Harry Willsmer was born in 1864 at Sturmer, Essex, England to William and Charlotte (Finch) Willsmer. Upon completion of his education, Willsmer held occupations including clerk, collector and farmer. He emigrated to Canada in April 1902 and settled briefly in Regina, North-West Territories (after September 1905, Saskatchewan). Between 1902 and 1906, he lived in various locations before settling permanently in Regina.
Willsmer was employed with the Government of Saskatchewan as its first chief clerk of the Department of Railways, Telegraphs and Telephones (ca. 1906-1913) and as an inspector of rural telephones with the Department of Telephones (ca. 1913-1917). He left the employ of the government briefly and was a representative for O'Hara & Co. bond brokers (ca. 1917). Subsequently, he was re-employed with the Government as an accountant with the Local Government Board, a position he held until his retirement in 1931. He was a founding member of the Saskatchewan Civil Service Association, and served as its first president in 1913.
Willsmer was active in several secret and benevolent societies. He was a past grand patron of the Grand Chapter of Saskatchewan, Order of the Eastern Star; a charter member of Floreat Lodge No. 64, I.O.O.F.; and held life membership to Wascana Lodge No. 2, A.F. & A.M.; Wascana chapter, Royal Arch Masons; Shepherds of Gabriel's White Shrine of Jerusalem; and the Scottish Rite. Among Willsmer's other hobbies were sketching, cartooning and illustrating, particularly on programmes, certificates, and greeting cards.
Harry Willsmer died in Regina on January 1, 1950. He was interred at Regina Cemetery.