Adult Program OIC/Site Manager

In by Caitlyn Ridgely

Website Courageous Sailing

Reports To: Adult Program Director

Status: Part-Time/Full-Time Seasonal

Description Last Updated: 3/1/2024

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.

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 from all walks of life out on the water. 

Dates/Time: Part-time and Full-time shifts are available seasonally. Schedules can be tailored to individual availability; Mon-Sun, May 1st-Oct 31st.

Position Overview

Courageous Sailing is seeking Site Manager (Also known as Officers in Charge) to manage our sites at Jamaica Pond and Charlestown.  


Participate in and contribute to a safe, engaging, and respectful work environment by:

  • General:
    • Open and close the site (12PM-sunset weekdays, 10AM-sunset weekends)
    • Provide clear, effective, and timely communication with leadership staff
    • Assist with scheduling and course oversite
    • Leave Courageous better than you found it
  • Safety (minimizing risks while maintaining an approachable and engaging environment for students, members, patrons, and fellow staff members):
    • Lead all staff, students, and members through our established emergency management procedure in the event emergencies occur
    • Monitor weather and make decisions regarding inclement weather in cooperation with the Site Director and Youth Program Director 
    • Responsibly manage risk so that students, members, and patrons feel comfortable stepping outside of their comfort zones, asking questions, and engaging with the facility on various levels. 
    • Approve member’s daily float plans, and, as needed, discuss ways to execute their plans more effectively or safely 
    • 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 all vessels are navigating the harbor appropriately and assist with towing boats out of the way of traffic as needed.  
    • Comply with and encourage students and members to learn Courageous’ set of sailing safety standards and reiterate their importance whenever possible. 
    • Exercise sound judgment and decision-making. Assess and mitigate foreseeable hazards.
  • Engagement (maintaining the expectation of individual responsibility for students and members):
    • Build rapport with students, members, and patrons
    • Provide active and engaged feedback to daily questions and interactions
    • Lead, facilitate, and participate in on-land responsibilities for general upkeep of the boathouse during downtime. 
    • Able to communicate clearly, directly, and calmly at all times. 

*Job training days are position dependent and vary from position to position. 

  • US Sailing Level 1 Instructor Certification, equivalent or more advanced preferred
  • At least 2-3 years of sailing instruction experience, 1-2 years of 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
  • Comfortable giving and receiving feedback to and from peers, participants, and supervisors
  • Able to build rapport easily with participants and coworkers
  • Comfortable working outdoors, regardless of weather
  • 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

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

To apply for this job please visit