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Simon Draper has a long history of work experience, beginning in 2009 when they founded and became the CEO of Resolutions MSP. In 2009, they also founded and became the CEO of SaaS Distribution & Consulting. In 2016, they became the Director of Evolve-IT Consulting Ltd, a company focused on enterprise software development. Simon also became a Deal Maker for HippoCorn, an Investment Bank for Startups, and Co-Founder of Hastee Pay, a company focused on faster, smarter, and ethical payments. In 2019, they became an Advisor & Investor for Parsyfal® and a Board Advisor & Investor for HR DataHub. In 2020, they became a Board Member for Hammock and Founder of Monspire. In 2021, they joined the Advisory Board for Red Dot Foundation-Safecity, a platform that crowdsources personal stories of sexual harassment & abuse in public spaces.

Simon Draper attended Oxford Brookes University.