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Instructor Trainer, IIT Program

Reports to: IIT Program Coordinator and Head Instructor Trainer
Status: Seasonal, Full-Time
Date of Last Revision: March 13, 2015

Position Summary:

At Courageous Sailing Center, we run an intensive Instructor-in-Training ("IIT") Program for a diversified group of Boston teens ages 15-17. We have 16 instructors-in-training, each with varying levels of skill in sailing, teaching, and professionalism. The primary goal of the IIT program is to prepare them to become full instructors, capable of passing the US Sailing Level 1 examiniations, within one to three summers of training. The Instructor Trainers play a critical role in facilitating this transformation. Instructor Trainers are also responsible for leading teambuilding and creating a welcoming, supportive, and positive learning environment for all of our IITs. For more description of the IIT program, take a look at the IIT Program page: http://www.courageoussailing.org/youth/iit-program


These inculde, but are not necessarily limited to the following:

  • Attend all 4 days of staff orientation (Mon June 29 - Thu July 2)
  • Create a sail plan each day with the IIT Program Coordinator and/or Head Instructor Trainer that is shared with the Site Director
  • Provide individualized coaching in sailing and sailing instruction for your assigned group of IITs in accordance with IIT Program teaching objectives
  • Facilitate chalk talks and on-the-water instruction
  • Manage time efficiently to maximize student's time on the water but making sure to be back on land when required
  • Lead chores at the end of each day
  • Attend staff meetings
  • Be a cooperative member of the Youth Program staff
  • Maintain a fun, positive, friendly atmosphere for your students
  • Instill a sense of respect and safety for the Courageous fleet, Boston Harbor, and for each person


Minimum qualifications include:

  • 2-3 years sailing instruction experience
  • US Sailing Level 1 Instructor Certification, equivalent or more advanced
  • Current First Aid/CPR certification
  • Positive and enthusiastic attitude
  • Outstanding communication and team management skills
  • Excellent references
  • A passion for sailing, the ocean, mentoring, and working with teens
  • Prior experience working with or mentoring teens or young adults is strongly preferred

About Courageous

Courageous Sailing is a non-profit sailing center dedicated to transforming the lives of underserved populations of youth through sailing. The program has been in continuous operation since 1987 and is based in the Charlestown Navy Yard on Boston Harbor. The youth program is supported by the operation of the adult program, grants, corporate sponsorships, individual donations and fundraising events. With a fleet of Rhodes 19s (25) , J22s (9), J24s (3), J80s (2), 420s (9), Lasers (12), and a small assortment of cruising boats, Courageous is one of the largest nonprofit, keelboat-based sailing schools and community sailing programs in the northeast. In addition to youth programs, we offer adult memberships, instruction, and racing. Courageous is a fun place to work, with a large but congenial staff and an atmosphere that encourages initiative and self-direction. In 2014, Courageous Sailing employed over 100 seasonal staff members, including over 60 sailing instructors.

COURAGEOUS SAILING is an Equal Opportunity Employer.

Courageous Sailing does not discriminate in employment on the basis of race, color, religion, sex, sexual orientation, national origin, age, genetic, disability or veteran/Reserve/National Guard status.