Our Quality Promise
Excellence is achieved through relentless effort. Our sailing community is the heart of our business: students, guests, managers, captains, crew, vendors, dock hands, maintenance technicians, and everyone who keeps our ship moving forward.
We never compromise on quality. Our culture of high values and support defines our brand and serves as our compass.
The Employee Promise
Our crew members are our greatest asset as we strive to provide the best guest experiences. We are committed to supporting you in realizing your potential.
By upholding trust, honesty, respect, integrity, and commitment, we nurture talent for the benefit of all. Go Sail Vacations creates a workplace where diversity is valued, quality of life is enhanced, individual aspirations are realized, and memories are made.
Go Sail Vacations is an equal opportunity employer. All applicants are considered based on merit, competence, and qualifications, regardless of race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, or any other protected category under federal, state, or local law.
GSVI is the only school with 3 Outstanding 2024 Instructors!
We invite you to grow with our company and enrich your own sailing journey. Our team features three instructors who rank in the top 1% of all American Sailing Instructors. Visit our Captain’s and Crew page to learn more. Working with us is deeply rewarding; we carefully select team members to support long-term careers and foster a sense of family among our crew.
If you feel called to a life at sea, ready to leave behind the daily grind, you’ll find likeminded sailors here. Join a community where you can share your passion and stand out as a leader.
We offer full-time, part-time, and fractional employment opportunities for experienced candidates. Explore our available positions below—or, if you bring something unique, let us know.
Our crew knows that fitting in is not always the goal, when some of us were made to stand out.
Sales Manager Job Summary
If you are passionate about sailing and the opportunities it brings, consider joining our team as a Sales Manager.
As Sales Manager, you’ll be the primary point of contact at Go Sail Vacations, offering our unique learn-to-sail trips and bareboat charter bookings. You will manage relationships with prospective, current, and returning guests, provide real-time support, arrange travel, upsell VIP packages, and answer questions.
Our Sales Manger sales position offers a potential annual income of $55,000 to $80,000 (Based on Commission).
In This Role You Will
- Offer “learn to sail vacations” tailored to trips and customer interest
- Provide customized private course charters, group courses, and bareboat bookings
- Coordinate travel arrangements and upsell options
- Make 10-20 outbound calls daily to guests who have requested information (no cold calling)
- Answer inbound sales calls and address questions about destinations, amenities, and pricing
- Develop new opportunities to drive sales with company partnerships.
- Maintain comprehensive CRM records and ensure prompt follow-up with every lead
- Embrace feedback, remain coachable, and pursue sales goals with drive and initiative
To Be Successful, You Will Need
- Sailing experience
- 5+ years of sales experience in a high-end travel or sales environment
- A proven record of consistently exceeding sales and revenue targets
- Experience working independently with inbound and outbound interactions
- Excellent communication and relationship-building skills
- Comfort with technology and CRM systems such as Conversions Assist, Drip, Google Workspace, and virtual tools like Google Meet and Zoom
- Flexible scheduling for evenings, weekends, and holidays to serve guests in different time zones
- A dedicated home office with wired high-speed internet (minimum 25 Mbps) and a quiet workspace
Additional Skills
- Commitment to exceptional customer service
- Positive and pleasant interactions with customers and colleagues
- Excellent written and verbal communication skills
- Ability to learn policies and procedures for reservations and assisting callers
- Desire to master all aspects of the product to enhance sales and service
- Maximize sales by offering additional amenities and ancillary products
- Ability to follow the Go Sail Vacations Sales Process
- Ability to learn and use the Fareharbor reservation system
Expected Hours of Work
- Full-time (40 hours per week)
- Shift-based hours, 9 AM to 6 PM Atlantic time, sometimes evenings and weekends based on call hours.
- Available for weekends and public holidays
Captain/ASA Instructor Full Time.
Types of ASA Courses
We are looking to hire a full time committed American Sailing Instructor with expert level experience. This is a serious seasonal commitment from November – July.
If you have strong teaching, sailing and boating experience on 40-50 FT cruising catamarans and sailing yachts, we want to talk to you.
You would teach courses Sunday – Saturday at least 2 consecutive weeks a month, possibly 3. We never ask you to work more than 3 in a row for your sake as well as the students. We want you to have fun and enjoy yourself without getting burned out.
We have experience teaching in this capacity at other sailing schools, we know firsthand how rewarding and hard the job is. We know how a boat that is in disrepair can be the difference between a good week and a bad week for you and the students. We can understand why you might be slightly traumatized if you worked for a school that overworked you, underpaid you, and asked you to teach on poorly maintained yachts. This is NOT how we operate.
We operate this business on a much higher level of quality than the standard. We use 2021 – or newer charter boats from several local charter companies, which means you never have to maintain the vessel. You call for maintenance and they come to fix it. We always spend extra to make sure the vessel is new, has a generator, water maker, and air conditioning.
I would encourage you to look at our reviews on Google. We have nothing but 5 stars because we do not compromise on the yacht, the food, and/or support you need. Which results in happy customers because they received a better-than-expected level of service and happy instructors because all they had to do was teach the course. Your job is to take care of the guests and students. Everybody wins.
We take very good care of you. We pay what you think is fair, you always have a full-size cabin to yourself. The schedule always allows for a Saturday night off and you will not meet the guests until 5 PM on Sunday. Every course every week starts at 5 PM on Sunday and ends Saturday at 10 AM. You order the provisions from a local company, and then the provisions are delivered to the boat. You have discretionary funds to spoil the guests, like buying them dinner or cocktails.
When employed, we will ask you to provide a weekly Captain’s log report, 5, 10 second social media videos, 10 photos, and invoice in addition to teaching the ASA courses. You will also be asked to sign an NDA, non-compete, and employment contract. We require our Captains to work as independent contractors with your own health insurance.
If this is something you’re interested in, we would like to see your resume. You can email us after you have reviewed our website. Then if approved, we would schedule a 1-week training trip for you with a senior instructor at a reduced cabin rate. You will learn our best practices, standard procedures, and booking system functionality. Learning how to be the best sailing instructor you can be and will only improve the smooth sailing of our guests.
Technical Qualifications:
- USCG 50 Ton Master with Near Coastal Merchant Mariner license with Sailing endorsement.
- American Sailing Instructor ASA 201/203/204/214/205/206 certifications.
- STCW II/3 endorsement.
- If you do not meet some of these technical qualifications but are working on it let us know.
Mandatory Professional skills:
- Expert Level Sailing Skills 5 years +
- Excellent people skills.
- Unparalleled dedication to taking care of the crew you are leading.
- Kindness, respect, and patience for all people.
- Experience teaching in the Virgin Islands.
- Knowledge of the Virgin Islands and Caribbean sailing.
- Fundamental boat system knowledge.
- Detail orientated with focus on doing it right.
- Find pure joy in mentoring and inspiring others through sailing connections.
References: Please be prepared to provide three recent employer references.