Experienced Professionals

Bob Bailey

Chief Underwriting and Risk Officer

As one of our co-founders, Bob serves as both our Chief Risk Officer (CRO) and Chief Underwriting Officer (CUO).  With over 30 years of underwriting and product development experience, including time at Fireman’s Fund Insurance Company and CIGNA Insurance, Bob is primarily responsible for making sure the company is tracking our key areas of risk and making sure that our underwriting routines and price application are consistent with delivering a sustained top-tier performance. Bob spent his undergraduate years at the University of Oklahoma and earned an M.B.A. from Chapman University.

Meet the Leadership Team

Chief Executive Officer and President

Meet Larry

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 Technology and Operations Officer

Meet Darryl

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

Chief Investment Officer

Meet Nico

Chief of Staff & Head of Capital Markets

Meet Jeff