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Drew Poling has worked in a variety of roles since 1989. Drew began as a Department Manager and Assistant Buyer at Bloomingdale's 59th Street flagship store. From 2005 to 2009, they were an Assistant Web Editor, Social Media and Public Outreach at UNICEF. From 2013 to 2014, they were the Online Customer Service Manager at UNIONMADE, and from 2014 to 2018, they were an Assistant Store Manager at Hudson Grace, LLC. From 2018 to 2020, they were a Department Manager at Nordstrom. Currently, they are the Director of Club and Custom at Rowing Blazers.

Drew Poling received their Bachelor of Science (B.S.) degree in Marketing with a minor in English from Georgetown University in 1986. Drew then went on to receive their Masters of Music in Vocal Performance from the University of Iowa in 1997.