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Simon Diggins has extensive work experience in the ski industry. Simon started their career in 1992 as a Sales Manager at Solitude Mountain Resort, where they worked until 1995. After that, they joined Snowbird Ski and Summer Resort as the Director of Ski Tour & Travel Sales. In this role, they managed leisure sales for ski and summer seasons, including direct sales, travel industry sales, wholesale, group travel and events, incentives, and social groups.

Simon Diggins completed their education with a BA in History from the University of Cambridge, specializing in British and European modern history. Afterward, they pursued further studies at the City University of Manchester, where they obtained a Post Grad Diploma in Hotel and Catering Management.