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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* (see below) – 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
    • 2018             Mystic Seaport Museum’s America and the Sea Award recipient (one of 15 honorees)
    • 2018             Around Long Island Race, Set Course Record & 1st IRC (Numbers -JV66)
    • 2015             Millenium Cup – 1st Tactician on S/Y Silencio (50m Perini Nav)
    • 2015             Opera House Cup – 2nd Vintage Day Racer – Dolphin – Newport 29
    • 2015             NYYC Annual Regatta – 2nd IRC2 – Oakcliff – Farr 40
    • 2015             NYYC Queen’s Cup – 2nd – Temptation Oakcliff- Ker 50
    • 2015             2nd, IRC4 Round Block Island Race, Temptation Oakcliff, Ker 50
    • 2013             Perini Navi Cup, Porto Cervo – 1st Tactician on S/Y Silencio (50m Perini Navi)
    • 2012             NYYC Race Week – 1st IRC Tactician on Temptaion-Oakcliff (Ker 50)
    • 2011             3rd, IRC1 Halifax Race, Temptation Oakcliff, Ker 50
    • 2002             1st, IC45 World Championship
    • 2000             America True CEO and captain, America’s Cup
    • 1999             US Sailing’s Rolex Yachtswoman of the Year
    • 1999             1st, Santa Maria Cup
    • 1992             1st, Santa Maria Cup
    • 1995             Team captain America3 , the women’s team in the America’s Cup
    • 1993/94      Skipper of Heineken, the only all-women’s entry in the 1993-94 Whitbread Round-the-World Race
    • 1992             1st, Women’s Cup in Portofino, Italy
    • 1992             Pit person on America3, winner of 1992 America’s Cup; first woman with active role on an  AC team
    • 1989/90      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

*Dawn Riley has developed a unique organization in Oakcliff Sailing, with the primary goal of building American leaders through sailing. Over the past decade  as Executive Director, she has grown the organization into a world-class training  facility for sailors, umpires & marine industry professionals. They are partners  with American Magic, 11th Hour Racing Team, the World Match Race Tour, and  are a critical part of the pathway to the Olympics. Dawn has also successfully  transitioned Oakcliff to fully public non-profit, with a diverse funding base.

This past year during the COVID pandemic, Dawn led her team in developing new  socially-distanced boating protocols to get their teams and the local community  sailing safely. As a result, Oakcliff was able to host eight graded match races,  more than any other organization in the world during the pandemic. Dawn and  her team developed a novel method of socially-distanced umpiring that is more

effective than pre-COVID methods. And they also ran two Double-Handed  Offshore events with onboard live streaming – showcasing the viability of the new  Olympic Mixed Doubles Offshore Event.

Furthermore, Dawn expanded Oakcliff’s training by establishing an accredited  High Performance High School, including training in Florida during the spring  semester. Oakcliff has also recently partnered with the World Match Racing Tour  to run their official Match Race Academy.

Oakcliff’s 300+ graduates are now working and sailing on America’s Cup and  Ocean Race teams, managing sail lofts and rigging shops, and running offshore  racing programs around the world, all due to Dawn’s vision & leadership.

Oakcliff Highlights :

  • Oakcliff Sailing is an official training center of the US Sailing Team, 11th Hour Racing, NYYC American Magic, IYRS, and the World Match Racing Tour.
  • Boasts the world’s largest collection of Olympic class Nacra 17s, 49ers, and 49er FXs
  • Hosts more match racing events than anywhere else in the country
  • Organized and hosted 19 regattas including the Nacra 17/49er/49erFX US National Championship and the Oakcliff International
  • Celebrates multiple podium finishes for Oakcliff Sailing Offshore Teams
  • Sends competitors to grand prix events including the Mini Transat, Red Bull Youth America’s Cup, World Match Race Tour, Farr 40 Worlds, Caribbean 600 and many, many more.
  • Oakcliff also has sent teams to support the Volvo and America’s Cup World Tour.



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