Lieutenant Colonel Bossart was commissioned in August 2004 through the Platoon Leaders Course and was designated a Naval Aviator in May 2007. 

In November 2007, Lieutenant Colonel Bossart reported to the Black Knights of HMM-264, MCAS New River, North Carolina, for service as a CH-46E pilot. He deployed with HMM-264 (REIN) on the 26th Marine Expeditionary Unit (MEU) in August 2008 and remained with the squadron after this deployment as it transitioned to the MV-22B. As an MV-22B pilot, he graduated from the Naval Aviation Safety Officer School, the Weapons and Tactics Instructor Course, 2-12, and deployed with VMM-264 to Operation Enduring Freedom 11.1 and 13.1. 

In August 2013, he reported to Marine Aviation Weapons and Tactics Squadron One, MCAS Yuma, Arizona, and served as an MV-22B instructor, the Aviation Safety Officer, and the MV-22B Division Head. 
In June 2016, Lieutenant Colonel Bossart was a resident student at the U.S. Air Force Air Command and Staff College (ACSC), Maxwell AFB, Alabama. 

After graduating from ACSC in May 2017, Lieutenant Colonel Bossart reported to VMM-166, MCAS Miramar, California, where he served as the Aircraft Maintenance Officer and deployed with VMM-166 (REIN) on the 13th MEU in June 2018. 
In June 2019, Lieutenant Colonel Bossart transferred back to Maxwell AFB to attend the U.S. Air Force School of Advanced Air and Space Studies (SAASS). After graduating from SAASS in May 2020, he reported to the Deputy Commandant for Aviation to assume duties as the Marine Air-Ground Task Force planner. 

Lieutenant Colonel Bossart holds a Master’s Degree in Military Operational Art and Science and a Master of Philosophy in Military Strategy.