Program Manager; Discovery, Expeditions, and Training

Description

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.

Cathleen Stone Island Outward Bound’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.

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.

The Program Manager, Discovery, Expeditions and Training, is responsible for managing program logistics and the delivery of Discovery and Expedition programs with a focus on safety and quality of student outcomes.

Primary responsibilities include managing aspects of planning, delivery, and day to day operations of the assigned programs including client relationships, the training and oversight of staff, management and communication of program schedules, program content development, and clearly reporting on programmatic outcomes.

This role is responsible for informal management and coaching a team of up to 30 facilitators and course directors to deliver high‑quality Outward Bound programming to our retail clients and school partners.

The program manager team is part of a larger, dynamic, and collaborative team of managers and directors who share the responsibility of delivering mission‑driven programming on Cathleen Stone Island while maintaining the highest levels of safety and quality. This role reports to the Associate Director of Group Programs and Training. This position will manage members of our course director team and instructional staff.

Aug 21, 2026

• Oversee the direct partnership management for a portfolio of school partners and expedition partners.
• Develop, maintain and communicate program operations and schedules, in conjunction with Program Manager team, to appropriate departments (ie. Kitchen, Operations, etc.)
• Ensure programs are delivered safely and in a high‑quality manner quality as evidenced by surveys, observations and data.
• Support Course Director with programmatic needs for the duration of the course
• Build and maintain positive working relationships with community and school partners.
• Support the distribution, collection, and processing of student enrollment paperwork.
• Collaborate with the Admin team to analyze survey results and implement subsequent changes based on results.
• Assist Program Director in developing and reconciling an annual budget.
• Ensure that all course and incident data is entered into the appropriate databases.
• Collaborate with Family Engagement manager on student outreach and recruitment.

• Lead, manage, and coach a team of course directors and instructors to support students through social emotional learning.
• Collaborate with the Associate Director of Training and Group Programs to plan, develop, and facilitate regular training and professional development opportunities.
• Develop instructors as strong facilitators and leaders through their Outward Bound experience.
• Model leadership that…