Command Sergeant Major Caleb C. Webster is a native of Raleigh, North Carolina. He enlisted in the United States Army in January 2003 as a Field Artilleryman. He began his military career attending One Station Unit Training at Fort Sill, Oklahoma. 

CSM Webster has served in every leadership position in the Field Artillery. He has spent time as a Cannon Crew Member, Howitzer Gunner, Howitzer Section Chief, Drill Sergeant, Gunnery Sergeant, Platoon Sergeant, FA Master Gunner, BN Operations Sergeant, First Sergeant, Battalion Operations Sergeant Major, BDE Operations Sergeant Major SFAB, Battalion Command Sergeant Major of 1-77 Field Artillery Regiment, and the 41^st Field Artillery Brigade Command Sergeant Major.  

CSM Webster’s stateside assignments include 193^rd Fort Jackson South Carolina, 2-15 Field Artillery Regiment Fort Drum New York, 2-8 Field Artillery Regiment Fort Wainwright Alaska, and 4^th Battalion 3^rd SFAB FT Hood. His overseas assignments include D-Battery and B-Battery 173^rd Italy / Germany and the 41^st Field Artillery Brigade Grafenwoehr Germany. He has deployed to Iraq once in support of Operation Iraqi Freedom and Afghanistan five times for Operation Enduring Freedom, all in support of combat operations and joint contingency operations.

CSM Webster’s military education include Airborne School, Uniform Six Field Artillery Weapons Maintenance Towed Howitzer Course, Warrior Leader Course, Advanced Leaders Course, Drill Sergeant School, Combatives Level One, Senior Leaders Course, First Sergeant Course, Air Assault School, FA Master Gunner Course, Battle Staff, Cold Weather Leaders Course, Sergeants Major Academy Class 71, BN/BDE Pre Command Course and the Nominative Leader Course 26-02. He holds a Bachelor of Arts in Leadership and Workforce Development awarded by the Army Command and General Staff College. 

CSM Webster is accompanied by his wife Rebecca Webster of Fairbanks Alaska, his sons Elijah and Benjamin, and his daughter Emily.