Dailey is sworn in as the 15th sergeant major of the Army by Army chief of staff General Raymond T. Odierno on January 30, 2015.
Dailey's military education includes Basic Noncommissioned Officer's Course, the Bradley Master Gunner Course, the Advanced Noncommissioned Officer's Course, First Sergeants Course, the Force Management Course, the Keystone Course, the Sergeants Major Academy, and the Command Sergeants Major course. He has served in the 1st, 2nd, 3rd and 4th Infantry Divisions.
Dailey is decorated with the Bronze Star Medal with Valor for his leadership during the Siege of Sadr City. Later, he was selected as the 4th Infantry Division command sergeant major in 2009. Prior to his selection as the Sergeant Major of the Army, he served as the command sergeant major of the United States Army Training and Doctrine Command.
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. In August 2019, Dailey stepped down as Sergeant Major of the Army and was succeeded in his post by Command Sergeant Major Michael A. Grinston.[3] Dailey's official retirement date was January 1, 2020.[4]