Boss is in his second stint as an Austin FC Assistant Coach, having also served in the role during the 2023 and 2024 seasons. He led USL Championship side Lexington SC as the team's Head Coach in 2025.
Before his time in Austin and Lexington, Boss was the men’s soccer Head Coach at Oregon State University. Boss was named Pac-12 Coach of the Year in 2018 and 2021, earning a No. 1 national ranking and No. 1 seed in the NCAA Tournament in 2021.
Boss’ other previous experience includes time as Assistant Coach/Goalkeeper Coach for the United States Men’s National Team (2019), Associate Head Coach for the University of Virginia (2014-2017) and Assistant Coach for both Oregon State (2013-2014) and his alma mater, University of Tulsa (2012-2013).
Prior to becoming a coach, Boss played seven (7) seasons of professional soccer from 2005 to 2011, including stints with New York Red Bulls, Seattle Sounders FC, and the Puerto Rico Men’s National Team.