Dawn Riley

Dawn Riley is an American sailor recognized for her significant contributions to competitive sailing and sailboat racing. Riley was the first woman to manage an entire America's Cup syndicate and the first American, man or woman, to compete in three America's Cups and two Whitbread Round the World races. She is a member of the National Sailing Hall of Fame, the international America's Cup Hall of Fame, and the State of Michigan Sports Hall of Fame, the only individual to hold all three distinctions.

Riley's competitive sailing career includes joining the crew of Maiden, skippered by Tracy Edwards, which was the first all-women's boat to participate in the Whitbread Round the World Race. Serving as watch captain, diver, and engineer, Riley and her team brought increased visibility to women in sailing. The feature film "Maiden" tells the story of Riley and the crew's efforts in blue water racing. Riley later became the first woman to have an active racing role aboard an America's Cup contender as part of the America3 team, which won the America's Cup. She subsequently skippered Heineken, the only all-women's entry in the Whitbread race. Riley recounted her experiences in the book "Taking the Helm," co-authored with Cynthia Goss.

Riley's leadership extended beyond the racecourse. With America True, she became the first woman to serve as CEO of an America's Cup syndicate, managing more than 100 employees and volunteers and raising $24 million to fund the campaign. The America True team outperformed expectations in round robin and Semifinal competitions, including races against the New York Yacht Club and Stars & Stripes. The America True Foundation, established as part of the campaign, worked to make sailing accessible through programs across the United States, introducing at-risk youth to the sport. Riley was named Rolex Yachtswoman of the Year for her match racing victories and has won One Ton Cup and Women's Match Race World championships.

Off the water, Riley served on the board of the Women's Sports Foundation, founded by Billie Jean King, and was the only sailor to serve as its president. Mystic Seaport presented Riley and Oakcliff Sailing with the America and the Sea Award, recognizing achievements in maritime exploration, competition, scholarship, and design. Riley has appeared on ESPN, CNN, CNBC, Live with Regis and Kelly, and Late Night with David Letterman. As a public speaker, she shares insights on leadership, adaptability, accountability, and teamwork, drawing from her experience in elite sailing competition.

Riley became executive director of Oakcliff Sailing, a high-performance training center for advanced sailors. Oakcliff's mission is to build American leaders through sailing. The America True Foundation, under Riley's leadership, continues to introduce young people nationwide to sailing, providing opportunities for youth to benefit from the sport and its life lessons. From her role on Maiden to leading an America's Cup syndicate, Riley's career highlights the impact of leadership and innovation in the sailing industry.