Experienced Professionals

Bob Bailey

Chief Underwriting Officer

Bob is our chief underwriting officer and the last piece of our co-founders fellowship. He has a sharp wit that is surpassed only by his deep professional expertise – a master of the identification, assessment and management of all risks associated with our lines of business. With over 30 years of underwriting and product developing experience, he is a natural at leading our teams in the creation of customized business solutions for specific industry needs. His knack for accomplishing tasks “Sooner” rather than later may be a direct result of graduating from the University of Oklahoma. Oh, and Bob also earned an M.B.A. from Chapman University, however we’re still not sure where he acquired his illustrious storytelling capabilities.

Meet the Leadership Team

Chairman, President and CEO

Meet Joe

Chief Operating Officer

Meet Larry

Chief Customer Experience Officer

Meet Vivienne

Chief Claims Officer

Meet Paul

Chief Legal Officer

Meet Frank

Chief Human Resources Officer

Meet Frank

Chief Actuary Officer

Meet Lee

Chief Financial Officer

Meet Anthony

Customer Group President

Meet Erin

President at ProSight Direct

Meet Darryl

National Sales Officer

Meet Ric

Chief Information Officer

Meet Nestor

Customer Group President

Meet Joe