Step 3: Intermediate Sailing Leader


Job Description

The Step 3: Intermediate Sailing Leader’s (a.k.a. "Head Instructor") primary responsibility is to oversee and facilitate the day-to-day operation of the Advanced Sailing program at the Charlestown site. He/She reports to and will work closely with the Assistant Youth Program Director and Youth Program Director.  
The Step 3: Intermediate Sailing Leader is the point of entry for Courageous’ youth sailors into our Racing and Cruising programs, it is imperative that the Step 3 Leader be committed to preparing students for entry into these even more advanced and intensive courses.  Each Friday, the Step 3 leader shall hold a sailing test for those Step 2 students wanting to pass into Step 3. 
The leader must be a team player and strong role model, capable of motivating and mentoring his/her instructors and young sailors, as well as instilling within them a deep respect for Courageous’ fleet, the ocean environment and for one another.  
This person is also charged with maintaining a fun, friendly and positive environment.  The Step 3 Leader will assist the Step 2 leader in preparations for “Fun Fridays” and other events throughout the summer. 
Specific responsibilities include but are not limited to: helping maintain student records; planning classes; creating advance plans for rainy days; running classes from a support boat; training instructors; leading chalk talks; making sure all equipment for the class is cared for and well-maintained; working with the Assistant Youth Director to infuse sailing classes with environmental education and leadership training; communicating with leaders/coaches of other Steps to coordinate advancement of students; helping to warm up and fuel powerboats each morning; lead a team of 3 to 4 other Step 3 instructors; submitting instructor performance evaluations. 


    • U.S. Sailing Certified Level 1 Instructor or equivalent certifications 
    • Current First Aid/CPR certification 
    • Extensive safety boat experience and/or CSC motorboat qualified (mandatory in-house certification that is somewhat more rigorous than NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level I certification course) 
    • 3+ years experience teaching sailing 
    • Ability to communicate well with public, parents, partner organizations, etc. 
    • Experience in basic sailboat and powerboat maintenance 
    • Positive, enthusiastic, flexible, "can-do" attitude 
    • Self-starter with strong work ethic and attention to detail 
    • Team-oriented 
    • Outstanding references
    • A passion for sailing, the ocean, the environment and working with youth 

Other considerations for this position: 

    • Other certifications (Lifeguard, EMT, WFA, WFR, etc.) 
    • Prior experience in leadership role in a youth sailing program or other youth program that required you to lead others
    • Prior outdoor education or summer camp councilor experience 
    • Other teaching experience 
    • More advanced Racing or Cruising experience strongly preferred
    • Prior experience on Boston Harbor a plus



Kate Henderson, Director of Youth Programs

Phone: 617-242-3821 ext. 12




Apply to be a Step 3 Leader