Courageous Sailing, Inc.
One First Avenue
Boston, MA 02129
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 25 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 (you) 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 Instructor-in-Training (IITs), are the highest level of our Steps To Lead program, giving them the most autonomy as students as well as the most responsibility in regards to our Code of Conduct. The IITs are also the youngest members of our Young Leaders program (staff) and are expected to adhere to staff guidelines. Our Instructor Trainers are charged with helping them navigate the shift from student to staff.
Creating a safe, engaging, and respectful learning environment that focuses on social-emotional growth.
Understand the intention of management when giving instruction and utilize debriefs and check-ins to express concerns, give feedback, and help facilitate change
Provide clear, effective and timely communication with leadership staff
Leave Courageous better than you found it.
Safe (minimizing risks while maintaining a fun atmosphere for youth to stretch their limits which leads to real learning.):
Responsibly manage risk so that IITs feel comfortable stepping outside of their comfort zones
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
Attend all days of staff and senior staff training and staff meetings and/or complete online training
Exercise sound judgement and decision-making. Assess and mitigate foreseeable hazards.
Supervise IITs and oversee programming in a way that reduces risk.
Respectful (support and ensure that everyone can be successful):
Maintain the Courageous fleet and facilities by completing everyday tasks as discussed in training and documented in chore checklists
Reduce and help manage the disposal of waste in and around Boston Harbor
Cultivate a kind and inclusive community
Give clear and direct feedback to IITs that leads to growth as an instructor.
Engaging (give lots of responsibility, hands-on and experiential pedagogy with real-world consequences for behavior/choices):
Build rapport with students
Model best practices for the IITs
Provide active and engaged supervision to IITs both on-land and on-the-water
Teach and encourage IITs’ learning of sailing concepts using curriculum provided
Lead, facilitate, and participate in on-land activities during down time and/or when sailing is not feasible.
US Sailing Level 1 Instructor Certification, equivalent or more advanced
At least 2-3 years sailing instruction experience, 1-2 years powerboat experience for Head Instructors
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 and directly
Comfortable giving and receiving feedback
Able to build rapport easily with students and coworkers
Passionate about and dedicated to experiential education for youth from all backgrounds
Able to meet different learning-style needs by varying teaching techniques
Sufficiently physically fit to participate in all site and course activities while maintaining ample energy, strength, and focus to aid students
Comfortable working outdoors, regardless of weather
Able to practice proper self-care and energy management while on the water
Able to maintain composure, exercise sound judgment and decision-making, and assess and mitigate risk under extended periods of stress
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
Employer Contact Information
Courageous Sailing, Inc.
One First Avenue
Courageous Sailing transforms lives through sailing programs that inspire learning, personal growth and leadership.
Courageous Sailing is a community that embraces sailing as a platform for life-long learning, personal growth and leadership; a center of sailing excellence committed to removing barriers to access for all Boston youth, the public and people with physical and intellectual challenges.
Courageous Sailing was established in 1987 as a 501(c)(3) by the late South Boston sailing enthusiast Harry McDonough. It was Harry’s dream to use sailing to build character and camaraderie among Boston children from all economic and ethnic backgrounds. For 25 years, we have continued to grow and deliver our mission to transform children’s lives through sailing programs that inspire learning, personal growth and leadership. In Harry’s words, “Every child's perspective is improved 50-yards off-shore.”
Courageous is now a nationally recognized year-round educational center for community sailing and youth development. Courageous offers Boston-area youth free and low-cost out-of-school-time programs in sailing, environmental education, job skills development, and leadership training. In 2011 we were honored to be named one of the top 10 community sailing programs nationwide by both US Sailing and Sail Magazine.
How Courageous Got Its Name
The America's Cup 12 meter "Courageous" once lived at Pier 4 in the Navy Yard. This two-time America's Cup winner lent its name to Courageous Sailing in the late 1980s. The boat now resides at the Museum of Yachting in Newport, Rhode Island, where it has been restored and is still being raced.
Join a team of nearly 100 seasonal instructors, administrators, and coaches, all dedicated to delivering affordable, high quality sailing programs to thousands of Boston-area community members each year. Visit our website to view our most up to date job postings and to find the right opportunity for you. We look forward to hearing from you!