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.[4] In 2016, Callaway became the offensive coordinator for Samford.[5] For the 2020 season, Callaway was hired by the LSU Tigers to serve as an analyst.[6] In 2021, Callaway joined the New York Giants as an offensive assistant.[7] In 2022, Callaway joined the Florida Gators as a defensive intern.[8] For the 2023 season, Callaway was promoted by the Gators to coach the teams tight ends.[9] In 2024, Callaway was once again promoted by Florida this time to be the team's co-offensive coordinator and tight ends coach.[10]