Offshore Program Coordinator

In by Alexe Taylor

Website Courageous Sailing

Courageous Sailing Overview:

Courageous Sailing was established in 1987 as a 501(c)(3) by South Boston sailing enthusiast, Harry McDonough. It was Harry’s dream to use the sport of sailing to build character and camaraderie among Boston children from all economic and ethnic backgrounds. In Harry’s words, “Every child’s perspective is improved 50-yards off-shore.” For 25 years, we have continued to grow and deliver our mission to transform children’s lives through sailing programs that inspire learning, personal growth and leadership. 

Position Overview

Courageous Sailing is looking for a Offshore Program Coordinator to design and implement our Big Boat programming, which will include training staff, instructing, and coaching during the summer of 2022.

Offshore Program Overview 

In partnership with the College Offshore Sailing Circuit, Courageous will be taking on the management and use of two Beneteau Figaro 2s for use within our Adult and Youth Programs. This will be our pilot year and the curriculum is in development, but we envision this program growing to encompass long distance trip planning, big boat performance sailing and racing, and fundamental offshore seamanship and safety. 

Staff Responsibilities:
Participate in and contribute to a safe, engaging, and respectful work environment. 

  • General:
    • Create curriculum and lead training in big boat sailing, safety, and care. 
    • Conduct check-out sails for new staff. 
    • Teach youth and adult lessons on big boat sailing and systems, lead small groups during corporate events. 
    • Work with maintenance to ensure proper care of the boats. Assist with maintenance projects. 
    • Be proactive. Independently manage programming resources, scheduling, staffing, and curriculum. 
    • Communicate early and effectively with staff and management to realize the needs of the program. 
    • Leave Courageous better than you found it
  • Safety (minimize risks while maintaining an approachable and engaging environment for students, members, and fellow staff members):
    • Responsibly manage risk. 
    • Comply with safety standards. Communicate those standards and their importance to members, students, staff. 
    • Complete Courageous Staff training (training is mandatory and paid). 
    • 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. Review the Emergency Action Plan with a direct supervisor. 
  • Respect (support our community 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. Build rapport with students, members and patrons. 
  • Engagement (maintaining the expectation of individual responsibility for students and members):
    • 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 down time. 

Schedule and Availability Candidates must be available to work between 2-4 weekdays during our Summer Youth Program (June 28- August 15th) as well as some additional nights and weekends.  We anticipate this position working 10-15 hours/ week in the spring and fall and 25-30 hours per week during the summer, however we would be willing to discuss a more flexible schedule for candidates with the appropriate background and experience. 


  • USCG Captain’s license – OUPV minimum 
  • 2-3 years instructor experience 
  • Experience about cruising sailboats and familiarity with marine systems
  • Hold, or are willing to obtain before start date, current First Aid and CPR certification
  • Willing to authorize a federal background check
  • Positive and enthusiastic attitude. Excellent communication, team management, customer service, and behavior management skills. 
  • Able to communicate clearly and directly with a wide variety of age groups and populations from diverse backgrounds. 
  • Comfortable giving and receiving feedback.
  • Ability to relay needs, issues, and solutions between members, staff, and administration
  • Able to build rapport easily with students, members, patrons and coworkers
  • Excellent references 
  • A passion for sailing, the ocean, and teaching
  • Willingness to work weekday evenings and weekends within a consistent schedule. 
  • 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

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