Offshore Sailing School Employment Opportunities

View all current available openings at Offshore Sailing School, including sailing instructor jobs, sales positions and more below. You may download our Application for Employment here. When completed, please send to the contact person listed for each position.


This career position is based at our premier Florida location on Captiva Island. Key responsibilities include: Evaluate, train, schedule and supervise staff of full time and part time instructors; train, schedule, supervise and hold responsible cleaning and maintenance personnel; insure the entire Captiva Island fleet is maintained in A-1 cosmetic and mechanical condition (currently Jeanneau 439 and 479; Leopard 48 catamaran, 10 Colgate 26 keelboats, chase boat and ribs); prepare and submit any required reports on daily, weekly and bi-weekly basis, including payroll detail; maintain cosmetic and physical appearance and functionality of classrooms, office, storage areas and docks. This position reports to the Chief Operations Manager, and is expected to communicate with all other branch managers to share best practices and work closely with headquarters sales and marketing team to ensure branch revenue growth.

We want to talk to you if you have the following: Strong management experience; expert sailing skills and knowledge relevant to the courses we teach and boats we teach on; boat maintenance aptitude; expertise in coaching or teaching sailing, with willingness to attain US Sailing instructor certification at the highest levels if not already in hand; proficiency in Microsoft Office operating systems, CRM and reservations systems. Please fill out our employment application, send it with your work and sailing resume, and a cover letter highlighting why you are the right person for this position to Bryce Jackson, Bryce@OffshoreSailing.com.


We welcome inquiries for teaching positions at our six locations – four in Florida and two in the British Virgin Islands. Instructor candidates must have excellent sailing knowledge and experience, ability to communicate that knowledge to clients, humility, patience and be team players. This rewarding position requires excellent “people” skills, strong teaching experience on keelboats and cruising sail and power yachts. All Offshore Sailing School instructors must be US Sailing certified at the Basic Keelboat level or higher (or at time of hiring have the skills to pass these levels quickly), and hold a USCG license or have the experience to obtain one at the appropriate level. Candidates who wish to work in the United States must be U.S. citizens or carry a valid green card. Those who wish to work in the British Virgin Islands must have a valid work permit for that region. Since it takes several months to apply for and get a work permit, preference is given to those who are already able to work in the islands. Send your sailing resume and cover letter highlighting all aspects of your work experience to Bryce Jackson, Chief Operations Manager, Bryce@OffshoreSailing.com.


We have a full time sales associate position available at our Ft. Myers, Florida headquarters. This position requires sailing experience and a passion for sailing or a strong desire to learn to sail. The right candidate will have a proven track record in sales and a commitment to achieving individual and company sales goals, excellent oral and written communication skills, ability to quickly adapt to company’s reservations software and work with multiple customers at the same time. A college degree is preferred. You will be communicating with highly educated, successful clients. Our products are fun to sell. Leads are hot, emanating from direct response to marketing efforts. Compensation includes base pay and commission. Send resume and cover letter highlighting the three most important reasons why you are the right person for a sales position to Wendy Bishop, Sales Manager, Wendy.Bishop@OffshoreSailing.com.


Our sales department at company headquarters in Ft. Myers, Florida is seeking an assistant to help process contracts, and assist the Sales Manager in all aspects of completing the enrollment and follow-up experience for clients. This position needs someone who is accurate in handling multiple process steps, has excellent computer skills and facility with all Microsoft Office programs, is a team player and likes a busy office environment. Some college preferred. Full-time or part-time hourly position. Send resume and cover letter highlighting why you are the right person for this position to Wendy Bishop, Sales Manager, Wendy.Bishop@OffshoreSailing.com.