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Bob O'Leary currently serves as the Senior Vice President of Revenue Diversification at The Daily Gazette, a position held since October 2017, after previously holding the role of Vice President of Advertising there. O'Leary has extensive experience in the media industry, having served as Publisher for the New York Group at Digital First Media, overseeing multiple newspapers, and as General Manager at The Daily Freeman, where responsibilities included advertising revenue growth and audience retention. Earlier roles include Advertising Director at the Poughkeepsie Journal and various positions at Gannett, cumulatively demonstrating expertise in sales strategy, budget management, and team development. O'Leary holds an Associate of Arts and Sciences degree in Computer Science from Columbia-Greene.