Experienced Professionals

Darryl Siry

President at ProSight Direct

Darryl leads our direct-to-consumer technology platform for small businesses. He oversees a group of designers, developers, underwriters and marketers who deliver the best online commercial insurance experience in the industry. He is a dynamic leader whose previous roles at ProSight include CMO and CIO. Prior to joining ProSight, he founded a technology startup, led marketing and sales for Tesla and was CMO for Fireman’s Fund Insurance Company. Darryl earned a B.A. in Economics from Brown University.

Meet the Leadership Team

Founder and Executive Chairman

Meet Joe

President and Chief Executive Officer

Meet Larry

Chief Underwriting Officer

Meet Bob

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 Segment President

Meet Erin

National Sales Officer

Meet Ric

Chief Information Officer

Meet Nestor

Customer Segment President

Meet Joe

Customer Segment President

Meet Rob