The Oakcliff Sailing staff brings a vast amount of experience and knowledge to the program. Each staff member has a unique perspective on the sailing industry which gives everyone involved a more enriching experience.
As CEO and captain of America True, Dawn Riley was the first woman to manage an America’s Cup sailing team. She has raced on four America’s Cup and two Whitbread (now Volvo Ocean Race) teams. She is the former president of the Woman’s Sports Foundation, served on the board of US Sailing, and is an advisor to several public service organizations.
Bill Simon joined Oakcliff in 2010 and is our Race Program Director. He brings his 30-plus years of small business experience as CFO, COO and MBA in Finance to help support the Executive Director and the Oakcliff mission. An avid local sailor, Bill organizes the array of events offered at Oakcliff. In addition to scheduling our Grades 5-1 Match Racing regattas and Clinegattas, Bill also coordinates Oakcliff’s coaching clinics, Race Management, Umpire and Judge Seminars. He works with the Wednesday night Fleet Racing program and encourages all local sailors to join the educational fun. In his 40-plus years on the water, Bill has campaigned a Sonar and other class boats on Manhasset Bay and has enjoyed major regional racing, including crewing on a couple of Newport to Bermuda races. Most recently he participated in the Sonar North Americans in Manhasset Bay. While at Oakcliff, Bill took advantage of the seminars offered and is a Club Race Officer, Judge and Umpire. As a member of the US Sailing Match Racing and US Sailing Match Racing Championship Committees, Bill works diligently to grow Match Racing in the US and abroad. He is eager to combine his background and sailing passion into programs that will assist Oakcliff Sailing in its mission, as well as supporting Acorns and Saplings in preparing for sailing industry careers.
Ladi Oguntoyinbo grew up in Beaufort, South Carolina and attended Beaufort Academy, Cardigan Mountain, and Brooks School boarding schools. He played division 1 lacrosse and soccer at Hofstra University and continued his studies at the Seattle Maritime Academy. He headed out to sea as a merchant marine, traveling the world from Charleston to Kuwait and Seattle to South America. During this time, he crossed the equator twice, graduating from pollywog to trusty Shellback, a true Son of Neptune. Ladi’s sailing life has also been a journey. He began sailing at the Beaufort Yacht and Sailing Club and dreamed of racing sailboats. While home on leave after an exceptionally hard tugboat passage, Ladi got the call to join a race boat team and the rest is history. In 2006, his first year as a professional racer, the team won Block Island Race Week, Whidby Island Race Week, and the Round Statue of Liberty Race, among others. Ladi said he remembers hot summer days in Beaufort, sailing Sunfish and trying to jump tug boat waves. His life has come full circle, as he now works with Oakcliff Sailing to learn, train and coach.
Chris Kennedy sometimes finds time to actually go sailing. He loves to take things apart, and put them (mostly) back together. In the Fall of 2011, between finding a real job as an engineer, keeping the ’78 Chevy and ’83 Yamaha running, and building a chicken coop, he found a little time to sail Melges 24 Nationals, F18 North Americans, and C Scow Worlds. While the “real job” and some iceboating kept the thirst sated through the long, cold Wisconsin winter, as the weather warmed the need to be on the water grew. Chris headed off to Oakcliff to find out what Long Island Sound has to offer. Once at Oakcliff Chris continued to be industrious in the shop and with any project we could throw at him. At the end of his class we were happy to hear the words – “I can’t think of anywhere else I would rather be than at Oakcliff”. Chris has become a valued member of our team and on the sailing side he is one of our more talented match racing coaches, often sailing with Chris Poole’s Riptide Racing with much success.
SapGrad 2013 – Training Program Director Consultant
Elizabeth is a Canadian who is addicted to sailing, adores her dog Dodger, speaks three and a half languages, likes shiny things, digs real estate and loves being cozy. Her sailing career is diverse. She competed abroad in the International 470 class, raced One Design and big boats in Australia, instructed and coached under the RYA schemes in England, handled communication strategy for an Open 60 team in France and has racked up over +25,000 coastal and ocean miles over the years. Elizabeth spent 3 years working as the Director of Sailing/Race Director at the Royal Nova Scotia Yacht Squadron; her home club in Halifax, Nova Scotia. During that time she gained a wealth of experience in race management which uncovered a new passion leading her to become certified as Canada’s youngest National Race Officer. She is currently Vice President on the Board of Directors for the Nova Scotia Yachting Association. Elizabeth made her way back to Oakcliff as a force of nature and is now leading our Acorn and Sapling programs. She is uniquely suited to do so as she was a participant and is now a leader.
Tim Kent learned to sail on Lake St. Clair just north of Detroit, and did not start racing actively until his early 30s. He began keelboat racing, including the Port Huron and Chicago to Mackinac Races and really enjoyed the longer distance races. In the late 90s, he sailed in the first Chicago to Mackinac Solo Challenge, finding his niche in solo racing. After competing in two more Solo-Mac challenges, he took his purpose-built Open 50, Everest Horizontal, to the East Coast, and entered the 2002/3 Around Alone Race, a 26,000 mile solo race around the world with four stopovers. He successfully completed the race, finishing second in Class 2.
His passion for sailing has been passed down to his two daughters, who have captained their respective college sailing teams and who both work in the sailing world, teaching and managing sailing programs. Tim still enjoys shorthanded distance racing, but can be found buoy and distance racing in the company of a full crew as well. He lives aboard a boat right here in Oyster Bay.
Graduate Class of 2015
Ethan has been sailing for 9 years on offshore and inshore sailboats both large and small. He grew up sailing in high school competitively, shortly to begin coaching sailing. Before Oakcliff he spent each season coaching high school sailing and expanding STEM sailing in his hometown of Southern Maryland. Wanting to follow his dreams of sailing a Volvo Ocean Race he left everything behind to pursue the professional field.