He graduated from a commissioned officer's academy in Kyiv as an ensign in 1916, and served with the Latvian Riflemen regiment from 1917 until 1918.

[2] He commanded his unit during the Estonian War of Independence, and was promoted to lieutenant on 12 February 1920.

On 1 February 1940, he was appointed commander of the newly established 4th Division, based in Viljandi.

During the German occupation of Estonia in World War II, Maide was Chief of Staff, and later Commander of the Omakaitse (Home Guard), a militia based on the Estonian Defence League.

[1] In wake of the German retreat and the Soviet offensive in September 1944, Otto Tief's government made one last attempt to restore Estonian independence.