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Jim Massengill started their work experience in 1991 as a Sales Manager at Sears Holdings Corporation. Jim then moved on to Sears Logistics Services, Inc. where they held various roles including Market Operations Manager, Regional Trainer, and District Delivery Manager. In 2006, they joined Covenant as the Vice President of Supply Chain Services, where they were responsible for overseeing the supply chain operations and developing long and short-range planning.

Jim Massengill attended Walter State Community College, although it is not mentioned if they completed a degree or pursued a specific field of study.