Simon Weaver is an old boy of Cordwalles, having been a pupil at the school from 1970 to 1975. He then went on to Michaelhouse where he also did a Post Matric year.

Simon's qualifications: include a B.A. H.D.E from the University of Natal (Pietermaritzburg); B.A. (Hons) (UNISA) majoring in Counselling Psychology; and an M Ed in Educational Management (Wits) (Cum Laude). He has been intimately involved with the development of the Core Curriculum in Gauteng, a performance appraisal system, and studies on bullying. He is licensed as a lay minister with the Anglican Church and is a keen hockey player and cyclist.

Simon began his teaching career at Parktown Boys' High (1981-1988) before moving to St John's College (1989-1995). At St John's he became a housemaster, ran the careers and counselling department, was Master in Charge of hockey. He also taught Mathematics and Additional Mathematics to Matric level.

He was then appointed Deputy Headmaster of the Ridge (1995-1998). During this time he was Chairman of the Gauteng Prep Schools Athletics Association.

Simon was appointed as Headmaster of Pridwin from the beginning of 1999. He was involved in doubling the school from one class per grade to two classes per grade. This also meant project managing a major construction phase of the school which saw Pridwin being transformed. He was instrumental in developing a mutually rewarding partnership between Pridwin and St Vincent School for the Deaf.

Simon took over as Headmaster of Cordwalles at the beginning of 2004.