Sergeant Major Woodruff enlisted in the Marine Corps 16 November 2000, and attended recruit training at MCRD San Diego, CA graduating in October 2001. Upon graduation of recruit training, he was directed to Marine Combat Training, School of Infantry - West in December 2001. Following MCT he reported to Marine Corps Communication-Electronics School, Twenty Nine Palms, CA for Basic Field Wireman Course.
 
Upon graduation from communication school in February 2002, Private First Class Woodruff reported to 7th Communication Battalion, III Marine Expeditionary Force, Okinawa, Japan in March 2002.He participated in numerous field exercises and theater area operations in Thailand as a Field Wireman and Wire Supervisor. 
 
In June of 2003 he was promoted to the rank of Corporal and executed orders to report to Communication Platoon, Headquarters Company, 1st Marine Regiment, 1st Marine Division, Camp Pendleton, CA. While at 1st Marines he deployed with Headquarters Company, Regimental Combat Team 1 in support of Operation Iraqi Freedom OIF-II/A and OIF-II/B from February 2004 to March 2005. In July of 2004 he was promoted to the rank of Sergeant and was a participant in (2) major combat operations during this time: VIGILANT RESOLVE and PHANTOM FURY (Al Fajr)serving as a heavy crew served machine gunner for RCT-1 Security Platoon “Chesty”; RCT-1 Headquarters Police Sgt; Sergeant of the Guard for Camp Inchon, Camp Fallujah; and the RCT's forward Combat Operations Center within the Mayor's Complex inside the city of Fallujah, Iraq during Operation PHANTOM FURY from November to December 2004.
 
Following the 15 month deployment to Fallujah, Iraq, Sergeant Woodruff reenlisted and attended Drill Instructor School, MCRD San Diego, CA. From 2006 to 2009 he served as a Drill Instructor and Senior Drill Instructor with Charlie Company, 1st Recruit Training Battalion, and was meritoriously promoted to the rank Staff Sergeant in July of 2008. He completed his Special Duty Assignment tour as the primary first aid academics instructor with the Academics Instruction Platoon, Support Battalion, MCRD-SD.
 
Following SDA he reported to Wire Chief's Course again with MCCES, Twenty Nine Palms, CA and proceeded to his next duty station with Wire Platoon, Alpha Company, 9th Communication Battalion in April 2009. During his tenure with 9th Comm he completed two deployments to Camp Leatherneck, Helmand Province, Afghanistan in support of combat operations in Regional Command - Southwest, NATO Integrated Security Assistance Force, OEF rotation 10-2 as an Inside Plant Installation Chief following a combat meritorious promotion to Gunnery Sergeant in April of 2012 he deployed again during OEF 12-2 as the Alpha Company, Wire Platoon SNCOIC.
 
In June of 2013 he received orders to I-I 6th Communication Battalion, Brooklyn, NY reporting to Support Company Switching Platoon SNCOIC. In September of 2014 Gunnery Sergeant Woodruff was reassigned to the Battalion Operations Section as the Battalion Operations Chief until his selection to First Sergeant in December of 2015.
 
Following his selection First Sergeant, the Woodruff family executed overseas assignment orders and reported to Headquarters Battalion, 3d Marine Division, III MEF as the Truck Company First Sergeant in June 2016. Throughout his tour he served as the Company First Sergeant with all three companies in Headquarters Battalion; Truck, Communications, and Headquarters & Service companies. In February 2019 he executed a permanent change of assignment, following an in-place overseas tour extension, to further serve with Force Reconnaissance Company, III MEF as the Company First Sergeant.
 
First Sergeant Woodruff was selected to his current rank of Sergeant Major in November of 2020 and was reassigned within 3d Marine Division to serve as the Battalion Sergeant Major, 3rd Battalion, 12th Marine Regiment in December of 2020. In June of 2022, SgtMaj Woodruff remains within the artillery community and is currently on his second tour of I-I Duty with 3d Battalion, 14th Marines in Bristol, PA.
 
Sergeant Major Woodruff's personal decorations include the Meritorious Service Medal; Navy and Marine Corps Commendation Medal, with 2 gold stars; Navy Achievement Medal, with 3 gold stars; and the Combat Action Ribbon.