Winters Oliver Insurance Agency
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 Our Leadership Team


 Ben Winters CIC

Agency Principal & Commercial Lines Sales

Phone: (804) 746-5178 Ext: 112

Ben specializes in commercial property & casualty insurance with a focus on social & human services organizations, technology, and the healthcare industry.  He holds the distinguished Certified Insurance Counselor (CIC) designation and is currently earning his Registered Professional Liability Underwriter (RPLU) designation.  Ben was featured on the February 2014 cover of Independent Agent magazine, a national industry publication, where he was recognized for his success in niche marketing.  He is a board member of the Independent Insurance Agents of Virginia and serves on the Board of Northstar Academy, an independent school serving special needs children in central Virginia.  Ben graduated from Hampden-Sydney College where he earned a degree in Managerial Economics and is proud to be the fourth generation to join the agency.  Ben lives in Richmond with his wife and two sons.

Sherwood Bowditch
Agency Principal & Commercial Lines Sales

Phone: (804) 746-5178 Ext: 104

Sherwood Bowditch brings a broad range of insurance and risk management experience to working with small businesses. For nearly 15 years he has been working with a broad spectrum of businesses to arrange their commercial insurance and group benefits. A graduate of Hampden-Sydney College with double major in Economics and Political Science, Sherwood later earned his MBA from the Robins School of Business at the University of Richmond. Sherwood serves on the board of directors and advisor to several start-up companies and is active in the Boys & Girls Club. When he is not working Sherwood is most at home on the water in Gloucester where he grew up.


Winters-Oliver is a specialty insurance agency offering property & casualty insurance and employee benefits to small and middle market businesses.