Sergeant Major Olmstead was born in Huron, South Dakota in May of 1981.  He enlisted in the Marine Corps and attended Boot Camp at Marine Corps Recruit Depot, San Diego, California in September of 1999.  Upon graduation, he reported to the School of Infantry, Infantry Training Battalion, Camp Pendleton, CA, where he earned the Military Occupational Skill of 0311, Infantryman.
 
In January of 2000, he reported to 3rd Battalion, 7th Marines, Lima Company, 3rd Platoon at Marine Corps Air Ground Combat Center, Twentynine Palms, CA.  During this tour, he was trained as an Anti-Armor and Demolition Man and promoted to the rank of Private First Class.  Upon promotion to Lance Corporal, he served as a member of the Company's Super Squad until the time he was promoted to the rank of Corporal and assigned to be in charge the guard force to a Combined Joint Task Force in support of Operation Enduring Freedom (OEF) at Camp Doha, Kuwait, in September of 2001.  Later he went on to serve in Operation Iraqi Freedom with the initial push into Bagdad, Iraq and served as 1st Team Leader, 1st Squad Leader, and 3rd Platoon Sergeant.
 
In 2004, he reported to Weapons and Field Training Battalion at Edson Range, Camp Pendleton, CA.  During this tour, he was promoted to the rank of Sergeant and served as a Marksmanship Coach, Primary Marksmanship Instructor, and Chief Martial Arts Instructor.  In 2007, he reported to 1st Battalion, 1st Marines, Alpha Company, 3rd Platoon.  During this time, he served as 1st Squad Leader and deployed to Iraq in support of Operation Iraqi Freedom.  Also during this tour, he earned the rank of Staff Sergeant and served as Platoon Sergeant for 3rd Platoon and later Weapons Platoon.  In 2008, he reported to Recruiting Station Kansas City, 9th Marine Corps District, MO, and served as an Officer Selection Assistant.
 
In 2011, he reported to 3rd Battalion, 4th Marines in Twentynine Palms, CA, as the Platoon Sergeant for Lima Company, 3rd Platoon.  During this time he also served as a Camp Commandant and Company Gunnery Sergeant for OEF 131/132 in Musa Que Lah, Afghanistan.  In 2014, he earned the rank of Gunnery Sergeant and reported to Marine Wing Support Squadron (MWSS) 374 in Twentynine Palms, CA, to serve as the Operations Chief and  Air Base Ground Defense SNCOIC.   

In 2016, he reported back to 3rd Battalion, 7th Marines, Weapons Company as a Combined Anti-Armor Team Platoon Sergeant.  During this time he deployed with SPMAGTF CR-CC in support of Operation Inherent Resolve and later took over as the Weapons Company Operations Chief.  In 2017, he reported to I Marine Expeditionary Force (I MEF) G-3 Camp Pendleton, CA, and served as the Current Operations Chief and Senior Watch Chief.
 
In 2018, he was promoted to the rank of First Sergeant and assigned to 9th Communication Battalion, Camp Pendleton, CA, and served as the Charlie and Service Company First Sergeant.  In 2020, he was assigned to be the Lima Company First Sergeant of Headquarters and Support Battalion, School of Infantry (West), MCB Camp Pendleton, CA.  In 2021, he was reassigned to the Headquarters and Service Company, in this same battalion.

In March 2022 he received orders to serve as the command Sergeant Major for MWSS-371 in Yuma, AZ where he is presently stationed. 
 
Sergeant Major Olmstead's personal decorations include the Meritorious Service Medal, the Navy and Marine Corps Commendation Medal (gold star in lieu of third award), the Navy and Marine Corps Achievement Medal (gold star in lieu of second award), and the Combat Action Ribbon.