Sergeant Major Cuthbertson enlisted in the Marine Corps in November 1996 and graduated from Delta Company, 1st Recruit Training Battalion, Marine Corps Recruit Depot, Parris Island, SC. Upon completion, he reported to Camp Johnson where he received the Military Occupational Specialty of 3043, Supply Administration Operations. In March 1996 he reported to 2nd Forces Service Support Group (2nd FSSG) Battalion Supply, Marine Corps Base, Camp Lejeune, North Carolina. 

In 1999, Sergeant Major Cuthbertson served in Okinawa Japan with Electronics Maintenance Branch (EMB) Supply section. He subsequently augmented to Security React Team (SRT) to provide security for the 1999 G8 Summit in Okinawa Japan.

In March 2001, Sergeant Major Cuthbertson reported to Quantico, Virginia and served with Service Company H&S BN Material Readiness Branch. During his tour, Sergeant Major Cuthbertson was promoted to the rank of Sergeant and transferred to work as the Assistant Terminal Area Security Officer (TASO) within the Information Security Management Office (ISMO) and subsequently serve as the Facilities Maintenance Branch Supply Chief.

In April 2004, Sergeant Major Cuthbertson reported to Drill Instructor's School, Parris Island, South Carolina and assigned to Charlie Company, First Recruit Training Battalion where he served as a Drill Instructor, Senior Drill Instructor, Series Gunnery Sergeant Martial Art Instructor, Physical Training Instructor, Static Rope Suspension Technique Instructor (SRST) and Weapons Field Training Battalion Crucible Instructor. In June 2007, he would receive orders to report to Okinawa Japan and assigned to Headquarters Battery, 12th Marine Regiment. He would serve as Supply Chief, Platoon Sergeant and subsequently serve as the Quick Reaction Force (QRF) First Sergeant for Joint Special Operations Task Force Philippines (JSOTF-P).

In March 2008, Sergeant Major Cuthbertson serve a combat tour as an Embedded Training Team (ETT) Advisor during Operation Enduring Freedom (OEF) in Afghanistan and receive a Navy Commendation Medal for his actions.  While deployed Sergeant Major Cuthbertson would be selected to Gunnery Sergeant and upon redeployment be hand selected to fill the billet of Headquarters Battery First Sergeant with 12th Marine Regiment. In July 2010, Sergeant Major Cuthbertson would receive orders to Marine Forces Europe and Africa where he served as the Supply Chief and hand selected to serve as the Headquarters and Service Company First Sergeant.  In December 2012, Sergeant Major Cuthbertson was selected as a First Sergeant and receive orders to 1st Battalion, 11th Marines, Camp Pendleton California, to serve as Charlie Battery 1stSgt and Headquarters Battery 1stSgt subsequently.

In June 2014, Sergeant Major Cuthbertson deployed with Battalion Landing Team 2/1, 11TH MEU and served as the principal enlisted advisor for the BLT detachment aboard the U.S.S. Makin Island in support of Operation Inherent Resolve (OIR) and would receive a Meritorious Service Medal upon redeployment to 11th Marines. In January 2016, Sergeant Major Cuthbertson reported to 1st Supply Battalion, Combat Logistics Regiment 15, Camp Pendleton, CA, where he served as the Headquarters & Service Company and Supply Company First Sergeant.

In March 2017, Sergeant Major Cuthbertson was promoted to his current rank and assumed duties as the Sergeant Major for 1st Law Enforcement Battalion; 1st Combat Engineer Battalion in June of 2019 and in August 2020, would receive orders to Marine Corps Communications-Electronics School MCAGCC 29 Palms CA as the group Sergeant Major.

In May 2023 Sergeant Major Cuthbertson assumes his current role as the Security and Emergency Services Battalion Sergeant Major.

Sergeant Major Cuthbertson has attended all required resident and distance learning Professional Military Education (PME) courses. He holds a Masters of Arts Degree in Organizational Leadership, Bachelor of Science Degree in Organizational Leadership w/ Supply emphasis and Associates of Science Degree in Logistics Management.

Sergeant Major Cuthbertson personal awards include the Meritorious Service Medal with three gold stars, Navy and Marine Corps Commendation Medal with three gold stars, Navy and Marine Corps Achievement Medal, Outstanding Volunteer Service Medal and Combat Action Ribbon.