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General Description

The Sailing Instructor teaches sailing lessons while incorporating safe boating practices. Boats involved in the program include privately owned Optis, N10s, Lasers and club-owned 420s. Children in the Youth Sailing Program range in age from 9 through high school.

The Sailing Instructor is a role model for staff and participants in the sailing programs, exemplifying integrity and the key characteristics we expect of our employees: Commitment, Respect, Responsibility and Cooperation.

The Sailing Instructor is s full time summer employee working between 30 and 35 hours per week and is paid an hourly rate. As an hourly employee, he/she is required to submit a weekly timecard to the WBC Management for approval. Overtime would require advance approval. Work shifts may include, although not often, some nights and weekends for events such as regattas and other sailing activities such as pizza parties, field trips, award night, to be determined by the Sailing Program Manager under the direction of the Sailing Director. He/she must be available from the close of Winchester Public Schools through an end of season date to be negotiated with the Sailing Director (generally through the third week in August). Vacation time during this period is at the discretion of the WBC Management. (See Job Application for WBC Vacation Policy.

While on duty, the Sailing Instructor must wear the uniform specified by the WBC Management (Instructor's t-shirt, khaki shorts or other suitable clothing as specified by the WBC Management). When representing the Club at sailing events and club meetings, he/she should wear the uniform specified by the WBC Management (collared shirt, khakis or other suitable clothing as specified by the WBC Management).

Qualifications & Certifications

The Sailing Instructor must be 18 years of age or older. The Sailing Instructor must be US Sailing Association Small Boat Sailing (Level l Dinghy) certified and certified in CPR. We seek a candidate with prior sailing experience and willingness to motivate and encourage youth sailors.

Reporting/Management Relationships

The Sailing Instructor reports to the Sailing Program Manager, working under the direction of the WBC Management with input by the Sailing Director.

Primary Responsibilities

Duties of the Sailing Instructor include:

  • Teach Youth Program Sailing Classes
    • Work in a team with a particular lesson group (Beginner, Adv. Beginner, Intermediate, Tactics) to be determined by Sailing Director.
    • Help develop a season lesson plan to be approved by the Sailing Program Manager and/or Sailing Director.
    • Help write daily lesson logs to be reviewed with Sailing Program Manager.
    • Programs should include, where appropriate for class level:
      • Basic Sailing.
      • Rowing and boat retrieval.
      • Knot tying.
      • Basic boat maintenance.
      • Emphasis on sportsmanship and respectful behavior.
      • Protocol for the rigging and de-rigging of boats.
      • Introduction to racing tactics.
      • Introduction to racing rules.
      • Teaching in accordance with U.S. Sailing Instructor Guidelines.
  • Teach Adult Sailing Classes if determined by Sailing Director.
    • Help develop a season lesson plan to be approved by the Sailing Program Manager.
    • May required night work shifts.
  • Sailing Instructors may make private arrangements for lessons or assist members in hauling boats. This must be done off the clock and the WBC assumes no liability for such services. Employee must abide by private lessons/assistance policies.
  • Attend regattas if required. Determined by Program Sailing Manager.
    • On lake regattas include, but are not limited to Swanson/Opti Cup, Dillon/Opti Challenge, Generation and Raphael Regattas.
    • Help plan, coordinate, and attend end of year Class Regattas and Class Series. Help report results to Sailing Program Director, Sailing Director and office staff for trophies.
    • Off lake regattas include local events in Boston area.  Away regatta responsibilities include
      • Assist in coordination of boat transportation as required.
      • Assist in rigging and de-rigging while at regatta location.
      • Offer encouragement and tactical advice to sailors.
      • Check sailor standings while at regatta.
      • Attend award ceremony held at regatta with sailors.
      • Represent WBC in an appropriate manner, communicating with representatives and coaches from other clubs.
  • Attend and help present sailing program at Sailing Orientation Night, working under the guidance of the Sailing Program Manager and Sailing Director.
  • Attend preseason employee training as required including Sailing Instructor Training. This training is under the direction of the Sailing Program Manager, WBC Management and Sailing Director and includes the following:
    • Review of instructor roles and responsibilities.
    • Proper use of Queen (RC/instructor boat) and whalers.
    • Proper care and storage of the Club 420s.
    • Maintenance, safety and cleanliness of dock area.
  • Communicate effectively with sailing staff and other WBC staff.
    • Listen to and incorporate, if appropriate and beneficial, the ideas and suggestions of the other members of the sailing staff.
    • Communicate appropriately when required with pool and snack bar staff.
    • Provide direction and feedback to the Junior Sailing Instructors.
  • Communicate effectively on a regular basis with the Sailing Program Manager.
    • Accept direction and get approval from Sailing Program Manager while taking initiative to offer ideas to develop and implement a successful sailing program.
  • Communicate effectively with junior sailing program students.
    • Engage and encourage junior sailors.
  • Under the direction of the Sailing Program Manager, maintain boats and areas used by sailing staff and program sailors.
    • Coordinate and assist in pre-season and post-season maintenance of junior sailing equipment.
    • Coordinate and assist in maintenance of club owned 420s.
      • Ensure that boats are put away properly.
      • Complete routine maintenance on 420s (missing clips, pins, etc.).
      • Promptly report all damages to boats to the WBC Management.
      • Assist with boat cleaning when required.
    • Program area must be clear of trash and gear by end of program day.
    • Rowboats used during sailing class must be clear of trash and gear by end of program day.  Rowboats will be bailed on mornings after an evening rain.  Otherwise, maintenance staff is responsible for bailing boats each evening before club closing as well as throughout the day.
    • Motorboats used during sailing class must be clear of trash and gear by end of program day. Alert Sailing Program Manager to any required motorboat repairs.
    • Ensure that the locker room area is clean and sailors store their gear properly.
    • Instructors are responsible for cleaning up after themselves in any areas of the club that are used.
  • Follow water safety procedures.
    • Practice safe use of boats according to WBC policies.
    • Enforce WBC boating rules in accordance with policy in rear of Membership Directory.
  • Assist Sailing Program Director in organizing and attending Sailing Awards Night.
    • Participate in making trophy nominations.
    • Help to coordinate summer sailing slide show.
    • Help give program class presentations.
    • Help participate in presentation of trophies and awards by sailing staff.
    • Help in setup; and clean up where needed.


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