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Kai Gilsey has a diverse range of work experience. They started their career as an Account Executive at Bait & Tackle Ad Company in 2009, before moving on to mcgarrybowen as a Junior Producer & Assistant Account Executive. In 2010, Kai joined The Greenwich Hotel, where they held various positions including Assistant to General Manager, Front Office Supervisor, Assistant Front Office Manager, and finally Front Office Manager. In 2014, Kai transitioned to Baccarat Hotel & Resorts as the Director of Front Office. Currently, they hold the position of Director of Operations at Getaway since December 2016 and were later promoted to VP of Operations.

Kai Gilsey holds a B.A. degree in Psychology, Communications & Fine Arts from St. Lawrence University, which was completed between 2005 and 2009. In 2013, they obtained a Certificate of Financial Management from Cornell University's School of Hotel Administration. Additionally, in 2018, Kai completed a program titled "Leading with Finance" at Harvard Business School Online.