Prior to his tenure as the Sergeant Major of the Army,[1] he served as the Command Sergeant Major for the United States Army Training and Doctrine Command.

A native of Palmerton, Pennsylvania, Dailey entered the United States Army as an 11B (Infantryman) in 1989.

His civilian education includes a Bachelor of Science degree in history from Excelsior University.

Dailey is decorated with the Bronze Star Medal with Valor for his leadership during the Siege of Sadr City.

As Sergeant Major of the Army, Dailey served as the Chief of Staff of the United States Army's personal adviser on all enlisted-related matters, particularly in areas affecting soldier training and quality of life.