Shearer Automotive began with Chevrolet which, was founded in 1928 by Carl Shearer, a former railroad man from Massachusetts. Sometime after World War II, Carl's sons Jack and Bob (Bill's father) joined the business and ran it until 1987 when Bill Shearer left his real estate business and became the new owner of Shearer Chevrolet.

Since he took over the business, Bill has embarked on a steady, methodical expansion. In 1992 he purchased the Honda franchise in Rutland, which now operates as Shearer Honda. In 1995 he added the Pontiac, Oldsmobile and Cadillac franchises at 1030 Shelburne Road in South Burlington. Ten years later, in 2005, he purchased the Buick and GMC franchises from the Fitzpatrick family and moved them to the 1030 Shelburne Road location. In 2007 he built a brand new, state-of-the-art collision repair facility called Direct Autobody, in a bright shiny new building at the back of the Shearer Chevrolet lot. Finally, his latest purchase on July 1, 2009 was the former Lewis Motors at 1301-1325 Shelburne Road, which added Acura, Audi and Volkswagen to the Shearer Family of Dealerships.