Youth Program Site Director

Courageous Sailing, Inc.
One First Avenue
Boston, MA 02129
United States

Charitable / Not for Profit
Job Start Date
Job End Date
Application Closing Date
Manages Others
Experience Required
Degree Required
Security Clearance Required
Housing Provided
From $20.00 To $25.00
Per Hour
Employment Type
Summer Only
Work Schedule
Summer Only
No Travel

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.
Job Requirements
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
Jobs Courageous Sailing
One First Avenue
Boston MA 02129
United States
Courageous Sailing, Inc. Jobs Courageous Sailing
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