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Anthony Caldwell has a diverse work experience in various roles and industries. Anthony started their career as a Production Intern at Heatwave Interactive in 2010 and later became an Assistant to the CEO, a Quality Assurance Tester, and a Production Assistant in Social Games at the same company. In 2012, they joined Apple as a Junior Sales Representative, where they processed purchase orders and assisted school administrators. Anthony then worked as a Documents Review Analyst at NetSpend in 2014. From 2014 to 2019, Caldwell served as an Account Sales Manager at Hi-Rise Balloons and Floral Supplies. Currently, they are employed as a Sales Representative at Mayflower Distributing Company.

From 2005 to 2010, Anthony Caldwell attended Huston - Tillotson University, where they pursued a degree in Business Administration with a focus on Management.