Adult Sailing Instructor

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.

Dates/Time: Part-time and Full-time shifts available seasonally. Schedules can be tailored to individual availability; Mon-Sun, May 1st-Oct 31st. Partial availability within the season is welcome. A full-season commitment is not mandatory. 

Position Overview

Courageous Sailing is seeking instructors to teach courses and private lessons at our Charlestown and Jamaica Pond sites. Most classes run on the weekends and weekday evenings.

Responsibilities:

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

• General:

• Be proactive

• Provide clear, effective, and timely communication with leadership staff

• Leave Courageous better than you found it

• Teach private lessons

• Teach Learn-to-Sail courses

• Safety (minimizing risks while maintaining an approachable and engaging environment for students, members, patrons, and fellow staff members):

• 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.

• Comply with and encourage students and members to learn Courageous’ set of sailing safety standards and reiterate their importance whenever possible.

• Attend all days of staff training and staff meetings and/or complete online training.*

• Exercise sound judgment and decision-making. Assess and mitigate foreseeable hazards.

• Remain up to date on what roles and responsibilities you may take on in the event of an emergency and review the EAP with your direct supervisor.

• Respectability (support and ensure that everyone can be successful):

• Maintain the Courageous fleet and facilities by completing everyday tasks as discussed in training and documented in daily checklists

• Reduce and help manage the disposal of waste in and around Boston Harbor

• Cultivate a kind and inclusive community

• 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.

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