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Offshore Sailing School Announces Promotion of Key Financial Expert to Executive Leadership Position

July 19, 2023

On July 17, 2023, Offshore Sailing School’s current Controller, Dana Matthews, assumed the role and responsibilities of Executive Vice President and Chief Financial Officer. 

“We are pleased to announce this executive move as part of our on-going development of new leadership roles as we head into Offshore Sailing School’s 60th year,” announced Offshore Sailing’s President and CEO, Doris Colgate. “With 30 years of experience in financial management, business leadership, and corporate strategy and growth, Dana has already made a lasting impact in helping us develop our team for substantial growth in the future,” Colgate continued.

Prior to joining Offshore Sailing School in early 2022, Matthews worked in finance roles at various property management companies, spent over 11 years at the Internet Society in leadership positions, culminating in Director of Financial Reporting & Accounting, and she served as CFO-COO for the American Bird Conservancy. She holds a Bachelor of Business Administration and Accounting degree from George Mason University.

Offshore Sailing School was founded in 1964 by Olympic and America’s Cup sailor, Steve Colgate, and has been run by the Colgate husband and wife team together since 1969. Steve Colgate was inducted into the National Sailing Hall of Fame in 2015, Doris Colgate was inducted in 2022. Their dedication to enhancing lives through sail and power boat education has made Offshore Sailing School the pre-eminent sail and power school company over its long history. The Company has had locations on Captiva Island, Florida since 1975; in St. Petersburg, Florida since the 1990’s; and in the British Virgin Islands since 1974. All levels of sailing instruction are taught from basic sailing, to cruising, passage making, and racing on a fleet of 26’ to 50’ monohull and catamaran yachts. Powerboat courses are provided on 37’ to 51’ power cats. Visit

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