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Jonathan Holmes has a diverse work experience in various roles and industries. Jonathan started their career as an Assistant Controller at South Carolina Tees in 1984, where they supervised departments and implemented accounting and cash flow management systems. Jonathan later worked as an Employee & Consultant at CFRE Certified Fund Raising Executive from 1992 to 1999. In 1999, they joined i4 Design as the Director of Sales & Marketing, where they served until 2001. From 2001 to 2005, Jonathan worked as the Director of Business Development & Marketing at Rock Paper Scissors. Jonathan then became a Partner at Mighty 8th Media in 2005, where they specialize in digital marketing and branding. In 2022, they joined Pinnacle Bank as a Board Member.

Jonathan Holmes received their Bachelor of Science in Business Administration from the University of South Carolina Darla Moore School of Business in 1984. Jonathan double majored in Finance and Management during their time at the university.