Henderson studied at Winchester College, and later received a bachelor degree and Postgraduate Certificate in Education (PGCE) in history from the University of Oxford where he was a student of Brasenose College, Oxford.
Henderson first worked as a history and politics teacher at The Windsor Boys' School, before joining Eton College in 2001; he soon became head of history at the school. From 2009, he served as Deputy Head of Sherborne School. He left Sherborne in 2011 when he was appointed Headmaster of Bradfield College.
In 2015, Henderson was appointed Head Master of Eton College, being the youngest so far at 39 years old. In the same year, he became a governor of Holyport College and the London Academy of Excellence.

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