Adult Program Cruising Instructor

Job Posted 1/31/2024
Courageous Sailing, Inc.
One First Avenue
Boston, MA 02129
United States
Experience Required
Housing Provided
Job Start Date
Job End Date
$25.00 to $30.00 Per Hour
Job Description
Courageous Sailing

Courageous Sailing is a nonprofit community sailing and youth development organization committed to providing people of all ages and backgrounds with opportunities to learn, sail, and enjoy the waterfront. We work at two locations in Boston: the Charlestown Navy Yard on Boston Harbor, and the Historic Jamaica Pond boathouse in Jamaica Plain. Our mission is to transform lives through sailing programs that inspire learning, personal growth, and leadership.

Why Courageous? 

Working at Courageous is an opportunity to join a close-knit and diverse community committed to fostering a positive educational environment for staff and participants on and off the water.

Courageous Staff receive paid training and professional development as well as recreational access to our fleet of boats which range from dinghies to mid-size keelboats and cruising boats. 

By joining our team you will make a meaningful and positive impact on the lives of our participants and will be a critical part of fulfilling our mission to get people from all walks of life out on the water. 

Dates/Time: This is a part-time seasonal position, with shifts available Mon-Sun, May 1st-Oct 31st. Courageous hosts most cruising courses on weekends throughout the season, full season availability is not mandatory but appreciated. 

Position Overview

Courageous Sailing is looking for Cruising Instructors to join our staff and participate in coaching within the Adult Program during the summer of 2024. The position can also include instruction within our Summer Youth Program based on schedule and availability preferences.


Participate in and contribute to a safe, engaging, and respectful work environment by:

  • General:
    • Teach US Sailing or ASA Basic Cruising and Bareboat according to the curriculum as laid out by US Sailing and Courageous Sailing
    • Teach in-house Cruising courses such as “First Mate” and “Boston Harbor Navigation”
    • Conduct check-out sails for new cruising members
    • Teach private lessons
    • Lead small groups during corporate events
    • Act as a liaison between membership and maintenance to ensure proper care of the cruising fleet.
    • Assist members in planning overnight sails; conduct reviews of submitted overnight sail plans prior to member departure
    • Be proactive
    • Provide clear, effective, and timely communication with leadership staff
    • Leave Courageous better than you found it
  • Safety (minimizing risks while maintaining an approachable and engaging environment for students, members, patrons, and fellow staff members):
    • Responsibly manage risk so that students, members, and patrons feel comfortable stepping outside of their comfort zones, asking questions, and engaging with the facility on various levels. 
    • Complying with and encouraging students and members to learn Courageous’ set of sailing safety standards and reiterate their importance whenever possible. 
    • Attend all days of staff training and staff meetings and/or complete online training.*
    • Exercise sound judgment and decision-making. Assess and mitigate foreseeable hazards.
    • Remain up to date on what roles and responsibilities you may take on in the event of an emergency and review the EAP with direct supervisor.
  • Respectability (support and ensure that everyone can be successful):
    • Maintain the Courageous fleet and facilities by completing everyday tasks as discussed in training and documented in daily checklists
    • Reduce and help manage the disposal of waste in and around Boston Harbor
    • Cultivate a kind and inclusive community
  • Engagement (maintaining the expectation of individual responsibility for students and members):
    • Build rapport with students, members, and patrons
    • Provide active and engaged feedback to daily questions and interactions
    • Lead, facilitate, and participate in on-land responsibilities for general upkeep of the boathouse during downtime. 

*Job training days are position dependent and vary from position to position. 

Job Requirements
Qualifications USCG Captain’s license 2-3 years of coaching/instructor experience US Sailing Keelboat Instructor or equivalent ASA certification; (for Adult Program) US Sailing Basic Cruising Instructor or Bareboat Cruising Instructor certification preferable - All qualified applicants are encouraged to apply regardless of US Sailing certifications Extensive J80 or comparable sport boat sailing and racing experience is preferable Racing experience and knowledge of the Racing Rules of Sailing Completion of NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level I certification course Hold, or be willing to obtain before start date, current First Aid/CPR certification Positive and enthusiastic attitude Outstanding communication, team management, and positive behavior management skills Excellent references Excellent customer-facing skills and attitude A passion for sailing, the ocean, and teaching Willingness to work weekday evenings and weekends within a consistent schedule. Ability to relay needs, issues, and solutions between members, staff, and administration At least 2-3 years of customer service experience is a plus Can work and communicate effectively with a wide variety of age groups and populations from diverse backgrounds Able to communicate clearly and directly Comfortable giving and receiving feedback Able to build rapport easily with students, members, patrons, and coworkers Comfortable working outdoors, regardless of weather Able to practice proper self-care and energy management while on the water or behind a desk for extended periods of time Able to maintain composure, exercise sound judgment and decision-making, and assess and mitigate risk under extended periods of stress Positive and enthusiastic attitude Willing to authorize a federal background check
Jobs Courageous Sailing
One First Avenue
Boston MA 02129
United States
Courageous Sailing, Inc. Jobs Courageous Sailing
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