Ontario-born Ronald Maitland moved to Vancouver at a young age and got his start in sailing by constructing home-made canoes and navigating them through the Burrard Inlet. By the 1910s he had become involved in yacht racing and joined the Royal Vancouver Yacht Club, where he served as Commodore in 1924. In 1932 he was the helmsman of the Santa Maria, which represent Canada in the 8 metre class at that year’s Summer Olympics, with a crew consisting of Ernest Cribb, Peter Gordon, George Gyles, Harry Jones, and Hubert Wallace. Despite losing all four races, the Canadians brought home a silver medal from the Games because the only other nation to enter the 8 metre tournament was the United States.
Maitland’s career as a businessman began in 1904, when he left his job as a clerk at the Royal Bank of Canada and was hired by Macaulay Nicolls, a real estate and insurance firm that eventually became part of Colliers International. He became a partner in the early 1920s and is credited with helping the firm survive the Great Depression. He was also involved in the operation of the North Arm Steamship Company in the early 1910s. His brother Royal was a prominent politician in British Columbia, who served as provincial Attorney General from 1941 through 1946.