The Offshore Sailing School Team

The photo above is a recent photo of Offshore Sailing School headquarters located in Ft. Myers, Florida. This is where Steve and Doris Colgate (our founders and owners) have their offices, along with:

  • The executive team handling finances, marketing, operations
  • Our sales manager and most of the sales team
  • And the administrative sales and operations team

To contact members of the Offshore Sailing School headquarters team, please email; call 800-221-4326, or 1-239-454-1700.

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888-454-7015 or 239-454-1700

Steve and Doris Colgate – Chairman (Steve), President & CEO (Doris)

The Colgates inspire all of us to give 110% to the art of teaching sailing. Their passion for delivering the best on-water education in fun settings started in 1964 when Steve Colgate founded Offshore Sailing School in New York City. On the recommendation of her then employer Yachting Magazine, Doris Colgate met Steve while taking a Learn to Sail and then Racing course at Offshore Sailing School. The rest is history. Read their complete story and the reasons for their dedication to sailing here.

Dana Matthews – Executive Vice President & Chief Financial Officer

Dana is responsible for all the company’s financial functions including accounting, corporate finance, banking, and corporate growth; in addition to overseeing  and managing human resources and payroll activities. Her career spans 30 years of experience in financial management, business leadership, and corporate strategy and growth. Dana holds a Bachelor of Business Administration and Accounting from George Mason University. In her spare time she enjoys Florida’s many beaches, boating, cruising, traveling, spending time with her family and dog, and now sailing.

Beth Oliver – Vice President, Director of Sales & Marketing

Beth has more than 25 years of experience with large corporations and entrepreneurial businesses, including Hiram Walker/Allied Domecq, General Motors and its automotive brands, The Walt Disney Company, Warner Bros., film and television production. Beth managed automotive relationships with the Olympic Games, MLB, NASCAR, Country Music, celebrity endorsements, and sponsorships. Her team at agency Campbell Ewald in Detroit executed more than 3,000 event days a year. After relocating to Southwest Florida with her husband in 2010, Beth managed sponsorships for the thought-leader Imagine Solutions Conference in Naples, and owned her own marketing services consulting business. Beth was elected to the Sail America Board of Directors in 2023, and previously served as a Board member for CHEF: the Culinary & Hospitality Education Foundation of Southwest Florida, and on the Advisory Council of the Southwest Chapter of the Leukemia & Lymphoma Society.

Josh Julow – Director of Operations

Josh Julow relocated to Florida in 2014 from the Midwest, trading fresh water for salt water. He grew up in the Metro-Detroit area and spent a decade in Milwaukee after attending Marquette University for Secondary Education. Having grown up in the Great Lakes area, time on the water has always been a part of Josh’s life. He spent over 6 years at Offshore Sailing School starting as the Sales and Marketing Intern before eventually shifting his focus to operations. Having spent 2 years away from Offshore at Rice Windows and Doors as a Production Manager during the Covid pandemic Josh was delighted to return to the sailing industry at the end of 2021, saying “It is more enjoyable to sell people their dream lifestyle as opposed to a dream home.” When not on the water, Josh spends his free time moderating the largest ice hockey forum in the world, and taking advantage of Florida weather, playing golf and enjoying time on Florida’s many beaches. Please see the Our Faculty page for information about our instructors!

Wendy Bishop – Sales Manager

Wendy moved to Florida from Milwaukee with her husband in 2007. She studied business at Eau Claire University in Wisconsin and has worked in Sales and Administration with GE Medical and Verizon. An entrepreneur, Wendy has owned and operated two small business in Milwaukee and Cape Coral, Florida. Growing up near Lake Michigan Wendy enjoyed sailing in the summers with her husband and three daughters. Her hobbies include fishing, boating, and traveling.

Diana Smith – Sales Associate

When her two sons left the nest, Diana elected started sailing on Highlanders in Indianapolis, IN. In 1997 her General Motors job moved to Detroit where she raced on a C&C35, J120s and NA40s at Bayview Yacht Club – one season as skipper and seven seasons as crew chief. She has sailed “her favorite boat,” the Colgate 26, since its introduction in 1997 and has taken every course Offshore Sailing has to offer. During her four years as President of the National Women’s Sailing Association, she taught at Women’s Conferences, led Caribbean flotillas and Chesapeake schooner sailing programs. Diana joined Offshore in 2004.

Jill Harwood – Sales Associate

Jill grew up on the waters of Lake George and Saratoga Springs, NY. She has worked in Sales and Marketing for 20 years. As a recent empty nester, Jill realized that you must move yourself and your dreams to the front of your priorities. After years of selling for companies looking for financial gain, she was drawn to Offshore Sailing to be able to provide people with the opportunity to live their passions and dreams of sailing, and not put off the good stuff to focus on the daily grind and what everyone else needs from us. She often can be heard saying, “if not now, when?” Jill’s hobbies include, competitive darts, crafting, refurbishing furniture, boating and stand-up comedy.

Cheryl Jones, SHRM-CP – HR & Finance Specialist

Cheryl is a Navy daughter and a Navy wife.  She grew up on Maryland’s Eastern Shore and Southeast Virginia and has always loved being around waterways. When her husband left the Navy, they moved to the Roanoke Valley and they would have to plan trips to visit friends and family in order to get back to the water. When Cheryl’s husband accepted a job with a major commercial shipping line, it allowed them to move wherever they wished, and they happily settled in Southwest Florida, where family and Cheryl’s water awaited. Cheryl enjoys spending time on her lanai, enjoying the views and reading books.

Nikita Graveney – Sales and Operations Assistant

Nikita grew up in Mandeville, Jamaica, and moved to Florida in 2012.  She gained customer service experience in fitness, hospitality, and flooring industries before joining Offshore Sailing School in 2022. An adventure seeker, Nikita loves the water and spends most of her time on the beach soaking in the sun and doing fun water activities. She says her best yet water activity was the first time she sailed on the legendary Colgate 26 while taking her Basic Keelboat course at Offshore Sailing School. In addition to doing her studies in the field of data science, Nikita’s hobbies include reading, writing and editing.

Sign Up For A Course Today!

888-454-7015 or 239-454-1700