OBP Facilitator

CATHLEEN STONE ISLAND OUTWARD BOUND
Boston, MA

Job Description

Job Description

Description:

Who are we?

Cathleen Stone Island Outward Bound School is a National and State Park located in the heart of the Boston Harbor Islands, With a 200-year legacy of serving children in Boston and a 48-year partnership with the Boston Public Schools (BPS), 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 11 Outward Bound schools in the U.S., with a shared mission to change lives through challenge and discovery.

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 School’s core mission is to build stronger, more equitable school communities by delivering free experiential learning programs that boost academic success and foster personal growth. Our research-based programs blend STEM, social-emotional, 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 programs for Boston Public School middle school and high school students, fee-for-service programs for school and youth groups, and leadership development programs for professionals. We also fund our transformational programs by hosting private and corporate events and weddings.

Position Summary

Responsible for delivery of Outward Bound Professional program in collaboration with Senior Director, Outward Bound Professional, and colleague Facilitators. The OBP Facilitators are part of a dynamic and collaborative team whose shared responsibility is that of delivering programming of the highest quality of excellence and safety to adult professional groups. Program delivery is based on the client’s specific goals.

Cathleen Stone Island Outward Bound School Education Center’s Professional programs deliver customized adult programs designed to yield high-performance teams, cultivate a positive, supportive, and empowering culture, and form greater trusting relationships amongst colleagues. Set amidst the serene wilderness of our 204-acre island preserve or designed in the location of your choosing, our programs stimulate creative development and incorporate a global perspective to meet the diverse challenges of today’s organizations. OBP programs operate year-round.

ESSENTIAL DUTIES AND RESPONSIBILITIES

  • Design and deliver OBP program Initiatives based on client goals, if an ‘open’ program.
  • Deliver OBP pre-designed ‘tell’ program, if requested by the client.
  • Manage safety for clients and colleagues during the program.
  • Manage all equipment needed for the program including Initiatives and if climbing, helmets/harnesses/ropes, or raft building equipment, etc.
  • Complete attendance, Evaluation tally, end-of-course report, and incident/accident forms if necessary in a timely manner.
  • Fully become part of and participate in the Outward Bound Professional community.

Requirements:

QUALIFICATIONS

  • Understanding of and/or interest in adult team and leadership development.
  • Understanding of and/or interest in the Outward Bound Process and/or facilitation.
  • Familiarity with experiential education, specifically pertaining to professional development.
  • 3+ years’ business/work experience preferable.
  • Current WFA or WFR certification and Adult CPR required.
  • Aptitude for and experience with technical climbing is a plus.
  • Ability to work collaboratively with colleagues as a team member.

WORK CONDITIONS

  • Work environment is dynamic and changing. Work may include time spent outside in inclement/harsh weather, sitting at a desk 6+ hours per day, or traveling to schools/client sites.
  • Commute includes a 25-minute boat ride to and from Thompson Island.
  • Must be willing to stay on Island occasionally the night before OBP programs.

PHYSICAL REQUIREMENTS

  • All CSIOBS employees are asked to assist in loading/unloading cargo from the boat as able. This involves lifting and walking with parcels upwards of 50lbs on and off moving docks and up/down ramps.
  • Must be able to be on feet an average of 6+ hours per day.

COMPENSATION AND BENEFITS

Competitive pay commensurate with experience. Worker’s Compensation Insurance. Optional Accident Insurance. Access to professional discount programs for gear and clothing.

Cathleen Stone Island Outward Bound School 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.

Posted 2026-06-05

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