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; , 10 Colgate 26 keelboats, 2 chase boats); 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.
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.
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. 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.


Offshore Sailing School is looking for a high energy and dynamic Sales Development Representative to provide pre-sales support. The SDR is tasked with identifying and generating sales opportunities through inbound chats and outbound calling activities. The right candidate will be one who works well under pressure, easily initiates related but informative two-way conversations with prospects, and is highly self-motivated. This important role is one of the first touch points for prospects and has the opportunity to set the tone for the sales cycle to follow.


  • Respond to, engage with, and qualify inbound chat requests and inquiries
  • Effectively expand awareness and educate prospects about sailing and boating education packages provided by Offshore Sailing School at six resort locations
  • Place 40-50 outbound calls daily to existing prospects and customers to identify new opportunities, ask for referrals, and develop account intelligence
  • Set follow-up tasks, calls and appointments for a Sales Associate when a lead reaches a qualified stage
  • Ensure successful follow-through of sales cycle by maintaining accurate activity and lead qualification information in CRM application
  • Collaborate with sales and marketing team members on strategic sales approach
  • support the sales team in achieving sales goals and quotas

Qualifications and Required Work Experience:

  • 1-3 years of prior telephone sales and customer service experience, working in an office setting, communicating via phone, chat, email and text
  • Exceptional communication skills, both oral and written, coupled with excellent listening skills and a positive and energetic phone presence
  • Highly self-motivated with a diligent work ethic
  • Experience with CRM applications preferred
  • Demonstrated success in prospecting and mining an existing database of prospects
  • Ability to quickly become a knowledgeable expert on Offshore Sailing School products
  • 2-4 year college degree preferred
  • Sailing and boating experience or the desire to learn the skills to become a competent sailor and boater
  • Computer accuracy and adaptability including use of Office 365, Microsoft products, CRM and reservations systems
  • Ability to quickly become a knowledgeable expert on Offshore Sailing School products
  • Absolute accuracy in quoting packages to clients and entering client information in CRM and reservations systems

Please download and fill out the Offshore Sailing School Application for Employment, scan and send it with an email to our Sales Manager, Wendy Bishop (wendy.bishop@offshoresailing.com). In your email tell us why you feel you are the right fit for this position.


We are interviewing for qualified instructors to work in Florida and the British Virgin Islands. Considered the best sailing jobs in the industry, Offshore Sailing School instructors are known for their excellent sailing knowledge and experience, and the ability to communicate that knowledge to clients with humility and patience. If you have excellent “people” skills, plus teaching experience on keelboats and cruising sail and power yachts we want to talk to you. 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. If you do not currently have one, we will help you with this process. Please download and fill out the Offshore Sailing School Application for Employment, scan and send it with your sailing resume to Bryce Jackson, Chief Operations Manager, Bryce@OffshoreSailing.com.