Chubb taps Dave Roberts to lead Westchester

Chubb has named Dave Lupica executive chairman of Westchester , its North American wholesale E&S business, while appointing Dave Roberts as division president, effective immediately.

In his new role, Lupica will provide governance oversight and advise on strategy for Westchester’s wholesale E&S operations. During his 26 years with Chubb, he helped build the company’s Financial Lines practice, launched its first Small Business division, led Westchester’s digital transformation, and oversaw the growth of Healthy Paws into a leading pet insurer. He was inducted into the Insurance Business America Hall of Fame in 2024.

Roberts, previously Westchester’s chief operating officer, will assume executive responsibility for the business, overseeing the delivery of specialty E&S products for wholesale brokers. A more than decade-long Westchester executive, he previously led the division’s digital, middle market, and small business operations.

The leadership transition comes as Westchester continues to expand its specialty E&S franchise, with Chubb highlighting Roberts’ underwriting discipline and use of data analytics in portfolio management, while retaining Lupica in a strategic oversight role.