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Jerry Underwood began their work experience in 1986 as the Vice President of Sales at Land and Sky Manufacturing. Jerry managed an outside sales force in the bedding industry and conducted key dealer meetings, developing marketing programs for top retailers. Jerry also directed product development in new categories. In 1999, they joined HOM Furniture as the Executive and Director of Marketing, where they focused on brand development and managed web traffic growth, website UI, and advertising budgets and revenue.

Jerry Underwood attended the University of Nebraska at Omaha from 1973 to 1975, but did not obtain a degree or specify a field of study.