History of Winters-Oliver

The origins of Winters-Oliver Insurance Agency date back to 1945, when E. Ray Winters Sr. founded an independent insurance agency in the Broad-Grace Arcade building near Grace & 5th Streets in Richmond. Three years later in 1948, Ray Sr. partnered with Harry James to form the Winters-James Insurance Agency. At some point, Winters moved his family from Richmond’s West End to Hanover County. After establishing roots in a new community and growing tired of the commute from Hanover to Richmond, Winters sold his shares in the Winters-James Insurance Agency to his partner, Harry James.

In 1959, Winters partnered with Stuart Oliver who was then president of Tri-County Bank, and together they purchased an existing insurance agency in Mechanicsville, Virginia. The agency was renamed the Winters-Oliver Insurance Agency. The agency was located at 8022 Mechanicsville Turnpike where it remained until 2019 before outgrowing that space and moving back to Richmond.

In 1964, E. Ray Winters Jr. joined his father in the insurance business, and in 1972 Ray Sr.’s eldest son, James A. “Jimmy” Winters made a career change from the farm equipment business to join the agency. Upon Ray Sr.’s retirement, Ray Jr. and Jimmy led the agency until Jimmy’s retirement in 1990 at which point Jimmy’s son, Steve, purchased his shares. Steve was now the third generation to co-lead the agency. Prior to Steve joining the agency, Winters-Oliver was solely a property & casualty agency selling and serving personal lines and small commercial lines accounts in the community.

In 1973 Steve saw an opportunity to expand the agency’s capabilities and he led the agency into the life and health insurance business. This new offering created an opportunity for Winters-Oliver to better serve its existing P&C clients but also served as a catalyst for growth as the agency leveraged its broader capability to gain new clients. Over the next 40 years, the agency continued to expand by bringing on more insurance company contracts and moving upmarket to target more commercial business while continuing to serve its personal lines clients.

In 2010, Winters-Oliver welcomed the fourth generation of the Winters family to the agency. In May of that year Steve’s son, Ben, left a career in real estate to join the family business. Ben started out selling personal lines, commercial lines, and group medical insurance. He soon realized that the insurance industry is too complex for any one person to be an expert in all these areas. As a result, the agency became more granular and focused with each person playing their specific role.

In 2012, Ray Jr. retired after 48 years in the insurance business; all with Winters-Oliver. Steve Winters became sole owner and led the agency until 2018, retiring in April 2019.

In 2012, Ben called his friend and Hampden-Sydney classmate, Sherwood H. Bowditch, and invited him to join the agency. Sherwood was working for a well-known and successful independent agency in Hampton, Virginia. In July 2013, Bowditch joined Winters-Oliver. With Steve’s support, Ben and Sherwood began to transform Winters-Oliver into a modern agency. Significant investments were made in technology. The agency upgraded the agency management system and eliminated paper files to become fully automated. The agency invested in a risk management platform to help clients better analyze and understand their risks and began offering online enrollment for employee benefits clients. The agency began to focus on how it could assist clients with risk management in addition to placing insurance coverage.

Today, Winters-Oliver continues to enjoy strong ties to the Greater Richmond community and has expanded its reach to serve clients up and down the east coast.