In Depth
Colin Bennett on Creating His Own Road Map for Career Opportunities
When Colin Bennett joined Skims in July 2023, he did so as the first General Counsel and Chief Compliance Officer at the company—a team of one overseeing all its legal and compliance work. In the time since, Skims has rapidly evolved from an almost purely e-commerce enterprise into an omni-channel organization with a growing U.S. and international retail store presence. The mix of business advisory and legal work he and his team handle now is everything Colin envisioned when he left private practice in pursuit of in-house opportunities at venture-backed companies. In this interview, he details the lessons he gleaned from Cravath and through other formative experiences along the way.
Colin Bennett recalls that when he worked at Cravath as a corporate associate from 2010 to 2013, there were fewer obvious career paths to which he could transition in-house at an early stage company, versus the multitude of opportunities that seemed available at large blue chips and financial institutions the Firm was known for representing at the time.
“Finding that precise route took a bit of personal exploration,” he says, “but once I got there, I was so grateful for the breadth of work I had at Cravath as a young associate.”
He cites his experiences in the rotation system of training at the Firm—during which he spent time in the banking, M&A and securities practices—for preparing him to task switch and to be comfortable within the “controlled chaos” inherent to building and growing a company.
Since joining Skims as General Counsel and Chief Compliance Officer in July 2023, his day to day has been as much about business advisory work as it has legal work. The challenge in the role, Colin says, has been in juggling competing priorities and learning to navigate the unknowns of scaling a successful business.
“This is the first time I’ve joined a company as the first lawyer, and it’s been incredibly valuable and gratifying to get to construct something from scratch and really put your mark on it,” he explains.
That sense of being able to choose your own adventure is one of the reasons Colin wanted to pursue in-house opportunities at growth-stage companies, backed by the confidence and skills he gained in his early years as an associate.
“There is legitimate anxiety that comes from trying to find a new role in an unknown industry,” he says. “But the flexibility that Cravath instills in its associates gave me the assurance to then come into three different industries that I’d never had any exposure to before, and I’m now on my fourth.”
Colin grew up in Florida, where his father was a local litigator and his mother was an art critic. “I was aware of law as a profession and I would go hang out in my dad’s office during the summer sometimes when I was young, but I wasn’t one of those kids who dreamed about becoming a lawyer,” he explains. “I was drawn mainly to writing and creative work.”
He attended Yale as an undergraduate, studying English literature, and afterwards taught the language abroad for a couple of years—according to him, to buy time to figure out what he actually wanted to do.
“I can’t pinpoint the moment I decided I was going to be a lawyer,” Colin says. “But when I realized that I wanted to take a real shot at it, I did a lot of research into what the profession entailed. The more I learned, the more I taught myself about American jurisprudence, the more interested I became in it conceptually and philosophically.”
When Colin got to law school at the University of Michigan, already captivated by the legal industry, he recalls writing a letter to Cravath asking about the recruiting process. Several weeks later, he received in the mail a pamphlet on recruitment and the history of the Firm, which he leaned against the wall on his desk throughout his 1L year.
Why Cravath specifically? Colin says he had read a lot of online commentary, studying rankings, industry reporting, message boards and whatever else he could find to inform the goals he would set for himself.
“And what I kept seeing over and over was about the uniqueness of Cravath, so I kind of got it in my head that this was the place for me. I think it made me work extra hard that first year,” he explains. “At on-campus interviews, I felt very confident in every single interview except for Cravath because that was the one firm I desperately wanted.”
When Colin arrived at the Firm as a summer associate, he recalls feeling like a deer in headlights but being thrilled to have achieved his goal. He says he came out of those months with a real taste of substantive work, even as the 2008 recession continued to throw doubt over the job market as he headed into his final year of law school.
Coming through the door again as a first year, with the economic downturn ongoing, was a hit-the-ground-running moment for him. “I felt from the start it was my job to make sure that I’m a valuable team member, and pull my weight as quickly as I can,” Colin says. “Cravath still gave us all the responsibility we showed we were ready to take.”
One early memory that stands out to him is the first meeting he was called into with now-retired corporate partner Jim Cooper. It was Colin’s first week of his first year as an associate at Worldwide Plaza, where the partner offices were “imposingly” organized by suites.
“Jim had a deal he wanted some help with, so he sat down with me and talked about things that I’m sure were a complete waste of his time—it would have been very easy for him to tell me to go read the credit agreement and figure it out,” he says. “I later learned that he famously had parts of the credit agreement templates for all the big banks named after him because he invented the provisions, and there he was sitting there teaching me about them.”
Getting that practical advice and knowing someone was there as a mentor for him was incredibly important, Colin adds. It helped alleviate early fears in receiving assignments and his own questions about whether he was qualified to be handling that work.
Also essential to his development was Tatiana Lapushchik, whom he remembers as a patient teacher: "I took way more time than I probably should have to understand some of the nuances of how credit agreements work, and she was integral to my getting up to speed. She and Jim were the most important partner mentors to me, because as that scared first-year, they made me feel as though I could actually do this.”
There were others, too, who instilled in Colin the importance of team camaraderie among associates and the ethos that everyone at Cravath was “in it together.”
“That approach was so meaningful to me,” he says. “Working with mentors who were always so thoughtful and approachable, despite the volume of work they had at the time—they modeled for me how I could evolve and learn how to become a leader.”
Colin adds: “That sort of trust was transformative for me, and it gave me the confidence to come into jobs where it’s a green space and you don’t have anyone telling you, ‘Here’s what you should do,’ or ‘Here’s how I’ve done it.’ You’re building it as you go along, in many cases.”
Around the time Colin was a third-year, he started thinking about next steps in his career, which included an honest self-assessment. “I did the math and thought about what it might look like if I wanted to stay,” he says, “and I liked working at Cravath, but I also didn’t want to be in a situation where I had lost the window to find the next best thing.”
This was right around the second boom of Silicon Valley in the early 2010s, which Colin notes made it compelling for him to try and establish a legal career in the Bay Area.
“Being untethered in terms of family or other commitments, I interviewed with a lot of firms before I decided to lateral to Morrison Forster,” he says. “And I was really happy there, too. It was a different model and system, but the mentality in people’s commitment to excellence, and the camaraderie and collegiality, made it the perfect place for me to land.”
His pivot paid off a year and a half later, when Colin received a cold outreach about an opportunity to join Counsyl, a biotechnology company preparing for a prospective IPO that was later acquired by Myriad Genetics. The general counsel had an intellectual property background and was looking for someone with corporate experience to join the team.
“Frankly, I probably should have been more nervous about the job because I was lawyer number two, which meant I wasn’t just doing corporate work,” Colin says. “There were also HIPAA and insurance reimbursement issues, and things like that that came to my desk in week one.
“Without the skills that Cravath and my time in private practice had helped me build in my ability to problem solve, I probably would not have had the confidence to go take a job like that.”
Colin quickly found he enjoyed the type of legal work that early stage companies offered. Following that initial jump in-house came opportunities at SaaS platform Yext, where he was Assistant General Counsel and guided the company through its IPO, and at German meal-kit provider HelloFresh, where he started as Head of Legal and Compliance for North America before taking on the GC role for the North American business during his almost six years at the company.
At a peak during the pandemic, Colin notes that HelloFresh’s U.S. business had grown roughly 25x since he’d joined. “At one strange point, we had a bigger market cap than Deutsche Bank,” he notes. He describes the quickness with which his previous employer scaled during the early 2020s as a sort of “crucible” for him as a mid-career lawyer, to be thrust into an organization grown to that size and leading a legal function for the first time.
“Having those experiences validated for me that passion in wanting to really be a lawyer that focused on growth-stage companies, and particularly venture-backed companies that are looking for either their next stage of growth or an exit,” he says.
“Having those experiences validated for me that passion in wanting to really be a lawyer that focused on growth-stage companies, and particularly venture-backed companies that are looking for either their next stage of growth or an exit.”
– Colin Bennett
That pace hasn’t slowed down any for Colin at Skims, which is moving along on its own express track. In progress are the continued openings of multiple retail stores across the United States and internationally, new category and channel launches, and continuing to evolve the NikeSKIMS partnership.
“I have visibility into almost every aspect of the business, which gives me a uniquely broad view that I find incredibly valuable,” he says. “I sometimes have to take off my lawyer hat, but I always keep it in one hand. That is the challenge: knowing what to focus in on, and what to let lie.
“Weighing those things takes time and experience, but, the more companies I’ve been at, the more I’ve learned there are common themes that, as a lawyer, you really can be a difference maker in addressing.”
Colin says those decisions all trace back to the foundation he built as a young lawyer, and trusting in that skillset and himself to establish a career path that matched his ambitions.
He adds: “For anyone who’s considering that jump and asking, ‘Could my work at Cravath translate?’ I hope that my experience is at least one datum of, yes, it can, and it actually is a competitive advantage.”
