A native of Washington, D.C., Webster arrives in DeLand with extensive NCAA Tournament experience, both as a player and as a coach. During his tenure at Virginia Tech, the Hokies made five consecutive NCAA Tournament appearances, highlighted by a run to the Sweet 16 in 2019.
At Virginia Tech, Webster was a key figure in both opponent scouting and recruiting, helping the Hokies secure six ESPN Top 100 recruits and a Top 20 national recruiting class in his first year. His impact on the recruiting trail and in player development earned him a spot-on ESPN's 40 Under 40 list in 2020, recognizing the nation's top young coaching talent in Division I men's basketball.
Before joining the Hokies, Webster spent the 2015-16 season at UCF, serving as an assistant coach at just 25 years old. His coaching career began at Harvard, where he spent two seasons helping guide the Crimson to a 49-13 record and back-to-back NCAA Tournament appearances. Harvard's 2014 Tournament run included a memorable upset of No. 5 seed Cincinnati.
Webster was invited to join Harvard's staff after a standout playing career with the Crimson. A four-year starter, he graduated in 2013 as the winningest player in program history with 90 victories, including three straight Ivy League titles and two NCAA Tournament berths. He ranks fifth all-time in 3-pointers made with 176 and second in games played at 117 in school history. He earned his degree in psychology from Harvard.