Instructor-in-Training Trainer

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Website Courageous Sailing

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Courageous Sailing

Courageous Sailing is a nonprofit community sailing and youth development organization committed to providing people of all ages and backgrounds with opportunities to learn, sail, and enjoy the waterfront. We work at two locations in Boston: the Charlestown Navy Yard on Boston Harbor, and the Historic Jamaica Pond boathouse in Jamaica Plain. Our mission is to transform lives through sailing programs that inspire learning, personal growth and leadership.

In the Courageous Sailing Summer Youth Program, sailing is the platform for youth aged 8-18 to develop leadership skills, gain confidence, explore Boston Harbor, and delve into hands-on science.

Why Courageous? 

Working at Courageous is an opportunity to join a close-knit and diverse community committed to fostering a positive educational environment for staff and participants on and off the water.

Courageous Staff receive paid training and professional development as well as recreational access to our fleet of boats which range from dinghies to mid-size keelboats and cruising boats. 

By joining our team you will make a meaningful and positive impact on the lives of our participants and will be a critical part of fulfilling our mission to get people of all walks of life out on the water. 

Dates/Time: This is a Full time summer position, 8:00 am to 4:00 pm Monday through Friday

Job Description Courageous Sailing is looking for an Instructor-In-Training (IIT) Trainer to help prepare our IITs with the teaching, leadership, and sailing skills they will need to be instructors at Courageous after they complete the program. The IIT Trainers work in a pair to oversee a team of 20-30 IITs (10-15 per year of the program) and report to the Youth Program Director. 

At Courageous Sailing, we run an intensive Instructor-in-Training (IIT) program for a diverse group of Boston teens ages 15-18.  We have up to 30 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 team building and creating a welcoming, supportive, and positive learning environment for all of our IITs.

Our Instructors-in-Training (IITs) are graduates of our summer program or other sailing programs who are interested in furthering their sailing education by learning the skills required to become instructors. During the first year of this program, IITs focus on honing their sailing skills on a variety of boats and learning fundamentals of teaching. In the second year of the program IITs practice teaching by shadowing and assisting in all of the programs at Courageous. They are the youngest members of our staff and are expected to adhere to staff guidelines. Our Instructor Trainers are charged with helping them navigate the shift from student to staff.



  • Responsibly manage risk so that IITs feel comfortable stepping outside of their comfort zones
  • Deliver high-level sailing instruction following Courageous Curriculum, preparing IITs to pass our In-House Sailing Evaluation and independently teach beginner sailors
  • Create a safe place to make mistakes by clearly establishing limits and boundaries for the IITs behavior and independence
  • Complying with, teaching, and encouraging of IITs’ learning of Courageous’ set of sailing safety standards
  • Model best practices for the IITs, especially best practices in professionalism in the workplace, sailing and teaching on the water, cleanliness and organization, care for Courageous boats and resources, and safety
  • Provide active and engaged supervision to IITs both on-land and on-the-water
  • Organize and lead at least one off-site camping trip for IITs to the Boston Harbor Islands

Management and Supervision

  • Supervise and oversee IIT programming, including scheduling IITs to work across different programs and program sites
  • Schedule and hold regular meetings with IITs to check in on work projects and give feedback. 
  • At least once per season, hold performance reviews with each IIT to exchange job performance feedback


  • Attend all days of mandatory training and/or complete online training
  • Be proactive and communicative. Provide clear, effective and timely communication with supervisors and staff. Ask questions if the scope or intention of work is unclear, express concerns when they come up, give feedback regularly to peers and supervisors, and help facilitate positive change

Safety and Risk Management: 

  • Comply with Courageous safety standards and policies on and off the water and teach participants how to do the same
  • Model safe, respectful, and responsible behavior to participants and peers at all times. 
  • Exercise sound judgment and decision-making. Treat safety as the highest priority. 
  • Leave Courageous better than you found it. Treat Courageous property with respect. Maintain the cleanliness and functionality of workspace and tools

Diversity, Equity, and Inclusion: 

  • Cultivate a kind and inclusive community where everyone at Courageous can feel like they belong

At Courageous Sailing, our highest priority is finding the best candidate for the job. Research has shown that people of color and women are less likely to apply for jobs if they don’t believe they meet every one of the qualifications described in a job description. We encourage you to apply, even if you don’t believe you meet every one of our described qualifications or you have a less traditional background. We are looking for applicants with the following qualifications:


  • US Sailing Level 1 Instructor Certification, equivalent or more advanced
  • At least 2-3 years sailing instruction experience, 1-2 years powerboat experience.
  • Completion NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level I certification course
  • Can work effectively with a wide variety of age groups and populations from diverse backgrounds, role modeling inclusive behavior and building positive group culture
  • Able to communicate clearly, directly, and calmly at all times. 
  • Comfortable giving and receiving feedback to and from peers, participants, and supervisors
  • Able to build rapport easily with participants and coworkers
  • Passionate about experiential education for youth from all backgrounds
  • Comfortable working outdoors, regardless of weather
  • Positive and enthusiastic attitude
  • Willing to authorize a federal background check
  • Hold, or are willing to obtain before start date, current First Aid and CPR certification
  • Three references


  • Experience working with young adults
  • Performance sailing, racing, and/or navigation and trip planning skills


The pay range for this position is $20-25/hour depending on experience and relevant certifications. 

2023 Mandatory Dates:

  • Senior Staff Training: June 17th-21st
  • All Staff Training: June 24th- 28th
  • Regular Season : Monday-Friday, from Monday, July 1st – Friday, August 9th
  • End of Season Staff Day: Monday, August 12th
  • Additional work is available before and after these dates from mid-April through mid-September. Staff may work other jobs at Courageous within different departments (ex. Adult Programs, Maintenance) during non-youth program time. 

To apply, go to Direct questions to Learn more about Courageous Sailing’s Summer Youth Programs at

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