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Rupert May has over 25 years of experience in financial and business management. Rupert started their career in 1992 as a Broker Consultant at Friends Provident. In 1994, they joined KPMG Audit as a Senior and was promoted to Senior Manager. In 2001, they moved to RPO Management Consultants as a Consultant. In 2002, they became a Partner at Grant Thornton LLP where they focused on growing the value of owner managed businesses. In 2010, they co-founded 2Mevents.com and Cycle Component Network, where they served as CFO & Co-Founder. In 2017, they were appointed Vice President of Equestrian Canada's Board of Directors. Since 2019, they have been the Chief Financial Officer at Interpodia Technology.

Rupert May attended Hampton School from 1981 to 1988. Rupert then went on to earn a B.A. Hons. in History from The University of Manchester from 1988 to 1991.