Sayre's involvement with the theatre began around 1891 when he took a job at the Seattle Opera House folding programs. In 1899, Sayre began working as an advertising director for theater manager John Cort and soon opened Seattle's first theatrical advertising agency. In late 1907, he began his career as a theatrical critic with one of Seattle’s weekly papers, "The Argus". He worked briefly for the "Seattle Star" in 1909, then returned to the "Seattle Daily Times", where he edited the paper’s theatrical department and wrote reviews. He worked as the manager of the Seattle Symphony from 1908 to 1909. From 1924 to 1936 he worked as an independent promoter of theatre productions and films and wrote several books on the history of Seattle. One of these books, "This City of Ours", was a standard history text in Seattle public schools for many years.