First Sergeant Jonathan E. Sypole enlisted in the Marine Corps and attended Recruit Training at Marine Corps Recruit Depot Parris Island, South Carolina in March 2003. He then reported to the School of Infantry, Camp Geiger in Jacksonville, North Carolina for Marine Combat Training. He was then assigned to Navy Supply Corps School Athens, Georgia where he completed the Aviation Logistics Tactical Information Systems course earning the military occupational specialty (MOS) of 6694. He was promoted to Private First Class in September 2003.
In March 2004, Private First Class Sypole reported for duty to Marine Aviation Logistics Squadron 11, Marine Corps Air Station Miramar, California. He was promoted to Lance Corporal in May 2004 and meritoriously promoted to Corporal in March 2005. In September 2005, Corporal Sypole took part in a Unit Deployment Program with Marine Fighter Attack Squadron (All-Weather) 225 to Iwakuni, Japan; Okinawa, Japan; and Osan, South Korea.
In October 2006, Corporal Sypole was assigned to Marine Aviation Logistics Squadron 29, Marine Corps Air Station New River, North Carolina. In January 2007, he deployed to Al Asad Air Base, Iraq in support of Operation Iraqi Freedom. During this deployment, he was promoted to Sergeant in June 2007.
In January 2008, Sergeant Sypole transferred back to Marine Aviation Logistics Squadron 11, Marine Corps Air Station Miramar, California. In March 2010 he was augmented to Marine Aviation Logistics Squadron 16 where he deployed to Kandahar Airfield, Afghanistan in support of Operation Enduring Freedom.
In January 2011, Sergeant Sypole reported to Marine Corps Recruit Depot Parris Island, South Carolina for duty as a Drill Instructor. He was subsequently assigned to Second Recruit Training Battalion, Company H upon completion of Drill Instructor School. In March 2011, he was promoted to Staff Sergeant. Staff Sergeant Sypole held the billets of Drill Instructor, Senior Drill Instructor, and Chief Drill Instructor with Company H and Chief Drill Instructor and Operations Chief with Company F.
In May 2015, Staff Sergeant Sypole transferred to Marine Aviation Logistics Squadron 36, Marine Corps Air Station Futenma, Okinawa, Japan. During this tour, he held the collateral duty of Deputy Director for the Marine Corps Air Station Futenma's Command Sponsored Corporals Course. He was promoted to Gunnery Sergeant in September 2016.
In December 2017, Gunnery Sergeant Sypole reported to Marine Corps Recruit Depot San Diego, California for a second tour of duty as a Drill Instructor. He was subsequently assigned to Second Recruit Training Battalion, Company H. Gunnery Sergeant Sypole held the billets of Chief Drill Instructor with Company H and Company First Sergeant with Company G and 2d Recruit Training Battalion's Headquarters Company.
In March 2020, he was frocked to First Sergeant and reported to 3d Battalion, 1st Marine Regiment, 1st Marine Division where he served as the Weapons Company First Sergeant. During this tour, First Sergeant Sypole deployed in support of the Special Purpose Marine Air Ground Task Force-Crisis Response-Central Command 21.1 to Camp Buehring, Kuwait.
In April 2022, First Sergeant Sypole reported to 4th Light Armored Reconnaissance Battalion where he currently serves as the Inspector-Instructor First Sergeant for Company B in Fort Detrick, Maryland.
First Sergeant Sypole's personal awards include the Navy and Marine Corps Commendation Medal with three gold stars in lieu of fourth award and the Navy and Marine Corps Achievement Medal with three gold stars in lieu of fourth award. He holds an Associate of Arts Degree in General Studies from the University of Phoenix and a Bachelor of Science Degree in Digital Media and Web Technology from the University of Maryland Global Campus where he graduated Summa Cum Laude.