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How 7 lawyers landed jobs as general counsel at fintechs like Lemonade, Toast, and Stash.

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GCs at some of the most exciting fintechs spoke with Business Insider about their career paths.

Stash; Gemini; Albert


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  • In-house gigs at companies are often highly coveted among young lawyers seeking to zero in on a single business and finding generally better work-life balance.
  • Fintechs especially rely on their general counsel to provide legal advice, as they tend to operate in complex regulatory landscapes.
  • Seven GCs at some buzzy fintechs, like newly-public insurance company Lemonade, spoke with Business Insider about how they landed their jobs, and what skills they think are essential for working in-house. 
  • Visit Business Insider’s homepage for more stories.

While most attorneys start their careers at traditional law firms, many go in with the intention of eventually moving in-house.

There are a myriad of reasons for this desire to be general counsel at a company, including the ability to depart from the infamous billable-hour model, a better work-life balance, and the opportunity to focus on a single client.

The fintech world is booming, scooping up $34.5 billion in funding throughout 2019, as previously reported by Business Insider. Given the complex regulatory landscapes that these fintechs operate in — from insurance to cryptocurrency — GCs have an increasingly crucial role in offering legal advice that shapes startups’ innovation and business decisions.

Business Insider spoke with seven lawyers who landed general counsel jobs at major fintech startups about their career paths and what skills they think are essential in-house.

Jeff Apfel, general counsel at Albert

Jeff Apfel, GC at Albert.

Albert


Current position:General counsel at personal finance app Albert 

How he landed at Albert:Apfel was originally a software engineer before pivoting toward law, working in software development at ABN AMRO Bank and Accenture. After several years, though, he found himself wanting to work on “the bigger picture,” which contrasted with the individual projects he worked on as a software engineer, and pivoted toward law.

After graduating from the Loyola Law School in 2003, Apfel went straight in-house, landing an associate counsel position at IAC, a media and Internet company. After stints at car sales platform, TrueCar.com, and Groupon, Apfel returned to Accenture — this time as their software product attorney — in 2013.

One day, over lunch with a friend, Apfel talked about how he wanted to transition from a large company like Accenture to an in-house position, which he felt would allow him to work on a variety of matters. Shortly after, the friend happened to bump into the CMO of Albert at the time, and discovered the startup was looking to hire a GC.

What is an important skill as GC at a startup?

Lawyers are notorious for speaking in legalese, and Apfel said that communication skills are extremely important as GC.

“You have to essentially distill for the business folks complex legal arguments and regulations from all over the place”, he said, specifically from industry watchdogs like the Financial Industry Regulatory Authority, the US Securities and Exchange Commission, and the Federal Deposit Insurance Corporation. “It’s the alphabet soup of agencies in the financial services space. You need to be able to distill those complex regulatory structures and communicate, in plain English, to the business leadership what the risk is in doing X, Y, or Z.”

Sydney Schaub, general counsel at Gemini

Sydney Schaub, GC at Gemini.

Gemini


Current position:GC at cryptocurrency startup Gemini

How she landed at Gemini:Schaub, who discovered in her first year of law school that she wanted to work in the tech industry in a legal capacity, landed a position in Google as a policy specialist. She knew that the policy team worked closely with the legal team, and, three years later, became associate corporate counsel at Google.

Seeking to get a broader set of skills, Schaub transitioned to Square, the payments startup famously launched by Jack Dorsey, as associate GC, in 2011. Five years later, Schaub moved to the women-led fashion startup, Rent the Runway, as its GC.

Schaub was connected to Gemini through a friend in the cryptocurrency space, and discovered that the startup was looking for a GC after speaking with Beth Kurteson, who’s now Gemini’s managing director.

What is an important skill as GC at a startup?

Schaub said that an open-mindedness to innovation is key to being GC at a startup, especially since lawyers are typically trained to spot risk and identify problems, whereas companies look to their in-house counsel to come up with creative solutions.

“I think that’s a critical skill, and doing it in a way where you share the sense of adventure that the rest of the company has,” Schaub said. “Are you bought into the vision, as opposed to being the wet blanket? I’m coming at it with a spirit of optimism, while protecting the company and flagging the risks in a way that also allows it to innovate and move forward.”

Read more:Meet 9 legal tech startups that top VCs say are poised to take off as law firms look to cut costs and boost productivity

Tracy Bowden, general counsel and head of compliance at Hippo

Tracy Bowden, GC at Hippo.

Hippo


Current position:GC and head of compliance at insurtech startup Hippo

How she landed at Hippo:Bowden’s career path was always steeped in insurance. After spending eight years at the insurance law firm, Thompson Coe Cousins & Irons, she moved in-house at various insurance companies, including: TIG Insurance, RenRe Insurance, and Alliant Specialty Insurance.

Bowden was at the law firm Mitchell, Williams doing insurance corporate regulatory work, when she met Richard McCathron, now the chief insurance officer at Hippo, during a joint venture project. When the then-GC of Hippo moved to a different company, Bowden was offered the position. 

What is an important skill as GC at a startup?

Knowledge of the core business is the lynchpin of in-house work, according to Bowden.

“You don’t have the time to learn that core business on the fly — you have to immerse yourself and know what the issues are in your core business. There are too many chances that big things could go wrong,” she said. “At the end of the day, the general counsel is making the key decisions around the core business.”

William Latza, general counsel at Lemonade

Screenshot of the Lemonade App.


Courtesy of Lemonade



Current position:General counsel at online insurance company Lemonade

How he landed at Lemonade:From the moment he graduated from law school in 1981, Latza worked in the insurance space, first at a small insurance specialty firm, D’Amato & Lynch. He was then recruited by Stroock & Strook & Lavan, a Wall Street general practice firm, to join their new insurance practice group as an associate. Over the next three decades, he was promoted to partner, and ultimately the head of the firm’s insurance practice.

Latza was connected to Daniel Schreiber and Shai Wininger, the founders of Lemonade, by someone at D’Amato & Lynch. Latza was engaged as outside counsel shortly after the company launched in 2015, and developed a great working relationship with the nascent Lemonade team — “except of course for paying Wall Street legal fees.” He was ultimately brought in-house as general counsel at the firm, which went public in July.

What is an important skill as GC at a startup?

Aside from “lawyerly fundamentals,” which are a given, Latza said that an understanding of the founder’s vision is a key skill for a GC at any startup. Although the issues across the insurance industry are familiar, the resolutions reached at startups tend to be different because they’re tied to the company’s mission.

“At Lemonade, it’s no longer enough to know the rules, you also have to find new ways to apply the rules to achieve the vision,” he explained.

Another difference that Latza had to adjust to as he transitioned from his 30 years at a Wall Street law firm to a startup was the culture. “Finding myself the oldest person in the company was clearly an adjustment, but the comparative youth of my colleagues frankly was one of the reasons I joined Lemonade,” he said.

Read more:The notoriously old-school legal industry is finally warming up to tech. Here are the winners and losers as law firms turn to startups to cut costs.

Brian Elworthy, general counsel at Toast

Brian Elworthy, GC at Toast.

Toast


Current position:General counsel at restaurant point-of-sale system Toast

How he landed at Toast:Elworthy followed the more traditional path, kicking off his career after law school as an associate at the law firm, Ropes & Gray, where he continued to build his repertoire of corporate skills, especially spotting, identifying, and explaining risk.

Elworthy left Ropes after five years for two main reasons: First, he wanted to start a family, which was challenging to do with the partner model typically found at firms. Second, he’d grown tired of “the cyclical nature of work at law firms.”

Serendipitously, he’d worked with inVentiv Health while at Ropes, and moved in-house as assistant GC in 2014. During Elworthy’s two and a half years there, the company held a liquidity event for major shareholders, and he ran a dual process M&A IPO. When that closed, Elworthy was connected with Toast.

What is an important skill as GC at a startup?

Elworthy said that being able to work hard with less is important, describing his experience in going from a fully decked-out law firm like Ropes & Gray, where he had two secretaries and document processing teams, to a startup with relatively fewer resources.

“It was a big thing for me when I started at Toast just to get a printer. When I requested a printer, our CFO, asked me if I next needed an abacus because it seemed so antiquated,” he told Business Insider with a laugh. “Lawyering is hard work, but it’s different when you’re working on a startup where you lose that sort of infrastructure, and go from being the revenue generator to being a support team member.”

Meredith Smith, general counsel at Stash

Meredith Smith, GC at Stash.

Stash


Current position:General counsel at investing and banking app Stash

How she landed at Stash:Smith kick-started her legal career at Sullivan & Cromwell’s financial institutions group, which sought to train attorneys in a generalist philosophy. Smith and her colleagues advised different client groups, from investment banks to asset managers, which Smith said “sets you up to be GC.”

After eight years of working at Sullivan & Cromwell, Smith was connected to an executive at Stash by one of the partners she worked closely with in the firm’s financial institutions group. She landed a job as head of legal and compliance at the startup in 2017, and, one year later, became GC.

What is an important skill as GC at a startup?

One of the biggest differences between working at an established law firm and a startup is the pace, said Smith. The change in speed was something she had to get used to as GC at Stash.

“You have to be able to make decisions quickly based on facts you were able to collect, and potentially get up to speed with a whole new set of laws that you weren’t aware of, to make a decision and being comfortable with that decision — knowing you didn’t run every fact down and didn’t run down every legal nuance,” she explained. “Because at S&C, we were paid to be extremely precise, to run down every loose end, to think through every possibility. You have to really gather what you can in the timeframe and rely on your judgment.”

Read more:Stash’s CEO says LendingTree’s participation in its $112 million funding round will help the fintech’s expansion into lending

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