Bob O'Leary

Philadelphia Insurance Companies

CEO & President




Mr. Robert D. O’Leary’s insurance career began in 1977 as an Industrial Sales Representative for American Mutual Insurance Company. Mr. O’Leary later joined Universal Underwriters Insurance Company as a Commercial Sales Representative in 1979. In 1982, he joined Maguire Insurance Agency as a Regional Manager for the New England Region. He was named Regional Vice President of Philadelphia Insurance Companies in 1986 and managed the Great Lakes area in addition to New England and New York. As the Company’s business became more concentrated, Mr. O’Leary’s territory became the Northeast Region, which encompassed New England and New York. In April of 2006, he was named Senior Vice President for the Eastern Territory, and two years later he was promoted to Executive Vice President of Marketing. Mr. O’Leary took over as Executive Vice President and Chief Marketing Officer in January of 2012, before being named President and CEO in February 2013. Mr. O’Leary holds a B.A. in Economics from Trinity College in Connecticut and also holds the Chartered Property Casualty Underwriter designation.

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