Simon has had an extensive international career in education, working as a teacher, leader and consultant across Australia, and in South East Asia, China, New Zealand, the United Kingdom and the United States. Simon was Head of St Michael’s Grammar School, an inner-city, co-educational independent school in Melbourne, from 2000 to 2017. In 2015, Simon was featured as one of Australia’s most innovative and influential education leaders in “The Educator” magazine’s 2015 ‘Hot List’ and conferred with a Medal of the Order of Australia (2020). From 2018 to 2019, Simon was CEO of The Song Room, a national not-for-profit organization delivering professional mentoring programmes in Arts Learning to teachers in high needs communities.
Simon has held Board level positions with Independent Schools Victoria and the Council of the Centre for Strategic Education, and currently is Chair of Council at Trinity Grammar School, Melbourne. He works in the consultancy areas of Governing Board Reviews and Principal and Senior Leadership Reviews at Hutton Consulting.