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

Dawn’s story started when a sailor fell in love with a local girl as his boat was docked at her Mediterranean island. Growing up on the Pacific in Southern California, and spending summers in the Mediterranean, she was always in or on the water – body boarding, fishing or sailing. It was a huge life change when she took a promotion in Colorado. Her passion has always been focusing on the customer; from starting a successful private label brand to helping restaurants be profitable. As a former All-American Soccer Player at the University of San Diego, she found time along the way to coach professionally and play in the WPSL. But more significantly, on the field is where she met her incredible husband! Dawn and her family recently relocated to Southwest Florida to be close to family. Being back on the water and joining Offshore Sailing’s amazing sales team has been a dream come true for this California girl. Her direct line is 239-985-7524; email Dawn@OffshoreSailing.com.



Sales Associate

Jen moved to Fort Myers Beach in 2010 from St. Louis, MO with her family. Jen served as an Operations Specialist in the US Navy Reserves and loved growing up in a military family. She has held numerous licenses including Real Estate and Mortgage licenses and is currently a licensed Notary. During her time in Real Estate she earned multiple designations and awards including the 5-Star Realtor Award with St. Louis Magazine. Prior to joining our team at Offshore, she spent her career in Retail Management running multi-million dollar businesses such as Camping World, Pilot Flying-J and Sears. She has a passion for helping others and has volunteered for many different programs including the Foster & Adoptive Care Coalition, Junior Achievement and the Fort Myers Beach Elementary School. Having spent most of her life around numerous lakes and rivers, Jen has spent a lot of her free time on the water. Her favorite hobbies still include boating, jet skiing and kayaking as well as any outdoor activity. Her direct line is 239-985-7525; email Jennifer@OffshoreSailng.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