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Jonathan Leahy has a diverse work experience in sales and marketing roles. Jonathan started in 2003 as the Director of Sales and Marketing at Highland Green Adult Resort Community and Golf Club, where they hired and managed sales staff and also worked as a top sales agent. In 2008, they joined Legacy Properties Sotheby's International Realty as Vice President, where they specialized in marketing and public relations to promote the brand and achieved significant sales. Currently, since 2019, Jonathan is the Director of Sales & Marketing at Highland Green, where they oversee sales and marketing initiatives.

Jonathan Leahy earned a Bachelor of Arts degree in Sociology & Business from Eastern Illinois University between the years 1986 and 1989.