[2] In 1999, Tryson joined Roush Racing to become the crew chief for Kevin Lepage and Johnny Benson.
He was able to become one of three other crew chiefs to make the Chase for the Sprint Cup in its first three seasons, with the others being Robbie Reiser and Chad Knaus.
[3] Midway through the 2007 season, he left Roush again, moving to Penske Racing to become the crew chief for Kurt Busch and the No.
He remained in that capacity through 2009, when at the end of the season, he decided to move to Michael Waltrip Racing to become the crew chief for the new No.
In 2014, Tryson joined Turner Scott Motorsports in the Nationwide Series as crew chief for rookie Dylan Kwasniewski.
After being replaced by Paul Clapprood starting at Kentucky, for the rest of the 2015 season, Tryson worked for Hattori Racing Enterprises.
In 2017, Tryson returned to TMG, which became Circle Sport – The Motorsports Group, to serve as crew chief of the No.
That year, the car was driven by multiple drivers: Derrike Cope, James Davison, Joey Gase, Chris Windom, J. J. Yeley, and Bayley Currey.
23 car of Anthony Alfredo, replacing Kenneth Roettger Jr.[11] On January 17, 2025, it was announced that Tryson would crew chief Matt DiBenedetto and their No.
Tryson graduated from West Chester University, where he earned a Bachelor of Arts degree in Business Administration.