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Heather Winnie has worked in various roles since 2007. Heather began as a Sales Recruiter for UBS in 2007 and then moved to Reynolds American Inc. as a Commercial Account Manager in 2008. In 2010, they took on the role of Sales Recruiter at City College. In 2012, they became a Sales Executive at New Media Investment Group Ventures, and in 2015 they were an Event and Sponsorship Coordinator at UF Innovate | The Hub. In 2017, they took on the role of Senior Sales Executive at eventPower and in 2020 they became a Sales Executive for Costpoint at Deltek. Currently, they are a Sales Executive at CXT Software.

Heather Winnie attended the University of Florida from 2002 to 2006, where they obtained a Bachelor of Arts in History.