Bob Roland

Bob Roland is Executive Vice President, Chief Administrative Officer and Chief Operating Officer for the CopperPoint Family of Insurance Companies.

He joined the company in 2017 with more than 30 years of experience in the property and casualty industry. In 2021, Roland was promoted to assume the responsibilities of Chief Operating Officer. His responsibilities include claims and related processes, data management and analytics, corporate development, internal audit, information technology, program management, Pay as you Go and the integration of alternative growth and acquisitions.

With deep knowledge of property and casualty insurance, he is a respected expert in data management. He has significant experience in merger integrations, having led more than 17 financial integrations, as well as in strategic systems development in which he has led more than 20 large-scale systems development projects.

Previously, Roland served as Senior Vice President of Corporate Financial and Actuarial Operations at The Travelers Company. During that time, he also supported business insurance, effectively managing the flow of data throughout the enterprise and to many external reporting functions. While at Travelers, Roland served on the Business Insurance Strategic Leadership group, the CFO Counsel and numerous steering groups.

He holds a Bachelor of Science in Management with a Human Resources Concentration from the University of Connecticut.