Stewart's coaching experience began in 1999 when he accepted a position as a varsity coach at Niskayuna High School as an undergraduate. There he coached the Silver Warriors for two seasons helping them to their first victory after two prior winless seasons (0-36 previous record). Just two years later, in his final season with the team, Stewart's Warriors posted a 13-5 record and finished third in the Suburban Council tournament. Since September of 2001, Stewart has been a certified official, overseeing various high school and collegiate matches in the Capital Region.
During his tenure with the Siena women's program in 2005-06 season, Stewart extended his coaching career acting as head coach for the Siena Men's Club Volleyball team, and head coach of the Adirondack Women's Open volleyball team for the Empire State Games.
Stewart was president and captain of the men's club volleyball team at Siena in 2000-2001 and participated all four years as a setter for the team. He participated in the Empire State Games in 1996 and 2004, and has played in the USA Adult National Tournaments in Atlanta (2004), Denver (2005), and New Orleans (2006). Additionally, Stewart is a managing member and tournament director for Capital District Grass Doubles, where he conducts 10-12 two-on-two grass volleyball tournament's each summer, which are sanctioned by the Association of Volleyball Professionals (AVP).
Off the court, Stewart has worked in the Capital Region as a risk and advisory associate for KPMG LLP and is currently pursing a master's degree in Education at the State University of New York at Albany.