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Harry Bowlby has a extensive work experience, starting in 1987 as a Chartered Accountant at BDO Binder Hamlyn. Harry worked there until 1993. After that, they joined Spitfire Network Services Ltd in 1993 as a Finance Director. Harry later became the Finance Director and Joint Managing Director until December 2018. From December 2018 onwards, they have been serving as the Managing Director of the company.

Harry Bowlby attended City of London Polytechnic from 1983 to 1987, where they earned a 2:1 degree in Business Studies.