Land Based Site Director

In by Abbie Doane-Simon

Courageous Sailing Inc.

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. 

Summer Youth Program Description: 

Courageous Sailing operates an extensive summer program for youth ages 8-18 at multiple sites throughout the Boston area. At our main site on Pier 4 in Charlestown Navy Yard, we have a six-step program that takes students from beginner classes through Instructors-in-Training (IITs) as well as a program that provides free sailing, swimming and science programming to Boston Public School students. We are also looking for instructors at our Jamaica Pond site which offers beginner and intermediate level sailing opportunities. Our instructors are skilled sailors who act as role models to their students and function well as a team. We teach on a variety of boats including Rhodes 19s, RS Quests, RS Ventures, J80s, 420s, and Lasers. Please find the descriptions of each step below (more detailed descriptions on our website), for all which we are hiring head sailing instructors and sailing instructors.

  • Swim Sail Science is a five-week summer program for Boston children that blends academic support with sailing lessons, swimming instruction, and hands-on marine and physical science. Instructors sail in each boat. 
  • Step 1 is a one-week basic sailing course offered to children ages 8 and up. Students are introduced to sailing theory and gain sailing experience in Boston Harbor. Instructors sail in each boat. 
  • Step 2 is a three-week intensive beginner sailing course that takes place over three weeks and provides an in-depth introduction to sailing, theory, and boat handling. Instructors sail in each boat.
  • Step 3 is a three-week intermediate sailing course for children age 10 and up. Students learn to sail more independently in Rhodes 19s without instructors consistently in the boat. Instructor supervision is provided from a motorboat.
  • Step 4 is a three-week introduction to dinghy course. Students experience sailing capsizable boats, RS Quests, for the first time. Instructor supervision is provided from a motorboat.
  • Step 5 is a three-week advanced dinghy course. Students learn the basics of racing in 420s and Lasers. Instructor supervision is provided from a motorboat.

Staff Responsibilities:

The Land Site Director is responsible for coordinating on-land activities across the Summer Youth program, supporting on-water staff in program implementation, and communicating with parents and stakeholders. 

Create a safe, engaging, and respectful learning environment that focuses on social-emotional growth in these ways:

  • General:
    • Be proactive
    • Understand the intention of management when giving instructions and utilize debriefs and check-ins to express concerns, give feedback, and help facilitate change
    • Provide clear, effective and timely communication with staff
    • Leave Courageous better than you found it 
    • Open and close the site each day (7:45AM – 4PM) 
    • Manage the division of site resources between head instructors and their respective classes, including communicating with the Fleet Manager about any maintenance concerns
    • Assign chores and ensure they have been completed and the facility is clean and ready for other programs 
    • Coordinate and help lead activities for days in which students cannot be on the water 
    • Track student attendance 
    • Provide support to other coordinators in terms of communicating supply needs, and delivery of supplies
      • Manage organization of physical front desk space, as well as associated digital/informational spaces
      • Maintain attentiveness on multiple platforms, especially during times of incoming weather or emergency
      • Maintain the resources and tools of Courageous in coordination with other staff
  • Safe (minimizing risks while maintaining a fun atmosphere for students to stretch their limits which leads to real learning.):
    • Create a safe place to make mistakes by clearly establishing limits and boundaries for student behavior and independence
    • Attend all days of staff and senior staff training and staff meetings and/or complete online training
    • Exercise sound judgment and decision-making. Assess and mitigate foreseeable hazards
    • Communicate with parents regarding student programmatic needs. 
    • Communicate with parents regarding student attendance 
    • Maintain an injury log and ensure all incident reports are completed and delivered to the Youth Program Director in a timely fashion
    • Respond to minor first-aid and behavior incidents among students and staff
    • Assist with the development and implementation of staff training
      • Remain up to date on what roles and responsibilities you may take on in the event of an emergency and review the EAP with a 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 chore checklists
    • Reduce and help manage the disposal of waste in and around Boston Harbor
    • Cultivate a kind and inclusive community
    • Give clear and direct feedback to staff that leads to staff growth
  • Engaging (give lots of responsibility, hands-on and experiential pedagogy with real-world consequences for behavior/choices):
    • Build rapport with students and staff
    • Model best practices for staff members
    • Lead, facilitate, and participate in on-land activities during down time and/or when sailing is not feasible


  • Can work effectively with a wide variety of age groups and populations from diverse backgrounds, role modeling inclusive behavior and building positive group culture
  • Able to communicate clearly and directly
  • Comfortable giving and receiving feedback
  • Able to build rapport easily with students and coworkers
  • Passionate about and dedicated to experiential education for youth from all backgrounds
  • Sufficiently physically fit to participate in all site and course activities while maintaining ample energy, strength, and focus to aid students
  • Comfortable working outdoors, regardless of weather
  • Able to practice proper self-care and energy management while on the water
  • 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


  • $22-$26 per hour depending on experience 

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