Summer Youth Program Jobs

We seek highly motivated, skilled sailing instructors and educators, those who will ensure that our students are safe, have fun, and have the optimal setting to grow and learn as blossoming sailors.

Each year, Courageous hires over 100 seasonal staff and instructors. Our instruction team is enthusiastic, energetic, and diverse, united by common passions for sailing, the ocean, and working with kids. They range in age and experience from high school and college sailors, to NOLS instructors, to tall ship crew and seasoned cruisers. We also hire experienced educators, naturalists, and outdoor educators who enhance our summer programs with their unique expertise.

Our staff members also enjoy a wide range of benefts, including: racing opportunities, opportunities to work for our adult program, professional development support, connection to the growing Courageous alumni network, and the satisfaction of having a job that makes a difference. Come spend your summer sharing your passion, making a difference, and being part of an exceptional team of instructors who are united by their dedication to the Courageous mission.

Applications for 2017

Available positions for the summer will be posted in early 2017.

Site Director and Assistant Site Director

Reports to: Youth Program Director
Status: Seasonal, Full-Time
Date of Last Revision: May 2016
Please note that while the Site Director position has been filled, we are still accepting applications for the Assistant Site Director position.

Description:

Courageous Sailing operates summertime youth sailing programs at three different locations: the Charlestown Navy Yard on Boston Harbor; Camp Harbor View, located on Long Island in Boston Harbor; and Jamaica Pond, a smaller, freshwater venue located in the heart of the city of Boston.

At each site, a Site Director and Assistant Site Director are responsible for overseeing the day-to-day operation of the youth programs at that site. The Site Directors report to the Youth Program Director, and supervise Head Instructors (5-7 at Charlestown; 2-3 at Jamaica Pond; 2-3 at Camp Harbor View).

Each Site Director functions like their site’s principal and operations manager. This position is a great leadership opportunity for the sort of individual who, for example, has previously been a Head Instructor at another program and is interested in gaining more staff/logistics management experience.

Responsibilities:

  • Training and Communication
  • Collaborating with the Youth Program Director and Youth Program Outreach Coordinator to plan and conduct Staff
  • Orientation, Staff Development Clinics, and weekly staff meetings
  • Attending all Senior Staff meetings
  • Communicating daily events, needs, issues and successes to the Head Instructors, Youth Program Director, Youth
  • Program Outreach Coordinator, Evaluation Coordinator, Fleet Manager, and Adult Program Director, as needed or as appropriate.
  • Site Management
  • Opening and Closing the site each day (8 am – 4 pm)
  • Managing the division of site resources between Head Instructors and their respective classes
  • Communicating via radio with all Head Instructors to coordinate the safe departure and return of each class at the beginning of the day, lunchtime, the end of the day, and during any emergency management procedure (e.g. bringing boats home before incoming weather event).
  • Communicating via radio with passing ships, ferries, barges and others for whom the youth sailing program may pose a navigational obstruction or hazard
  • Ensuring all boats are tied down and equipment is stowed properly at close of each program session
  • Ensuring the facility is clean and ready for the next day or programs beginning after 4 pm
  • Staff and Student Management
  • Promoting a culture of safety, fun, and learning
  • Work with the Youth Program Director and Outreach Coordinator to create a strong sense of community and support among the staff members at your site
  • Working to track students’ attendance
  • Working to ensure all staff time cards are complete and accurate
  • Ensuring all youth programming proceeds on time
  • Approving Head Instructors’ Daily Float and Lesson Plans, and, as needed, discussing ways to execute their plans more effectively or safely
  • Resolving any issues with students, parents, and staff members, as well as passing these on to the Youth Program Director if problems persist
  • Enforcing all safety and instructional standards, and leading the Emergency Action Plan
  • Maintaining an injury log and ensuring all incident reports are completed and delivered to the Youth Program Director in a timely fashion
  • Interim and end-of-season evaluations of Head Instructors and any other supervisees
  • Performing additional related tasks as designated by the Youth Program Director

* Please note that specific duties, schedule, responsibilities vary slightly by site, and listing each difference here would be inefficient. The Charlestown site, which puts over 100 youth and instructors on the water daily, is far larger than either the Jamaica Pond or Camp Harbor View sites. Site Directors in these locations function more like traditional Head Instructors. Clarification and more details will be discussed during the candidate’s interview.

Qualifications:

  • Experience leading teams of staff members within youth development, sailing, education, or camp settings
  • Experience making weather-related programming decisions utilizing a combination of online tools, sensory cues, past experience, and sound judgement
  • Comfort with VHF radio communication
  • Ample experience in sailing and sailing instruction
  • Current First Aid and CPR certification, or more advanced, is required
  • A love for mentoring younger staff and for creating a sense of community and camaraderie among co-workers
  • Current US Sailing Small Boat Level 1 Certification or its equivalent is preferred but not essential
  • Competency in driving a range of small outboard powerboats (e.g. center-console, 17′ Boston Whalers and Easterns)

2016 Schedule:

Senior Staff Training: June 22-24
All Staff Training: June 27-July 1
Monday-Friday 8:00 AM – 4:00 PM, from Tuesday, July 5 – Friday, August 19

Team Leader, Swim Sail Science!

Reports to: Swim Sail Science Coordinator
Status: Seasonal, Full-Time
Date of Last Revision: December 17, 2015

Description:

Swim Sail Science (SSS) is a no-cost, fun, six-week program in conjunction with Boston After School and Beyond and Boston Public School students going into grades 4th and 5th who are identified as being at risk of summer learning loss and who can most benefit from summer programming. During our program we provide participants with inquiry-based instruction and activities in English language arts, math, sailing, swimming lessons, and marine science. The students targeted are from low-income neighborhoods and will receive transportation to and from Charlestown as well as breakfast and lunch all at no cost.

Responsibilities:

  • Ride on the buses to ensure students get to and from the sailing center each da
  • Monitor student’s behvaior while on the buses
  • Monitor breakfast and lunch each day
  • Oversee behavior management of students
  • Engage students during transitions with games and other activites
  • Attend 3 days of senior staff orientation and 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

Qualifications:

  • Experience in and/or interest in working with underserved populations and students with behavioral difficulties
  • Desire for personal growth and opportunities to learn in a unique program enviroment
  • Behavior management and teaching skills
  • 2-3 years of youth development or teaching experience at schools, camps, or other informal learning settings
  • Current First Aid/CPR certification
  • Positive and enthusiastic attitude
  • Team-oriented
  • Excellent references
  • A strong interest in and/or experience with sailing and the marine environment

2016 Schedule:

Senior Staff Training: June 22-24
All Staff Training: June 27-July 1
Monday-Friday 7:00 AM – 4:00 PM, from Tuesday, July 5 – Monday, August 15

Instructor in Training Program Coordinator/Head Trainer

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

Description:

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.

Responsibilities:

  • 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

Qualifications:

  • 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

Instructor in Training Assistant Head Trainer

Reports to: IIT Head Trainer
Status: Seasonal, Full-Time
Date of Last Revision: December 17, 2015

Description:

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.

Responsibilities:

  • 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

Qualifications:

  • 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

Sailing Instructor

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

Description:

Courageous Sailing operates an extensive summer program for youth ages 8-18 at three different sites throughout the Boston area. At our main site on Pier 4 in Charlestown Navy Yard we have a five-step program that takes students from basic classes through instructors in training (IIT) as well as a program that provides free sailing and science programming to Boston Public School students. We are also looking for instructors at our Jamaica Pond and Camp Harbor View sites. Our instructors are skilled sailors who act as role models and function well as a team. Please find the descriptions of each step and other summer programs on our website, all for which we are hiring sailing instructors.

Responsibilities:

  • Sail in boat with students
  • Have students assist with sailing the boat
  • Teach sailing safety
  • Follow directions given from your step leader
  • Attend all 5 days of 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

Qualifications:

  • Exceptional sailing ability
  • Current First Aid/CPR certification
  • At least one year of sailing instructor experience for Step 1 and SSS
  • At least two years of sailing instructor experience for Steps 2 and 3
  • Positive and enthusiastic attitude
  • Outstanding communication and team management skills
  • Excellent references
  • A passion for sailing, the ocean, and working with kids

2016 Schedule:

All Staff Training: June 27-July 1
Monday-Friday 9:00 AM – 4:00 PM, from Tuesday, July 5 – Friday, August 19