Major Kesterson reported to Marine Corps Recruit Depot San Diego, California, in April 1998 for recruit training. Upon completion of Naval Aircrew Candidate School in Pensacola, Florida he was assigned to Marine Helicopter Training Squadron 303 and served as a Crew Chief and mechanic on the UH-1N Huey and AH-1W Cobra. In 2003, Sergeant Kesterson was accepted into the Broadened Opportunity for Officer Selection and Training program and spent a year in Newport, RI. After completion of training, he matriculated into the Marine Enlisted Commissioning Education Program and attended the University of Colorado. Staff Sgt. Kesterson graduated with a Bachelor of Science degree in Business Management and was commissioned a 2nd Lt. in the Marine Corps on December 21st, 2007.

2nd Lt. Kesterson subsequently reported to Quantico, Virginia for training at The Basic School. Following graduation in November 2008, he reported to Naval Air Station (NAS) Pensacola, Florida for initial flight training. After completing Aviation Preflight Indoctrination, 2nd Lt. Kesterson transferred to NAS Whiting Field for Primary Flight Training with Training Squadron 2. Following primary flight training, 1st Lt. Kesterson reported to Helicopter Training Squadron 28 for Intermediate Helicopter training. Upon completion he transferred to NAS Corpus Christi for Advanced Multi-Engine training. 1st Lt. Kesterson received his wings on December 17, 2010 at NAS Corpus Christi. He then reported to Marine Medium Tiltrotor Training Squadron (VMMT) 204 at Marine Corps Air Station (MCAS) New River, North Carolina for training in the MV-22B Osprey and was subsequently assigned to Marine Medium Tiltrotor Squadron (VMM) 266. He served in the squadron from 2011 to 2016.  He held billets as the Pilot Training Officer, Assistant Operation Officer and Squadron Weapons and Tactics Instructor. During this time he deployed with the 26th Marine Expeditionary Unit in 2013 and with Special Purpose Marine Air-Ground Task Force (SPMAGTF)-Crisis Response - Africa in 2015.  In 2016, he earned a Master of Arts (MA) in Leadership studies from Marshall University.

In May of 2016, Capt. Kesterson reported to the Philadelphia Consortium, Naval Reserve Officers Training Corps, serving as the Marine Officer Instructor for Villanova, Pennsylvania, Drexel, and Temple University. Maj. Kesterson was promoted to his current rank on November 1, 2017. In 2019 he earned a Master of Business Administration (MBA) degree from Villanova University.

In June 2019, Maj. Kesterson reported to MCAS Miramar and was assigned to VMM-166.  After completing the MV-22B refresh syllabus with VMMT-204, he assumed the duties as the Aircraft Maintenance Officer. He deployed with the squadron in March of 2020 with SPMAGTF-Crisis Response - Central Command 20.2. Upon returning from the deployment he assumed his current duties as the Executive Officer of the squadron.

Maj. Kesterson’s personal awards include the Air Medal with numeral 2 and the Navy and Marine Corps
Commendation Medal (gold star in lieu of second award).