Sergeant Major Olander reported to the Marine Corps Recruit Depot, Parris Island, South Carolina in July of 2001. Upon completion of recruit training Private First Class Olander attended Marine Combat Training at Camp Lejeune, North Carolina and Engineer Equipment Operator course at Fort Leonard Wood, Missouri where he was meritoriously promoted to the rank of Lance Corporal.
 
In March 2002 Lance Corporal Olander reported to MWSS-172 in Okinawa Japan, where he performed duties as a heavy equipment operator. Lance Corporal Olander reported to First Marine Division in February of 2003. In March 2003 he was deployed to Kuwait in support of Operation Iraqi Freedom as a combat replacement where he was assigned to Company G, 2d Battalion 6th Marine Regiment, and later to 2d Supply Battalion. During his deployment he was promoted to the rank of Corporal.
 
In October 2003 Corporal Olander reported to First Combat Engineer Battalion where he served as a heavy equipment operator and deployed to Fallujah, and Ramadi Iraq in support of Operation Iraqi Freedom.
 
In May of 2006 Sergeant Olander conducted a lateral movement to the MOS 6174, UH-1 Crew Chief. In October 2006 he received orders to HMLA/T-303 where he completed all necessary training to be qualified as a Crew Chief, and in July 2007 was designated UH-1N Crew Chief. Upon his designation he was permanently assigned to HMLA/T-303. In July 2008 Sergeant Olander reported to HMLA-267 where he performed duties as a UH-1N Crew Chief. During this time he was promoted to the rank of Staff Sergeant.
 
In September 2008 Staff Sergeant Olander reported to Marine Aviation Detachment China Lake where he served as a UH-1Y Crew Chief. Staff Sergeant Olander held the billets of Flight Line Staff Non-commissioned Officer in Charge for AH-1Z Operation Evaluation, and detachment Martial Arts Instructor. 
 
In November 2011 Staff Sergeant Olander reported HMLA-269 where he performed duties as a UH-1Y Crew Chief.  In May 2013 Staff Sergeant Olander graduated Weapons and Tactics Instructor (WTI) School at MCAS Yuma. In February of 2014 Staff Sergeant Olander deployed with VMM-263 (REIN) on the 22d MEU.
 
In June of 2015 SSgt Olander reported to Camp Geiger, North Carolina for duty as a Combat Instructor and was promoted to the rank of Gunnery Sergeant. Upon completion of Marine Combat Instructor Course Gunnery Sergeant was assigned to Marine Combat Training Battalion where he served as a Squad Instructor, Company Gunnery Sergeant and Company First Sergeant.
 
In September 2018 Gunnery Sergeant reported to HMLA-269 where he served a UH-1Y Crew Chief, squadron WTI, and Enlisted Aircrew Training Manager.
 
In July 2019 Gunnery Sergeant Olander was frocked to the rank of First Sergeant, and reported to Site Support Terre Haute, Indiana where he served as the Inspector-Instructor First Sergeant for Company B, 1st Battalion 24th Marines, 25th Marine Regiment.
 
In May 2022 First Sergeant Olander reported to 2d Combat Engineer Battalion where he served as the company First Sergeant for Engineer Support Company, During this time he deployed to Norway in support of Marine Rotational Force-Europe 23.1.
 
In May of 2023 First Sergeant Olander was frocked to the Rank of Sergeant Major and reported to MWSS-272 where he currently serves as the squadron Sergeant Major.