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Thomas Oliver has a long work history, beginning in 1997 with Heartland Bank (Midland States Bank as of 4/20/15), where they served as System Operator / Internet Specialist. In 2015, they joined DShofer Inc. as District Manager, Office Manager, and Independent Contractor. In 2017, they moved to REI BlackBook, where they have since held the roles of Director of Customer Success, Software Quality Assurance, and Tier 2 Tech Support.

Thomas Oliver attended Saint Louis University from 1993 to 1997, where they obtained a Bachelor of Science in Business Administration.