His insurance career spans more than three decades and includes a record of success in complex underwriting and claim functions. Prior to joining CNA in 2009, Bob served as chief operating officer of Commercial Markets for Zurich North America. During his Zurich career, he led the turnaround of the company's middle market business, opening new offices, refreshing current products, adding proprietary products, and changing the geographic mix and segmentation.

He decided on an insurance career when he received a college scholarship through Kemper Insurance as a “Kemper Scholar.” He went on to work for Kemper and, over a 28-year period, rapidly advanced from underwriter to several branch, regional and business leadership roles. In his last two positions at Kemper, Bob served as president of American Manufacturers Mutual, Kemper's small and middle market commercial business, and was Kemper's chief claim officer.

Bob received a bachelor's degree in business economics and industrial relations from the University of San Francisco, and holds the CPCU designation. Bob has served twice as board member of the National Council on Compensation Insurance (NCCI).