Our Sales Team

The Offshore Sailing School Sales Team

The people you meet on the phone, at boat shows and through emails, work at Offshore Sailing School headquarters in Ft. Myers, Florida. They are all avid sailors and boaters, have taken or about to take one or more Offshore Sailing School courses, and are very knowledgeable about our locations. Our Sales Team is inspired by Beth Oliver, Director of Marketing on our Executive Team.



Sales Manager

Wendy moved to Florida in 2007 from Milwaukee with her husband. She studied business at Eau Claire University in Wisconsin and has worked in Sales and Administration with GE Medical and Verizon. An entrepreneur, she has owned and operated two small business in Milwaukee and Cape Coral, FL. Growing up near Lake Michigan Wendy enjoyed sailing in the summers with her husband and three daughters. Her hobbies include fishing, boating, and traveling. Her direct line is 239-985-7509; email wendy.bishop@OffshoreSailing.com.




Sales Associate

Will has spent most of his life on and around boats, both power and sail, and holds a USCG Master license with over 5,000 miles of sailing logged. Will is an avid racer and competes in events from Charlotte Harbor down to the Florida Keys on several boats, including his own Allied Mistress 39 and Herreshoff Scout 18. He joined Offshore Sailing School as a Senior Sailing Advisor after working for nearly a decade in the role of Sales and Marketing for a general contracting firm based in Fort Myers. Will lives in Fort Myers with his wife Paula and their cat Federico.  His direct line is 239-842-8358; email Will@OffshoreSailing.com.




Sales Associate

Sheri comes to Offshore Sailing School with over 20 years of Sales and Marketing experience. Sheri and her husband have been visiting and boating in Southwest Florida for the last 25 years, as part time residents, and finally settled in as full-time residents in 2016. Sheri and her husband live in Fort Myers, FL and enjoy boating, fishing, biking and cooking. You can reach Sheri at 239-985-7524; email Sheri@OffshoreSailing.com.




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. Her direct line is 239-985-7506; email DianaSmith@OffshoreSailing.com.



Sales and Operations Coordinator

Josh moved to Florida from Milwaukee where he received a Bachelor’s Degree in History and Secondary Education from Marquette University. In 2011 he received a Bachelor of Science Degree in Interdisciplinary Studies from Hodges University. Before joining Offshore he worked as production specialist for MSX International, office assistant for Hunter Robert’s Homes, and Target. He lives in Bonita Springs, FL and is responsible for managing resource inventory and our booking system, while assisting the Director of Operations in whatever it takes to make branch operations run smoothly. His direct line is 239-985-7500, email Josh@OffshoreSailing.com.



Sales and Marketing Assistant

Gabrielle was born and raised in Ft. Myers, Florida. She attends Florida Gulf Coast University and is pursuing a degree in Communications with a minor in Spanish. She doesn’t have a specific career in mind yet, but wants to travel to Spain and other countries to take classes abroad before she graduates. Her direct line is 239-985-7507; email Gabrielle@OffshoreSailing.com.

Sign Up For A Course Today!

Call 888-454-7015 or 239-454-1700
Email Sail@OffshoreSailing.com