In by

Courageous Sailing

Apply for this job

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. 

Through this 7-week summer job-training program, students make the transition from student to instructor, developing their abilities to teach, lead, and inspire the next generation of Courageous kids. Under the guidance of our senior instructor team, participants first attend a one-week, pre-season training session and then participate in six weeks of intensive professional training, covering everything from teaching theory and classroom management, to long-distance cruising and camping, safe powerboat operation, and racing.

Instructors-in-Training (IIT) are the highest level of our Steps To Lead program, giving them the most autonomy as students as well as the most responsibility in regards to our Code of Conduct. The IITs are also the youngest members of our Young Leaders program  (staff) and are expected to adhere to staff guidelines. Below please find our staff responsibilities and student code of conduct. 

Staff Responsibilities:
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 leadership staff
    • Leave Courageous better than you found it
  • Safe (minimizing risks while maintaining a fun atmosphere for youth to stretch their limits which leads to real learning.):
    • Assist with responsibly managing so that students are able to safely step outside their comfort zones
    • Assist with creating a safe place to make mistakes by clearly establishing limits and boundaries for student behavior and independence
    • Comply with, teaching, and/or encouraging of students’ learning of Courageous’ set of sailing safety standards  
    • Act as a role model for our Step 4 and 5 students by modeling appropriate student behavior.
    • 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.
  • 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
  • Engaging (give lots of responsibility, hands-on and experiential pedagogy with real-world consequences for behavior/choices):
    • Build rapport with students
    • Provide active and engaging supervision to students
    • Teach and encourage students’ learning of sailing concepts using curriculum provided
    • Lead, facilitate, and participate in on-land activities during down time and/or when sailing is not feasible

Student Expectations:

Values & Expectations

We value all Courageous students, staff, and community members, and expect them to treat each other with kindness, respect, tolerance, and compassion. We value our differences and find strength in our diversity of backgrounds, experiences, and points of view.

Code of Conduct

 All youth program students and staff must behave in accordance with the values and expectations articulated above. Students and staff must work cooperatively together to ensure that all Courageous activities (on water and land) are conducted in a manner that maximizes respect, safety, and fun for everyone involved.

Discipline and Guidance

 We believe that discipline and guidance should be consistent and based, as much as possible, upon an understanding of each individual. We also recognize that to maintain a safe and supportive environment for our whole community, certain guidelines and parameters must be clearly articulated and understood.

Courageous program managers reserve the right to dismiss or suspend any student or staff when their behavior interferes with the rights and safety of themselves or others. These behaviors may include but are not limited to the following: 

  • Weapons of any kind
  • Threatening another student or staff or behaving in a threatening manner
  • Endangering or purposefully hurting another student or staff
  • Bullying
  • Hazing
  • Harassment
  • Inflammatory language
  • Sexual misconduct
  • Leaving the group without permission
  • Stealing
  • Purposefully destroying property
  • Engaging in inappropriate or illegal behavior

Each incident is reviewed on a case-by-case basis and consequences are issued at the discretion of Courageous program managers.

Consequences for behavior that is inconsistent with the Courageous code of conduct, but not at the level of warranting suspension or separation from the program may include time-outs, reduction in privileges, discussions with senior staff, and phone calls with parents, as appropriate. 

The following consequences are strictly prohibited: corporal punishment, cruel punishment, humiliation or verbal abuse; the denial of food, sleep, restroom privileges or shelter; and any punishment for soiling, wetting, or toilet use.


  • Must be 15 years old by July 1
  • Must be able to swim 25 yards (one lap), any stroke, and tread water for 90 seconds without assistance
  • At least one summer of experience sailing in a program like Courageous Sailing, Community Boating, or Piers Park and/or equivalent experience elsewhere and/or (ideally) intermediate sailing competency
  • Complete an application form, which includes a short essay on why you would like to be an IIT
  • Complete an in-person job interview with the Director of Youth Programs and Outreach
  • Harbor a love of water, sailing, the outdoors, working with kids, and teaching
  • Desire to keep learning and furthering skills in sailing, teaching and mentoring
  • 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 students
  • Able to meet different learning-style needs by varying teaching techniques
  • Sufficiently physically fit to participate in all site and course activities while maintaining ample energy, strength, and focus to aid students
  • Comfortable working outdoors
  • Able to practice proper self-care and energy management for extended periods of time
  • Able to maintain composure, exercise sound judgment and decision-making, and assess and mitigate risk
  • Possess an open-mind and a positive and enthusiastic attitude
  • Willing to authorize a federal background check
  • Hold, or are willing to obtain before start date, current First Aid and CPR certification

2022 Mandatory Dates:

  • All Staff Training: June 27th- July 1st
  • Monday-Friday 8AM – 4PM, from Monday, July 5th – Friday, August 12
  • Staff Retrain Day: Monday, July 25 
  • End of Season Staff Day: Monday, August 15th
  • Additional work is available Tuesday, August 16 – Friday, August 19

To apply for this job please visit