Sergeant Major Ashley enlisted in the Marine Corps in November 1998 and attended recruit training in February 1999 at Parris Island, South Carolina where he graduated as the platoon honor graduate and was meritoriously promoted to the rank of Private First Class. After completing Marine Combat Training at Camp Geiger, North Carolina he then transferred to Camp Johnson, North Carolina where he attended Personal Administration School. Upon graduation he transferred to 3d Marine Regiment, Marine Corps Base Kaneohe Bay, Hawaii for duty as a Unit Diary clerk.
In October 1999, Private First Class Ashley participated in Operation CROCIDLE in Gladstone, Australia where he served as an administrative clerk. Upon his return he was promoted to the rank of Lance Corporal. During his tour he also participated in the Rim of the Pacific Exercise aboard the USS Boxer and returned back to Australia where he participated in Operation TADNEM THRUST.
Upon his return he was promoted to the rank of Corporal and continued his duties as the Unit Diary and Promotions Chief. In October 2002, he was promoted to the rank of Sergeant.
In February 2003, Sergeant Ashley transferred to Headquarters Battalion Camp Pendleton, California for duty where he served as a Manpower Information System Support Specialist.
In May 2005, Sergeant Ashley transferred to 12th Marine Corps District, Orange County, California for duty where he served as a Canvassing Recruiter for Recruiting Sub Station Fullerton. During this tour, Sergeant Ashley was promoted to the rank of Staff Sergeant.
In April 2008, Staff Sergeant Ashley transferred to Headquarters Battalion, Marine Corps Base Kaneohe Bay, Hawaii for duty where he served as the Administrative Chief for the Installation Personnel Administrative Center. During his time there, he was promoted to the rank of Gunnery Sergeant.
In January 2010, Gunnery Sergeant Ashley deployed to Liberia, Africa in support of Operation ONWARD LIBERTY. Upon his return he was assigned to the Pu'uloa Rifle Training Facility were he served as the Staff Non Commissioned Officer in Charge.
In August 2012, Gunnery Sergeant Ashley transferred to Marine Corps Recruit Depot Parris Island, South Carolina for duty where he served as a Drill Instructor and Experienced Drill Instructor for First Battalion Alpha and Delta Company. He also served as the Company First Sergeant for Instructional Training Company.
In July 2015, Gunnery Sergeant Ashley transferred to 1st Battalion, 7th Marine Regiment, Twentynine Palms, California for duty where he served as the Battalion Administrative Chief and Battalion Adjutant. During this tour, he deployed with the SPMAGTF 16.1 GCE to Al Jabar, Kuwait in support of Operation INHERENT RESOLVE.
In January 2017, Gunnery Sergeant Ashley was promoted to the rank of First Sergeant. He then transferred to Marine Corps Communication Electronics School, Twentynine Palms, California for duty where he served as the Company First Sergeant for Alpha Company.
In October 2017, First Sergeant Ashley transferred to 3d Battalion, 7th Marine Regiment, Twentynine Palms, California for duty where he served as the Company First Sergeant for Weapons Company. During this tour, he deployed with the SPMAGTF 18.2 GCE to Syria in support of Operation INHERENT RESOLVE.
In January 2019, First Sergeant Ashley transferred to Marine Corps Recruit Depot San Diego, California for duty where he served as the First Sergeant for Third Recruit Training Battalion Kilo Company. During this tour, he was hand selected to serve as the School First Sergeant for Drill Instructor School. He was promoted to the rank of Sergeant Major in June 2021.
In July 2021, Sergeant Major Ashley transferred to Marine Medium Tiltrotor Squadron-164, Marine Aircraft Group 39, 3rd Marine Aircraft Wing, Camp Pendleton, California for duty. During this tour, he supported with two Deployment for Training exercises in preparation for the Squadrons deployment with the SPMAGTF-CR 24.2 ACE to Djibouti, Africa. In June 2023, Sergeant Major Ashley transferred over to Marine Aviation Logistics Squadron 39 for duty as the Squadron Sergeant Major.
Sergeant Major Ashley's personal awards include the Meritorious Service Medal, the Navy and Marine Corps Commendation Medal with combat “C” device and 1 gold star in lieu of 2nd award, the Navy and Marine Corps Achievement Medal and the Outstanding Volunteer Service Medal.