Jamaica Pond Site Manager

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

Sailing Management
Job Start Date
Job End Date
Manages Others
Experience Required
Housing Provided
From $20.00 To $25.00
Per Hour
Employment Type
Summer Only
Work Schedule
No Travel

Job Description
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: This is a full time seasonal position.* Schedules can be tailored to individual availability; Mon-Sun, March-Oct 31st.

*March-April: >25 hours per week

May-Oct: 40 hours per week

Position Overview

The Jamaica Pond Site Manager is responsible for: 


  • Manage the staffing schedule and payroll approvals 
  • Train, assist, and supervise staff members who work at Jamaica Pond Boathouse.
  • Communicate with the parks department about weather closures and boathouse issues
  • Communicate with the management team to organize / prepare / troubleshoot issues
  • Open and close the site 4 or 5 days a week (the site is open 12PM-sunset weekdays and 10AM-sunset weekends). And on these days, be the Officer in Charge (the person responsible for the site and the boating activities that day.)
  • Report weather closures and boathouse or dock maintenance requests to the Boston Parks Department.
  • Operate the business aspects of the boathouse such as inventory management, ordering supplies, and report on revenue vs costs. 
  • Write an end of season report detailing boat usage, community engagement, and a financial summary.
  • Coordinate with contractors such as a bathroom cleaning service.
  • Provide clear, effective, and timely communication with leadership staff.
  • Build the staffing schedule and approve payroll hours.
  • Lead efforts to further engage the Jamaica Pond community through marketing, attending public events, and social media. 
  • Organize 3 Open House events.

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 exploring the pond. 
  • 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 staff members.
  • 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. 
  • Lead efforts to further engage the Jamaica Pond community through marketing, public events, and social media. 

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

Job Requirements

Background in management, specifically educational or non-profit program management, camp, or summer waterfront management.
Experience in supervising staff, administering financial transactions, and customer service.
Strong preference for substantial sailing or general boating experience.
Familiarity with boat maintenance and repair.
US Sailing Level 1 Instructor Certification, equivalent or more advanced preferred
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
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
Other certifications (Captain’s License, Lifeguard, WFA, WFR, etc.) a plus
Jobs Courageous Sailing
One First Avenue
Boston MA 02129
United States
Courageous Sailing, Inc. Jobs Courageous Sailing

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