Daniel Callaway joined the United States Marine Corps in March 2005, enlisting and deploying twice with the 24th Marine Expeditionary Unit in 2006 and 2008. He then completed Officer Candidate School (OCS) and commissioned as a Second Lieutenant.

Following graduation from OCS in December 2008, Second Lieutenant Callaway enrolled in and completed The Basic School in July 2009, with follow-on orders for aviation training at Naval Air Station Pensacola, Florida.

In March 2012, he was designated a Naval Aviator. First Lieutenant Callaway then reported to Marine Medium Tiltrotor Training Squadron 204 aboard Marine Corps Air Station (MCAS) New River, North Carolina for training in the MV-22B.

Following completion of MV-22B training in August 2012, First Lieutenant Callaway reported to Marine Medium Tiltrotor Squadron 365 (VMM-365). Billets held included S-5, Embarkation Officer, Logistics Officer, Aviation Life Support System Division Officer-in-Charge (OIC), and Tool Room OIC.

In January 2015, he reported to VMM-263. Billets held included Schedule Writer and Ground Training Officer. While at VMM-263, Captain Callaway deployed to Morón, Spain in support of Special Purpose MAGTF Crisis Response-Africa.

Following his time with VMM-263 in September 2016, Captain Callaway reported to School of Infantry East (SOI-E) aboard Camp Geiger, North Carolina to serve as the Air Officer for Advanced Infantry Training Battalion East (AITB-E). While at AITB-E, he also served as the Battalion Operations Officer.

In December 2018, he reported to Marine Aircraft Group 12 (MAG-12) aboard MCAS Iwakuni, Japan to serve at Marine Wing Support Squadron 171 (MWSS-171). During his time at MWSS-171, Major Callaway held the billets of Company Commander for Airfield Operations Company and Headquarters Company, and Squadron Executive Officer.

Following his time with MWSS-171, Major Callaway reported to MAG-12 in January of 2022 to serve as Operations, Activities, and Investments Manager in the Operations Department.

Throughout his time serving the Marines and sailors of MAG-12, Major Callaway also served as an Operational Support Airlift pilot for Headquarter and Headquarters Squadrons, MCAS Iwakuni. Throughout his career, he has logged over 1900 mishap-free flight hours.

Major Callaway's personal decorations include the Navy and Marine Corps Commendation Medal with two gold stars, Navy and Marine Corps Achievement Medal with two gold stars.