Caldwell was named the Head Women's Soccer Coach on April 8, 2024 after a successful high school coaching career and serving as an assistant for the LCU men's program for a season. 

Caldwell joined the LCU men's soccer coaching staff prior to the 2023 season, while remaining as the head girls soccer coach at Lubbock's Coronado High School. In a little over seven years as the head coach, Caldwell has led the program to five District titles, five Bi-District, five Areas, five Regional Quarterfinals and four Regional Tournament appearances. With the girls program, he has a record of 145-37-14. In 2024, Caldwell led the Mustangs to a 21-3-4 record and a regional semifinal appearance. 

During his lone season as goalkeeper coach for the LCU men's program, Caldwell was crucial to the success of All-LSC Second Team goalkeeper Tom Miles. Miles finished the season with 89 saves, the sixth most in NCAA Division II and the most in the Lone Star Conference. Miles recorded six shutouts and made 5.56 saves a game, 12th most nationally. The Chaps finished the season with a 6-4-7 record and went 2-3-4 in Lone Star play. 

Caldwell is no stranger to LCU, as he was the starting goalkeeper and Captain for the men's program during their inaugural season in 2010. That season, the Chaps finished 10-5-2, and recorded five shutouts. Caldwell was the starting keeper in LCU's first ever game, a 3-1 victory over Southwest. He also recorded the first shutout in program history on Sept. 1, 2010, picking up two saves in a 1-0 win over McMurry. 

The Kilmaurs, Scotland native graduated from LCU in 2013 with a bachelor's degree in physical education. Prior to that, he was the starting goalkeeper at Eastern New Mexico University, where he now holds a master's degree in Sport Administration.

Caldwell came through the youth ranks of Kilmarnock FC and represented Scotland at U15 and U18 levels. Professionally, he spent time as a Goalkeeper for Ayr United in the Scottish First Division, while also being a part of their Youth Academy.

Caldwell and his wife Lacy, who is a former starting goalkeeper for the Lady Chaps, reside in Lubbock with their children, Callum and Arran Kate.