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A qualified chartered accountant and IT entrepreneur, Rupert set up Pirum, a fintech start-up focussed on automating operational processes in the global securities finance markets in 2002. He served as Pirum¡¯s Chief Executive until 2014 and the business was sold to a private equity buyer in 2015. He remains involved with the company, as both a management consultant and non-executive director.

Rupert has been a Governor of St Andrew's Healthcare since 2017 and was appointed as a Board Member and Trustee in December 2022.