Sergeant Major Pegram enlisted in the Marine Corps at RSS Fort Myers, Florida and reported for recruit training at Marine Corps Recruit Depot Parris Island, South Carolina, on 18 July 2000. Upon completion of recruit training, he reported to Camp Geiger, North Carolina for Marine Combat training. Upon completion of Marine Combat training he reported Naval Air Station Pensacola, Florida for Aviation Life Support Equipment course and was assigned the MOS of 6048 Flight Equipment Technician.
In February of 2001, upon successful completion of MOS school, Lance Corporal Pegram reported to Marine Corps Air Station Cherry Point, North Carolina for service with Marine Aviation Logistics Squadron 14 as a flight equipment technician. In January 2003 he deployed aboard the USS Bataan in support of Operation Iraqi Freedom. In March 2003, he was promoted to the rank of Corporal. In November 2004, he was promoted to the rank of Sergeant and was assigned as the 81B Work Center Supervisor.
In October 2005, he reported to Marine Aviation Logistics Squadron 49 Stewart Air National Guard Base Newburgh, New York. Where he served as the 800 Division Chief and the Corporal's Course Chief Instructor. In May 2008, he was promoted to the rank of Staff Sergeant.
In May 2009, he reported to Marine Aviation Logistics Squadron 31, Marine Corps Air Station Beaufort, South Carolina to serve as the 800 Division Quality Assurance Representative. In January 2011, he attached to II MEF Forward as an individual augment in support of Operation Enduring Freedom. Upon return in March 2012, he was assigned as the 800 Division Chief.
In March 2013, he reported to Marine Corps Recruit Depot San Diego for Recruiting School and was assigned to Recruiting Station Orlando, Florida Recruiting Sub-Station Lakeland as a Canvasing Recruiter. In January 2014, he was reassigned to Recruiting Sub-Station Winter Haven as the SNCOIC. In July 2015 he was promoted to the rank of Gunnery Sergeant.
In May 2016, he reported to Marine Medium Tiltrotor Squadron 265 Marine Corps Air Station Futenma, Okinawa Japan, where he served as the Flight Equipment Division Chief and Squadron Gunnery Sergeant. In May 2017, he deployed twice with 31st Marine Expeditionary Unit. In July 2018, he transferred to Marine Wing Headquarters Squadron 1, where he served as the Aviation Life Support Systems Class Desk and Aviation Logistics Management Assessment Team Inspector.
In May of 2019, he was promoted to the rank of First Sergeant. He was assigned to Communication Training Battalion, Marine Corps Air Ground Combat Center, Twentynine Palms, California. Where he served as the Bravo and Headquarters Company First Sergeant before assuming the responsibility of Battalion Senior Enlisted Advisor. In November 2022, he was promoted to his current rank.
In January 2023, he reported for duty as the Marine Fighter Attack Squadron 115 Sergeant Major. Where he took part in the squadron's unit deployment to MCAS Iwakuni, Japan.
His personal awards include the Meritorious Service Medal, Navy and Marine Corps Commendation Medal with (2) gold stars and the Navy and Marine Corps Achievement Medal with (1) silver star.