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Henry Loveless has a diverse work experience history. Henry began their career at D.E MASTER BLENDERS 1753, where they held the roles of National Accounts Executive and later National Account Manager. Henry then moved to pladis Global, where they served as the Market Strategy & Planning Manager and later as a Business Account Manager. Following that, they joined Gympass as a Senior Business Development Manager. Currently, they are employed at ClassPass, where they have held various positions including Corporate Sales Manager, Senior Corporate Sales Manager, and Corporate Pricing Programme Manager. At ClassPass, they are responsible for the development and management of the Corporate Wellness Programme in the UK and EMEA.

Henry Loveless attended the University of Leeds from 2008 to 2011, where they completed their Bachelor of Science degree in Medical Sciences. Henry specialized in the field of Biomedical Sciences, focusing on general studies within this discipline.