ProPlaintiff.ai adds ex-Paradox COO Marc Chesley as advisor and investor

By AI, Created 7:46 PM UTC, June 01, 2026, /AGP/ – ProPlaintiff.ai has named Marc Chesley, the former COO of Paradox AI, as a strategic advisor and investor as it pushes its AI platform for personal injury law firms. The move ties a legal-tech startup to an executive with experience scaling AI and SaaS businesses and a background as an attorney.

Why it matters: - ProPlaintiff.ai is trying to bring enterprise-style AI automation into personal injury law, where firms want faster case work without giving up attorney control. - Marc Chesley adds both startup scale experience and legal credentials, which could help the company win trust in a cautious market. - The company says its platform can improve operational efficiency by 80% for personal injury firms.

What happened: - ProPlaintiff.ai named Marc Chesley, former COO of Paradox AI, as a strategic advisor and investor. - Chesley helped lead Paradox AI to a $1 billion acquisition in August 2025, after driving 1,000% growth at the company. - Chesley also served as CTO and Head of Product at Infusionsoft, now Keap, where revenue grew from $1 million to $100 million. - As president of OfferPad, Chesley helped guide the company into one of Arizona’s fastest-growing real estate tech startups to reach $100 million in revenue. - Chesley holds a law degree from Brigham Young University and has active bar admission in Arizona, the U.S. District Court for Arizona and the U.S. Supreme Court.

The details: - ProPlaintiff.ai automates case management, demand letter drafting, medical chronology building, evidence analysis and legal document generation. - The platform is built specifically for personal injury attorneys. - The company says attorneys keep complete control over every case decision while using the system to reduce manual work. - ProPlaintiff.ai was named a winner of the AZ PHX FWD Innovation Challenge. - The company was also a finalist in the Phoenix Business Journal’s 2026 AZ Inno Fire Awards, presented by the Arizona Commerce Authority. - ProPlaintiff.ai says it is backed by a growing roster of personal injury law firms across the country.

Between the lines: - The Chesley hire is a credibility signal as ProPlaintiff.ai tries to move from startup promise to broader legal-industry adoption. - His mix of AI, SaaS and legal experience fits a market where buyers want proof that automation can improve output without creating professional risk. - Jason Turnquist, ProPlaintiff.ai co-founder and CEO, said Chesley helped prove the company’s playbook around vertical AI built for a specific workflow and executed with operational discipline. - Chesley said he is investing because he believes the platform can improve outcomes for law firms and their clients.

What’s next: - ProPlaintiff.ai will likely use Chesley’s experience and network to expand its sales into more personal injury firms. - The company is positioning for more recognition as it builds on industry awards and adoption by law firms. - No new product launch or funding round was announced in the release.

The bottom line: - ProPlaintiff.ai is betting that legal-tech buyers will respond to a familiar enterprise AI playbook: narrow focus, measurable efficiency gains and an advisor with proven scale.