In November 2003, he reported to Naval Recruiting District Kansas City and was assigned to Naval Recruiting Station Rogers Arkansas. There he served as the Recruiter-in-Charge earning the Distinguished Graduate Bakarian Award.
In November 2006, he reported to Littoral Combat Ship Pre-Commissioning Detachment San Diego and served as the Leading Petty Officer before transferring to USS Dewey (DDG 105) in April of 2008.
In October 2010, he reported aboard USS Sterett (DDG 104) where he served as CA Division Leading Chief Petty Officer, and deployed twice in support of OND and OEF.
In June 2012, he reported to Commander Naval Surface Atlantic Norfolk, VA where he served as Force Sonar Technician. His follow on orders were Commander Surface Squadron Fourteen Mayport, FL as the Anti-Submarine Warfare Officer in 2015 and in USS The Sullivans (DDG 68) serving as Departmental Leading Chief Petty Officer in 2018. During this time, he earned an Associates Degree in Business, attended the Senior Enlisted Academy, and was selected into the Command Senior Chief Program.
CMDCS Callaway currently serves aboard USS Little Rock (LCS 9) Blue Crew in Mayport, FL as the Command Senior Chief.
His awards include the Navy and Marine Corps Commendation Medal (3), Navy Achievement Medal (6), Navy Good Conduct Medal (6), and various unit and campaign awards.