Seasonal Field Instructor

Description

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.

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.

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

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

• 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

• 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

• 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…