Youth Program Site Director and Assistant Site Director

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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. 

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 staff 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:
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 
    • 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
    • Ensure all boats are tied down and equipment is stowed properly at close of each program session
    • Assign chores and ensure they have been completed and the facility is clean and ready for other programs 
    • Monitor weather and make calls regarding inclement weather in cooperation with the Youth Program Director 
    • 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
  • Safe (minimizing risks while maintaining a fun atmosphere for students to stretch their limits which leads to real learning.):
    • Responsibly manage risk so that students are able to safely step outside their comfort zones
    • Create 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  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 staff and oversee programming in a way that reduces risk
    • Lead staff meetings 
    • Communicate via radio with all head instructors to coordinate the departure and return of each class at the beginning of the day, lunchtime, the end of the day, and during any emergency management procedure (e.g. bringing boats back to Courageous before incoming weather event) 
    • Communicate via radio with passing ships, ferries, barges and others for whom the youth sailing program may pose a navigational obstruction or hazard 
    • Communicate with parents regarding student programmatic needs, including camping trips and trips to Spectacle Island 
    • Communicate with parents regarding student attendance 
    • Approve head instructors’ daily float and lesson plans, and, as needed, discuss ways to execute their plans more effectively or safely 
    • Communicate with head instructors during off-site trips including Spectacle Island and camping trips 
    • 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
  • 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
    • Model best practices for more junior staff members
    • Provide active and engaged supervision to students and staff both on-land and on-the-water
    • 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


    • 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
    • Able to maintain composure, exercise sound judgment and decision-making, and assess and mitigate risk under extended periods of stress
    • 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
    • Comfortable working outdoors, regardless of weather
    • Able to practice proper self-care and energy management while on the water
    • 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 27th- July 1st
  • Monday-Friday 8AM – 4PM, from Monday, July 5th – Friday, August 12
  • Staff Retrain Day: Monday, July 25 for C-Town; Monday July 18 for JP
  • End of Season Staff Day: Monday, August 15th
  • Additional work is available Tuesday, August 16 – Friday, August 19

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