Youth Program Team Leader

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Courageous Sailing

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Courageous Sailing
Courageous Sailing is a nonprofit community sailing and youth development organization committed to providing people of all ages and backgrounds with opportunities to learn, sail, and enjoy the waterfront. We work at two locations in Boston: the Charlestown Navy Yard on Boston Harbor, and the Historic Jamaica Pond boathouse in Jamaica Plain. Our mission is to transform lives through sailing programs that inspire learning, personal growth and leadership.

In the Courageous Sailing Summer Youth Program, sailing is the platform for youth aged 8-18 to develop leadership skills, gain confidence, explore their local waterways, and delve into hands-on science.

Why Courageous? 

Working at Courageous is an opportunity to join a close-knit and diverse community committed to fostering a positive educational environment for staff and participants on and off the water.

Courageous Staff receive paid training and professional development as well as recreational access to our fleet of boats which range from dinghies to mid-size keelboats and cruising boats. 

By joining our team you will make a meaningful and positive impact on the lives of our participants and will be a critical part of fulfilling our mission to get people of all walks of life out on the water. 

Dates/Time: This is a seasonal full time hourly position for the 7-week summer youth program season. Hours are 7:45 AM to 3:45 PM Monday through Friday from late June through mid-August. One week of All Staff Training in late June is mandatory and paid for this position. 

Job Description: Courageous Sailing is looking for Team Leaders to lead groups of campers at our summer youth program reporting to the Swim Sail Science Coordinator.

  • Co-lead a group of 15-18 students (ages 8-11) through the day. With another team leader, supervise students through classroom lessons, swimming lessons, and sailing lessons (all taught by subject-specific instructors, with team leaders there to support) and chaperone student travel throughout the Courageous site. 
  • Lead games, STEM activities, and social-emotional learning during student free time. 
  • Serve as a liaison with and between teachers, sailing instructors,  and other camp staff. Communicate student needs, strengths and weaknesses, behavioral incidents, and relaying any other  necessary information throughout the day. 
  • Teach and/or encourage students’ learning, in particular academic support for Swim Sail Science students
  • Build rapport with other staff working with your students. Work with other Team Leaders to facilitate a positive group experience and create a sense of community within the student group. 
  • Assist with classroom management and individual student engagement during lessons taught by other staff or partner organizations


  • Attend all days of mandatory training and/or complete online training. 
  • Be proactive and communicative. Provide clear, effective and timely communication with supervisors and staff. Ask questions if the scope or intention of work is unclear, express concerns when they come up, give feedback regularly to peers and supervisors, and help facilitate positive change.

Safety and Risk Management:

  • Create a safe place for youth to learn and make mistakes by clearly establishing limits and boundaries for participant behavior and independence. 
  • Comply with Courageous safety standards and policies on and off the water and teach participants how to do the same. 
  • Model safe, respectful, and responsible behavior to youth and peers at all times. 
  • Exercise sound judgment and decision-making. Treat safety as the highest priority. 
  • Leave Courageous better than you found it. Treat Courageous property with respect. Maintain the cleanliness and functionality of workspace and tools.

Diversity, Equity, and Inclusion:

  • Cultivate a kind and inclusive community where everyone at Courageous can feel like they belong.

At Courageous Sailing, our highest priority is finding the best candidate for the job. Research has shown that people of color and women are less likely to apply for jobs if they don’t believe they meet every one of the qualifications described in a job description. We encourage you to apply, even if you don’t believe you meet every one of our described qualifications or you have a less traditional background. We are looking for applicants with the following qualifications:

  • Enthusiastic about working with young people and able to work effectively with a wide variety of age groups and populations from diverse backgrounds, role modeling inclusive behavior and building positive group culture.
  • Passionate about experiential education for youth from all backgrounds
  • Able to communicate clearly, directly, and calmly at all times
  • Comfortable giving and receiving feedback to and from peers, participants, and supervisors
  • Comfortable working outdoors, regardless of weather
  • 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
  • Three professional or academic references


  • Prior experience working with children


The pay range for this position is $16 – $22 depending on experience and relevant certifications. 

2024 Mandatory Dates 

  • All Staff Training: June 24th- 28th
  • Regular Season: Monday-Friday 8AM – 4PM, from Monday, July 1st – Friday, August 9th
  • End of Season Staff Day: Monday, August 12th
  • Additional work is available before and after these dates from mid-April through mid-September. Staff may work other jobs at Courageous within different departments (ex. Adult Programs, Maintenance) during non-youth program time.

To apply, go to Direct questions to Learn more about Courageous Sailing’s Summer Youth Programs at

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