Training Programs Jobs in Massachusetts (NOW HIRING)

Job Type
Full-time
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, 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.
Start Date
Aug 21, 2026
What will you do?
Program Management

• 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.

Personnel Management

• 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 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.
• Complete performance reviews and individual development plans (IDP).
• Oversee timecards for course directors and instructors, ensuring overtime policies and expectation of hours worked is accurate and aligned with staffing schedule.

General Workplace Responsibilities

• Attend and participate in CSIOBS Staff Meetings and other site activities/events.
• Course direct, facilitate, site manage (if certified), and/or belay monitor (if certified) as needed or requested by a supervisor.
• Other duties as assigned.

Requirements
Qualifications

• A bachelor's degree and 5 years of commensurate experience.
• Knowledge and field experience with urban school-based programs and/or Outward Bound.
• At least two years of experience supervising employees.
• At least three years of program management experience.
• Passion for social justice, environmental stewardship, climate change responsiveness, natural resource and facilities management, and the outdoors.
• Fluency (writing and speaking) in Spanish is a plus.
• Familiarity with computer-based systems like Microsoft Outlook, Word, Excel, Teams and Google Drive. Experience with Customer Relations Management databases (i.e. Salesforce) or booking system (Triple Seat) a plus.

Work Conditions

• While the position will work primarily on the island, expect to spend some time working remotely or at our partner schools.
• 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

• All positions reporting hours to the island are asked to assist loading/unloading cargo from the boat as able. This involves lifting and walking with parcels upwards of 50 lbs on and off moving docks and up/down ramps
• Must be able to be on feet an average of 5+ hours per day.
• Must be comfortable on board a variety of boats and working around the water.
• Must have the mental and physical stamina to maintain a high quality of job performance while working in a dynamic fast-paced environment, often performing hours exceeding typical workday.

Compensation and Benefits
Salary Range
$59,000 - $63,000
Competitive salary, commensurate with experience. Employer sponsored health insurance with the option to select between three comprehensive plans. Premier dental and vision plan. 401(k) retirement plan with competitive match. Generous paid time off including, vacation, holidays, personal days, parental and sick leave. Flexible scheduling, pursuant to position. Work that engages a diverse and dynamic community of educators and other professionals, with the shared vision of shaping a better future for Boston's youth. A quality work life in Boston's vibrant Seaport district with frequent access to the natural wonders and positive impacts of Cathleen Stone Island.
Cathleen Stone Island Outward Bound School 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 justice-centered organization that fosters a work environment where people from all backgrounds are welcomed and valued.
Salary Description
$59,000 - $63,000