Webster is a licensed coach with the United States Soccer Federation and the United Soccer Coaches, holding his A, B, C & D licenses along with the highly respected Premier Diploma and the much sought Director of Coaching Diploma. In January 2017, Webster successfully completed his United Soccer Coaches Master Coach and Soccer Leader diploma, graduating with a distinguished pass. He also holds the Advanced National Goalkeeping Diploma.
Webster grew up in São Paulo, Brazil, and North London, England, attending some of the biggest club soccer matches in the world. Webster began his soccer coaching career at Occidental College, Los Angeles, as the men's assistant to Lowell Thomas. In his one season with the Tigers, Webster helped the team to 2nd place in the Southern California Intercollegiate Athletic Conference.
He then moved to Windward High School, Los Angeles, to become the Head Coach of the Boys' Varsity team. In his first season, the Wildcats won the first of eight League Championships. As an unseeded school, the Wildcats won their first-ever boys' CIF Southern Section title, defeating Carpentaria High School 2-1. Webster was named CIF Southern Section Division VI Coach of the Year.[2]
In May 2012, Webster was appointed 1st team coach for Cal FC under the management of Eric Wynalda. The team from Thousand Oaks embarked on a historic run in the US Open Cup, beating the Kitsap Pumas, the Wilmington Hammerheads, and the Portland Timbers, the first time an amateur team had ever beaten an MLS team in the US Open Cup. The run was finally ended by the three-time defending champions, Seattle Sounders FC.
In the 2014 edition of the US Open Cup, Webster reprised his role as Head Coach and led the team against the LA Galaxy II (USL) in the 2nd round of the tournament. He also assisted Eric Wynalda and the Atlanta Silverbacks in their 5th round tie against the Colorado Rapids. A match that saw 5 red cards for the Silverbacks, including that of Wynalda and his first assistant, leaving Webster with 8 players. Webster designed a tactical plan with his remaining players, and the Silverbacks ran out 2-1 winners for one of the most dramatic wins in the competition's long and storied history.
On March 1, 2015, Webster won the United States Youth Soccer Association National Championships with CalSouth Boys' U17, beating Iowa in the final.
In the fall of 2017, Webster was the volunteer men's assistant coach for Cal State Dominguez Hills as they won the CCAA Championship.
Webster has coached numerous club teams in the Southern California region, winning multiple league and tournament titles.
In late 2018, Webster again teamed up with Eric Wynalda at the Las Vegas Lights FC in the United Soccer League, working with the first team on how to win the mental game.
In the spring of 2020, Webster began coaching at UCSB and assisting with the women's Division 1 program under Head Coach Paul Stumpf, and assisted with the Gauchos for two seasons. In 2023, he took over the boys' soccer program at Venice High School, leading them to the Los Angeles City Finals in his first season, an undefeated first league title in over twenty years in his second season and retaining that title in 2026.
