Tim Montgomery joined the Culver Academies' Student Life department in 1990 as a Military Tactical Officer for the Band and Black Horse Troop. In 2001, he joined the counseling ranks as Counselor of Company A until 2004, at which point he moved to the Black Horse Troop. In 2007, he became the Counselor of Black Horse Troop B. He continues to remain very involved in the Horsemanship Program and the Black Horse Troop Lancer Platoon, and has accompanied the Black Horse Troop to three Presidential Inaugural parades.

Mr. Montgomery attended Ball State University and earned a Bachelor's degree in Management from Bethel College. He is married to Kathleen and has three children: Heather, CGA '02, T.J. W'99, and Christopher.