IIT Assistant Head Trainer

Reports to: IIT Head Trainer
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 other trainers to create a comprehensive lesson plan for the whole summer
  • Prepare lessons for days when sailing is not possible
  • Manage IITs and aid in their leadership development
  • Organize and chaperone camping trips, BBQs, race nights, and other fun events for IITs throughout the summer 
  • Create a sail plan each day with the other trainers that is shared with the Site Director
  • Provide individualized sailing instruction to 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 3-day senior staff orientation and all 5 days of all staff training
  • 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


  • 2-3 years sailing instruction experience
  • US Sailing Level 1 Instructor Certification, equivalent or more advanced
  • 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)
  • 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 

2016 Schedule:

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