Mark R. Isakson

Mark R. Isakson is CEO of Chesapeake Employers’ Insurance Company. Mr. Isakson became CEO of Maryland’s largest workers’ compensation insurance company on April 3, 2023. In this leadership role, he is responsible for developing the company’s vision, culture, and financial strength. He also leads engaging stakeholders in the creation of the company’s long-term strategic direction with an emphasis on innovation and growing Chesapeake Employers’ mission into the future.

Prior to joining Chesapeake Employers, Mr. Isakson was Senior Vice President, Chief Customer Officer at Pinnacol Assurance in Denver, Co., one of the nation’s 25 largest workers’ compensation carriers. In this capacity, he was responsible for corporate strategy development and executives leading the organization’s insurance operations, information services, and agency/distribution sales management. Mr. Isakson’s strategic leadership shaped the organization’s mission-driven culture of caring, growth, and operational excellence. He also spearheaded the development of new enterprise-wide strategies and capabilities in the areas of business growth, customer experience, diversity, equity and inclusion, and innovation. Prior to his senior VP role, Mr. Isakson also served as vice president, operations; associate vice president, underwriting and business operations; business director; and senior underwriter. Mr. Isakson began his career at Pinnacol Assurance in 2001.

Mr. Isakson holds an MBA, Financial Management, from the University of Colorado Denver and a bachelor’s degree in Business Administration from the University of Northern Colorado where he graduated cum laude and with highest academic distinction.

Mr. Isakson is a native of Colorado where he was raised on his family’s farm. He is married, has four children, and enjoys traveling with his family, reading, and volunteering in the community.