In-house counsel often jump industries, but few moves have been as drastic as that by former DraftKings General Counsel Tim Parilla.

Two years ago, he moved from the fantasy sports and gambling giant to LinkSquares, an artificial intelligence-powered contract drafting and management platform. Founded in 2015, LinkSquares a year ago completed a $100 million Series C funding round, bringing its total fundraising haul to $161 million and giving it an $800 million valuation.

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