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Ryan Fleming
Director
Ryan brings with him more than 30 years of experience as a player, coach, and leader within the tennis industry, along with a deep passion for fostering community through racquet sports. A native of the mountains of North Carolina, Ryan was a standout collegiate player for legendary coach Chuck Kriese at Clemson University before competing professionally. Over the years, he has held numerous leadership roles, including Director of Tennis at The Birchwood Club, Adult Director at College Park Athletic Club, and most recently as Regional Director and Head of Staff for TennisBloc, where he managed and trained hundreds of coaches across the Carolinas. Ryan’s extensive background combines business acumen, player development, and education. He has founded his own tennis school, collaborated with national coaching organizations, and worked closely with renowned tennis educator Steve Smith for more than two decades. Ryan has already developed an exciting lineup of new programs for Wintergreen’s racquet community, bringing fresh energy and a long-term vision to the mountain. Now settled in at Wintergreen with his wife and children, Ryan looks forward to growing all aspects of racquet sports from tennis and pickleball to events and programming.