Adult Sailing Instructor

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

Job Start Date
Job End Date
Manages Others
Experience Required
Degree Required
Housing Provided
From $18.00 To $25.00
Per Hour
Employment Type
Part Time
Work Schedule

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.


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.


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.

Job Requirements
US Sailing Level 1 or Keelboat Instructor Certification, equivalent or more advanced preferred
A passion for sailing, the ocean, and working with students
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 and directly
Comfortable giving and receiving feedback
Able to build rapport easily with students and colleagues
Passionate about and dedicated to experiential education for students
Able to meet different learning style needs by varying teaching techniques
Sufficiently physically fit to participate in all site and course activities while maintaining ample energy, strength, and focus to aid students
Comfortable working outdoors, regardless of weather
Able to practice proper self-care and energy management
Able to maintain composure, exercise sound judgment and decision-making, and assess and mitigate risk under extended periods of stress
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
Jobs Courageous Sailing
One First Avenue
Boston MA 02129
United States
Courageous Sailing, Inc. Jobs Courageous Sailing
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