Women @ RopesTalk: Conversation with Jennifer Wilen, Bombas

March 24, 2022
26:34 minutes

In this episode of Women @ RopesTalk, hosted by IP transactions partner Megan Baca, data, privacy & cybersecurity partner Fran Faircloth interviews Jennifer Wilen, vice president of legal at Bombas. Jen shares her experience growing the legal team at Bombas from the ground up, and how being in-house counsel compares to her prior roles at a global law firm and a leading investment bank. As a manager, she discusses the importance of empowering team members, which includes allowing others to make mistakes. Jen concludes by talking about the culture at Bombas, which celebrates individuality, and how the company is holding itself accountable on its DE&I goals.


Megan Baca: Welcome, and thank you for joining us on our latest installment of Women @ RopesTalk, a podcast series brought to you by the Women's Forum at Ropes & Gray. In this podcast, we spotlight extraordinary women who have had successful careers and interesting lives, and who are also making a positive impact in their workplaces and in their communities. We feature women attorneys at Ropes & Gray in conversation with prominent women clients, industry leaders, entrepreneurs and others, about their careers, what's led to their successes, the challenges they’ve faced, and the hard-earned wisdom they've acquired. I’m Megan Baca, a partner at Ropes & Gray with a practice focusing on intellectual property and technology transactions, and I’m also co-head of the firm’s digital health initiative. I’m based in Silicon Valley. On this episode, I’m joined by Fran Faircloth, who’s based in Washington, D.C. Fran, to get things started, can you please introduce yourself and provide a brief overview of your practice?

Fran Faircloth: Thanks, Megan—I’d be happy to. I’m a partner in Ropes & Gray’s data, privacy & cybersecurity practice. I’m based in our Washington, D.C. office. As part of that practice, I help clients who are dealing with complex data issues—these can range from technology and data-driven questions to privacy compliance, or cybersecurity crisis preparedness and incident response. Our practice represents clients who are navigating really difficult data issues—things like security breaches and ransomware attacks, online brand protection, social media or ecommerce questions, and compliance with federal, state and foreign laws related to the collection, handling and protection of data.

Megan Baca: Who’s the special guest you’ll be interviewing on this episode?

Fran Faircloth: Today, I’ll be interviewing my client, Jennifer Wilen, who’s vice president of legal at Bombas. If you’re not familiar with Bombas, they’re an online apparel brand that’s focused on making comfortable, colorful socks and other apparel. I’m a big fan of their socks, and I love that they have a mission of providing these essentials to people who are in need.

Megan Baca: That’s awesome. I love Bombas socks so much, so I’m very excited for this interview. How did you meet and start working together?

Fran Faircloth: I’ve been working with Jen for a few years now. Ropes & Gray advised Bombas as they navigated a couple of cybersecurity incidents, and we represented them through the investigations and enforcement actions that followed from those. The incidents actually happened when the company was just starting to grow, and it was before Jen actually joined. It was impressive to see her step into this role and really lead on these legal issues.

Megan Baca: What would you say is most notable about Jen’s career?

Fran Faircloth: I think firsthand, how wonderful it is to work with Jen. Even when things are really stressful or difficult, she’s very positive and level-headed. She’s done an awesome job of growing the legal team at Bombas from the ground up. She was their very first in-house attorney, and I’m not surprised, as you’ll hear from our discussion, that she’s very intentional and thoughtful about building those mentoring relationships with her team and other attorneys, and paying forward the kind of support that she’s received in her career.

Megan Baca: That’s fantastic—I can’t wait to hear the interview. With that, I will turn it over to you and Jen.

Fran Faircloth:  Jen, thanks so much for joining us today. Just to kick us off, can you introduce yourself to our listeners?

Jennifer Wilen: Absolutely, and thank you so much for having me. My name is Jen Wilen, my pronouns are “she” and “her,” and I am the SVP of legal at Bombas.

Fran Faircloth: Can you tell me a little bit about your career trajectory—how you got to Bombas?

Jennifer Wilen: I started my career as a corporate associate at Kramer Levin—I was focusing on M&A and securities there. After about four years at the firm, I went to Morgan Stanley—I worked there in the company law group where we focused on corporate governance. It was extremely exciting. I got to sit on the board and committee meetings at Morgan Stanley, and the board and executives, of course, are extremely bright. I learned so much sitting in the board meetings, working on related SEC reporting and governance issues. It's an extremely large organization, and as a result, it was naturally pretty siloed there. I started to have a desire to focus on a broader array of matters after about four years. I took some time, because it was very exciting. I had this desire to focus on a mission-driven company, or work for a nonprofit, but I hadn't quite figured out exactly what it was. I had this inkling that my next move was going to be my big move, and this thing that solidified my career, but I needed to figure out what it was.

A friend of mine had seen Dave Heath, who's our CEO—he posted on social media that he was looking for someone to run the legal department, so my friend sent that over to me and said, "I think you might be interested in this," and I took a look at it. I had heard of the company actually because my brother is a huge Shark Tank fan, and had purchased the socks very early on and was telling me about them. The more I looked into the company, I saw the mission-driven and the one-for-one motto. I thought this could combine everything in one, and it's probably my dream job. I realized throughout the interview process that it definitely was my dream job, and I'm happy to report that I'm still very happy and feel the same way three and a half years later.

Fran Faircloth: That's great. From what I know about Bombas from working with you over the last couple years, it sounds like that was a perfect fit for what you are looking for. Can you tell our listeners a little bit more about what you do there?

Jennifer Wilen: If the listeners don't know, Bombas is a comfort-focused premium basics brand—think socks. Most of you are familiar if you know Bombas—tees and underwear. And we have a mission to help those in need, so for every item purchased, a specially designed item is donated to the homeless community. To date, we're at 60+ million items donated, which feels pretty amazing to be a part of something like that. As mentioned, I'm the head of the legal department. We have a mighty team of four, currently, and we cover all aspects of the business on the legal side. I think what's interesting for me, being in-house (at Morgan Stanley I was in-house also, but I think it was a more specified area) and covering the legal department from a company like Bombas that's relatively smaller, you're really working on all areas of the law. For me, I thought it was really important to build a legal team that seems part of the business, rather than separate. I wanted to make sure our legal team was viewed as problem solvers, rather than those "no" people that you're kind of scared of. So, I wanted to make sure we engendered the trust of the whole company at once, and it makes it really fun, because we get to solve problems all day. And, of course, we're advocates for the company. Our job is to manage risk and protect the company, but I think a big part of our role is to problem solve and find creative solutions to make sure we can get the business team's goals accomplished.

Fran Faircloth: That's a really cool, holistic approach to in-house counsel. What kind of things are keeping you up at night at work these days?

Jennifer Wilen: I'm sure this is the case for many lawyers, I definitely am kept up a lot—probably more of my personal anxiety than anything else. But I think, currently, the first thing that comes to mind is that I'm really proud of the team we've built. It's so cohesive, but everyone's extremely unique. It feels that everyone really enjoys working together—at least I feel that way—but I feel pretty confident that the rest of the team does, as well. We'll be hiring more roles soon, and one of the things I think, and frankly worry about, is how the team culture and the company culture will change as we hire new individuals. That being said, to date, every single person we've hired has only made the team so much better, so I’m working on turning that fear into excitement because change is always scary, but it's also really exciting. I'm excited to see what future members of the team are going to bring.

Fran Faircloth: That's a wonderful approach. I like that phrase of “turning fear into excitement.” I feel like, as lawyers, we often tip over into the anxious, fearful side, but there's a lot of excitement underlying that. How has COVID affected you and your team?

Jennifer Wilen: Every single member of my team was hired during COVID, which has been very interesting. I think that I learned so much in my career at the firm, listening to partners on conference calls, sitting down with a senior associate marking up a purchase agreement, going to the printer and working with the team to try to get a registration statement filed—all of those in-person moments where you're observing other people, I think people really do take that in and take that forward. Obviously, it's been a little hard to replicate that in the virtual world. I've been trying to be creative and figure out ways to work with the team to get some of those experiences. Maybe not quite the same, but little things like marking up a contract over Zoom—not as fun as being in a conference room, but I think it helps a bit. And most important to me, especially at a company like Bombas, is ensuring the team has fun together. I think especially in the legal world, it can be stressful, it can be hard, and the ideal is to get us to all have fun while we're in those moments. Some of my favorite memories at the firm are, and maybe this is a little masochistic, but staying up late with a group of people at the printer and getting things filed, because it feels really good to have accomplished that as a team. We certainly miss a lot not being in-person—I think just sitting next to people, chatting about your day, and forming relationships. I try to just make meetings about having fun and getting to know each other, rather than getting too down in the weeds of what we're doing, because that tends to happen naturally throughout the day. So, trying to ensure my team gets as much of that as possible and gets as much of the Bombas culture as possible.

Fran Faircloth: I feel like we've all had to find new ways to make connections during these weird times. What do you see as some of the most important changes, either in the law, in your business or technology for Bombas recently?

Jennifer Wilen: I think this goes off of the COVID conversation and continuing to learn to operate in a virtual or a hybrid-virtual world. Bombas has done a bit of both. We did return to the office for a bit, but then, in light of Omicron, had to rework it again. Our plan is generally a hybrid situation, where if you want to be in the office, you can be an HQ employee, and if you prefer to work remotely generally, you'd be a flex employee. I think it's a really interesting challenge and opportunity, figuring out not only how to work virtually, but how to work when some people are in-person and some are virtual. I do like to go into the office personally, so I've been heading in when it's okay to do so. And some of my team members feel comfortable doing that, so it's been really great to have that in-person opportunity, but at the same time, not everyone is there. So, I think it's really interesting trying to figure out how to ensure everyone feels part of the team, even more broadly from a company scale when some people are in-person, some are not, or in times when COVID flares up and everyone is remote.

On the legal side, not just on the cultural side, but I think information flow makes me a bit nervous. It was very easy when we were in the office. You stop by someone's desk, have a conversation, people see you, it might spark a question that they didn't even realize they had. You just talk to people more, you're in more meetings, seeing more things happen, so you feel more comfortable that you're getting the information you need. There's been a lot of new hires during COVID, and I maybe don't know them or have not had the opportunity to get to know them yet, but I perhaps would have had in-person. So, I think since the pandemic started, I've been really trying to ensure that not only we're including everyone from a cultural perspective, but also ensuring they feel comfortable and empowered to share information with the legal team, and ensuring I engender that same amount of trust to the whole company. That was easier to get in-person—finding ways to maybe set up a coffee date with a new hire to ensure they get to know us as well and feel just as comfortable in the virtual world.

Fran Faircloth: That's really wonderful. It sounds like you've had so many interesting experiences in your time at Bombas, juggling during COVID, and even in your time before Bombas in your legal career. What are you most proud of in your career to date?

Jennifer Wilen: I think that's kind of easy, interestingly. I guess we're having a theme here, because the thing that I would say I'm definitely most proud of is the team I've built. They're just such smart, hardworking, funny, and very kind individuals. I truly love working with them, and I love watching them learn and thrive. Prior to Bombas, I never really managed anyone before. When I was at the firm, there were junior associates working with me, and paralegals working with me at Morgan Stanley, but I never had anyone reporting into me. I think before I came to Bombas, I'm not sure I had a manager that was the ideal role model of what I would want to be as a manager. And when I came to Bombas, it was the first time I really felt people empowering me with their trust in me, and I learned off of that, even if it wasn't a lawyer above me. The executive team was so supportive and so trusting, and I wanted to take that and make sure I filtered that down to my team. As lawyers, a lot of us have come from big firms, and it's a different culture—not bad or worse in any way, but just very different—but also a very different culture from Bombas. So, trying to ensure that everyone feels safe and empowered, and mistakes happen and they're okay. I think the more comfortable you are that a mistake is okay, in my experience, the less likely you are to make them. And if you do make them, we figure it out and move on. I think the team is just really wonderful. I'm so proud of them, and I think the thing I'm most proud of generally.

Fran Faircloth: I love your focus on your team and the people that you're surrounding yourself with, because that really is such a big part of practicing law. Who do you think has had the greatest influence on your career?

Jennifer Wilen: That's tough—it depends how far back we want to go. I think what I said before—it really boils down to the people that have empowered me and believed in me. On that note, we can certainly give my parents a shout out. But it was not until I came to Bombas, as I mentioned, that I think I really felt truly empowered. I wasn't being micromanaged—I just had this trust placed in me off the bat. My manager directly when I was hired, and my manager now on the executive team, their trust in me made me want to do a great job. I can admit, I'm a Type A personality—I've always been a self-motivator and always wanted to do great, but I think trust is something you definitely don't want to lose. Their confidence in me gave me the confidence that I could do a great job. I mentioned this before, but I knew that if I made a mistake, it would not be the end of the world, and I wouldn't be berated for it. And ironically, knowing it's okay to make mistakes, I think you're less likely to make them and you're more focused on protecting the company, making sure everything goes as well as you can to the extent you can control that. I think we all have a bit of impostor syndrome, at least I do, but I do really think the people that have had the confidence in me, gave me the confidence in myself. Whenever people have confidence in you, I think it often makes you realize that you're capable of even more than you think.

Fran Faircloth: It's so true that we depend on these people around us who believe in us. So much of our careers are built on relationships with other people. Can you talk about how you build and maintain your most important relationships now in your career?

Jennifer Wilen: I think I am very lucky in this regard. Going back, the individuals I've maintained professional relationships with from my prior roles are the individuals I developed friendships with throughout my time, whether it's at the firm, at Morgan Stanley, or now. I found it's particularly important for me moving in-house, when I was the only lawyer for a while. I didn't have the experience or expertise in a lot of matters. I was a corporate lawyer. I did securities M&A. I never did employment law or IP. On that note, it's kind of funny—you never know the things that will end up being very useful, like that trademark class you may have took in law school, but somehow, things do have a way of coming back. It was really helpful for me to have some of those relationships and be able to bounce something off of someone. A friend that I used to work with at the firm, who was an employment lawyer, I could call and bounce something off of. And what's happened through my time at Bombas is a lot of the people I've worked with over time, like you, Fran, for example, end up becoming really important relationships with, because, of course, you're our outside counsel and advisor, but I feel very comfortable going to you and bouncing things off of and having a discussion, rather than it just being, "Hey, can you do this for me?” I think those things tend to be really helpful, because that's how you end up learning the most from my perspective. You can't know every answer, so I think it's always great to have friends and colleagues that you can work with and get their advice on.

Fran Faircloth: That's true. We all have so much to learn from each other and to give to one another. It sounds like you've had some wonderful mentors, and you've also focused on mentoring your team and building these relationships. How do you see the importance of mentoring in your career?

Jennifer Wilen: I think it's so important. I definitely had some mentors at the firm, and I recently developed a very meaningful mentor relationship, and I think the key generally throughout these has been that they've developed naturally, and have evolved over time. Interestingly, one of my current mentors was introduced to me through a mentor at the firm who I'm still friends with. I was working on setting up some of the needs we have for Consumer Privacy Act compliance. He introduced me to a friend of his who used to be counsel at the firm, as well (but not when I was there), and was working as a consultant to two law firms and in-house counsel, working on setting up just various privacy obligations. It started off as just a business relationship, and from there, has grown to an extremely meaningful mentorship. Because this individual has been GC at various different locations, has worked under people, has worked at public companies and private companies, has a wide array of experiences, and is frankly a privacy expert—Fran, similar to yourself—it has really developed into such a special relationship, and a friendship. It's someone who I feel at this point is helping me not just in the specific issues I may have, but more broadly as my career develops, and where I want to go and what I want to accomplish. It's been really special. And because I've been lucky enough to have these relationships, it's been really important to me wherever I can to give that to others. Again, this kind of goes with impostor syndrome, where you feel a little funny saying I'm a mentor to somebody, but I do think sharing experiences is so important and the littlest thing can have a much bigger impact than anyone thinks. I think it's easy to think about the obvious mentorships—your teammates and other people at the company—but I think mentor relationships can come from unexpected places.

For me, an interesting situation is that when I was hiring for one of my roles, I had just some outstanding candidates, and weren't necessarily exactly right for the role, but I thought they were just so phenomenal. After we went through the process, I reached out to them and let them know, "If you ever need anything, I would love to keep in touch." Certainly, in my mind, I would love to hire them for a future role, but also, I just thought it'd be great relationships to maintain. We actually planned to meet for coffee in the coming months, so we'll see how it develops. But I think they can come from unexpected places, and you never know where you might make an impact on someone.

Fran Faircloth: That's so true, and I think that building these mentoring relationships is so crucial to helping build diverse legal teams. What do you see as the advantages of having greater gender and other diversity in law?

Jennifer Wilen: That is a great question, and to me, I think it's hard to overstate the importance. I would say in the professional and in our personal lives, our greatest assets are the things that make us different. If you're surrounding yourself with people that look and think like you do, and come from the same place that you do, not only you're not going to learn, you're going to be missing out on really important viewpoints. This just reminds me of a little personal anecdote that has stuck with me. A few years ago, I was at a women's panel discussion, and the head of a department at a very large bank was speaking on this panel. One of the managing partner’s asked for advice on essentially how women can better fit into the boys’ club, and the department head responded by saying, "Why would you want to fit in if your greatest asset is that you are different?" I know this is cliché, but it was kind of this “aha moment”—it stuck with me truly. And I think it applies to DE&I more broadly. It pushes me to focus on diversity, not only on my team, but with our external partners as much as possible. I think the real key is that we shouldn't be fitting in, because the greatest thing about us is that we might have a different viewpoint and we may think differently about whatever it is, and I think that goes for absolutely anything.

As for gender diversity, I'm very lucky that at Bombas, I've been empowered to highlight other women in the legal field. It just so happens that my team is currently, coincidentally, all female, which has been really amazing and fun, particularly given that most of the people on my team have come out of more male-dominated workplaces. But that being said, I really look forward to adding more gender diversity to the team and to lean into hiring other underrepresented groups. I think I'd be remiss not to mention the barriers to entry in the legal industry, so something I definitely think about is how we can be better in terms of providing more accessibility in that regard.

Fran Faircloth: I love that anecdote. I do think that we're finally starting to see a shift away from the old boys’ club to more of an everyone's welcome club. I love that you have an all-women team at Bombas. Are there any other efforts or successes at Bombas regarding diversity and inclusion that you're particularly proud of and would like to share?

Jennifer Wilen: I think Bombas is a place where individuality is celebrated, which was very different for me at first, in the best way. Not only is it celebrated to be different, but people are really encouraged to come as you are, be quirky. Since day one, creating an inclusive, fun, and positive work environment was always a priority for the company and the co-founders. I think certainly there's always work to do, but I do think that basis has really been a good facilitator for DE&I at the company. From Bombas's perspective, I think we all think there's always work to do, but we have been actively making incremental improvements to try to be better as an organization. One thing in particular that I am proud of is that in the summer of 2020, we made a public commitment to being better and ensuring that we can continue to be a diverse, equitable, and inclusive place to work. In that regard, we made public DE&I goals on social media, outwardly, and we're committed to not only reporting on those goals, but holding ourselves accountable. And that public ability and requirement to hold ourselves accountable I think meant a lot to me personally, and hopefully to a lot of other people. I really am proud of that.

Fran Faircloth: That's such an accomplishment and a wonderful approach from Bombas to helping to solve this problem. Thank you so much for all of this, Jen. We really appreciate talking with you today—thanks for joining us.

Jennifer Wilen: Thank you so much for having me—it was such a pleasure.

Megan Baca: Fran and Jen—thank you so much. As always, thanks to our listeners. For more information about Ropes & Gray's Women's Forum and our women attorneys, please visit www.ropesgray.com/women. You can also subscribe to this series wherever you typically listen to podcasts, including on Apple and Spotify. Thanks again for listening.

For more information or to contact Jen Wilen, please visit her LinkedIn profile.

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Jennifer Wilen
Vice President of Legal, Bombas
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