Adult Program Cruising Instructor

In by Hugh Freund

Courageous Sailing

Reports To: Adult Program Director
Status: Part-time
Date of Last Revision: January 2020
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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. 

Courageous Sailing is looking for a Cruising Instructor to join our staff and participate in coaching within Adult program during the summer of 2020. Position can also include participation in our Summer Youth Program based on schedule and availability preferences.

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

  • General:
    • Teach US Sailing Basic Cruising and Bareboat according to the curriculum as laid out by US Sailing and Courageous Sailing
    • 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
    • Be proactive
    • Provide clear, effective and timely communication with leadership staff
    • Leave Courageous better than you found it
  • Safe (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 judgement 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. 
  • Respectful (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
  • Engaging (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 down time. 

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


  • USCG Captain’s license
  • Extensive J80 or comparable sportboat sailing and racing experience preferable
  • 2-3 years coaching/instructor experience
  • US Sailing Keelboat Instructor or equivalent certification; (for Adult Program) US Sailing Basic Cruising Instructor or Bareboat Cruising Instructor certification 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
  • 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 customer service a plus
  • Can work effectively and effectively communicate 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
  • Excellent references
  • Willing to authorize a federal background check
  • Hold, or are willing to obtain before start date, current First Aid and CPR certification

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