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Simon Forester has a diverse work experience spanning various industries. Simon started their career in 2008 as a US & Global Property Reinsurance Broker at Aon Benfield, where they worked for eight years. In 2015, they took a sabbatical and completed a 12-week professional cookery course at Dublin Cookery School, gaining culinary experience in fine-dining restaurants.

In 2016, Simon joined Syft as a Business Development Manager and later took on roles as a Senior Business Development Manager and Senior Client Executive. Simon continued their employment at Syft as an Enterprise Business Development Manager until 2021 when the company was acquired by Indeed Flex. Simon then transitioned to the role of Enterprise Business Development Manager at Indeed Flex and received several accolades for their work, including the Technology Award of the Year 2019 and the Brave Award 2019.

Simon's career also includes roles as an Investor in various companies, such as Nix & Kix, Paradym, Foodstuff, and Lifesaver. Currently, they serve as an Account Director at NuBreed Hotels and EventBedsTM, taking on the position of Global Account Director.

Simon Forester earned a Master of Arts (M.A.) in Luxury Hospitality Management from the University of West London in 2016-2017. Prior to that, they obtained a Philosophy BA(Hons) 2.1 from the University of Leeds during the period of 2005-2008. Simon also completed their secondary education at Charterhouse from 1999 to 2004, focusing on subjects such as Maths, English, and History. In addition to their formal education, Simon has obtained several certifications, including WSET Level 2 from WSET — Wine & Spirit Education Trust in July 2018, Food Hygiene & Safety Level 2 from The Nationwide Caterers Association (NCASS) in March 2017, and Cert CII from the Chartered Insurance Institute. The month and year of obtaining Cert CII are not specified.