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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 Boston Harbor, 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 part time summer position, 8:30 am to 3:30 pm, Monday through Friday.

Job Description:

Through this two-year 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.

Our Instructors-in-Training (IITs) are graduates of our summer program or other sailing programs who are interested in furthering their sailing education by learning the skills required to become instructors. During the first year of this program, IITs focus on honing their sailing skills on a variety of boats and learning fundamentals of teaching. In the second year of the program, IITs practice teaching by shadowing and assisting in all of the programs at Courageous. They are the youngest members of our staff and are expected to adhere to staff guidelines.



  • 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


  • 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 participants to learn and make mistakes by clearly establishing limits and boundaries for 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 participants 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:


  • Must be 15 years old by July 1
  • 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
  • Completed application form, including a short essay on why you would like to be an IIT
  • Complete an interview with the Director of Youth Programs and Outreach
  • Desire to keep learning and furthering skills in sailing, teaching and mentoring
  • Willing to work with a wide variety of age groups and populations from diverse backgrounds, role model inclusive behavior and build positive group culture
  • Passionate about sailing, the ocean, and 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, young sailors, and supervisors
  • Able to build rapport easily with students and coworkers
  • 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


  • Intermediate sailing competency or higher. 
  • Experience working with youth, particularly youth of diverse backgrounds


The pay rate for this position is $15/hour. 

2024 Mandatory Dates:

  • All Staff Training: June 24th- 28th
  • Regular Season : Monday-Friday, 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.

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