Command Sergeant Major Conroy joined the Army in April 1992 as a Fire Support Specialist (13F). He attended AIT at Fort Sill, Oklahoma. His assignments include: Platoon Forward Observer, Company Fire Support NCO, Assistant Battalion Fire Support NCO, Battalion Fire Support NCO, 2nd Battalion, 75th Ranger Regiment, Ft. Lewis, WA; Battalion Fire Support NCO, 1st Battalion, 160th Special Operations Aviation Regiment, Ft. Campbell, KY; Brigade Fire Support NCO and Fire Support Operations Sergeant, 505th Parachute Infantry Regiment, 3rd BCT, 82nd ABN DIV, Ft. Bragg, NC; First Sergeant, Able Battery, 1st Battalion, 319th Airborne Field Artillery Regiment, 3rd BCT, 82nd ABN DIV, Ft. Bragg, NC; Battalion Sergeant Major, 1st Battalion (P/EMC) (FA), 290th Regiment, 205th IN BDE (TSB), Camp Atterbury, IN; Brigade Operations Sergeant Major, 18th Fires Brigade (Airborne), 82nd ABN DIV, Ft. Bragg, NC; Battalion Command Sergeant Major, 2nd Battalion (Airborne), 321st Field Artillery Regiment, 4th BCT, 82nd ABN DIV, Ft. Bragg, NC; Battalion Command Sergeant Major, 3rd Battalion, 321st Field Artillery Regiment, 18th Field Artillery Brigade, XVIII ABN Corps; Command Sergeant Major, 18th Field Artillery Brigade (Rear Detachment).
Command Sergeant Major Conroy is a graduate of the Primary Leadership Development Course, Basic Non-Commissioned Officer Course, Advanced Non-Commissioned Officer Course, First Sergeant Course, United States Army Sergeants Major Academy Class 62, Basic Airborne Course, Air Assault School, Jumpmaster School, and Ranger School. Command Sergeant Major Conroy holds a Bachelor of Science degree in Public Relations from Illinois State University.
His awards include the Bronze Star with two Oak Leaf Clusters, Meritorious Service Medal with four Oak Leaf Clusters, Air Medal, Joint Service Commendation Medal, Army Commendation Medal with four Oak Leaf Clusters, Army Achievement Medal with Oak Leaf Cluster, Air Force Achievement Medal, Armed Forces Expeditionary Medal, Afghanistan Campaign Medal with two Campaign Stars, Iraq Campaign Medal with Silver Campaign Star, Global War on Terrorism Expeditionary Medal, Global War on Terrorism Service Medal, National Defense Service Medal with Campaign Star, Overseas Service Ribbon with Numeral 3, Master Parachutist Badge, Air Assault Badge, Ranger Tab, and Combat Action Badge.