Step 1: Sailing 101 Assistant Leader
Step 2: Beginner Sailing Assistant Leader 


Job Description

Our Assistant Leaders and Assistant Coaches (or “Senior Instructors”) are our talented and versatile mid-level instructors. They are employed at all three sites to work with our youngest sailors in our Learn-to-Sail, Advanced Sailing, Racing and Cruising.  They report directly to their respective Step Leaders.  Senior instructors typically have 1-2 years previous instructing experience, but do not necessarily have experience leading a class on their own.

Senior instructors must be team players and strong role models, capable of motivating and mentoring Courageous’ youngest sailors, as well as instilling within them a deep respect for Courageous’ boats, the ocean environment and for one another.  They are also responsible for creating a fun and positive atmosphere, one that gets students excited about hopping in the boats and getting out on the water all summer long!  As safety boat drivers, they are also directly responsible for monitoring and ensuring the safety of our students.

The ideal senior instructor would specialize in teaching a certain course at a certain site all summer long, but, in a pinch, would also be willing and capable of filling in for other staff members teaching other courses.  As Senior Instructors are encouraged to apprentice with our Step Leaders and Coaches, this position is particularly suited to individuals interested in advancing through the instructor ranks at Courageous and in becoming assistant or head coaches.

Specific responsibilities include but are not limited to: helping to plan and run classes; teaching students and new instructors to respect boats and equipment, and reporting damage and breakdowns when they occur; teaching students about the environment and leadership in addition to the fundamentals of sailing from within the sailboat; helping to maintain and clean the docks, boats and grounds; participation in regular staff skill-building clinics.

Step 1 & 2 Assistant Leaders

Step 1 & 2 Assistant Leaders are responsible for leading chalk talks and running the safety boats.  The assistant leader is primarily responsible for leading the instruction team in teaching students the skills and competencies outlined in the Courageous Sailing “Blue Book” in preparation for advancement into higher levels of the Courageous’ program.  As Steps 1 & 2 are the point of entry for the vast majority of Courageous’ youth sailors, the Step 1 & 2 assistant leaders must be highly energetic and excited about sailing and teaching sailing. 


    • US Sailing Level 1 Small Boat Instructor Certification (or equivalent)
    • Current First Aid/CPR certification
    • 1-2 years previous sailing instruction experience
    • Safety boat driving experience
    • Passing sailing skills check-out with Youth Director
    • Positive and enthusiastic attitude
    • Team-oriented
    • Excellent references
    • A passion for sailing, the ocean, the environment and working with kids

Other considerations for this position:

    • Other certifications (Lifeguard, EMT, WFA, WFR, etc.)
    • Other teaching experience
    • Prior experience on Boston Harbor a plus
    • Keelboat experience
    • (not required but a plus) Interest in racing for Courageous in local, regional and national PHRF and one-design events as a member of the youth racing team


Kate Henderson, Director of Youth Programs

Phone: 617-242-3821 ext. 12




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