Sergeant Major Olson is a native of Tahlequah, Oklahoma. He enlisted in the United States Marine Corps in August 2007 and attended recruit training at Marine Corps Recruit Depot San Diego, California. Upon graduation, he reported to Infantry Training Battalion (ITB) in Camp Pendleton, California, where he earned the MOS of 0341, Infantry Mortarman. After ITB, he reported to Marine Corps Security Forces Training Company in Chesapeake, Virginia, where he earned the additional MOS of 8152, Basic Security Guard. Sergeant Major Olson was the Honor Graduate for his class and was meritoriously promoted to Lance Corporal. He was then transferred to Marine Corps Security Forces Battalion Kings Bay, Georgia and was assigned as a Basic Security Guard.
In July 2008, Sergeant Major Olson attended the Marine Corps Security Force Close Quarters Battle Team Member Course in Chesapeake, Virginia, where he earned the additional MOS of 8154, Close Quarters Battle Team Member. He returned to Marine Corps Security Forces Battalion Kings Bay, Georgia and was assigned to Recapture Tactics Team (RTT) 1. In November 2009, Sergeant Major Olson attended the Martial Arts Instructor Course in Kings Bay, Georgia, where he earned the additional MOS of 0916, Martial Arts Instructor. In May 2010, First Sergeant Olson attended the Martial Arts Instructor Trainer Course in Quantico, Virginia, where he earned the additional MOS of 0917, Martial Arts Instructor Trainer.
In September 2010, Sergeant Major Olson received orders to 3rd Battalion, 2d Marines in Camp Lejeune, North Carolina, where he was assigned to Weapons Company, 81MM Mortar Platoon as a Squad Leader. In February 2011, he was deployed to the Musa Qala District in the Helmand Province of Afghanistan for combat operations in support of Operation Enduring Freedom. In July 2012, Sergeant Major Olson reported to Basic Recruiters Course at MCRD San Diego, California. Upon completion, he earned the additional MOS of 8411, Recruiter, and was assigned to Eastern Recruiting Region, 6th Marine Corps District, Recruiting Station Jacksonville, Florida, Recruiting Sub-Station Gainesville, Florida as a canvassing recruiter and Staff Non-Commissioned Officer in Charge (SNCOIC). In January 2015, Sergeant Major Olson was meritoriously promoted to the rank of Staff Sergeant for his performance while on recruiting duty.
In June 2015, Sergeant Major Olson reported to 1st Battalion, 3d Marines at Marine Corps Base Hawaii, Kaneohe Bay, Hawaii. From December 2015 to June 2016 and June 2017 to December 2017, he was forward deployed to Okinawa, Japan as part of the Unit Deployment Program. His duties while at 1st Battalion, 3d Marines included Platoon Sergeant for Company "B", 3rd Platoon and Weapons Platoon. He also served as the Battalion S-3 Training Chief, Battalion Force Fitness Instructor, and Battalion Martial Arts Instructor Trainer.
In February 2018, Sergeant Major Olson reported to Eastern Recruiting Region, 6th Marine Corps District, Recruiting Station Jacksonville, Florida, Recruiting Sub-Station Gainesville, Florida to assume duties as the SNCOIC from February 2018 to December 2019. He was promoted to the rank of Gunnery Sergeant in November 2018 and was selected to lateral move into MOS 8412, Career Recruiter, in July 2019. From January 2020 to June 2020, he assumed the duties as SNCOIC of Recruiting Sub-Station Jacksonville, Florida. From June 2020 to November 2020, he assumed the duties as the Military Entrance Processing Station LNCO for Recruiting Station Jacksonville, Florida. From November 2020 to June 2022, he assumed the duties as the Assistant Recruiting Instructor for Recruiting Station Jacksonville, Florida.
In July 2022, Sergeant Major Olson reported to Maintenance Company (-), CLB 453, Waco, Texas, where he served as the Inspector-Instructor First Sergeant. In July 2025, Sergeant Major Olson reported to Marine Wing Support Squadron-272, Marine Corps Air Station New River, North Carolina, where he served as the Headquarters and Service Company First Sergeant and was subsequently selected to Sergeant Major. In August 2026, Sergeant Major Olson reported to 2d Light Armored Reconnaissance Battalion, Camp Lejeune, North Carolina, where he is currently serving as the Battalion Sergeant Major.
Sergeant Major Olson's personal awards include the Meritorious Service Medal, Navy and Marine Corps Commendation Medal (with two gold stars in lieu of third award), Navy and Marine Corps Achievement Medal (with two gold stars in lieu of third award), Combat Action Ribbon, and Military Outstanding Volunteer Service Medal. Sergeant Major Olson holds a Bachelor of Arts in Business.