Woolridge applied for a job in the Service Department at the Triumph Engineering Company, after national service in the Royal Air Force. After a few years in the Service Department, Harry joined the team in the Experimental Department until he was promoted to the position of Assistant Quality control Manager. Later, he became Inspection Foreman for Motorcycle Assembly and Production Development. With the formation of the Meriden Co-operative, Harry served as Warranty/Service Manager until the factory closed in 1983.