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Jesse Gregg has a diverse work experience in the finance and hospitality industries. Starting in 2017, Jesse worked at The Club at Admirals Cove as a Manager in Training, where they gained extensive knowledge in managing club restaurants, private events, and banquet functions. In 2018, Jesse joined Woodfield Boca Raton as a Food and Beverage Supervisor, where they effectively managed multiple restaurant openings and closings while maintaining high service and cleanliness standards. Jesse then transitioned to Golden Lion Capital Investments in 2020, initially working in investments before being promoted to the role of VP of Investments in 2023. Throughout their career, Jesse demonstrated strong leadership skills and a commitment to delivering excellent service to clients and members.

Jesse Gregg completed their high school education at Southwick Tolland Regional High School from 2009 to 2013. Following this, they pursued a Bachelor of Science (BS) degree in Hospitality and Tourism Management from the Isenberg School of Management at UMass Amherst, graduating in 2017.