Sergeant Major Flynn entered recruit training in June 1992, at Marine Corps Recruit Depot, Parris Island, SC. After attending Marine Combat Training, PFC Flynn received orders to Camp Johnson, NC as a 3533 Motor Transport Operator.
In January 1993, PFC Flynn received orders to Bravo Company, 8th Motors Transport Bn, 2d Force Service Support Group, Camp Lejeune, NC, serving as a Logistic Vehicle System operator. He deployed on the 24 Marine Expeditionary Unit, participating in Operations Restore Hope, Somalia and Provide Promise, Bosnia and Haiti.
In December 1995, Cpl Flynn returned to 8th Motors where he was promoted to Sgt in December 1996.
In March 1997, Sgt Flynn was assigned to Marine Wing Support Group, Cherry Point, NC, serving as instructor and chief instructor.
In September 2000, Sgt Flynn was assigned to Marine Corps Detachment, Fort Leonard Wood, MO where he was promoted to SSgt and served as a class commander, Instructor, chief instructor and awarded the Transportation instructor of the year for 2005.
In July 2005, SSgt Flynn was assigned to G-4 Head Quarters and Service Company, 3rd Marine Division, Okinawa Japan, serving as director of the Division Driver School.
In January 2007, SSgt Flynn was attached to 3d Bn 7th Marines in support of Operation Iraqi Freedom, serving as convoy commander and SNCOIC.
In July 2008, GySgt Flynn reported to Camp Pendleton, CA, to attend Marine Combat Instructors Course. After completion GySgt Flynn served as the Student Administration Company Gunnery Sergeant and Hotel Co 1stSgt.
In March 2011, 1stSgt Flynn was assigned to 3d Bn 11th Marines, 29 Palms CA, where he deployed with the 31st MEU and UDP with Kilo and India Btry.
In July 2014, 1stSgt Flynn was assigned to 2d LAAD Bn, Cherry Point, NC, and served as the Bravo Btry 1stSgt deploying to Norway, H&S Btry 1stSgt, and SgtMaj.
In February 2018, SgtMaj Flynn was assigned to 3d Battalion, 23d Marines, where he serves as the Inspector Instructor Sergeant Major.
Sergeant Major Flynn’s personal awards include the Meritorious Service Medal, Navy Commendation Medal (3 gold star in lieu of forth award), Navy and Marine Corps Achievement Medal (with 3 gold stars in lieu of forth award), Outstanding Volunteer Medal as well as numerous unit and service awards.