DraftKings uses LinkSquares to organize their contracts and keep up with a rapidly scaling business.

Learn how DraftKings uses LinkSquares Analyze to save hours of manual work each week.

Digital Sports Entertainment
Sean Hickey - Director of Legal, Dean Fiotto - Associate Corporate Counsel

Meet DraftKings


Boston, MA


Digital Sports Entertainment



Founded in 2012, and headquartered in Boston, DraftKings is a digital sports entertainment and gaming company with products that range across sports betting, iGaming, Daily Fantasy Sports, free-to-play products, digital media, and a NFT marketplace. With over 3,500 employees and millions of users across the United States, and globally, DraftKings is one of the country’s leading sports and entertainment companies.

To support its legal needs, DraftKings has several legal groups devoted to specific aspects of the business, including litigation, government affairs, and intellectual property, among others. One of these groups is the commercial transactions team, which reviews and negotiates every commercial contract entered into by DraftKings. This team, which includes Sean Hickey, Director of Legal, and Dean Fiotto, Associate Corporate Counsel, is among the company’s busiest. Each of the commercial transactions groups’ five attorneys field multiple business-critical requests from within the organization and tend to over a dozen contracts per day, from one-off agreements with social media influencers to large-figure deals with sports leagues like the NFL, NHL, PGA TOUR, NBA, and MLB, among others.

The Visibility Challenge

When Hickey joined the company in 2016, his first major project was to locate every DraftKings contract, identify the information they contain, and determine how to keep them organized for easy access.

“This was a massive challenge,” remembers Hickey. “We had contracts stored across multiple shared drives with different folder structures and naming conventions, it was hard to even know where to start.”

This lack of insight became even more apparent when it came time to complete a company capital event. The team needed to quickly find answers to critical, granular questions about specific contracts over a certain dollar amount or that contained specific contractual provisions. “We ended up straining ourselves needlessly because we did it all manually,” Hickey said.

LinkSquares was exactly the tool we needed. We started by bringing our thousands of contracts into Analyze, where the system pulled out key information and kept every agreement organized.

Sean Hickey

The company’s rapid expansion began to stress the manual processes they had in place, especially during the contract drafting and execution process. With a growing list of VPs working on strategic contracts for the business, Hickey was fielding several status update questions each day, pulling him away from his other time-sensitive work.

“There were lots of incoming emails and messages, each one more urgent than the next,” said Hickey. “We needed a better way to provide answers to these stakeholders.”

Between Hickey’s initial directive, lessons learned from previous transactions, and a rapidly growing company, it became clear to DraftKings team that they needed a platform that could get them organized and automated assist in effectively scaling.

Getting Organized and Automated

When it came time to put a new system in place, DraftKings knew they needed a secure repository, accurate optical character recognition (“OCR”) and data extraction capabilities, a robust reporting engine to surface contract details, and a way to keep stakeholders updated.

“LinkSquares was exactly the tool we needed,” says Hickey. “We started by bringing our thousands of contracts into LinkSquares Analyze, where the system pulled out key information and kept every agreement organized in one place.”

For the commercial transactions team, this centralization with clause-level search proved critical to keep things moving efficiently. They accelerated their drafting process, while reducing risk, by quickly surfacing prior contracts with the same counterparty or similar types of agreements to understand how specific terms have been used in the past.

Centralization has also proved invaluable for maintaining their portfolio. Contracts are uploaded from the respective data room into Analyze where the DraftKings team can quickly understand what has been agreed to and other key information.

The reporting saves us hours that we can now spend getting something else done for the business.

Dean Fiotto

As for newly executed contracts, they now flow automatically from their e-signature tool into Analyze, effortlessly keeping their repository up-to-date. This is useful for maintaining DraftKings’ records, a key responsibility for a publicly traded company.

With every contract and key data stored in one place, the team leverages the LinkSquares reporting capabilities to run portfolio-wide reports in seconds, providing insights into key dates and terms that would normally take significant time combing through documents.

“The reporting saves us hours that can now be spent getting something else done for the business,” says Fiotto.

While LinkSquares makes Legal more efficient, it’s also driving value for other teams across DraftKings.

“When other departments across the organization need a specific agreement, we can pull it up immediately, allowing us to be less of a speedbump,” says Fiotto. “For instance, the finance team benefits because we can quickly ensure that contractual conditions are met before they write a check. Most folks look to lawyers as a source of infinite information, so being able to quickly get an answer is super valuable.”

Five years after adopting LinkSquares, DraftKings has continued to integrate the platform deeper into their workflow. With the recent purchase of LinkSquares Finalize, contracts are now being drafted within the platform, providing key stakeholders with the ability to view a contract’s status without requesting an update from Legal.

As Fiotto remarked, “Being able to locate specific contract information and draft agreements at the rate LinkSquares allows is huge. Our business moves quickly, and we have to be quick, too.”

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