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Rupert Jenner has held various roles in the IT industry since 1995. Rupert began their career as a Software Developer at Deloitte, where they developed a major document archiving system for Smithkline Beecham. In 1998, they moved to Pfizer, where they worked in the Developmental Research division, developing document management applications using the Documentum product suite. In 2000, they became a Freelance IT Consultant for Jentech Solutions Ltd, providing document management IT services to many clients. In 2014, they founded and became the CEO of Playwaze Ltd.

Rupert Jenner attended The Skinners School from 1978 to 1985. Rupert then pursued a Bachelor of Science in Business Information Systems from the University of Portsmouth from 1991 to 1995.