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Jim Wilkinson Sr. has a diverse work experience spanning across various industries. Jim started their career in 1983, working in customer service roles for NewAir, Pilgrim, and Business Express Airlines. From 1986 to 1998, they served as a restaurant server and manager for multiple restaurants, including Chuck Steak House, Margarita's Restaurant, and Ledge Light Brew Company. In 1990, Jim became a co-owner of On Par Golf Inc, where they managed day-to-day operations, including sales, marketing, finances, inventory control, and golf club repair. In 1996, they joined Mohegan Sun as the Vice President of New Markets, responsible for establishing and building new business relationships and maintaining existing ones. Currently, Jim is working at Mohegan Pennsylvania as the Director of Casino Marketing.

Jim Wilkinson Sr. attended Fitch Sr High in Groton, CT from 1980 to 1983. However, no specific degree or field of study was mentioned. Additionally, they obtained several certifications from LinkedIn, including "Delivering an Authentic Elevator Pitch," "Excel: Introduction to Charts and Graphs," "Sales Pipeline Management," "The Mindful Workday," "Coaching Skills for Leaders and Managers," "Improving Your Listening Skills," "Marketing Foundations (2014)," "Mission and Vision Statements Explained," "Navigating Awkward Situations at Work," "Communication Foundations," and "Excel 2016 Essential Training." The dates of these certifications range from 2020 to 2022.