Instructor-in-Training Trainer

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Courageous Sailing

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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. 

At Courageous Sailing, we run an intensive Instructor-in-Training (IIT) program for a diverse group of Boston teens ages 15-18.  We have up to 25 Instructors-in-Training, each with varying levels of skill in sailing, teaching, and professionalism. The primary goal of the IIT program is to prepare them to become full instructors, capable of passing the US Sailing Level 1 examinations, within one to three summers of training.  The Instructor Trainers play a critical role in facilitating this transformation. Instructor Trainers are also responsible for leading team building and creating a welcoming, supportive, and positive learning environment for all of our IITs.

Our Instructor-in-Training (IITs), 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. Our Instructor Trainers are charged with helping them navigate the shift from student to staff. 

Staff Responsibilities:
Create a safe, engaging, and respectful learning environment that focuses on social-emotional growth by:

  • General:
    • Be proactive
    • Understand the intention of management when giving instruction 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.):
    • Responsibly manage risk so that IITs feel comfortable stepping outside of their comfort zones
    • Create a safe place to make mistakes by clearly establishing limits and boundaries for IIT behavior and independence
    • Complying with, teaching, and encouraging of IITs’ learning of Courageous’ set of sailing safety standards  
    • Attend all days of staff and senior staff training and staff meetings and/or complete online training
    • Exercise sound judgement and decision-making. Assess and mitigate foreseeable hazards.
    • Supervise IITs and oversee programming in a way that reduces risk
  • 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 IIT that leads to growth as instructors
  • Engaging (give lots of responsibility, hands-on and experiential pedagogy with real-world consequences for behavior/choices):
    • Build rapport with IITs
    • Model best practices for the IITs
    • Provide active and engaged supervision to IITs both on-land and on-the-water
    • Teach and encourage IITs’ 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


  • US Sailing Level 1 Instructor Certification, equivalent or more advanced
  • At least 2-3 years sailing instruction experience, 1-2 years powerboat experience for Head Instructors
  • Completion of NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level I certification course
  • 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
  • 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, 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

2022 Mandatory Dates:

  • Senior Staff Training: June 21-24
  • All Staff Training: June 27- July 1
  • Monday-Friday 8AM – 4PM, from Monday, July 5 – Friday, August 12
  • Staff Retrain Day: Monday, July 25 for C-Town
  • End of Season Staff Day: Monday, August 15
  • Additional work is available Tuesday, August 16 – Friday, August 19

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