In 2006, inspired by the success of business process outsourcing company Office Tiger, which RR Donnelley acquired that year for $250 million, Ajay Agrawal and Daniel Reed founded UnitedLex, one of the earliest legal process outsourcing companies. Within months, it was providing legal services to clients such as HP, IBM and Microsoft. Within four years, the company had achieved a valuation of $100 million.

But Agrawal was becoming increasingly intrigued by a problem a client had described to him as one of “contract education” — the gap between the promises made in an organization’s contracts and the promises ultimately delivered. It is a problem, he estimates, into losses for businesses of $2-3 trillion a year. So in 2011, he sold his stake in UnitedLex to begin working on a solution.

That led him to found SirionLabs in 2012, where he is using artificial intelligence technology to disrupt the field of enterprise contract lifecycle management. In May, the company raised $44 million in a Series C round, bringing its total raise to $66 million. Just this month, it announced several patent-pending upgrades to its AI technology.

Based in New York City, Agrawal recently joined me from New Delhi, India, where he is awaiting travel restrictions to lift so he can return home.

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#97 Triathlete/Big Wave Surfer - Clint Kimmins