Youth Program Site Director

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Website 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. Senior Staff training and All Staff Training in late June are mandatory and paid for this position. 

Job Description: Courageous Sailing is looking for an On-Water Site Director to lead each of our sites at Charlestown and Jamaica pond. Site Directors oversee summer programming and manage teams of Head Instructors, Assistant Head Instructors, and Sailing Instructors in teaching safely on the water. The Site Director is responsible for overseeing  boat and resource allocation across different youth programs, risk management and safety decision-making and communications (especially around on-water commercial traffic and weather), organizing site setup and cleanup,  and providing hands-on assistance as needed to different programs throughout the day.  The Site Director reports to the Youth Program Director and manages other sailing staff.



  • Open and close the site each day (7:45AM – 3:45PM)
  • Monitor weather and make decisions regarding inclement weather in cooperation with the Youth Program Director 
  • 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 sailing staff to ensure that each program is navigating the harbor appropriately and assist with towing boats out of the way of traffic as needed.  
  • Assist Head Instructors with planning, management, and communication during off-site trips including Spectacle Island and camping trips 
  • Communicate with parents regarding student attendance and programmatic needs, including camping trips and trips to Spectacle Island 
  • Coordinate and help lead activities on days in which students cannot be on the water 
  • Provide support to other staff by receiving and communicating supply needs, ordering and delivering of supplies. 
  • Approve head instructors’ daily float and lesson plans, and, as needed, discuss ways to execute their plans more effectively or safely 
  • 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
  • Ensure all boats are tied down and equipment is stowed properly at close of each program session

Management and Supervision:

  • Supervise staff and oversee programming in a way that reduces risk
  • Lead weekly staff meetings and daily check-ins with Head Instructors 
  • Manage the division of site resources between head instructors and their respective classes, including communicating with the Maintenance Department about any maintenance concerns
  • Assign chores, ensure they have been completed and that the facility is clean and ready for other programs
  • Schedule and hold regular meetings with supervisees to check in on work projects and give feedback. 
  • At least once per session, hold meetings with each program team to give and receive job performance feedback


  • 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 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 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:

  • US Sailing Level 1 Instructor Certification, equivalent or more advanced
  • At least 2-3 years sailing instruction experience, 1-2 years powerboat experience
  • 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, directly, and calmly at all times. 
  • Comfortable giving and receiving feedback to and from peers, participants, and supervisors
  • Able to build rapport easily with participants and coworkers
  • Passionate about experiential education for youth from all backgrounds
  • 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 references


The pay range for this position is $20-25 per hour depending on experience and relevant certifications.

2023 Mandatory Dates:

  • Senior Staff Training: June 17th-21st
  • All Staff Training: June 24th- 28th
  • Regular Season : Monday-Friday 7:45AM – 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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