Callaway got his first career coaching job as a defensive analyst for the Alabama Crimson Tide.
[1] He was part of the Alabama coaching staffs that won the National Championship ifor the 2011 and 2012 seasons.
[2] In 2013, Callaway was hired by the Murray State Racers to serve as the teams wide receiver coach and recruiting coordinator.
[3] In 2015, Callaway decided to join the Samford Bulldogs as the teams wide receivers coach.
[9] In 2024, Callaway was once again promoted by Florida this time to be the team's co-offensive coordinator and tight ends coach.