Employment Opportunities

Join Us

Cathleen Stone Island Outward Bound is part of a national network of experiential and outdoor education programs for youth and adults. We use the inherent challenge of the island's outdoor spaces, as well as virtual spaces, to teach people of all ages to be compassionate leaders, serve their communities, and build character to ultimately reveal the full potential within all of us.

At Cathleen Stone Island Outward Bound, you will work with a team of passionate individuals with the shared vision of helping create a better future for Boston’s youth. As an organization, we strive to offer the same excellence to our staff that we do to our students: integrity and compassion are part of our values; collaboration, effective problem solving, and creativity play an essential role in our workplace culture; and community is at the core of everything we do.

Current Openings

Director of Major Gifts: Cathleen Stone Island Outward Bound is on the move! At an exciting point of momentum and growth as we prepare for the first phase of our five-year strategic plan implementation, we are seeking a Director of Major Gifts to ensure we are well positioned to meet our aggressive major giving goals for 2026 and beyond. Click here to learn more about the position and how to apply.  

Senior Director of Human Resources:The Senior Director of Human Resources (SDHR) will shape every facet of the employee journey, from talent strategy and recruitment to performance, culture, and well-being. Collaborating closely with the CEO and President, and senior leaders, the SDHR will help foster a thriving, inclusive organization deeply committed to youth development and the energy of our events-driven location. Click here to learn more about the position and how to apply.  

Field Instructor (Full time, Seasonal): Cathleen Stone Island Outward Bound is seeking seasonal instructor(s) who are passionate or have an interest in experiential learning, outdoor education, and working with Boston Public School students! We are seeking Seasonal Instructors for our Spring 2026 season to ensure we are well adapted to serve and grow our students for this season and beyond. Click here to learn more about the position and how to apply.

Equal Opportunity Employer

Cathleen Stone Island Outward Bound 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.

Questions? Feel free to reach out to [email protected].