Gregory’s has served in a variety of leadership and staff assignments to include Platoon Leader, and Rifle Company Executive Officer in 1st Battalion, 327th Infantry Regiment, 1st Brigade Combat Team, 101st Airborne Division (Air Assault) and deployed to Iraq serving in Hawija.
Following the Military Intelligence Captains Career Course, Gregory served as a Battalion Intelligence Adviser to the Iraqi Army in Baghdad, Diyala and Maysan Provinces. Upon return from Iraq, Gregory attended the Counterintelligence Special Agents Course and then served as an MI Detachment Commander and Company Commander in 308th MI Battalion, 902nd MI Group, and as Headquarters and Headquarters Company (HHC) Commander in Special Operations Command Korea (SOCKOR). Gregory then deployed to Afghanistan as the CJ2X for International Security Assistance Force Special Operations Forces (ISAF SOF).
Following graduation from Command and General Staff College, Gregory served as Assistant Chief of Staff G2 and Intelligence Planner for 1st Theater Sustainment Command (TSC), and Brigade S2 for 505th Parachute Infantry Regiment, 3rd Brigade Combat Team, 82nd Airborne Division. Gregory's next assignment was at Supreme Headquarters Allied Powers Europe (SHAPE) J2 as the Identity Intelligence Branch Chief. Gregory then served as the Aide-de-Camp to the NATO Special Operations Headquarters (NSHQ) Commander, and later as the Deputy Director of the Commander’s Action Group (CAG), NSHQ. Gregory most recently served as the Technical Services Battalion Commander in Army Counterintelligence Command.
Gregory’s awards and decorations include the Bronze Star Medal (2OLC), Defense Meritorious Service Medal (1OLC), Meritorious Service Medal (2 OLC), Army Commendation Medal, Iraq Campaign Medal (4th award), Afghanistan Campaign Medal, Combat Infantryman Badge, Expert Infantryman Badge, Ranger Tab, Parachutist Badge, and Air Assault Badge.
Gregory and his wife have two children.