Jeffrey C. O'Shaughnessy, JD

Jeffrey C. O’Shaughnessy, JD, is President and Chief Executive Officer of HSB Group Inc., parent company of The Hartford Steam Boiler Inspection and Insurance Company with insurance and engineering affiliates worldwide. He assumed responsibility for this position in 2026.

Mr. O’Shaughnessy most recently served as President of Portfolio Risk Solutions, managing HSB’s assumed reinsurance from September 2020 – March 2026. He oversaw the division’s products, underwriting, and relationships with client insurance companies and strategic partners. In his role, he focused on delivering innovative product and service solutions that align HSB’s capabilities with clients’ strategies and objectives, as well as helping clients generate revenue and positioning them to better respond to today’s emerging risks.

Mr. O’Shaughnessy served as Global Chief Underwriting Officer at HSB from 2017 – 2020. He was responsible for defining the group’s underwriting appetite, ensuring that the portfolio of business stays true to that appetite, empowering the field underwriting organization to make decisions within that framework, and managing the underwriting services organization.

Joining HSB in December 2002 as assistant vice president of product development, Mr. O’Shaughnessy led the development and enhancement efforts of a number of HSB’s strategic products. From 2012 to 2017, he served as the Chief Underwriting Officer of HSB’s Treaty division in charge of Treaty underwriting and product management. Mr. O’Shaughnessy has also served as a member of the Board of Directors of HSB’s international insurance affiliates, HSB Canada, and HSB U.K.

Prior to joining HSB, he spent four years at Royal & Sun Alliance and four years at American International Group in various underwriting management roles in Boston, Mass.

Mr. O’Shaughnessy holds an undergraduate degree in history from Boston College and a law degree from Suffolk University in Boston, Mass.