In-House Counsel

Constructively Channeling Passion Into Success

While “pursue your passion” can often-times seem like an overused cliché, it can work for you.

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Thumbs up! successWhile “pursue your passion” can often-times seem like an overused cliché, when combined with a structured approach to professional development, risk-taking and getting comfortable with being uncomfortable, it is a key ingredient in achieving a higher overall level of job satisfaction. Sarah Feingold, General Counsel at Vroom, Inc. (Vroom.com), is the embodiment of these qualities and she shares the three key ways in which she has managed to build a career optimized for overall professional and personal satisfaction.

Constructively focus on what you love

“I have always been artistic. When I stumbled upon silversmithing, I knew I found my creative calling,” Feingold explains, “I wanted to make sure I keep my passion close to me even as I embark on a legal career.” In law school, she convinced the administration to allow her to take graduate level metalsmithing and jewelry-making 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. The key takeaway here is that instead of waiting for your passion to lead you to something fulfilling, it’s still your responsibility to harness it into something tangible.

The unconventional job hunt

Feingold’s approach to getting her first in-house legal job after graduation mirrored this approach. She was working at a law firm and selling her jewelry on a, at the time, small website: Etsy. When she started reviewing the company’s then-existing policies, she saw some issues.  Never one to sit back, she reached out directly to the CEO. “As an artist I felt a responsibility towards the creative community. This drove me to take risks that I, perhaps, wouldn’t have taken otherwise,” Feingold says. Nothing about what Feingold did next could be described as conventional: after talking to the CEO, she told him that she wanted to become their in-house counsel. As Feingold retells the story, “I went one step further. I booked a flight to New York City and told him I’m coming down for an interview to get hired as your first lawyer. It was bold, but I also had my pitch down and made it clear I wouldn’t be wasting his time.” Feingold was, unsurprisingly, hired on the spot and, over her nine-year career there, she was integral in Etsy’s explosive growth and successful IPO.

Let unconventional lead to your uncomfortable

Unsurprisingly, taking Etsy public was exciting, but also quite stressful. Additionally, as often-times happens, the company Feingold started at was very different from the company she worked at almost ten years later. “Etsy comprised a significant portion of my legal career and personal life. I started as the 17th employee only a few years out of law school. By the time I left, Etsy was a public company with over 800 employees and I was chasing my three-year old son. Even so, contemplating leaving was very difficult,” Feingold explains. Feingold knew that deep down she was ready for a change. “It’s always hardest to embrace change when the status quo is actually really good and quite comfortable,” Feingold says, “so I knew that what would drive my next move would have to be something other than a long list of reasons Etsy was no longer fulfilling.” Feingold could rely on a skill that she had started perfecting a long time ago: taking charge of your needs. As Feingold explains, “realizing I was comfortable drove me to make the change to continue growing.” She joined Vroom.com because she was impressed with the company, its business model, and the management.  She was also energized to learn a new industry and apply all the cumulative skills she acquired at Etsy. “I wanted to make sure I left Etsy for the right place, and after having numerous conversations with the Vroom 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!” Feingold adds. 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.

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Pass your knowledge on

“There have been so many people who have openly shared their lessons learned, supported me throughout my creative and career journey and, ultimately, were instrumental in my success. At some point, I realized the best way to contribute to the legal and creative community is to pay it forward,” Feingold explains. Feingold created a cohesive presentation and speaks about her top five takeaways 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, face the fear of saying “yes”. Feingold says, “by “borrowing” each other’s brain power, imagine how much more successful each one of us would be!” Feingold has been giving the cannonball talk at companies, law firms, and conferences. Unsurprisingly, the feedback has been nothing but positive.

Feingold’s ability to marry her creativity with her career as an attorney at two very successful startups is a lesson anyone can benefit from. In abstract, passion can be nebulous; however, focusing on concrete goals and creating your own opportunities can help push a career forward.  Feingold’s commitment to keeping her passion alive has led her to embrace being different, demonstrate the value in standing behind what she believes in and, ultimately, pushing herself to new heights.

Olga V. Mack and Katia Bloom are startup enthusiasts who embrace the current disruption to the legal profession. Long gone are the days when in-house legal departments simply manage outside counsel or provide services. Today’s legal department is a sophisticated business unit that co-manages the company’s bottom line, embraces technology, and analyzes risks constructively. Mack and Bloom love this change and are dedicated to improving and shaping the future of the legal profession. Together they passionately collect and share inspiring stories of legal leaders who are thriving through the ongoing tectonic shift. Mack and Bloom are convinced that the legal profession will emerge from this revolution even stronger, more resilient, and inclusive than before. They are currently co-authoring a manual of the skills and traits lawyers need to succeed in — and even enjoy — today’s rapidly evolving in-house legal departments. You can reach them at olga@olgamack.com and katia@katiabloom.com or @olgavmack and @bloomkatia on Twitter.

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