About Us

Who We Are

Winters-Oliver is a fourth-generation, independent insurance agency headquartered in Richmond, Virginia providing risk management, property & liability insurance, and employee benefits solutions to individuals and businesses on a regional scale. When working with clients, we seek first to understand then to educate. We believe it is crucial to fully understand our client’s business so that we can identify risk, and then work to mitigate or transfer that risk through insurance.

Through our relationships with regional and national insurance companies, we can deliver a tailored insurance solution. We believe in making the insurance buying process easy and efficient. We invest in technology resources that allow clients to spend less time on insurance paperwork and better understand their cost of risk.

Every Winters-Oliver client gets a dedicated agent and account manager. By having a dedicated team serving you, we can build better relationships and deliver the results and client experience you expect.

Who We Serve

Businesses – Property & Casualty

Winters-Oliver works with a range of small to medium-size businesses (SMB) throughout Virginia. Many small and medium-size businesses find themselves in growth stages where they may need additional resources such as a Human Resources Director or a dedicated Risk Manager, but budget and cash flow do not allow for these valuable hires. At Winters-Oliver, we aim to fill that void. Any insurance agency can put an insurance policy in place, but few have the knowledge and resources to augment your staff’s efforts to improve safety, develop a risk management strategy, or assist with human resources initiatives. Think of us not as just your insurance broker, but your outsourced risk management department. We have the resources to provide a new business with something as basic as an employee handbook and assist a larger business with a Return-To-Work Program that reduces workers’ compensation claims.

Businesses – Employee Benefits

In addition to being your trusted advisor for property, liability, and workers’ compensation insurance, we can also partner with you to deliver an employee benefits solution that helps you attract and retain talented staff. Winters-Oliver specializes in working with groups ranging from 10-100 lives to arrange group medical, vision, dental, short-term disability, long-term disability, and voluntary worksite benefits. When it comes to employee benefits, we work together with your management team to select the benefits that are the best fit for your group. Winters-Oliver is experienced in setting up fully insured, level-funded health plans, and self-insured health plans. We can also offer an array of options for employer-paid or employee-paid ancillary benefits. Click on Employee Benefits or contact us today to learn more!

Individuals & Families – For more than 75 years Winters-Oliver has been working with individuals and families to make sure their assets are protected. Our personal lines insurance staff is knowledgeable, experienced, and they truly care about our clients. When you speak with our staff, you will find the conversation to be consultative as they help you to understand what is at stake and then develop a solution to properly insure your home, cars, jewelry or collectibles, vacation home, boat, and more.



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 & 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 we began offering online enrollment for our employee benefit 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.