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Rupert Hillier has a diverse work experience. Rupert co-founded Learnlight in 2007, where they served as the Co-Founder & COO. Rupert'sresponsibilities included leading the strategy, design, and development of their learning platform, managing the team's performance, and guiding company-wide change projects. Prior to Learnlight, Rupert was a partner and COO at Training Express from 2007 to 2017, where they designed innovative products and services and led the management team through growth. Rupert also founded Breakthrough L&D in 2002, offering language and management skills training programs before merging with Training Express. Rupert co-founded niima.com, a start-up aimed at combining research findings with web-based tools for informed decision-making. Rupert began their career at Gartner in 1996 as a Research Analyst and Research Director.

Rupert Hillier attended Sherborne School from 1987 to 1992, but no specific degree or field of study is mentioned. Following this, they pursued a Bachelor of Science (BSc) in Psychology at the University of Leeds from 1993 to 1996.