Bob O'Leary

Chairman

Mr. Bob O'Leary's insurance career began in 1977 as an Industrial Sales Representative for American Mutual Insurance Company. He later joined Universal Underwriters in 1979. In 1982, Mr. O'Leary joined Maguire Insurance Agency, which became Philadelphia Insurance Companies (PHLY) in 1987. Mr. O'Leary has held several titles throughout his years at PHLY, becoming President & CEO in February of 2013. He was named Chairman in January 2020.

Mr. O'Leary holds a B.A. in Economics from Trinity College in Connecticut, and he earned the Chartered Property Casualty Underwriter designation in 1987. He is married with three sons.