Legal tech startup LinkSquares has hired former DraftKings GC Tim Parilla as its first chief legal officer.  

Parilla spent seven years with the Boston-based sports betting operator as its first ever GC before making the jump to fellow Boston firm LinkSquares, which specialises in using AI to provide end-to-end contract lifecycle and analytics services to legal departments.  

During his time with DraftKings, Parilla guided the company through a series of legal challenges surrounding the legality of fantasy sports betting in different states across the US. His work as GC eventually paved the way for DraftKings’ entrance into the online casino and sports betting arena. 

Parilla also notably played a leadership role in the company’s public market debut through a SPAC merger with Diamond Eagle Acquisition Group and SBTech. The company is reportedly set to bring in nearly $1bn in revenue this year as states look to relax rules around online sports betting. 

Parilla told Bloomberg Law the move reflected his desire to return to the startup environment, adding that he was keen to become part of the fast-paced legal technology space that is “ripe for disruption.”  

His new role at LinkSquares will see him act as a strategic legal advisor to the company’s management and corporate counsel customer base. 

As a LinkSquares customer himself, Parilla gained firsthand experience with the product in his role at DraftKings, saying it has the ability to “transform” legal operations at a company. He’s been a part of the firm’s advisory board since 2016 and was an early investor in the company soon after it was founded in 2015. 

“In fast-paced, high-growth companies and industries, the legal function needs to find and implement tech that enhances an attorney's ability to really drive substantive legal work,” he said. “LinkSquares is a company that is making the data-savvy legal future a reality.”  

LinkSquares says it has expanded significantly over the past year as legal departments look to mitigate risk and accelerate deals in the face of the pandemic, posting nearly 800% growth since 2019. Big-name clients include fitness technology company Fitbit, e-commerce platform Wayfair and cloud communications company Twilio.  

Parilla previously worked as internal counsel for online gambling platform Everest Gaming, now BetClic Everest Group, before joining DraftKings in 2014.   

A report published by Thomson Reuters earlier this month found that nearly a third of legal departments globally are upping their spend on technology, with 44% increasing their use of tech tools.