Webb has an extensive support system to help students make the transition to boarding school life. Each student is assigned a faculty/staff advisor. There are approximately eight students for every advisor. Advisors and advisees meet weekly and build very strong relationships. Advisors monitor students’ progress in three main areas: academics, extra-curricular activities and residential life. In addition, each dorm has a faculty member assigned as the dorm head. This faculty member resides in or next-door to their assigned dorm. Dorm heads oversee the dorm program, conduct weekly dorm meetings and are the senior adult in charge in case of emergencies. Upperclassmen also play a critical role in helping new students adjust to life at Webb. All students can readily turn to a senior student leader, known as a dorm counselor (girls) or a dorm prefect (boys), who is available to help with a whole variety of situations from providing study-break pizza to lending a sympathetic ear. Also, all new students are assigned a Peer Advisor who helps with meeting people and becoming integrated into the community.

Webb School of California students largely have single rooms, while Vivian Webb students largely have a roommate.