Our Headquarters Team

Steve and Doris Colgate – Our Chairman (Steve) and CEO/President (Doris) encourage all of us in a very special way to give 110% to the art of teaching sailing. Their passion for giving you the best education in a serious, yet fun setting started in 1964 when Steve Colgate founded Offshore Sailing School in New York City. Doris Colgate met Steve while taking a Learn to Sail course on the recommendation of her then employer – Yachting Magazine. The rest is history. You can read their complete story and the reasons for their dedication to sailing here. You can reach Doris on her direct line 239-985-7511 or Steve at 239-985-7505. Emails are Doris@OffshoreSailing.com and Steve@OffshoreSailing.com.

Charlie Adams – Our Director of Operations, moved from Massachusetts to join our management team in Ft. Myers, Florida. A competitive sailor since he was 12 years old Charlie has raced everything from around the bouys in Lasers, 420’s, Shields and Etchell 22’s to blue-water experience in the Newport Bermuda Race. Combining his love for the sailing lifestyle with a strong business management background Charlie will help continue the growth of Offshore Sailing School while tackling the many hats required for overseeing the daily operations of all of our branch locations.
You can reach him at 239-985-7539; charlie@OffshoreSailing.com. 

Sheila Leppanen – Our Controller, has been with Offshore Sailing School for over 15 years, handling with aplomb the complicated daily course of financial matters for the company. She is as dedicated to Offshore Sailing School as the Colgates, maintaining the highest ethical level. Sheila has two adult daughters and a husband who loves to play ice hockey here in Florida where we are headquartered. Her direct line is 239-985-7513, email Sheila@OffshoreSailing.com.

Terri Bryan - Our Director of Sales, oversees Offshore's headquarters and branch sales. She is an avid sailor and boater who learned to sail at Offshore Sailing School with her husband years before joining our team. Her sales, management and leadership experience ranges from real estate to one of the largest marinas in SW Florida. When not working tirelessly at Offshore, Terri enjoys relaxing at her island home, cruising in the Caribbean and enjoying the waters here at home. Her direct line is 239-985-7537, email Terri@OffshoreSailing.com.

Erin Williams – Landed on the doorstep of Offshore Sailing School in June of 2011. With over 22 years of Sales and Customer Service experience, she decided that it was time to pursue her passion for sailing. Having lived in the Ft. Myers/Cape Coral, FL area for over 15 years surrounded by water, what better way to pursue her dreams than working for the most reputable and respected teachers in the industry.  In addition to her passion for learning to sail, Erin is very passionate about her two children; one of which is now hooked on the sport at the age of 11! Erin believes that everyone should try sailing at least one time!  "There is no better feeling than being out on the water with nothing but the wind to guide your way. It is an excellent confidence builder as well as a way to truly develop a respect for the ocean," she says. Her direct line is 239-985-7500; email Erin@OffshoreSailing.com.
 

Diana Smith – Decided it was time to do something for herself when her two sons left the nest. So she got into sailing – first on Highlanders in Indianapolis. When her Gerneral Motors job moved to Detroit in 1997, she started racing at Bayview Yacht Club; on a C&C 35, J120s and NA40s with one season as skipper and 7 as crew chief over 12 years. She has sailed "her favorite boat," the Colgate 26 since its introduction in 1997 and has taken every course Offshore has to offer. Diana gives seminars at Offshore's Women's Weeks and during her four years of president of the National Women's Sailing Association's taught at Women's Conferences, led flotillas in the Caribbean and schooner sailing programs in the Chesapeake. Diana has been with Offshore for nearly five years. Her direct line is 239-985-7506; email Diana@OffshoreSailing.com.

Kathryn Olesak – Came to Offshore from South Seas Island Resort on Captiva Island, FL - home to Offshore's largest southern branch since 1975. There she was senior conference service manager. With long experience in real estate and hospitality industries she has also been a horse trainer, giving lessons, showing hunters and jumpers competitively nationwide. A graduate of Lewis and Clark College in Portland, Oregon, Kathryn enjoys talking to customers and finding the right program to meet their desires. Her direct line is 239-985-7531, email Kathryn@OffshoreSailing.com.

Janet Kreft – Takes care of our customer management systems, and works with our sales team to make sure that our customer's experience does in fact "change their lives." Her unwaivering support of the team is felt across the organization in the operations arm of Offshore as well as the executive suite. Branch schedules, changes, and customer requests are funneled to Janet for execution. She plays a pivotal role in making sure that our customers needs are met and exceeded. Janet is a Wolverine through and through from the great state of Michigan. Her direct line is 239-985-7522, email Janet@OffshoreSailing.com.