Casper General Counsel Jonathan Truppman always knew he wanted to “get his hands dirty” – build something that would have an impact on the world.

At first, he thought that was journalism, but after working for a leading newsroom, he says “I knew that was something I never wanted to do.” Then he thought he would get a Ph.D. in philosophy but “writing by candlelight was a played-out cliche.”

So law school was his path, with the goal of working in government. But right before his final interview (“a formality”) at the U.S. attorney’s office, the sequester hit. There was no more money for hiring.

Jonathan had met Casper CEO Philip Krim in a social context, and they’d hit it off with some “intellectual banter.” Philip approached Jonathan about joining the team and eventually talked him into taking a completely different path in his career, but one Jonathan calls “a different manifestation of the same impulse.”

Now, as Casper’s GC, Jonathan is helping build the company that Fast Company called one of the most innovative of 2017. Casper, the first global sleep company, is one of the fastest growing consumer brands of all time.

When Jonathan joined Casper, he joined a small team of 15-20 employees. Three years later, Casper has more than 300 employees.

He offers four tips for in-house counsel who are navigating the changing demands and dynamics involved in growing with a rapid-growth company.

“Inevitably as a company grows, the team becomes more specialized.”

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1. Sweep the floor.

Jonathan was not hired at Casper as its general counsel. In fact, until February 2017, Jonathan’s title was VP of Business Development & Legal.

“We were 10 people in a walk-up apartment on bond street with a shareroom as our office,” Jonathan says. “I was doing everything from payroll and onboarding to sweeping the floors. It was all hands on deck.”

Jonathan describes his first role as “a blended one”: 70% business and 30% legal. He spent the majority of his time focused on business development partnerships.

“The company was so small that Casper didn’t need a full-time GC when I joined, but – like with any early-stage company – as we grew and expanded into new markets and built new products, it was no longer feasible for me to run business development and handle the amount of legal work we had,” he says. “Legal needed to be someone’s central focus.”

It was a gradual specialization as Jonathan “cast off more hats.”

“The transition was natural,” Jonathan says. “Departments were built out with leaders who have significant experience with, for example, business development. Inevitably as the company grew, the team became more specialized.”

Now three years later, Jonathan is Casper’s first general counsel.

“Think about issues not as legal ones but issues for growing a business with law as your toolset.”

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2. The law is just your toolset.

Jonathan says that his experience on Casper’s business side has given him unique insight into the company’s priorities and the importance of putting the business side first.

“The drive at a company should never be legal,” he says. “Legal should help operationalize and make sure that business decisions are done in the correct fashion, but you’re part of a business. You’re not just a lawyer.”

Casper is building a business focused on sleep in all facets. He says he’s just another member of the team with the same focus.

“I’d recommend that any new GC joining a business remember to think about issues not as legal ones but issues for growing a business with law as your toolset,” he says. “Your role is not about the law. What’s most important is making a good business decision.”

Jonathan defines his success the same way that Casper’s business team defines success.

“Just like everyone else at Casper, I have to ask myself what is right for the customer?” he says. “The primary challenge as the new kid on the block is that we keep our customers happy. If they’re happy, then that is success. Everything else is just icing on the cake.”

3. Don’t be the suit.

The legal department needs to understand the underlying business dynamics when making legal decisions, Jonathan says.

“Get to know employees on a face-to-face basis. Meet people. Don’t be the lawyer in the suit.”

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“General counsel have to get to know everything they can about the business to be effective,” he says. “A key way to achieve this is to really know the employees. Get to know them on a face-to-face basis. Meet people. Don’t be the lawyer. The more you can come across as a real person and someone who is there to help them, then people will come to you.”

“If you’re the lawyer in the suit, then people aren’t going to come talk to you, and you won’t be naturally part of the important conversations,” he adds.

Part of getting to know the employees, he says, is learning to speak their language.

“At a rapid growth company, you often will have a young employee base,” Jonathan says. “For a lot of people, it’s their first jobs. I need to overshare, over comfort, over discuss, make sure I’m always having conversations, because most people aren’t going to know what the legal issues are.”

“There’s even a cartoon that captures this concept. It’s a priest speaking ‘thou shalt not,’ and a young kid walking by him texting and looking down at his phone,” he adds. “The kid is not paying attention and the caption is ‘lost in translation.’”

4. Jump in, learn by doing and follow your gut.

Casper’s communications team likes to joke that Jonathan “made the leap to sleep,” and back then, Jonathan couldn’t have known how successful Casper would become.

“When you join a team of 15-20 people, success in not preordained, so I tell anyone considering taking an in-house position to consider what experiences they’ll gain in the role that will give them the tools to be marketable for the next step,” he says.

“Sometimes you just have to go with your instinct, follow your gut.”

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Jonathan doesn’t shy away from saying that that in-house roles at rapid-growth companies can be uncomfortable. To help the company hit its growth goals, GCs have to move quickly, and they’re often exploring new legal territory. Risk, he says, doesn’t feel safe at a law firm.

“A big part of the job is figuring out your risk appetite. Sometimes you just have to go with your instinct, follow your gut,” Jonathan says. “Like everyone else on the team, legal has to be entrepreneurial and scrappy.”

After all, taking chances, he says, is how Casper was built.

“Every step Casper has taken over the years wasn’t some master plan we came up with on day one,” Jonathan says. “We listen to the desires of our customers, the market, unlike at a law firm, that openness to the unknown is deeply rooted in the culture at Casper.”

“It’s uncomfortable at first, but you get your sea legs, that’s the beautiful part,” he adds. “You just gotta jump right into it.”

“Casper can do for sleep what Nike did for sports.” – Forbes

Casper is a global sleep company that launched in 2014 with an obsessively engineered, outrageously comfortable mattress sold directly to consumers. Its critically acclaimed sleep surface was developed in house, has a sleek design, and is delivered in a small, “how did they do that?”-sized box. The company is one of the fastest-growing consumer brands of all time, and its product line has expanded to include sheets, pillows, a matching foundation, and a dog mattress. Casper was named one of Fast Company‘s Most Innovative Companies in the World, and its eponymous mattress was crowned one of TIME Magazine‘s Best Inventions.

About the author

Courtney Cregan

Courtney Cregan

Courtney Cregan has more than five years of experience working at AmLaw 100 law firms. Courtney earned a bachelor's degree in women and politics from Trinity College in Hartford, Conn.

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