Paul J. Hennessey

Paul J. Hennessey

Assistant Vice President

Paul is an Assistant Vice President in Cool Insuring Agency’s Commercial Lines Division and an Officer of the company. He joined Cool Insuring in 2004 as an Account Executive, and has been in his current position of Assistant Vice President since January 2011.  Prior to working for Cool Insuring Paul was an Assistant Underwriter at Travelers Insurance Company.    For several years Paul worked in the National Accounts Division at Travelers, where his focus was on loss sensitive programs including retrospective plans, deductible plans, and self insured retention placements.   At Cool, Paul maintains a large book of business and provides brokerage and risk management consulting services to large public and private entities.


  • Magna Cum Laude Bachelor of Science Degree in Marketing / Management, Siena College


  • Licensed NYS Property and Casualty Agent