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Drew Wilderman has a diverse work history, starting in 1994 when they served as a Specialist Combat Engineer for the Army National Guard. Drew later worked for Paychex Payroll Company as a Sales Representative, and Enterprise Rent-A-Car as a Branch Manager. In 2005, they joined CareerBuilder as a Senior Account Manager, where they monitored job postings for performance and trained clients in job posting optimization tactics. After moving on to Arrow Electronics, they worked as a Senior Inside Sales Representative, Sales Manager for IBM Power and Storage Systems, and Brand Marketing Manager, managing budgets exceeding $1 million and generating $500 million+ in IBM HW sales. In 2016, they became Regional Marketing Manager and later National Partner Marketing Manager at Promethean. Drew continued their work in marketing as Product Sales Marketing Manager at Aptean in 2020 and Product Marketing for Carestream Dental from 2021 to 2023. Currently, Drew Wilderman is the Marketing Director at Edge Solutions & Consulting Inc starting from June 2023.

Drew Wilderman earned a Bachelor of Science in Marketing from Southern Illinois University, Carbondale from 1998 to 2003. There is no other information available about their education history.