Sergeant Major Holloway joined the United States Marine Corps in 2003. He attended recruit training at Marine Corps Recruit Depot, San Diego, CA and graduated as Platoon Honorman. Upon completion of recruit training Private First Class Holloway transferred to The School of Infantry located at Camp Pendleton, CA for training as a Basic Rifleman. Upon graduation he was promoted to Lance Corporal (meritoriously). 
 
In 2004 Lance Corporal Holloway was assigned to Company F 2nd Battalion, 4th Marines and subsequently deployed to Ar Ramadi, Iraq in support of Operation Iraqi Freedom II as a Squad Automatic Rifleman. In 2005 Lance Corporal Holloway was deployed to Okinawa, Japan with Battalion Landing Team 2/4, 31st MEU as a team leader and was promoted to Corporal (meritoriously) for recognition as the BLT Marine of the Quarter. In 2006 Corporal Holloway deployed again with BLT 2/4 on the 15th MEU in support of OIF 5-07 as a Squad Leader and was subsequently promoted to Sergeant.
 
In July 2007, Sergeant Holloway reported for duty as a Combat Instructor with C Co, Infantry Training Battalion, School of Infantry (West). During his tour Sergeant Holloway was recognized as the SOI (W) NCO of the year and meritoriously promoted to Staff Sergeant.
 
Upon successful completion of his tour at SOI in 2010, Staff Sergeant Holloway reported to 1st Marine Logistics Group, G-3 and deployed to Afghanistan in support of Operation Enduring Freedom 10-2, as a Joint Fires Observer and SNCOIC of the Group Tactical Air Control Party. Staff Sergeant Holloway redeployed to CONUS in 2011 and became the chief instructor for the Basic Combat Skills package at the Combat Skills Training School. In 2012, Staff Sergeant Holloway deployed again in support of OEF 12-1 as a Joint Terminal Attack Controller attached to Combat Logistics Battalion 4. During this time he was promoted to Gunnery Sergeant (combat meritoriously).  Once Gunnery Sergeant Holloway returned to CONUS, he assumed the duties as Operations Chief, Combat Skills Training School.
 
In March 2013, Gunnery Sergeant Holloway reported for duty at The Basic School, Quantico, VA. He served as the Infantry Platoon Sergeant, Warfighting Instructor Company; First Sergeant, Company F and Company D, and lastly as the Chief Instructor, The Basic School.
 
Upon completion of his tour at TBS, First Sergeant Holloway report to Company F, 2d Battalion 4th Marines and deployed to Okinawa, Japan in support of the 31st MEU. Upon redeployment to CONUS, First Sergeant Holloway was transferred to Company G where he deployed to Australia as part of Marine Rotational Force - Darwin.
 
In February 2019, First Sergeant Holloway reported to Company A, Marine Barracks Washington and after two parade seasons, was transferred to H & S Company. In 2020, he was selected to Sergeant Major and was subsequently frocked in June, 2021.
 
Sergeant Major Holloway's personal awards include the Purple Heart Medal, Meritorious Service Medal (with gold star), Navy Marine Corps Commendation Medal (with two gold stars), Navy and Marine Corps Achievement Medal (with gold star), Army Achievement Medal, and Combat Action Ribbon (with gold star).