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Derek Gilroy has worked in a variety of roles since 1997. Derek began their career as a Trader at the Chicago Board of Trade. In 2014, they took on the role of Real Estate Investor at Masa Realestate LLC. In 2020, they joined Xpresso Delight USA as Vice President. In this role, they are responsible for their recent partnership with Xpresso Delight, which is a coffee machine for the office that allows users to make all the same coffees that they can buy at a coffee shop.

Derek Gilroy attended Northern Illinois University from 1989 to 1993, where they earned a Bachelor of Arts in Political Science Pre-law.