Sergeant Major Singley graduated from MCRD Parris Island in July of 1998. After graduating as an Infantry Rifleman from Infantry Training Battalion, School of Infantry East in 1998, he reported to Co L 3d Battalion 8th Marines for duty. In 1999, he deployed with the 26th MEU. Upon returning from the 26th MEU then Corporal Singley reported to the battalion Scout Sniper platoon and participated in the unit deployment program to Okinawa.
In May 2002, Sergeant Singley reported to II MEF Special Operations Training Group to serve as an amphibious raids instructor. In 2003 he attended Army Airborne School and Ranger School. In May 2004 he deployed to central Africa as part of the Pan-Sahel Counter Terrorism Training Team and in October 2004 deployed to Iraq as a member of an advisor support team in support of Operation Iraqi Freedom II.
Sergeant Singley reported to Company A, 1st Battalion 25th Marine Regiment, in November 2005. In 2006 he deployed with the unit to Iraq as a Platoon Sergeant in support of OIF 5.7. While deployed he was promoted to Staff Sergeant.
In October of 2008, Staff Sergeant Singley reported to 3d Light Armored Reconnaissance Battalion where he served as the Company B 81mm Mortar Section Leader and LAV-25 Platoon Sergeant. During this time he deployed with the battalion in support of OIF 9-1.
In 2010, Staff Sergeant Singley was promoted to Gunnery Sergeant and reported to Combat Instructor School, School of Infantry East. Upon graduation from CIS Gunnery Sergeant Singley reported to Marine Combat Training Battalion where he served in the billets of Combat Instructor, Platoon Commander, Chief Instructor, Company Gunnery Sergeant and Company First Sergeant.
In 2013, Gunnery Sergeant Singley was promoted to First Sergeant and reported to the Inspector Instructor Staff 3d Force Reconnaissance Company. In 2015 he completed the Joint Special Operations Forces Senior Enlisted Academy and the Army Sergeant's Major Academy (non-resident).
In 2016, First Sergeant Singley assumed duties as the Headquarters Company, Naval Amphibious Force, Task Force 51/5th Marine Expeditionary Brigade First Sergeant. In 2016 he completed the Navy Senior Enlisted Academy.
In 2018, Sergeant Major Singley was promoted to his current rank and assumed the duties as Battalion Sergeant Major for 2d Law Enforcement Battalion, and attended the Cornerstone Course.
In February 2020, he reported to the I&I Staff, CLB 453 for duty as the I&I Sergeant Major.
In March 2022, he reported to 4th Marine Regiment for duty as the Regimental Sergeant Major.
Sergeant Major Singley's personal awards include the Bronze Star Medal with combat distinguishing device, the Meritorious Service Medal with Gold Star in lieu of second award, the Joint Service Commendation Medal, the Navy and Marine Corps Commendation Medal with Gold Star in lieu of fifth award, the Navy and Marine Corps Achievement Medal with Gold Star in lieu of second award and the combat distinguishing device, and the Combat Action Ribbon with Gold Star in lieu of second award. He graduated Summa Cum Laude from Norwich University in 2017 with a BS in Strategic Studies and Defense Analysis.