IIT Program Coordinator/Head Trainer

Reports to: Site Director
Status: Seasonal, Full-Time
Date of Last Revision: December 17, 2015


At Courageous Sailing, we run an intensive Instructor-in-Training (IIT) Program for a diversified group of Boston teens ages 15-17. We have up to 22 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 examinations, 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.


  • Work with IIT Asst. Trainers to create a comprehensive lesson plan for the whole summer
  • Work with IIT Asst. Trainers to create a float plan each day that is shared with the site director
  • Make sure all students and staff adhere to the designated schedule
  • Prepare lessons for days when sailing is not possible
  • Facilitate chalk talks for IITs
  • Oversee IITs as they give chalk talks and instruction
  • Manage IIT Asst. Trainers and IITs and aid in their leadership development
  • Lead chores at the end of each day
  • Manage time efficiently to maximize students' time on the water 
  • Organize and chaperone camping trips, BBQs, race nights, and other fun events for the IITs throughout the summer
  • Complete MWBLP for all IITs and staff
  • Distribute evaluation surveys
  • Attend 3-day senior staff orientation and all 5 days of all staff orientation
  • Attend staff meetings
  • Be a constructive and friendly member of the Courageous team
  • 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


  • Bachelor's degree or currently in school for High School education or outdoor education
  • 3-5 years experience teaching teens
  • 2-3 years team management experience
  • US Sailing Level 1 Instructor Certification, equivalent or more advanced
  • 2-3 years of sailing instruction experience
  • Courageous Sailing motorboat qualified (mandatory in-house certification equivalent to completion of NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level 1 certification course)
  • Passion for working with urban teens
  • Commitment to creating a positive IIT team
  • Current First Aid/CPR certification
  • Positive and enthusiastic attitude
  • Outstanding communication and team management skills
  • Excellent references


2016 Schedule:

Senior Staff Training: June 22-24
All Staff Training: June 27-July 1
Monday-Friday, from Tuesday, July 5 – Friday, August 19