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Bob Henning began their work experience as the Northwest Manager for Sunset Magazine in August 1992. Bob then moved on to Wizards of the Coast in October 1995, where they served as the Advertising Sales Director. After that, Bob held a position as the Director of Corporate Partnerships at Live Nation from January 2003 to January 2008. Following this role, they joined Key Brand Entertainment in January 2008 as the Director of Corporate Sponsorship. Finally, Bob retired in February 2019.

Bob Henning attended Woodside High School from 1976 to 1979, although they did not obtain a degree or focus on a specific field of study during this time. Following their high school education, Bob Henning enrolled at the University of Southern California from 1979 to 1983, where they earned a Bachelor of Arts degree in Economics.