Profile
Dave Roberts brings nearly 20 years of industry experience, having held several regional and national leadership roles prior to joining Westchester in 2014.
Before this most recent appointment, he served as executive vice president at Westchester, with executive operating responsibility in small business underwriting, middle market underwriting, programs underwriting, operations, and information technology.
Roberts holds CPCU and RPLU industry designations. He earned a Bachelor of Science degree in management, with a minor certification in Spanish, from Pennsylvania State University.
3 Country View Road, Malvern, PA
484 321 4180
david.roberts@westchester.com
westchester.com/en
Dave Roberts
Chief Operating Officer
Westchester, A Chubb Company
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Bio
Milestones
2007–2012
2014–2019
2021–2022
2023–2024
2025
2007: Started insurance career at USLI
2012: Promoted to Regional Underwriter Leader at USLI
2007–2012
2014: Joins Westchester
2015: Promoted to Vice President at Westchester
2019: Promoted to Senior Vice President at Westchester
2014–2019
2021: Promoted to Head of Westchester Small Business
2022: Westchester Big Audacious Goal Award
2021–2022
2023: Promoted to Executive Vice President of Westchester Digital & Middle Market, Westchester Business Unit of the Year
2024: Westchester Business Unit of the Year
2023–2024
Promoted to COO of Westchester
2025
Milestones