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Robert O'Leary has extensive experience in the hotel industry, primarily in franchise sales and development. Robert began their career at Choice Hotels International as the Director of Franchise Sales, where they generated new business through long-term franchise agreements. Robert then joined The Plasencia Group as a Vice President, advising clients on marketing and selling hotel assets in the Southeastern United States. O'Leary later served as the Director of Business Development at Haywood Street Press, overseeing the marketing and sales efforts for a legal thriller publication. Robert then joined WoodSpring Hotels as the Regional Vice President of Franchise Development, responsible for new construction franchise development in several states. O'Leary currently works at Choice Hotels International as the RVP of Franchise Sales and Development for the Southeast region.

Robert O'Leary earned a Bachelor's Degree in Economics and Management from the University of Pennsylvania Wharton School of Business from 1989 to 1992.