LtCol Montgomery enlisted in the Marine Corps Reserve in May 2001 and served with Delta Company, 4th Combat Engineer Battalion. Corporal Montgomery attended split Platoon Leaders Course and was commissioned upon graduating from the University of Tennessee in May 2005.
Upon completion of the Basic School, Second Lieutenant Montgomery attended the Logistics Officers Course and in October 2006 was assigned to Combat Logistics Battalion-6. He deployed twice to Iraq serving as a Motor Transportation Platoon Commander and Forward Logistics Detachment Commander. He assumed command of Transportation and Support Company upon return from his second deployment. In April 2009, Captain Montgomery transferred to Headquarters Marine Corps where he served as a Facilities Planner and Aide de Camp to the Deputy Commandant, Installations and Logistics (I&L).
In August 2011, Captain Montgomery transferred to the Selected Marine Corps Reserve and served with Reserve Support Program (RSP), Marine Corps Individual Reserve Support Activity. In February 2013, Captain Montgomery mobilized as the Logistics Officer, Marine Special Operations Support Group, Marine Special Operations Command (MARSOC). Captain Montgomery remained with MARSOC as an Individual Mobilization Augmentee until 2015. He then rejoined the RSP.
In January 2017, Major Montgomery mobilized as a Policy Analyst, Reserve Affairs, Manpower and Reserve Affairs. From July 2017 until June 2018, Major Montgomery attended resident Marine Corps Command and Staff College where he earned a Masters of Military Studies.
In June 2018, Major Montgomery joined the Active Reserve and was assigned as the Deputy Assistant Chief of Staff G-10, II Marine Expeditionary Force. In August 2019, Major Montgomery transferred to 2d Marine Expeditionary Brigade G-3 where he served as the Current Operations Officer until August 2020 and then as a Future Operations Planner until June 2021.
In July 2021, Maj Montgomery was assigned to I&L, Logistics Division where he served as an Action Officer, Division Operations Officer, and Section Head for the Logistics Current Operations Section. In June 2023, he transferred to the Marine Corps Office of Legislative Affairs where he served as the I&L Portfolio Manager.
In May 2024, LtCol Montgomery assumed command as the Inspector-Instructor for Marine Corps Advisor Company Alpha and Site Commander for Site Support, Washington D.C. LtCol Montgomery’s personal decorations include the Meritorious Service Medal (with two gold stars), Navy Commendation Medal (with two gold stars), and Navy Achievement Medal.