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Jon Paradise has a diverse work experience spanning several industries. Jon started their career in 1985 as a Program Director at WHYR Radio, where they handled all on-air programming. Jon then moved on to WTVL Radio in 1988, where they served as the Vice President of Programming, responsible for on-air hiring and format decisions. In 1994, they became the Director of Marketing & Public Relations at Andover College, overseeing a significant increase in student population and awareness. From 1993 to 2001, Jon was the Public Address Announcer for the Portland Pirates hockey team, appearing on ESPN and NBC during game broadcasts. In 2000, they joined the Maine Credit Union League as the Vice President of Governmental & Public Affairs, later transitioning to the role of Vice President of Public Affairs and Engagement. In 2018, Jon joined Town & Country Federal Credit Union as the Vice President of Public Relations and Communications, and their role expanded in 2020 to become the Senior Vice President of Communications, Marketing, and Community Outreach. Additionally, since 2019, they have served as the Public Address Announcer for the University of Southern Maine. Throughout their career, Jon has demonstrated expertise in communications, marketing, media relations, and community outreach.

Jon Paradise received their education from various institutions. Jon started their academic journey at the University of South Florida in 1983, where they studied Communications. Jon then transferred to the University of Southern Maine in 1985 and completed their Bachelor of Arts degree in Communications in 1987. Later on, from 1996 to 1998, Jon attended the Muskie School & Cutler Institute at the University of Southern Maine, where they obtained their Master of Arts degree in Public Policy & Management.