[3] A native of Rock Island, Illinois, Gilland graduated from Sherrard High School in 1986.

[3][5] Gilland was commissioned from United States Military Academy at West Point in 1990.

He had previously participated in numerous deployments to the Middle East, Africa and Afghanistan.

[11][12] Around January 2021, the Office of the Chief of Staff of the Army announced that Gilland would become the deputy commander of III Corps at Fort Hood.

He assumed office as the 61st Superintendent of the United States Military Academy on 27 June 2022, succeeding Darryl A.