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DraftKings' First Lawyer Jumps to Contract Analytics Startup

March 16, 2021, 6:58 PM

DraftKings Inc.’s former general counsel and first ever in-house lawyer Tim Parilla has joined legal tech startup LinkSquares as its first chief legal officer.

Parilla spent seven years with the sports betting company before joining Boston-based LinkSquares on March 8, a move he told Bloomberg Law he made because he wanted to return to a startup environment.

LinkSquares, which uses artificial intelligence to provide contract management and analytics services to legal departments, reported nearly 800% growth in the last two years, according to a Tuesday statement.

The company raised $14.5 million in January 2020 in a Series A funding round led by Jump Capital.

“I really wanted to get into the B2B space because I’ve been in B2C my entire career,” Parilla said. “In particular, the legal technologies space is really, really interesting and is ripe for disruption. This is an interesting role because running a legal department is the business of the company.”

Parilla said he’s been on LinkSquares’ advisory board since 2016, and he was a LinkSquares customer as general counsel of DraftKings.

DraftKings went public last year through a SPAC merger and recently reported that its chief legal officer R. Stanton Dodge earned nearly $56 million in total compensation in 2020, three years after he joined the company. DraftKings also said it anticipates bringing in nearly $1 billion in revenue this year as states consider loosening the rules around sports betting.

“At the 2017, 2018 time frame, I knew that DraftKings was going somewhere big,” Parilla said. “When that happens, the role of in-house counsel just changes a little bit, and so I knew that I wanted to eventually get back into a startup.”

LinkSquares said in the statement that it has processed more than three million documents for clients such as fitness technology company Fitbit, Inc., restaurant chain TGI Fridays Franchisor, LLC, and cloud communications company Twilio.

Parilla worked for online gambling company Everest Gaming, later BetClic Everest Group, and co-founded a cryptocurrency startup before joining DraftKings in 2014.

To contact the reporter on this story: Ruiqi Chen in Washington, D.C. at

To contact the editors responsible for this story: Rebekah Mintzer at; Chris Opfer at