Callaway got his first career coaching job as a defensive analyst for the
Alabama Crimson Tide.[1] In 2013, Callaway was hired by the
Murray State Racers to serve as the teams wide receiver coach and recruiting coordinator.[2] In 2015, Callaway decided to join the
Samford Bulldogs as the teams wide receivers coach.[3] In 2016, Callaway became the offensive coordinator for Samford.[4] For the 2020 season, Callaway was hired by the
LSU Tigers to serve as an analyst.[5] In 2021, Callaway joined the
New York Giants as an offensive assistant.[6] In 2022, Callaway joined the
Florida Gators as a defensive intern.[7] For the 2023 season, Callaway was promoted by the Gators to coach the teams tight ends.[8] In 2024, Callaway was once again promoted by Florida this time to be the team's co-offensive coordinator and tight ends coach.[9]