Charter Experience Specialist

Waypoints Yacht Charters is looking for an energetic, customer-focused Charter Experience Specialist to join our Sales and Customer Service team in Annapolis. This isn't your typical sales job. One day you'll be helping a family plan the sailing vacation of a lifetime in the Caribbean, and the next you'll be welcoming excited guests as they begin their adventure on the Chesapeake Bay.

As the first point of contact for many of our guests, you'll play a key role in creating exceptional charter experiences from the first inquiry through their return to the dock. If you enjoy building relationships, exceeding expectations, and working in a fast-paced environment where no two days are the same, we'd love to meet you.

What You'll Be Doing

• Helping guests plan unforgettable sailing vacations for all bases (Annapolis, USVI, BVI, Bahamas, Belize, San Diego)
• Creating personalized charter quotes and assisting with itinerary planning
• Guiding prospective guests through the booking process
• Building strong relationships with clients before, during, and after their charter
• Providing exceptional support via phone, email, and in person
• Conducting guest check-ins and check-outs on a rotating weekend schedule
• Working closely with our charter operations team to ensure smooth sailing for every guest
• Solving problems with a positive attitude and a customer-first mindset
• Contributing to sales goals and helping grow the Waypoints client base

What We're Looking For

• Sales driven and a closer! Hungry for the money!
• A natural people person who loves helping others
• Someone who is motivated by performance-based earnings and achieving ambitious goals
• Ability to juggle multiple priorities while maintaining a positive attitude
• Hospitality, tourism, travel, sales, or customer service experience preferred
• Experience with Microsoft Office and CRM software
• Knowledge of sailing, boating, or the marine industry is a plus
• Previous experience as a sailing instructor, captain, charter broker, or marine professional is highly desirable
• A self-starter who takes initiative and enjoys being part of a collaborative team

Compensation & Benefits

• Base salary of $45,000 plus an uncapped commission structure, putting you in control of what you earn. Simply put: the more charters you book, the more money you make. Our sales team regularly generates $700,000–$800,000 in monthly charter revenue, and we have a strong pipeline of qualified leads ready to be converted into bookings. With high-value charter vacations and repeat clientele, there is real earning potential for someone motivated, relationship-focused, and who enjoys closing sales.
• Health insurance benefits following successful completion of the 90-day introductory period
• 401(k) program
• Paid Time Off
• Travel opportunities and sailing perks!!
• Career growth opportunities within a rapidly growing company

Schedule

• Full-time, on-site position in Annapolis
• Office hours: 8:30 AM – 5:00 PM
• 40-hour work week
• Weekend schedule to support charter operations and guest check-ins
• Flexibility with alternative days off during weeks that include weekend coverage

Why Waypoints?

At Waypoints, we're more than a charter company...We are a team that enjoys coming to work each day and loves creating lifelong memories for our guests. We love what we do! From first-time sailors to seasoned captains, our guests trust us to help them experience the freedom and adventure that only life on the water can provide.

If you're excited by travel, boating, hospitality, and helping people create incredible experiences, come join our crew.