Master Gunnery Sergeant Small enlisted in the Marine Corps on June 15, 1999. He graduated from MCRD, Parris Island, in September, 1999.
From November to January 2000, he attended the Navy and Marine Corps Intelligence Training Center for training as an Intelligence Specialist. Upon graduation, MGySgt Small checked into 2d Reconnaissance Battalion as a 0231.
In May 2000, MGySgt Small moved to Charlie Company, 2d Reconnaissance Bn to the Recon Indoctrination Platoon after successfully passing the Recon Screening. In September 2000, MGySgt Small attended Amphibious Reconnaissance Course at Ft Story, VA. After successfully graduating, MGySgt Small checked in to Alpha Company 2d Reconnaissance Bn. While in Alpha Company, MGySgt Small deployed twice to Iraq; once as an Assistant Team Leader and once as a Team Leader.
In October 2005, MGySgt Small checked in to 2d Force Reconnaissance Company, 3rd Platoon, as an Assistant Team Leader. In May 2006, 2d Force Reconnaissance Company became 2d Marine Special Operations Bn, which was later designated as 2nd Marine Raider Bn. MGySgt Small deployed with Golf Company in support of Operation Enduring Freedom aboard the 24th Marine Expeditionary Unit. Upon his return, MGySgt Small moved to the S-3 Training Cell at 2d Marine Raider Bn to train and evaluate deploying teams. In 2009, MGySgt Small transferred to Hotel Company and deployed twice to Herat Afghanistan in support of Operation Enduring Freedom serving as a Team Operations Chief and Team Chief.
In November 2012, MGySgt Small checked into the Marine Raider Training Center as the Chief Instructor of Irregular Warfare. MGySgt Small also served as the Staff Non-Commissioned Officer in charge of Special Operations Training Cadre 3 (Special Reconnaissance) and Chief Instructor of the Achilles Dagger Course. Following his tour at the Marine Raider Training Center, MGySgt Small checked back into 2nd Marine Raider Bn as a Team Chief for Marine Special Operations Team 8244, India Company. He deployed to Iraq in support of the Operation Inherent Resolve and participated in clearance of Mosul, Iraq. Upon returning, he assumed duties as India Company Operations Chief.
From January to July 2019, MGySgt Small deployed back to Iraq with India Company and served as the Special Operations Task Force North Senior Enlisted Advisor. Upon returning he assumed duty as the 3rd Marine Raider Battalion SOF Senior Enlisted Advisor. In July 2020, he was selected as the SOF Senior Enlisted Advisor of the Marine Raider Regiment.
MGySgt Small’s personal decorations include the Bronze Star Medal with gold star and combat distinguishing device, Meritorious Service Medal, Purple Heart Medal with gold star, Navy and Marine Corps Commendation Medal with combat distinguishing device, Navy and Marine Corps Achievement Medal with 2 gold stars and combat distinguishing device, and Combat Action Ribbon with 3 gold stars.