Alumni @ RopesTalk: Conversation with Jacob Comer, NovaQuest Capital Management

In the latest installment of Ropes & Gray’s alumni podcast series, Alumni @ RopesTalk, asset management partner Jason Brown interviews Jacob Comer, general counsel and chief compliance officer at NovaQuest Capital Management, a leading investor in life sciences and health care companies. Jacob began his career at Ropes & Gray in 2003 as an investment management associate and has since taken on legal, regulatory and compliance roles for a private equity firm, venture capital firm and hedge fund. Now at NovaQuest, Jacob talks about the challenges of moving in-house, interviewing for and accepting a new job during the pandemic, his experience working at Ropes & Gray, and his professional influences. Jacob also discusses what he looks for when engaging outside counsel and offers advice for attorneys considering a move in-house.


Podcast: Alumni @ RopesTalk: Conversation with Alon Rotem & Brianna Humphreville, thredUP

Time to Listen: 40:26

In the latest installment of Ropes & Gray’s alumni podcast series, Alumni @ RopesTalk, health care partner John Chesley interviews Alon Rotem, chief legal officer at thredUP, and Brianna Humphreville, associate general counsel at thredUP. Alon and Brianna met as summer associates at Ropes & Gray in 2006. While their careers took different paths after leaving Ropes & Gray—which they discuss in the podcast—they reunited at thredUP, an online consignment and thrift store. They talk about what it’s like to be lawyers at a tech company that’s environmentally focused, and share their experience of taking thredUP public during the pandemic. Looking back at their time at Ropes & Gray, they reflect on the cultural similarities between Ropes & Gray and thredUP. Finally, they give some advice for outside counsel looking to work with thredUP.

Ropes Alumni


John ChesleyJohn Chesley: I'm fortunate today to be joined by two former colleagues, Ropes & Gray alums Alon Rotem, who was recently promoted to chief legal officer at thredUP. Congratulations, Alon. And Brianna Humphreville, associate general counsel at thredUP. Let's start with your careers, post-Ropes—what was the most challenging thing about going in-house from law firm life?

Alon RotemAlon Rotem: I went from Ropes & Gray to another firm, and from there, I went in-house to a client. We had done a couple of financing rounds for that client, and I felt like I knew them pretty well. But once I got to the company, the eye-opening experience for me was learning how I didn't actually know how technology companies were structured internally, how product managers worked with engineers, the marketing team and the finance team. How did they collaborate? What were their struggles? Having been the first lawyer at the company (and also the first general counsel at thredUP), a big part of the role and a big part of the challenge is teaching people at a company what the lawyer's role is, because many of them have never worked with a lawyer before. Some of them thought I was like an internal affairs police officer who is looking to bust them on something they may be doing that may or may not have been nefarious. But the thing I tried to reassure people with was, "Yes, I'm here to make sure there's nothing unethical happening, but more than that, I'm really the bodyguard for the company." We have a set of objectives that we want to achieve and my job is to help the company achieve those objectives, both in the short-term and the long-term, and just helping people think a little bit more long-term was that challenge. Brianna, how about you?

Brianna HumphrevilleBrianna Humphreville: For me, having a manager was the most difficult challenge about going in-house from a law firm. At Ropes I had the ability to work for various partners and senior associates, not only in New York, but across all of Ropes' offices. There wasn't only one person that I had to answer to. When I left Ropes to work for a large, public-traded company I quickly understood how to work with the business team, but I couldn't really figure out how to work with my manager. I didn't understand how to have an effective one-on-one meeting. Over time I was able to crack that, but at first I didn’t understand how powerful one manager can be to your career. They can make or break it for you, and it was tricky for me to navigate that at first.

John Chesley: thredUP is a high-quality used apparel online retail company, if I've got that right. It's a fascinating blend of marketing and business all using what I think of as quintessential 21st century technology to make it happen. What led you to that company, to thredUP?

Alon Rotem: I think you described it mostly right. It's definitely a fascinating business in the sense that it's disrupting traditional retail by leveraging a managed marketplace and technology and all of that, but for me, it was really about the people. Just like my first general counsel stint, thredUP was a prior client of mine, and that's how I initially established that relationship. When it was time to look for that next role, I knew that thredUP was also looking for its first lawyer. So I set up a meeting with James Reinhart, our CEO, and we went to lunch and just immediately fell into our old groove. We were talking about technology and how much the company had progressed over time, and all the interesting challenges that they were having. From there, I got to meet the rest of the executive team, and that's really when I fell in love with the company. I just had a sense that I was going to learn from everybody around me. They were all very impressive in their own right, and so passionate about the company and its mission. Knowing that I was going to be in that position to learn from talented leaders like that, basically sold me on it, and from there, I basically fought for the role for about a month until the board of directors was finally convinced that I could do the job.

Brianna Humphreville: The reason I joined thredUP is because of Alon, and I'm not just saying that because he's my manager. Alon and I met back in 2006 when we were summer associates at Ropes & Gray. We remained connected through our professional networks, even after we both left Ropes to do different things. In 2019, I was working at another company in-house, and after successfully launching a new product I just knew it was time to try something else. I saw on LinkedIn that Alon was looking to expand his team so I reached out to reconnect. And the rest is history.

John Chesley: That's a great connection that the two of you have had over time. I want to hear more about how working together has been, particularly during this period of the pandemic.

Brianna Humphreville: Obviously, with the pandemic, we started to work remotely. I had only been at thredUP for a very short time before the pandemic hit, so my experience at thredUP is primarily working in a telecommuting manner. But Alon and I have a lot of shared values and goals, and a lot of shared background that we learned at Ropes and that helped us build our team. At a personal level, we both have kiddos that are about the same age. I think one of the coolest things from a personal perspective is Alon and I, back in the early days of the pandemic, when it was super hard on kids, were able to get both of our girls connected on the phone together and share their experiences back and forth.

Alon Rotem: Just stepping back about thredUP itself as a business—thredUP’s a managed marketplace for secondhand clothing. That means all of the supply that we end up selling online comes from people's closets through a clean-out bag. We use technology and operations expertise to help us scale that so we can do millions and millions of items each year. The exciting part that connects to the mission of thredUP is that this scaled solution, bringing secondhand clothing to the masses helps reduce the impact of retail fashion on the environment. We've done it as a core business for a long time and now we're trying to extend that to the rest of the retail industry, and that environmental mission has accelerated in the pandemic. Even from a corporate law standpoint, we know that ESG issues are coming to the forefront—environmental, social and governance issues—and if you look at our S1 that we drafted for the IPO, I think we were the first company ever to have a stand-alone ESG section. Not only did that connect to our mission, but the timing was right for it. The other thing is the overall transition to online and eCommerce for retail. I remember when I started four years ago, our walking around statistic was that three quarters of retail was still happening in brick and mortar stores, or even more than that. I think what we've seen through the pandemic is a multi-year acceleration of online, and that's played right into thredUP's strategic business model.

John Chesley: thredUP recently went public—what has changed and what's that transition been like?

Alon Rotem: Yes, lots of growing and changing. I can put it in a sports analogy context. thredUP's 11 years old. We essentially are like a talented young athlete—good speed, good strength, good overall raw talent. Then, all of a sudden, we get invited to this high-level tournament, the public company tournament, and it feels like we're going through puberty all at the same time. We're growing and changing week by week, and all the while, still just hoping we're worthy of being on this bigger stage. How that plays out outside of that analogy is, we've had a bunch of projects that we've been working on to get us to be public company-ready and really think about the company, both in that short-term window, like how are we going to actually get to the IPO and hit the capital markets? But a lot of the things that we're doing in order to get to the IPO are things we should be doing anyways to set us up better for the long-term, in the sense of implementing better controls, having a tighter cap table, and using a bunch of new vendors to do things in a way that's scaled for the long-run. Getting better at planning for the short-term and the long-term has been the key learning through the IPO process.

John Chesley: What you've described reminds me of a concept that Howard Gardner, the sociologist, articulated called "Good Work," something that engages you personally at a level of complexity that's interesting and that has a social significance that you can feel strongly about and committed to. So it's a great company, great model, and terrific to see it recognized by the public markets.

Alon Rotem: Actually, John, one thing I would also say is just having gone through this IPO process directly through the pandemic has been one of the things that kept me sane. We're all stuck in our home offices, and I know I'm looking around the four walls of the room that I'm in right now and I know how many hours I've spent in here over the last year. Working for a company that you believe in its mission and like working with the people, that's incredibly special. But to have a project like this, where it's been a long-term goal of mine, that's really helped keep our spirits up over the last year.

Brianna Humphreville: I completely echo Alon's sentiments. When we set out to do this, and then the pandemic hit, I thought, "Wow, this is kind of crazy. Can we really do this, in this ever-changing world where Alon and I are also responsible for keeping our employees safe, monitoring all the new regulations that are happening during the pandemic, and helping our distribution sales? Can we manage all of that and tackle the IPO?" So it made me a bit nervous at first, but it definitely, in the end, kept me focused and gave me a sense of purpose.

John Chesley: Good stuff, thank you. Teamwork is clearly something that's in your background and something that you depend upon in the work that you're doing. Let's go back to your days at Ropes—maybe start at the very beginning. How did you pick the one true firm, and how did you end up in the practice group that you were most active in?

Brianna Humphreville: You might not be surprised that I picked the law firm because of the people. Prior to law school, I worked as a paralegal at a couple of large East Coast law firms. So I had a taste and an understanding of how those firms ran and what it might be like if I joined as an associate. I decided, when on-campus recruiting came around, that I was looking for something different. I found Ropes really compelling because it was just starting its New York office at the time and I thought that the smaller atmosphere might be a good fit for me. I started in a general corporate pool, so for the first two years I took on any corporate project that came my way, from M&A, securities, to investment management.  I got a well-rounded base. I ultimately decided that I wanted to join the investment management and hedge fund group, and so that's where I specialized after my first two years.

Alon Rotem: Brianna, that's similar to my experience. I was at school at Berkeley and I was doing on-campus interviews. Ropes wasn't really on the radar in Berkeley, just because it was such an East Coast-centric firm, and the Bay Area office was just getting off the ground. But when I met the folks at Ropes, especially in San Francisco, what stood out to me was this entrepreneurial spirit that the office had. I was getting to be in a small office with great people who had taken a leap of faith, while also benefiting from this great tradition of teaching and training and collegiality that Ropes was known for. It probably sounds weird to folks that are sitting on the East Coast—maybe they went to Harvard or NYU or something—but in California back in 2005 or 2006, Ropes was like this undiscovered gem. Once I got accepted to the summer program, I ended up splitting it—I did half of my time in New York and half in San Francisco, just to get to know more people in the firm. I ended up working in the technology companies group—did a nice mix of venture, private equity and debt. John, I probably even did some hospital related deal with you at some point, when you needed a low-level associate to do some health care diligence.

John Chesley: So you were both at the firm around the same time but in different offices. Did you have a chance to work together, or at least cross paths?

Alon Rotem: Yes. The genesis was this summer split where I got a chance to be in New York for a period of time, where Brianna and her fellow summer associates were running around the streets of New York City in 2006, and that is when we overlapped. Brianna, what do you remember from that time?

Brianna Humphreville: I remember we ate a lot. And we had a tremendous amount of fun. Alon and I didn't necessarily work together; as summer associates our interactions were more on the social side. Once we both joined the firm as associates, I was on the East Coast, Alon was on the West Coast, and we worked in different practice areas, so didn't have a chance to overlap, per se, but what Ropes gave us is the connection. We had this shared language and core beliefs of teamwork, collaboration, and helping and inspiring and teaching the folks around us. A lot of the things that we learned as young lawyers at Ropes Alon and I bring to thredUP, and they're things we think about when we interact with our business teams. As we continue to scale and grow the thredUP legal team, our core values are inspired by our time together at Ropes.

John Chesley: I love this theme of Ropes & Gray as the training ground for your future careers. How about some prominent Ropes & Gray memories you could share?

Alon Rotem: I'll embarrass you a little bit, John. I remember having an awesome summer associate dinner at your home, and I remember this incredible vista in the heart of Marin County looking on the forest. As a real estate agent would probably say when you bought the house, "Location, location, location." I ended up moving to Marin County myself, so I'm sure that dinner had a huge impression on me. But in all seriousness, the favorite thing I remember at my time at Ropes was just walking through the hallway and stopping by everyone's office. Even the partners had their doors open, and I remember John stopping by and talking with you, Amy Olson, Scott Elliott, Christopher Austin, Brian Erb, Sara Stapleton, and of course the guy who recruited me to Ropes, Greg Davis. I just appreciated how much people cared about the firm and wanted you to be the best version of yourself, so that you could end up contributing in that way, too.

Brianna Humphreville: One of my favorite memories is actually bittersweet—the day that I decided to leave the firm. My husband also worked at Ropes & Gray, we happened to be in the same group and we were both leaving to head West. The partners threw a casual cupcake party—perfect for me. I remember thinking that these were people who had taught me everything I knew about being a lawyer. I’ll always remember that gathering and how exciting it was to be trying something new but how sad it was to be leaving a place where I could just pop out of my office to the partner next door—the door's always open—and just swing by, ask questions, chat about a baseball game.

John Chesley: That's a great image. It does speak volumes about Ropes and how we celebrate each other in the midst of all the hard work that we're doing. Were there any attorneys at the firm who really stood out as influences on your careers?

Brianna Humphreville: There are so many people, I am afraid that I am going to forget someone on my laundry list! There were a number of senior associates and partners in the hedge fund group in the NY office that played an instrumental part in my career. There are folks whom I still keep in touch with—Joel Wattenbarger, Laurel FitzPatrick, Isabel Dische, Mark Gurevich. Of course, I also have to mention my husband, Charlie Humphreville, who’s a counsel at Ropes. But one of the great things about Ropes is you get to work across offices, so there were partners on the West Coast, like Greg Davis, who I spent a lot of time working with, and who really mentored me and pulled me along, and Leigh Fraser in the Boston office. Another partner who both Alon and I worked closely with is the late Raj Marphatia, who definitely influenced my career. I can't help but mention Patrick Diaz, who recruited me to Ropes in the first place, and wouldn't let me say no. I thank him for being diligent and showing me how awesome Ropes would be for my career.

Alon Rotem: As a first-year associate, I had a one-year stint in the investment management group. I sort of knew that wasn't going to be my path for the long-term, but if I think back to attorneys that stood out to me and influenced me, you mentioned Raj. Also, Eric Wright, who worked with a lot of funds on that side. I remember soaking up everything he had to say, whether it was explaining to me how to markup a limited partnership agreement, or if it was just listening to him speak on the phone with clients and giving them really important information, but making it digestible, putting them at ease, that always impressed me.

John Chesley: Thank you—those are great. Those are some of the names that I, too, look up to. How do you think your time at Ropes prepared you for your current position?

Brianna Humphreville:  Ropes taught me that I'm responsible for being a teacher. One of the things I found powerful at Ropes is the associates ahead of me were so invested in my career and teaching me, whether it be how to run a markup, or how to negotiate a deal or a contract. I now feel it’s an honor for me to return to others, and so I'm deeply invested in teaching other people. Whether it be a direct report or business team member, I view my success as a lawyer at thredUP as my ability to teach, inspire, and pull other people along.

Alon Rotem: At thredUP, one of our core values is infinite learning. To echo what Brianna said, I think that I connected with that value very naturally because of my start at Ropes. To me, the law is still a noble profession, and I've stayed with it because I think we're really at our best when we are acting like trusted advisors to people and to businesses who are simply trying to make progress day-by-day. From my standpoint, I love enabling my clients to succeed. I guess the subtle difference is I'm internal to my client, but Brianna and I have lots of internal clients, whether it's the marketing department, the finance department, or the engineering team. So to me, doing that from the in-house role, in many ways, is very similar to doing it from the law firm role.

John Chesley: Pay it forward. The two of you have expressed one of the most satisfying parts of being a lawyer—stepping into that role of teaching and mentoring others and handing on the tradition. Here's a more business-oriented question for you: What advice do you have for outside counsel who are looking to get business from you to work with thredUP?

Alon Rotem: You used the right word, John, and that's "business." I know this is cliché, I heard it all the time at Ropes and elsewhere—you have to learn about the business and dig in. Once a lawyer has a surface-level understanding of the business and continues to ask questions about how things work and go deeper, the advice you end up giving becomes much more context-driven. I think you can really tell that difference once you start moving from reactive support, like the client asking you to do something and you say, "Yes, I can do it," and do a great job, to moving towards being that proactive partner. Brianna always uses this term, "Seeing around corners." I think she's right—the lawyer that can see around corners and anticipate where the company is going, that's the one that we love working with the most.

Brianna Humphreville: Alon hit the nail on the head. You've got to know our business in order to help us succeed. You've got to be practical, and you have to understand the enormous pressures that the in-house lawyer, like Alon and myself, are under. We don't want an outside lawyer to just give us a laundry list of all the risks that are out there—we know that risk is everywhere. We want someone who can help us strategize and practically evaluate risk by assessing, "What are the biggest risks that are out there? Why are they the biggest risks? Is there a regulatory thing going on? Are there monetary penalties? What actually makes it a big risk?" How can they work with us to creatively avoid or mitigate the problem?”

John Chesley: Actionable advice. All right, here's some lighter questions for our lightening round, and we'll wrap things up here. Here we go—fill in the blanks. My favorite food is…

Brianna Humphreville: My favorite food, I'm going to go with mashed potatoes.

Alon Rotem: I'm planning a vacation to Hawaii, so I have coconut shrimp on my mind. I'm going with coconut shrimp.

John Chesley: My ideal Friday night is spent…

Alon Rotem: Dinner with friends and then, we've been in a pandemic for a year, so a great game of cards, whether that's Gin or Sequence.

Brianna Humphreville: I'm going to go with food, as well. Family pizza night—every Friday night, we have pizza with another family that lives right down the block. There's a healthy competition between the two dads as to who can cook the best pizza.

John Chesley: If I wasn't a lawyer, I'd be…

Brianna Humphreville: Alon mentioned coconut shrimp, and now I can't stop thinking about coconut shrimp. So if money wasn’t an object and I could be anything, I think I would be a professional beachgoer sitting by the ocean with a drink in my hand.

Alon Rotem: I'll go even a little further out there. My dream would be to run a basketball camp for kids. If I could do that, I'd be happy.

John Chesley: Nice. The next one, I think I know the answer to, at least for Brianna. If someone handed me $25 million today, I would…

Brianna Humphreville: Move to Hawaii, and sit on the beach.

Alon Rotem: I would park it in Bitcoin and then just keep doing what I'm doing today.

John Chesley: We're going to switch this one around—you first, Brianna. In one word or phrase, what is it like to work for Alon?

Brianna Humphreville: Amazing! Here's why, truly—Alon has been my eighth manager working at a company. This is the third company I've been at, and I hit on this earlier, but your manager makes or breaks your career, your day, everything. Having Alon as my manager is a great fit for me. To go back to my earlier point, I think if you're looking to go in-house, you've got to keep that in mind.

John Chesley: Alon—one word or phrase for Brianna as associate general counsel?

Alon Rotem: I'll start by saying the word would be "blushing," because of what she just said, but you can't see that on this audio podcast. I would say "partner." One great thing about working with Brianna is we started off as summer associates together. We think of each other as peers, and I think one great way that our working relationship works so well now is we collaborate as peers on everything we do.

John Chesley: Last one—bring it back to Ropes here. Ropes & Gray is…

Alon Rotem: A great place to start your career.

Brianna Humphreville: I would say Ropes & Gray is a law firm filled with lawyers who value teamwork and teaching each other. It's an amazing place to be a young lawyer, and I really can't imagine starting my career elsewhere. I don't think I would be where I am today.

John Chesley: Thank you both. What you've said and shared today really reinforces for me the community of Ropes & Gray, past, present and future.

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