Step 5: Head Instructor Trainer


Job Description

The Head Instructor Trainer is primarily responsible for overseeing the Courageous Instructor-in-Training (IIT) Program. Please note that if funding allows, we may hire up to three or four Instructor Trainers for two separate IIT programs.  In each case, there will be one Head Instructor and an Assistant. Responsibilities and qualifications for each position are similar.

The IIT program is a rigorous two-summer-long job-skills training course that trains 15-to-18-year-old sailing students to become master sailors and skilled sailing instructors. The class typically consists of 12 to 18 students, and the curriculum focuses on topics including: advanced seamanship, boating safety, classroom management, public speaking, lesson planning, and techniques in sailing instruction. The course is similar to a US Sailing Level 1 or Basic Keelboat instructor course, but over the course of two summers covers that material in much greater depth.

To read more about the IIT program, visit:

If you are the kind of passionate and skilled teacher who has what it takes to inspire Courageous' next generation of sailing instructors, please contact Youth Program Director, Kate Henderson, as soon as possible. Send your resume and cover letter to


    • Bachelor’s Degree
    • US Sailing Smallboat Level 1 Instructor; more advanced instructor credentials preferred, but not required
    • Current First Aid/CPR certification; WFA, WFR or more advanced preferred
    • Comfort driving safety boats and using outboard engines on sailboats
    • 5-7 years experience teaching sailing
    • Substantial experience working with high school aged youth
    • Must be available for occasional (2-3 times per summer) overnight cruises and multi-night island campouts which serve as team-building opportunities
    • Experience developing curriculum and lesson plans
    • Positive and enthusiastic attitude
    • Self-starter with strong work ethic and attention to detail
    • Team-oriented
    • Outstanding references
    • A passion for sailing, cruising, the ocean, the environment and working with youth 

Other considerations for this position 

    • Other certifications (Captain, Lifeguard, EMT, WFA, WFR, etc.)
    • Previous experience cruising Massachusetts Bay and surrounding waters a plus
    • Conversational proficiency in other languages, including spanish and portuguese


Kate Henderson, Director of Youth Programs

Phone: 617-242-3821 ext. 12



Apply to be the Step 5 Head Instructor Trainer