Experienced Professionals

Darryl Siry

President at ProSight Direct

Darryl is president of ProSight Direct, our direct-to-consumer technology platform for small businesses. His team consists of designers, developers, underwriters and marketers who all work together to deliver the best online commercial insurance experience in the industry. He is a dynamic leader whose previous roles at ProSight include CMO and CIO. Simply put, the man is smart! Prior to joining our team, he founded a startup, led marketing and sales for Tesla, and was CMO for Fireman’s Fund Insurance Co. Many moons ago, Darryl earned a BA in Economics from Brown University. When he is not building the future of digital insurance, he’s cycling the beautiful hills of central New Jersey, as he is an avid cyclist.

Meet the Leadership Team

Chairman, President and CEO

Meet Joe

Chief Operating 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 Group President

Meet Erin

National Sales Officer

Meet Ric

Chief Information Officer

Meet Nestor

Customer Group President

Meet Joe