Dexter Stockdill graduated from the University of Manitoba in 1938. During his summers while in school he worked for John Graham Johnson in Victoria. Out of school he got a job with Northwood and Chivers in Edmonton where he stayed for a short time, and then with McCarter and Nairne in Vancouver. In 1939 Stockdill went into partnership with Johnson called Johnson and Stockdill. The partnership lasted until 1943 and significant projects included the Arthur Latham House (3040 Uplands Road, 1939) and the John Hodges House (2680 Queenswood Drive, 1940). In March 1946 Stockdill joined the new firm Birley and Wade, which became Birley Wade and Stockdill. Throughout the late 1940s, the 1950s, and 1960s Stockdill served as the design chief for the firm and was responsible for many of Victoria's modernist buildings. In 1939 Stockdill married Joyce Varley of Winnipeg. Their son Charles Peter (born 1941) became a prominent ophthalmologist, and their other son James Dexter became a general practitioner. After Joyce's death (ca. 1960), Dexter remarried in 1963 to Joan Drummond Taylor (1922-2005), the younger sister of John Wade's wife Margaret.