Paul A. Simpson
Account Executive
Paul is a seasoned commercial lines expert with more than 30 years of insurance experience. He joined Cleary in September 2026 after 25 years at Willis Towers Watson.
He began his career as an underwriting assistant at Liberty Mutual, which gives him a rare understanding of both the broker and carrier sides. As an Account Manager, Paul leads day-to-day client account service and partners with our producers on marketing and placement strategy, ensuring every client gets responsive, expert support. He attended Curry College in Milton, MA, and holds a Massachusetts Property & Casualty license. Off the clock, you’ll find Paul golfing, at concerts, or dancing.
617-305-0392
Fax: 617-305-0365



