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Robert Osborne has a long history of work experience, starting in 2006 as a Manager for TL Cannon Applebee's. In 2012, they joined Ingram Micro as a Solution Sales Executive for Citrix and later a Sr. Account Representative. Most recently, in 2023, they started working as a Federal Account Executive for Trilogy Innovations.

Robert Osborne attended the University at Buffalo School of Management, The State University of New York, where they obtained a Bachelor of Business Administration - BBA in Marketing.