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Glenn studied for a BA and an MA in Classics at the University of Otago. He moved to the United Kingdom in 1998 to undertake a PhD in ancient Greek tragedy at the University of Bristol. He started his career at Clifton College in Bristol, before becoming Head of Classics at Uppingham School. Both Clifton and Uppingham are co-educational boarding schools and members of the prestigious Rugby Group of independent schools.

From Uppingham, Glenn moved to Wycombe Abbey School as the Deputy Head Academic. In 2014 Glenn took up the post of Headmaster of Truro High School in Cornwall ā€“ the far south-western corner of the UK. In his spare time Glenn enjoys following rugby and cricket, playing golf, reading, travelling and spending time with his family. He is married to Vanessa and they have one daughter, Livia.