Colonel Charles L. Montgomery graduated from the University of Southern, Mississippi, Hattiesburg, Mississippi and commissioned through its Army ROTC program. He holds a Master’s of Science in Human Resources Management from Tarleton State University, Stephenville, Texas; Master’s in Military Arts & Science (MMAS) in Military Operational Art and Science, School of Advanced Military Studies, Fort Leavenworth, Kansas; and a Master’s of Strategic Studies, Air War College, Maxwell Air Force Base, Alabama.

His tactical and operational assignments includes service with: 2nd Armored Calvary Regiment (Fort Polk, Louisiana), 1st Cavalry Division (Fort Hood, Texas); 167th Theater Sustainment Command (Anniston, Alabama); 3rd Infantry Division (Fort Stewart, Georgia); Human Resources Command (Fort Knox, Kentucky); 1st Armored Division (Fort Bliss, Texas); Joint Multinational Readiness Center (Hohenfels, Germany); 1st Infantry Division (Fort Riley, Kansas); and the Combined Arms Command (Fort Leavenworth, Kansas).

His command assignments includes: Brigade Commander, Division Sustainment Brigade (DSB), 1st Infantry Division; Battalion Commander, 1st Armored Division, 123rd Brigade Support Battalion (BSB); Alpha Company Commander, 4th Infantry Division, 704th BSB; Alpha Company Commander, 1st Cavalry Division, 27th BSB.

He has three combat deployments to Iraq, and operational assignments overseas to Korea and Germany. In September 2018, he deployed his battalion to the Republic of Korea as part of the Regional Aligned Force.

Colonel Montgomery's military education includes: Transportation Basic Course, Sustainment Captains Career Course, Command and General Staff College, School of Advanced Military Studies, and the U.S. Air War College.

Colonel Montgomery’s awards and decorations includes: Legion of Merit, Bronze Star Medal (one oak leaf cluster), Meritorious Service Medal (six oak leaf clusters), Army Commendation Medal (two oak leaf clusters), Army Achievement Medal (three oak leaf clusters), Military Outstanding Volunteer, Parachutist Badge, and Pathfinder Badge.

He is the recipient of the Order of Saint Christopher, Order of the Spur, and Order of Saint Maurice.