Program Manager

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’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.

What is the opportunity?

The Program Manager role is responsible for co-managing and coaching a team of facilitators, and course supervisors to deliver high quality STEM and Outward Bound character development programming for Boston Public Middle Schoolers. This role takes on the partnership management of a portfolio of Connections partner schools.

This role is also responsible for managing all aspects of planning, delivery, and day to day operations their assigned program.

Start Date

Aug 3, 2026

What will you do?

Program Management

• Oversee the direct partnership management for a portfolio of Year-Round Connections schools including coordination between CSIOBS and assigned school teachers and leaders.
• Develops, maintains and communicates program operations and schedules.
• Ensures programs are delivered safely and in a high-quality manner quality as evidenced by surveys, observations and data.
• Build and maintain positive working relationships with community and school partners.
• Support the distribution, collection, and processing of student enrollment paperwork.
• Ensure that school-based programs are operating in accordance with Boston Public School policies.
• 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.
• Ensures all aspects of quality and safety of program delivery in both educational and work components of the program.
• Ensures that all course and incident data are entered into the appropriate databases (OBUSA, Salesforce).
• Ensures employees are appropriately supervised, oriented, and engaged.
• Ensures that work hours for direct reports are recorded and submitted.
• Collaborates with Family Engagement manager on student outreach and recruitment.

Program Management

• Lead, manage, and coach a team of Course Directors and Instructors to support students through academic and Social Emotional Learning.
• Develop Instructors as strong facilitators and leaders through their Outward Bound experience.
• Model leadership that reflects Outward Bound’s culture and values and create spaces that empower Instructors and Course Directors.
• Conduct regular observation and coaching sessions with Instructors to assess, strengthen, and grow their skill set.
• Collaborate with the Admin team to plan, develop, and facilitate regular trainings and professional development opportunities.
• Complete performance reviews and individual development plans (IDP).

General Workplace Responsibilities

• Attend and participate in CSIOBS Staff Meetings and other site activities/events.
• Course direct, facilitate, site manage (if certified), and/or…