Why Marc Chesley, Ex-COO of a $1B AI Exit Just Backed ProPlaintiff.ai

Marc Chesley, former Chief Operating Officer of Paradox AI, has joined ProPlaintiff.ai as a strategic advisor and investor.

Chesley was the COO at Paradox AI when the company was acquired for $1 billion in August 2025. Before that, he scaled Infusionsoft from $1M to $100M in revenue as CTO, and drove OfferPad to $100M as President. He holds a law degree from BYU and is admitted to the Arizona State Bar and the U.S. Supreme Court. He's backing ProPlaintiff.ai because he's seen exactly what happens when purpose-built AI automates a high-volume professional workflow at scale. And because he understands the legal side of that equation firsthand.

The Operator Behind a $1B Exit

Paradox AI built Olivia, a conversational AI that automated high-volume recruiting workflows for some of the largest employers on the planet: McDonald's, Disney, Unilever, Nestlé. Under Marc Chesley's operational leadership, Paradox grew 1,000% and scaled to more than 1,000 enterprise clients.

In August 2025, the company was acquired for $1 billion.

He understands AI at scale. He also understands what it means to practice law.

"Marc is the rare person who has both lived the vertical AI build at the highest level and understands the legal profession from the inside," said Jason Turnquist, Co-Founder and CEO of ProPlaintiff.ai. "He helped prove the playbook we're running. Having him as an advisor and investor gives us the guidance and credibility that serious companies earn after proving they work. ProPlaintiff.ai is proving it."

Marc's take on what he saw when he evaluated the platform:

"I've reviewed a lot of AI legal tech solutions, and ProPlaintiff.ai stands out for its laser focus on real-world PI workflows and its impressive agentic capabilities. I'm investing because I believe this platform will meaningfully improve outcomes for both law firms and the clients they serve. The team’s deep domain expertise combined with strong technical execution makes them a standout in the space."

‍— Marc Chesley, Strategic Advisor and Investor, ProPlaintiff.ai

Welcome, Marc.

The entire ProPlaintiff.ai team is grateful to have Marc in our corner. His experience, his legal background, and his belief in what we're building means a lot to us. We're just getting started, and having him alongside us makes that next chapter a whole lot more exciting!

See what a $1.5B AI operator is backing.

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