Bob Jessup

President, Chesterfield Companies Inc.


Bob has been the President of Chesterfield Companies Inc. since 2010, which provides commercial insurance brokerage services, commercial risk control services, and commercial claims administration services  in connection with General Liability, Commercial Auto, Commercial Property, Bonds, Boiler & Machinery, Cyber Insurance, Workers Compensation, Umbrella Liability, Travel & Accident, Employment Practices Liability, and Employee Benefits including Health, Life Insurance, Long Term Disability, Supplemental Insurance, and Flexible Spending Accounts. In addition, Chesterfield provides claims administration services for self-funded employer-based health plans and short-term disability plans.

Prior to joining Chesterfield, Bob served for twenty-five years as a Senior Vice President in the North-East and Mid-Atlantic regions for Zurich North American Insurance. He managed a casualty underwriting business portfolio in excess of $500 Million, comprised primarily of companies within the Fortune 1,000. He holds a B.S. in Engineering and Economics from Pennsylvania State University and attained a Chartered Property Casualty Underwriter designation in 1995.

All sessions by Bob Jessup