Experienced Professionals

Darryl Siry

Chief Technology and Operations Officer

Darryl is responsible for leading all technology and operations at ProSight. Previous roles within the company include CMO, CIO, and most recently, President of our direct-to-consumer online insurance platform. Prior to joining ProSight, Darryl founded a technology startup, led marketing and sales for Tesla, and was CMO for Fireman’s Fund Insurance Company. Darryl holds a B.A. in Economics from Brown University.

Meet the Leadership Team

Founder and Executive Chairman

Meet Joe

Chief Executive Officer and Co-Founder

Meet Larry

Chief Underwriting Officer and Co-Founder

Meet Bob

Chief Customer Experience Officer

Meet Vivienne

Chief Legal Officer

Meet Frank

Chief Human Resources Officer

Meet Kari

Chief Actuary Officer

Meet Lee

Chief Financial Officer

Meet Anthony

Customer Segment President

Meet Erin

Chief Sales and Marketing Officer

Meet Ric

Chief Information Officer

Meet Nestor

Customer Segment President

Meet Joe

Customer Segment President

Meet Rob

Chief Claims Officer

Meet Donna

Customer Segment President

Meet Kevin

Field Operations Officer

Meet Lee