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John Cheevers has been in the workforce since 1988, beginning their career in the Direct Mail Industry as a Mailing List Broker & Mailing List Manager. In 1997 they moved to Tiffany & Co. as a Corporate Sales representative, and in 2001 they transitioned to Ashford.com in the same role. From 2002 to 2005 they were a Corporate Sales representative at Zagat Survey, and then returned to eCompanyStore as a Team Leader / Account Executive. In 2013, Cheevers moved to Vantage Apparel as the Eastern Regional Sales Leader - Eastern USA & Canada. John returned to eCompanyStore in 2017 as the Director of Strategic Partnerships, and is currently employed by Pinnacle Promotions as a Strategic Partnerships representative.

John Cheevers attended Manhattan College from 1984 to 1991, where they earned a Bachelor of Arts in English and World Literature.