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.


Do you have a serious passion for creating, crafting, and editing video? Is story-telling your gift to the world? Are you looking for a full-time position that allows you the opportunity to create multiple videos every month while pushing your creative limits? Do you own your own video production equipment and suite of editing software? Are you familiar and experienced with social media creative formats? If so, the Offshore Sailing School might be a great choice for you.

As the in-house videographer, your job will entail producing video content for America’s #1 Sailing School that aligns with the brand, mission, and goals of our company. As the visual storyteller for our company, you’ll be responsible for story-boarding, shooting footage and editing, managing creative assets, and maintaining all video equipment.  You will accomplish the bulk of the technical tasks related to production and post-production. These duties may include the transport, setup, and operation of equipment; and assisting with staging, set preparation, and dressing. Most all video shoots will take place outdoors with natural light and ambient sound. You will work closely with the Director of Marketing to execute projects from concept through completion. Please read on and if you feel you fit the responsibilities and qualifications listed below, contact Beth Oliver, Director of Marketing – BOliver@OffshoreSailing.com, 239-985-7516.

Specific responsibilities include:

  • Supporting the marketing, sales and operations teams throughout the production process, which may include identifying interview subjects and locations, creating graphics, and presenting concepts and rough and final-cuts to management
  • Helping to sustain and guide video creative process
  • Assisting in maintaining the video hosting platform and understanding best practices
  • Developing short scripts, interview questions and storyboards
  • Staying up-to-date with all-new technological advances
  • Determining what camera equipment is necessary and obtain additional equipment with approval
  • Transporting, setting up, and operating various production equipment including cameras, audio and video recorders, lighting equipment, props, and microphones for location and office production
  • Operating and maintaining proper levels and calibration of cameras, audio and video recorders, and other production equipment
  • Collecting b-roll footage, as well as interviewing appropriate staff, clients, and resort partners
  • Uploading videos to website and assisting in the social-sharing of the video content (edit, upload, monitor and address any issues that arise, with management), as well as employee email video signatures
  • Most frequently, you will be responsible for single-camera shoots

Technical qualifications:

  • Proficient with Video Editing Software (Adobe Premiere or Final Cut Pro)
  • Experience with Adobe After Effects or Motion are preferred
  • Experience with Adobe Photoshop and Adobe Illustrator are a plus
  • Proficient at story-boarding, scripting, and conception
  • Understand basic and advanced composition techniques
  • Understand the fundamentals of branding
  • Very detail-oriented and able to identify and correct quality issues in audio and video

Personal and professional qualities:

  • Quick-thinking and a demonstrated proficiency in shooting video
  • Ability to provide examples of videos produced for websites and social media channels
  • Proven experience in working with a team, with a mindset and goal to develop the best video content
  • Ability to learn new skills and determine on-going learning opportunities for film techniques
  • An open mind about video production with the ability to make the company’s video strategy a reality
  • Owns the production process and does whatever it takes to make great content
  • Self-starting and treats the brand as your own
  • Deals well with criticism and able to collect and respond to feedback easily
  • Great communication skills and ability to make people comfortable in an interview
  • Energetic and able to excite people to be on camera
  • Looks at the content from the eye of the viewer to create the best experience
  • Lifelong learner and able to identify new learning opportunities
  • Professional and confident demeanor
  • Reliable transportation
  • Ability to easily get to HQ office in South Fort Myers, and locations in St. Pete, Cape Coral, Captiva Island and Ft. Myers Beach on a regular basis
  • Holds valid US Passport or will get one that doesn’t expire until 2020 or later – needed for occasional travel to/from the British Virgin Islands
  • Holds US citizenship or has valid US work permit
  • Fluent in English language

Bonus points if:

  • You have knowledge and experience with boats, sailing and boating, marinas
  • You have knowledge and experience with world-class resorts and amenities
  • Familiarity with motivational and aspirational messaging and communication
  • You have contagious enthusiasm that makes others around you light up when you enter the room
  • You are obsessed with improving your personal and professional skills, learning every day, and embracing new technology as it develops
  • You love feedback and are a major team player
  • You have an entrepreneurial spirit, and therefore, treat the position as if it was your own company
  • You’re awesome. And because you’re awesome, we absolutely want you to be part of our Offshore Sailing School family!


We welcome inquiries for teaching positions at our six locations – four in Florida and two in the British Virgin Islands. Instructor candidates for our US and Caribbean siling jobs 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 are always on the look out for full time sales associates, to work in 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.