Head and Assistant Head Instructor, Youth Program - Summer 2019

Courageous Sailing, Inc.
One First Avenue
Boston, MA 02129
United States

Job Start Date
Job End Date
Application Closing Date
Manages Others
Experience Required
Degree Required
Security Clearance Required
From $13.00 To $18.00
Per Hour
Employment Type
Summer Only
Work Schedule
Summer Only
No Travel

Job Description
• Step 1 is a Basic Sailing 101 is a one week course offered to children ages 8 and up. During this time, they are introduced to sailing theory and gain sailing experience in Boston Harbor.
• Step 2 is a more intensive Beginner Sailing course that takes place over three weeks and provides a more in-depth introduction to sailing theory and boat handling. Instructors sail in each boat.
• Step 3 is an Intermediate Sailing, three-week course offered to children ages 10 and up. Students learn to sail more independently in Rhodes 19s without instructors in the boat. Instructor supervision is provided from a motorboat.
• Step 4 is a three-week introduction to dinghy course. Students experience sailing capsizable boats, RS Quests, for the first time. Instructor supervision is provided from a motorboat.
• Step 5 is a three-week advanced dinghy course. Students learn the basics of racing in 420s and Lasers. Instructor supervision is provided from a motorboat.
• We have up to 20 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.

• Responsible for between 15-30 students both on-land and on-the-water
• Manage a team of up to 7 sailing instructors
• Create a lesson plan for each session
• Create a float plan each day that includes the day’s lesson plan, activities, boat needs and selected sailing area
• Coordinate boat resource usage with other Head Instructors and Site Director
• Prepare lessons and on-land activities when sailing is not possible
• Lead safe, fun and engaging activities both on-land and on-the-water
• Facilitate chalk talks for students
• Lead conversations in which students reflect on their experience
• Facilitate community building within your Step
• Oversee sailing instructors as they give chalk talks and instruction
• Manage student transitions between activities
• Manage minor student behavior management needs
• Lead staff chores at the end of each day
• Disseminate and facilitate student feedback surveys
• Facilitate the completion of student sailing skill progress reports
• Efficiently manage on-the-water and on-land time
• Manage sailing instructors and aid in their leadership development
• Complete a Courageous professional development plan (PPuP) for each of your instructors
• Attend 3 days of senior staff orientation and 5 days of all-staff orientation
• Attend staff meetings
• Be a constructive and amiable member of the Courageous team
• Maintain a safe, fun, positive, friendly atmosphere
• Instill a sense of respect and safety for the Courageous fleet, Boston Harbor, and for each person
Job Requirements
• US Sailing Level 1 Instructor Certification, equivalent or more advanced
• 2-3 years sailing instruction experience, 1-2 years powerboat experience for Head Instructors
• Completion of NASBLA-approved safety boat course through the MA Environmental Police and/or through the US Sailing Level I certification course
• Outstanding communication and teaching skills
• Current First Aid/CPR certification
• Positive and enthusiastic attitude
• Outstanding communication, team management, and positive behavior management skills
• Excellent references
• A passion for sailing, the ocean, and working with kids

2019 Mandatory Dates:
• Senior Staff Training: June 19-21
• All Staff Training: June 24-28
• Monday-Friday 8AM – 4PM, from Monday, July 1 – Friday, August 9
• Staff Retrain Day: Monday, July 22
• End of Season Staff Day: Monday, August 12
• Additional work is available Tuesday, August 13 – Friday, August 23
• All staff are eligible to request up to 3 vacation days
Employer Contact Information
Courageous Sailing, Inc.
Jobs Courageous Sailing
One First Avenue
Boston MA 02129
United States
Courageous Sailing, Inc. Jobs Courageous Sailing
Facebook LinkedIn Twitter
Our Mission

Courageous Sailing transforms lives through sailing programs that inspire learning, personal growth and leadership.

Our Vision

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.

Employment Opportunities

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!

View Count 2,567