina Ross: Yes. I had been doing that for nine months when some friends at Uber called and said, "We created this role for you. You can make of it what you want, and build out an ethical technology practice." I’d still be working with a lot of my favorite people and favorite product executives. And so, again, it felt really hard to say “no.” I had been interested in the policy space for a while, and indeed had been doing a little bit more pure policy work when I was consulting. So over the next six months, I started halftime with Uber while I wound down my consulting practice, and went back in.

Megan Baca: In your current role, tell us about what that entails for you.

Sabrina Ross: Running policy for Uber's ridesharing marketplace, as I alluded to, includes half internal facing work, and half external. So the work involves building out ethical technology practices, whether it's fairness in machine learning, or a principled approach to marketplace governance; working with product leadership. And then a bunch of my time is spent with the World Economic Forum, or the U.N., or others who are working in this space around, “How do companies do this well?” And, “How do you get to a rising tide with all boats across industry?” So that's roughly what I spend my time on.

Megan Baca: In the headlines over the last four or five years, there's been a lot going on at Uber, and a lot of change. How has that affected your job over the years? And how would you advise other lawyers experiencing tumultuous times, or difficult times at companies, on how to make that into an opportunity to grow their own role into something that is really the best for them?

Sabrina Ross: I love that question. I would say being in-house, in general, is more turbulent and political than being at a law firm, especially a collegial place like Ropes. Uber's an extreme example of that, where you particularly see it in the headlines. But to be very honest, I would say Apple and a startup named NAUTO I worked with had similar levels of turmoil, you just didn't see it reflected in the press quite as much. I think someone told me recently that LinkedIn similarly had all of their executives turn over at one point within about a year. So A, it's not uncommon. And I would say if you're going to go in-house, be aware of that, and think about how that fits with your personality.

As for advice for weathering change? This is hard, and I've had an opportunity to learn it several times over at Uber, because Uber, as you say, has had a lot of change. I would say stay clear-eyed and calm to the extent that you can. And that's a lawyer skill, right? Staying calm and, if everyone around you is feeling insecure and uncertain, and you're the person who just remains calm about it, I think that is to your benefit. The clear-eyed piece is, “Do be clear about what will work for you, and what won't.” It may be that there's such a change that you don't think it's great for you, and thinking through in advance what that is, is certainly useful. The last thing I would say about that is that a strong relationship with your business partner is going to be really helpful to you in times of change. So that not only in the good times, like helping you get a major promotion, but in bad times, if for whatever reason you're not going to get what you need from your leadership chain because they are under a lot of political stress, someone else can come in and be a solid voice for you. I would say, to that end, managing executives is an art. And so you have to really put yourself in their shoes about what they're interested in, and that way you can anticipate what kinds of answers and support you need to give them.

Megan Baca: So besides putting yourself in their shoes, any other tips for managing tricky executive teams? Broadening the question to people from other walks of life and other personality types: How have you gotten used to interacting with the non-lawyer sect?

Sabrina Ross: To me, this is a lot about reading a room, because you will have executives who are like a lawyer client, who want the details – they might want to see the legal memo. And then you have other executives who basically just want the answer, and they will be annoyed if you try to slow down with a lot of the reasoning. So reading the room – figuring out what level of detail they want. And they'll also have questions. At a law firm, very rarely was I asked to put a monetary figure, for example, to a different set of choices. And now I do that all the time. "If we take path A, the downside risk is this. If we take path B, the downside risk is that. And same on the upside.” So just learning the types of questions that they're going to ask that are not as core to the bread-and-butter legal analysis.

Megan Baca: That is so interesting. Let's talk about moving from big law into the in-house world. What are some of the biggest challenges? Learning these personality types is one. But what else has been interesting or a growth curve or difficult for you?

Sabrina Ross: I remember Ropes hosted a dinner two years back for new in-house counsel, and I still remember the vibrant discussion we had about this. I would say three things that are challenges, but they're joyful challenges. They're some of the fun areas of learning.

One is exactly what you referred to where you have many more stakeholders to manage and learning very quickly, “What do those stakeholders want and need?” Another is that, typically, you're the decision maker on most decisions in your day. And so whereas, as an associate at a law firm, maybe you're the architect of something, and a partner approves it on the way out the door, but then the client ultimately usually decides. When you're in-house, I'm making at least five major, substantive decisions a day, and getting comfortable with that. And then, lastly, is that risk tolerance has varied for me, both among my individual managers and in company culture. And so with one manager, you might bring them a recommendation, and they would say, “you've spent too much time researching this. You should've made the decision faster.” And another manager might say, “Whoa, this is a really big deal for our company. Let's slow down and get a second law firm's opinion.” So again, just getting used to really different styles of approaching problems.

Megan Baca: Backing up to the Ropes & Gray days, can you tell us how you ended up at Ropes, and also how your practice group decision to get into privacy evolved?

Sabrina Ross: I'll take them in reverse, because I fell into privacy law by luck, when I graduated in 2009. I went to Sidley Austin in D.C. first. And there was an amazing partner there named Ed McNicholas, who is now at Ropes. And I just fell in love with how quickly that area of the law was changing, with the variety of work that comes across your desk. And so I fell into privacy. Sidley at the time was not particularly strong on transactional privacy, with the bread and butter of negotiating contracts with customers or partners, and Ropes was really strong in that area. And at the time, I was looking to build out other parts of their privacy compliancy counseling. So it was an amazing opportunity for me to come learn more about privacy transactions. At the time, I think you and Jim DeGraw were looking for somebody mid-level, and so it felt like a really easy choice.

Megan Baca: And now Ed is here, so it's full circle. Any favorite Ropes & Gray memories?

Sabrina Ross: Well, my favorite one might be the time that I came to visit the Palo Alto office, (I was based in San Francisco). And you were wearing a full-on business suit, but hiking boots, because you were getting ready to go hike in Machu Picchu. And I thought “This is such a perfect embodiment of someone so professional but who also has a personal life.”

Megan Baca: That's hilarious. I forgot about that. So what attorneys stand out to you? One of the wonderful opportunities of being at a place like Ropes is the network that you build. But any memories of particular people that stand out in your mind?

Sabrina Ross: Yes. Jim DeGraw, who I mentioned earlier, and Ed Black, both of whom managed to be relentlessly excellent, but also real humans. I still remember that Jim would come by my office every morning and ask how I was, and he really meant it. And that was the kind of lawyer I wanted to be. And at the time, you were a very senior associate, which is a notoriously stressful time in law firm life. I think you were also getting close to being a new mom, and yet you were still generous in mentoring younger associates. And again, I thought “This is a model that I can see myself living by.”

Megan Baca: How did Ropes prepare you for your future career path? How has the training really panned out for you? Are there skills that you picked up here that have been most important to you?

Sabrina Ross: Yes, there are hard skills and soft skills. The hard skill, which I mentioned, was transactional privacy, which when I was interviewing to go in-house, each company kept telling me, “We want you to have more transactional privacy.” And I still use it, very regularly. And you also taught me about other kinds of transactions, which was helpful context to have, because that hadn't been part of my first few years of lawyering. In the softer skillset, I think efficiency and collegiality, and things that I come back to all the time as a core part of how I practice. When people come to me and say, “Now I'm thinking of actually going to a law firm. I haven't been before, but I feel like I want more of that rigorous, legal training.” I always say, “Absolutely. Do it. You get great training.”

Megan Baca: So for those folks who do start out in big law and are looking to move in-house, what advice do you have for them?

Sabrina Ross: At a law firm, you get to work with so many different people, and different kinds of companies, and different kinds of partners. And I would say take advantage of that, because once you're in-house, you can be susceptible to tunnel vision of the company, or tunnel vision of your particular manager. So I felt very lucky to work with a variety of companies and people, and that helps you suss out what you like and what you don't like. If you decide that you're going to go in-house, I would say talk to at least five in-house counsel because there's such a variety, as you say, of cultures, management styles, approaches to budget, and you have less choice once you're there – you're locked into that company's approach more or less. And so talk to people who will give you honest feedback about the pros and cons of their company.

Megan Baca: That's great advice. In your role now, I assume you work with a variety of outside counsel. So it's always interesting to me to ask the question of “What makes for really great outside counsel? What causes problems for you with outside counsel? What can folks can do better?” I know we are all always trying to improve on what we do, and make sure we're meeting our clients' needs.

Sabrina Ross: I just did a whole panel on this with the ABA, so I could go on for an hour, but I won't. I would say there are a couple of basic things like ensuring that you can meet your client where they are in terms of technology. I'm embarrassed to say this, but being able to use Google Docs, or Zoom, or whatever makes the speed and efficiency on their side work is invaluable, and I think continues to be challenging. And then if your client isn't telling you what they want clearly, ask a lot of questions. I love folks who just ask, “So is it a deck that you want, or a memo?” because the deliverable might be going to a variety of stakeholders in-house, and it’s important to get that right. I've also had firms ask for feedback after the fact, which I think is really effective. Recently a partner I worked with asked if she could request feedback from an executive we had prepared for a depo together, for feedback on the depo prep. And he gave her a long, thoughtful response, most of which was really good, but then a few little small bits of feedback. And that shows how much he values her as a partner, that he took the time to do that, and helped her move from “great” to “excellent” in terms of knowing how execs like to be prepped on this particular thing.

Megan Baca: So now, to wrap things up, I have some unscripted questions. It’s a lightning round, so quick answers off the top of your head. Tell me what your ideal vacation would be.

Sabrina Ross: I just got back from Vancouver Island, where we spent five days essentially eating and kayaking, and for those who can't see me, I'm eight months pregnant, but it turns out that spending time just kayaking and eating was good for that.

Megan Baca: Speaking of eating, if you had to eat one food every day, what would it be?

Sabrina Ross: Probably my husband's homemade soups.

Megan Baca: If you had three hours of kid-free, husband-free, work-free, obligation-free time, what would you do?

Sabrina Ross: I'd probably just roam around a part of the city that I haven't been to for a long time and stop in slowly anywhere I wanted.

Megan Baca: If you weren't a practicing attorney, what would you be?

Sabrina Ross: Well, interestingly at the moment, I'm not practicing as an attorney, so maybe I'm living that dream doing policy.

Megan Baca: “Ropes & Gray is...”

Sabrina Ross: Delightful.

Megan Baca: Thank you, Sabrina, for joining us. This has been really fun. As you know, we really value our alumni community here at Ropes & Gray. And hearing about what our alums are doing out there in the world with their phenomenal career development is so exciting. So for any alumni listening, obviously just stay in touch, and visit us at alumni.ropesgray.com to stay up to date on alumni news, firm news, and things going on with lawyers at the firm. Thank you so much for listening, and stay tuned for our next installment.