How’s GC Sarah Feingold Relied on Unconventionality to Succeed

Sarah Feingold, general counsel of Vroom, Inc. (, has always been artistic and considers the creative community “my people.” She has been a metalsmith for years and combined her passion for jewelry-making and law into a nearly decade-long career at Etsy, where she started as the 17th employee and first in-house counsel. Feingold’s commitment to being a self-described unconventional lawyer has influenced every part of her career. While many struggle with the path less travelled, Feingold has shifted her paradigm such that she relies on her differences as the key drivers of her success.

Unconventional beginnings

Instead of waiting for her passion to lead her to something fulfilling, Feingold knew it was her responsibility to harness it into something tangible. In law school, she convinced the administration to allow her to take graduate level metalsmithing classes as part of an independent study.

“By studying visual art alongside my legal studies, I learned, first-hand, about the business and legal issues impacting emerging artists. Too often, we rely on outside factors to magically make it all come together for us. I was always creative, but also analytical and I don’t believe the two have to be mutually exclusive,” Feingold says.

Feingold’s unique approach to law school cemented her interest to replicating the experience when searching for her first in-house legal job after graduation. After law school, she sold jewelry via a small startup: Etsy. When she reviewed the company’s then-existing policies, she saw some issues and reached out directly to the CEO.

“I felt a responsibility to the creative community. It drove me to take risks that I, perhaps, wouldn’t have taken otherwise,” Feingold says. After talking to the CEO, Feingold explains, “I informed him that I was coming to interview to become his first in-house counsel and that I had already booked my flight to New York City.”

“I had no fear of standing out because I could rely on a solid set of talking points that clearly explained the value I would add to the Etsy team,” Feingold continues. Feingold was hired on the spot and, over her nearly decade-long career there, was integral in the company’s explosive growth and successful IPO.  

An unconventional hunt for a new boss

As Etsy’s first lawyer, Feingold was dealing with any and every legal issue that came her way. As the company was going through explosive growth, she wanted to have an experienced legal mentor. “I realized that the standard path is to wait for a general counsel to be brought in when it looks like the company is steadfastly entering pre-IPO mode. But I felt that I could foresee what I needed in a boss the best,” she says.

It was important for Feingold to find a general counsel who had legal expertise and fit the company’s culture. She also ensured that the GC would value the contributions that her passionate approach brought to the table. As she explains, “to ensure an optimal environment for myself and the rest of our team (including the new general counsel), I wanted to make sure that I set us all up for success.” Again, Feingold demonstrated how going off the beaten path is integral to maximizing a successful outcome.

Sharing unconventional lessons learned

“There have been so many people who have openly shared their lessons learned, supported me throughout my creative journey, and, ultimately, were instrumental in my success. At some point, I realized the best way to give back to the legal and creative community is to pay it forward,” Feingold says.

Feingold regularly speaks about her key takeaways in a presentation via Project Cannonball. As Feingold explains, “the idea began with the notions that a cannonball is joyous and purposeful. It requires research, confidence, and coordination. By nature, a big splash is designed to make waves as it takes you out of your comfort zone.” Feingold wanted to help those in her community overcome imposter syndrome, overcome the fear of hearing “no,” and, conversely, the face the fear of saying “yes.”

“When we ‘borrow’ each other’s brain power, imagine how much more successful each one of us would be!” she says. Feingold has been giving cannonball talks at companies, law firms, and conferences. Unsurprisingly, the feedback has been nothing but positive. Feingold’s approach to sharing her lessons learned via her writing and speaking efforts helped demonstrate her expertise and increase her professional value — a win-win for everyone.

After almost 10 years at Etsy and years of speaking on embracing discomfort, Feingold realized she also needed to get out of her comfort zone — she said “yes” to a new opportunity even though she was at a job she loved. This is why in the summer of 2016, Feingold took a position as the general counsel of

“I knew I needed to grow, learn a new industry, and apply all the cumulative skills I acquired at Etsy,” Feingold explains. “I wanted to make sure I left Etsy for the right place, and after having numerous conversations with the team, I knew this job could also become a long-term home for me. After all, cars have enough metal that my creative passion is still with me!” Ultimately, Feingold realized that Etsy and Vroom had very similar issues: she needed to help build a company from the ground up and she had the legal and cultural experience to succeed.

Feingold ended her time at Etsy by presenting a company’s signature “Last Lecture,” where she talked about her nearly decade-long experiences, lessons learned, and desires for the company in the future. “I wanted to take the opportunity to not only reflect back on my experiences at Etsy, but to also thank the amazing team for all of their contributions,” she acknowledges.

Undoubtedly, Feingold’s commitment to her craft and dedication to sharing the lessons she has learned with everyone around her have propelled her forward. It is through her authentic nature and willingness to achieve greatness that have guaranteed both personal and professional success. An important and key lesson for us all: you don’t have to give up on who you are to succeed.