Caldwell began his career as a scouting assistant for the Carolina Panthers from 1996 to 1997.[3]
Indianapolis Colts
Caldwell spent ten years (1998–2007) with the Indianapolis Colts as an area scout. He was a member of the staff when the team won Super Bowl XLI in 2006.[3]
Atlanta Falcons
In 2008, Caldwell was hired by the Atlanta Falcons as their director of college scouting. In 2012, he was promoted to director of player personnel.[3]
Jacksonville Jaguars
On January 8, 2013, Caldwell was named the general manager of the Jacksonville Jaguars.[4] His first order of business with the team was to fire the head coach Mike Mularkey who had just completed his first season.[5] On January 17, 2013, the team hired former Seattle Seahawks defensive coordinator Gus Bradley as his replacement, who was eventually fired late in the 2016 season.[6][7] On February 23, 2018, the Jaguars extended his contract through 2021.[8]
On November 29, 2020, Caldwell was fired by the Jaguars following a 27–25 loss to the Cleveland Browns and a 1–10 start to the season.[9][10] He finished his tenure in Jacksonville with a 37–86 (.301) record and a 2–1 (.667) playoff record for a 39–87 (.310) career record.
Philadelphia Eagles
In 2021, Caldwell was hired by the Philadelphia Eagles as a personnel executive. On June 3, 2022, it was announced that Caldwell had assumed the roles of senior personnel director and advisor to the general manager.[11]