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Dawn Riley is both an expert big boat and match racing sailor. She was the first woman ever to manage an America’s Cup syndicate and the first American, male or female, to sail in three America’s Cups and two Whitbread Round the World races.

From her groundbreaking participation in the first all-women’s Whitbread team (Maiden), to winning the America’s Cup in 1992 with America3, to running her own America’s Cup campaign (America True), Dawn has competed and won at the top level of our sport. She now has a resume that includes 1999 Rolex Yachtswoman of the Year, 2002 IC 45 World Championship, first two-time winner of the Santa Maria Cup, and crew on the maxi yacht Morning Glory as they set the all-time course record in the 1996 Sydney to Hobart ocean race. She was team captain of America3, the historic all-women America’s Cup team in 1995, a member of the winning America’s Cup team America3 in 1992 and skipper of Heineken, the all-female team in the 1993-94 Whitbread Round the World sailing marathon. The French America’s Cup team AREVA brings her total to four America’s Cups.

Growing up in Detroit, Michigan, where she sailed on Lake St. Clair, Dawn became obsessed with sailboat racing at the age of 13. She joined North Star Sail Club and became Commodore of the junior sailing program. Dawn said it was difficult to break into professional sailing – she had to clean quite a few boat bottoms and learn to fix motors before people took her seriously.

A television host, author and experienced public speaker, Riley has spoken on topics ranging from entertaining sea stories to defining and attaining personal success, from risk assessment to competing in a co-ed world. Dawn’s experience creating and managing $20-35 million projects is used to make the topics of team building and achievement especially relevant to businesses.

A former member of the International Speakers Association, she has spoken to hundreds of clients including YPO, Oracle, Microsoft, Sweetbriar College, Franklin Covey, Association of Professional Fundraisers, Commonwealth Club, universities, women’s groups, and many sailing associations.

She continues as the CEO of America True Foundation, currently dedicated to providing youth with the opportunity to benefit from sailing and its inherent life lessons nationwide. She has gone on to succeed in leadership roles as a board member at US Sailing, president of Women’s Sports Foundation (founded by Billie Jean King), and now runs Oakcliff Sailing – providing race training to advance the skills of sailors. Dawn is also an advisory board member of the National Women’s Sailing Association, National Sailing Hall of Fame and a founding member of the International Women’s Match Racing Association, Agua Limpia, an environmental education effort and a Young Leader with the BMW Herbert Quant Foundation and the Aspen Institute.

Accomplishments and Honors






2nd IRC4

Round Block Island Race, Temptation Oakcliff, Ker 50


3rd IRC1

Halifax Race, Temptation Oakcliff, Ker 50



C45 World Championship


America True CEO and captain, America’s Cup


US Sailing’s Rolex Yachtswoman of the Year

1999, 1992


Santa Maria Cup


Team captain of America3, the women’s team in the America’s Cup


Skipper of Heineken, the only all-women’s entry in the 1993-94 Whitbread Round-the-World Race



Women’s Cup in Portofino, Italy


Pit person for America3, winner of 1992 America’s Cup and first woman to have an active role on an America’s Cup team


Watch captain/engineer on Maiden, the first all-women’s team in the 1989-90 Whitbread race


Leadership Roles

  • 2004-2007 General Manager K-Challenge America’s Cup 2007
  • America True Youth Program
  • Board member, US Sailing
  • Women’s Sports Foundation
  • Oakcliff Sailing
  • National Women’s Sailing Association
  • Advisory Board Member, National Sailing Hall of Fame

Major Appearances as a Featured Speaker

  • Outdoor Live Network, ESPN guest, athlete and commentator, Late Night with David Letterman, Live with Regis & Kathy Lee, CNN, CNBC, Lifetime, Oxygen, A&E network
  • Corporate clients have included: Oracle Corporation, Nortel, Novartis, NationsBank, Industrial Risk Insurance, Young Presidents Organization, Mazda, BMW, General Motors, Bell Atlantic Federal, Bank of America, The Southern Company, Silver Seas Cruise Line, Unisys Corporation

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