Seasonal Field Instructor

Who are we?

Cathleen Stone Island Outward Bound School is located in the heart of the Boston Harbor Islands. With a 200-year legacy of serving children in Boston and a 50-year partnership with the Boston Public Schools (BPS) district, the Island is a beacon for experiential education, empowering young people through hands-on learning and skill building and outdoor adventure and exploration. We are a proud member of the network of nine Outward Bound schools in the U.S., with a shared mission to change lives through challenge and discovery. We are members of the Outward Bound USA and International organizations. 

Education is at the forefront of our work. Funded by a combination of philanthropy and a robust private events business, our outdoor educational programs are offered at no cost to families.  

What is our mission and how do we achieve it?

Cathleen Stone Island Outward Bound’s mission is to build stronger, more equitable school communities by delivering experiential learning programs that boost academic success and foster personal growth. Our research-based programs blend social-emotional and character leadership, STEM, and challenge based learning, giving students a unique opportunity to build life skills alongside academic ones.

Whom do we serve (students, clients, customers)

We offer education programs for school and youth groups, leadership development programs for professionals, hospitality and catering, and rental services for on-site events.

What is the opportunity?

Instructors are responsible for the co-delivery of Youth Programs. A foundational understanding of Outward Bound philosophy and methodologies is critical to this position and to the overall success of course delivery. Candidates must display foundational technical, facilitation, group management skills, and show an understanding of the course area and structure. Successful candidates will be a minimum of 18 years of age and have facilitation and/or trip-leading experience. A minimum of Wilderness First Aid (WFA) with CPR is preferred for this position (or the ability to obtain one during training).    

Start Date

August 17, 2026

What will you do?

• Full commitment to safety, course outcomes, and student experience 
• Serve as a Youth Programs Facilitator  
• Actively participate in pre-course training and briefings, and post-course debriefs 
• Help ensure prompt execution of their course’s preparation and post-course paperwork and logistics 
• Help manage any in-field or program transitions 
• Be familiar with the student medical forms and other pertinent participant information 
• Maintain communication with the Course Director while courses are in the field 
• Provide written and verbal evaluation of co-instructors and Course Directors necessary for their Individual Development Plan (IDP) and improved delivery of future courses 
• Provide 24/7 support to co-instructors and students while on course  
• Deliver course curriculum and remain accountable to student and course outcomes 
• Enforce Leave No Trace and other pertinent wilderness ethics on Cathleen Stone Island and all other program areas 
• Perform additional duties and responsibilities at the direction of the Course Directors, the Program Managers, and/or the Director of Delivery and Program Operations

Qualifications:

• Bachelor’s Degree or two years equivalent field experience preferred 
• Wilderness First Aid and CPR preferred (or the ability to obtain one during training)   
• Minimum of ACA Level 2 Kayak Trip Leader certification required for sea kayak applicants (or the ability to obtain said certification during staff training)
• Relevant work experience in the following: Working with participants age 12-18+, Managing challenging student behaviors, Working with diverse communities, Teaching and facilitation tailored to different learning styles, Teaching and facilitation tailored to different program sites (virtual or in-person) and Experience working on high ropes challenge courses a plus

Work Conditions:

• In Person course delivery on Cathleen Stone Island, Boston Harbor, and Boston Public Schools depending on program needs
• Must commit to the full duration of each course they are instructing, including preparation, weekends, and overnights if the program requires it 
• Must respond to course delivery needs and/or behavioral/medical needs as prescribed in the CSIOBS (Cathleen Stone Island Outward Bound School) Manual  
• Expected ongoing coordination and collaboration with all Course Directors and co-instructors 
• Courses are dynamic, and demand sound decision-making within the scope of CSIOBS methodology 
• Instructors must be able to manage their course with appropriate autonomy, as determined by the Course Director  
• Environmental fluctuations are typical of the New England coast, and can include hot, humid weather, and unseasonably cool, rainy, and windy coastal weather; must be comfortable working outside in either of these extremes for extended periods of time  

Physical Requirements:

• Commute includes a 25-minute boat ride to and from Cathleen Stone Island
• Must be at least 18 years of age
• Must be able to lift/carry 50 lbs
• Must be able to be on feet and/or active an average of 8+ hours per day

Compensation & Benefits:

Salary Range: $19.36 - $19.36

Competitive salary, commensurate with experience. Cathleen Stone Island Outward Bound Education Center is an equal opportunity employer and actively seeks staff as diverse as the communities it serves. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status, or any other characteristic protected by law.

Outward Bound has a zero-tolerance policy for incidents of child abuse and neglect. Protecting our minor students against abuse and neglect is of the highest priority.

Our Commitment to Equity, Diversity, and Inclusion

With a staff that cares deeply about social justice and racial justice, we believe that diverse perspectives and backgrounds create a rich work environment and enhance our ability to pursue our mission. We are committed to building an organization with raised consciousness to impact how we work with students, as well as how we work together as a team. We hope you will join us as we continue to build a social justice-centered organization that fosters a work environment where people from all backgrounds are welcomed and valued.