Left to right: Cassie Sadowitz, Adam Gomolin and Jonathan Truppman.

It's happened more than once. Cassie Sadowitz was wearing her Jacksonville Jaguars apparel in an airport, when a stranger incorrectly assumed that she was a team cheerleader.

“Gotta love the stereotypes,” said Sadowitz, 29, who serves as general counsel for the Florida-based National Football League team.

It's unusual to find young lawyers early in their careers working in-house, let alone leading legal departments, but Sadowitz is among the small group of top in-house lawyers who fit into the millennial category. She, and others who spoke to Corporate Counsel, didn't take the traditional paths to becoming GCs— but that's not holding them back.

A Different Route

According to a 2017 survey from the Association of Corporate Counsel, 30 percent of in-house lawyers who are millennials, or those born between 1981 and 1997, did not have previous experience at a law firm.

Sadowitz's experience fits this nontraditional narrative. She started five years ago with the Anaheim Angels as a legal intern, a post she landed by sending an unsolicited LinkedIn message to the team's then-legal director. When he later moved to the Tampa Bay Buccaneers, he offered Sadowitz a full-time position in-house where she worked for nearly two years before joining the Jaguars in 2014.

“Typically when people ask about my role and I relay that I'm the team's general counsel, the reaction I get is a look of confusion and a response along the lines of, 'But how? You're so young,'” she said.

Despite the stereotypes, Sadowitz said she and the Jaguars' other two in-house lawyers —a chief legal officer and an associate GC who are also millennials—are embracing their age as an asset.

The three millennials have been able to think outside the box in many ways, according to Sadowitz, who said they've been instrumental in making changes such as allowing more flexibility for employees who want to work from home, something that not all older attorneys are willing to do.

Sadowitz said the trio bring a lot of what's considered “millennial” thinking to their work, which has been helpful for the team. They value ideals like transparency, social responsibility and flexibility in the Jaguars' organization.

“There is a general perception if you're in-house counsel or you're a lawyer for a larger company, you should be in your 50s sitting behind a wooden desk with all your law books on the shelf,” Sadowitz said. “That's just not who we are.”

Working for a professional football team involves quite a bit of travel, so Sadowitz and her colleagues encounter a lot of opportunities they want to document. About a year ago, they started using a hashtag on Instagram: #MillennialGCs.

“We jokingly called ourselves millennial GCs and it stuck,” Sadowitz said. “Using the hashtag is an easy way to archive our [activities] and showcase that the landscape of in-house lawyers is dynamic and evolving in today's age.”

Starting Out at Startups

Having a millennial in a GC role isn't too common in the sports world. General counsel in this generation are more readily found, it seems, in the startup world.

That's where Jonathan Truppman has landed. At 32-years-old, he's the top lawyer for Casper Sleep Inc.

Casper, which is frequently named as a fast-growing startup by major publications, brought on Truppman in 2015 as one of its first 15 employees. It now has more than 350.

“CEOs have different priorities,” Truppman said. “Some want the silver-haired fox in the boardroom and some need someone more scrappy who's willing to wear multiple hats and roll up their sleeves.”

As the mattress company's top lawyer, Truppman has found himself across the table from lawyers representing retailers such as West Elm and Target Corp. But he's not intimidated, he said.

“The lawyers I interact with most of the time are more seasoned,” Truppman said. “It's a good opportunity to have those experiences, to interact with them and be collaborative.”

And once the startup reaches a certain level and has the ability to bring on additional lawyers, there's always the option of recruiting more experienced attorneys, which is what Truppman has done.

“I think any hiring manager should recognize their own weaknesses… and hire people to help fill them out,” he said.

Outside of Casper, Truppman relies frequently on mentors he met from Paul, Weiss, Rifkind, Wharton & Garrison where he worked as a litigator for about three and a half years, and draws on his relationships with lawyers in the tech world he's met through networking groups.

“I can call the ZocDoc GC and he'll give me advice, or the Bonobos GC and he'll give me advice,” Truppman said.

Adam Gomolin, 33, takes a similar approach at his company Inkshares Inc., a crowdfunding startup for book publishing that he co-founded.

He said that his age doesn't hold him back as a lawyer. In many ways, it gives him more opportunities to learn from more experienced attorneys.

Promoted to CEO and general counsel in 2016, Gomolin is still Inkshares' only in-house attorney.

With the help of his outside counsel, Gomolin and his company have inked deals with major book publishers such as Penguin RandomHouse, and secured deals with Netflix Inc. and Lionsgate, among others.

The successes Inkshares has seen have exceeded Gomolin's expectations. “It feels pretty fucking good,” he said.

At the end of the day, he believes that while he might not have as much experience under his belt as some general counsel, he draws off of the critical principles he learned in law school, and he will continue to do so.

Sadowitz added that it's helpful for lawyers to always “lean on” mentors and colleagues, regardless of age.

“We're generalists and it's not expected we'd be subject matter experts in every area,” she said. “It's give and take.”

Left to right: Cassie Sadowitz, Adam Gomolin and Jonathan Truppman.

It's happened more than once. Cassie Sadowitz was wearing her Jacksonville Jaguars apparel in an airport, when a stranger incorrectly assumed that she was a team cheerleader.

“Gotta love the stereotypes,” said Sadowitz, 29, who serves as general counsel for the Florida-based National Football League team.

It's unusual to find young lawyers early in their careers working in-house, let alone leading legal departments, but Sadowitz is among the small group of top in-house lawyers who fit into the millennial category. She, and others who spoke to Corporate Counsel, didn't take the traditional paths to becoming GCs— but that's not holding them back.

A Different Route

According to a 2017 survey from the Association of Corporate Counsel, 30 percent of in-house lawyers who are millennials, or those born between 1981 and 1997, did not have previous experience at a law firm.

Sadowitz's experience fits this nontraditional narrative. She started five years ago with the Anaheim Angels as a legal intern, a post she landed by sending an unsolicited LinkedIn message to the team's then-legal director. When he later moved to the Tampa Bay Buccaneers, he offered Sadowitz a full-time position in-house where she worked for nearly two years before joining the Jaguars in 2014.

“Typically when people ask about my role and I relay that I'm the team's general counsel, the reaction I get is a look of confusion and a response along the lines of, 'But how? You're so young,'” she said.

Despite the stereotypes, Sadowitz said she and the Jaguars' other two in-house lawyers —a chief legal officer and an associate GC who are also millennials—are embracing their age as an asset.