Our Sales Team

The Offshore Sailing School Sales Team

The people you meet on the phone, at boat shows, virtually and through emails, work at Offshore Sailing School headquarters in Ft. Myers, Florida. They are all avid sailors and boaters 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! Getting 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

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 Coordinator

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. Her direct line is 239-985-7530, email Cheryl@OffshoreSailing.com.



Operations Coordinator

Jerri moved to Florida in 2003 from Lansing, Michigan.  She attended Edison College in Ft. Myers earning an Associates degree and later transferred to Florida Gulf Coast University earning a Bachelor of Science degree in Human Resource Management.  Prior to coming to Offshore Sailing, Jerri worked various customer service positions in the banking and hospitality business and most recently as a manager in human resources at a local resort.  Her hobbies include spending time with her dog Mia, participating in 5k mud and obstacle course events, boating and fishing, watching and attending college and professional football games.  Jerri’s direct line is 239-985-7500, email is Jerri@offshoresailing.com.


Sign Up For A Course Today!

888-454-7015 or 239-454-1700