Westchester, a Chubb Company, Appoints Dave Roberts Chief Operating Officer

WHITEHOUSE STATION, N.J., June 19, 2025 – Westchester, Chubb's Excess and Surplus (E&S) Lines Division, today announced that Dave Roberts, Executive Vice President, Head of Digital and Middle Market, has been appointed to Chief Operating Officer of Westchester, effective immediately.

Dave will have operating responsibility for Westchester’s recently formed Property, Casualty and Financial Lines Business Practices which includes Digital, Middle Market, Programs, Operations and IT. He will report to David Lupica, Vice President, Chubb Group, and Division President, Westchester.

“Under Dave's leadership, Westchester has experienced remarkable growth, transforming our Small Business practice into a fully digital operation while significantly enhancing our efficiency and market reach,” said Lupica. “His strategic vision will drive innovation and position us to respond to emerging opportunities while navigating the complexities of the excess and surplus market.”

As a nearly 20-year veteran of the insurance industry, Dave has spent over 10 years with Westchester. Prior to his current role, he held numerous senior leadership positions, including overseeing Westchester's Small Business products and business development, underwriting operations, and profitability performance.

About Chubb

Chubb is a world leader in insurance. With operations in 54 countries and territories, Chubb provides commercial and personal property and casualty insurance, personal accident and supplemental health insurance, reinsurance and life insurance to a diverse group of clients. The company is defined by its extensive product and service offerings, broad distribution capabilities, exceptional financial strength and local operations globally. Parent company Chubb Limited is listed on the New York Stock Exchange (NYSE: CB) and is a component of the S&P 500 index. Chubb employs approximately 43,000 people worldwide. Additional information can be found at:  www.chubb.com.

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