Director Stone Island Jobs (NOW HIRING)

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 Programs Course Director (CD) is responsible for the overall quality, consistency and safety of the Cathleen Stone Island Outward Bound (CSIOBS) courses. A candidate for this role needs to demonstrate an outstanding ability to supervise and train others, as well as have experience leading youth programming. The Course Director's primary role is to ensure course delivery meets program standards for safety and quality. While in the field, Course Directors will observe and mentor staff, focusing on course safety, instructor development, and educational outcomes. Course Directors should be at a level of skill with their course elements wherein they could comfortably replace a Lead Instructor in the field if the need presented itself. The Course Director is often coordinating with other departments, islands or outside entities to ensure the courses run safely and smoothly. Course Directors must display the highest level of professionalism, dedication and commitment to safety both in the field and at base and are expected to be on call 24 hours a day for the entire duration of their course. A minimum of Wilderness First Aid (WFA) with CPR certification is preferred for this position (or the ability to obtain one during training). 

Start Date

Aug 10, 2026

• Ensure the delivery of the Outward Bound Mission and educational programming by the instructional teams.  
• Support course delivery by providing logistical support, conducting coaching observations, and mentoring field staff.  
• Ensure course delivery aligns with CSIOBS's instructional tools, preferred practices, and policies and procedures.   
• Provide 24/7 support to field staff to manage medical or behavioral evacuations and early departures; arrange medical support; manage impending inclement weather that may necessitate itinerary adjustment, and any other potential or real threat to safety or course objectives 
• Ensure timely execution of instructor course prep and post-course wrap-up 
• Produce all necessary course paperwork by the prescribed deadline 
• Provide consistent and professional communication with staff, students, and families during and post-course.  
• Make necessary arrangements with kitchen, waterfront, site management, staffing, and all other aspects of Cathleen Stone Island as necessary for course delivery 
• Manage student medical forms and other paperwork 
• Provide written and verbal evaluation of instructors necessary for their professional growth and improved delivery of future courses 
• Maintain communication with the Program's Team Admin (including program managers, coordinators and directors) 
• Participate in student recruitment efforts, including in-school recruitment events and island-based open houses 
• Utilize booking and client management systems (Triple Seat and Salesforce) to support programs, as needed, creating internal forms to communicate client needs, tracking and updating operations and ferry information, etc.
• Work with the Program Directors, Managers, and other Course Directors to deliver staff training and PDs. 
• Serve as a Connections, Green Ambassadors, or a Discovery Program Course Director or Instructor, as dictated by staffing needs 
• Work with assigned Program Manager on the design and execution of assigned summer programming 
• Perform additional duties and responsibilities at the direction of the Program Manager Team 

Accountabilities

Supervision:  

• Lead Instructors 
• Instructors and/or Crew Leaders 
• Interns 
• Students  

Key Relations: 

• Director of School Programs 
• Associate Director of Group Programs and Training 
• Associate Director of Impact  
• Logistics Manager 
• Program Managers 
• Vice President of Safety and Administration  
• Course Director Team 
• Instructor Team 
• Safety Team 
• MVOB Captains and Deckhands 

Requirements

Qualifications

• Bachelor's degree preferred 
• 3-4 years relevant field experience in the following: 
• Working with participants ages 11-18+ 
• Managing challenging student behaviors 
• Working with diverse communities 
• Teaching and facilitation tailored to different learning styles and program sites 
• 1-2 years relevant management experience, including training, development and management of staff.
• Ability to demonstrate emotional regulation, good judgement and balanced decision-making in stressful situations.   
• Serve as role model for students, staff and community, able to manage a range of student behaviors in a positive and professional manner.  
• Ability to build and maintain a positive group culture.   
• Flexible, adaptable and open to change.  
• Wilderness First Responder & CPR certification required 
• Intermediate computer skills, working knowledge of Microsoft Office Suite (Word, Excel and Outlook).  
• Spanish proficiency preferred  

Work Conditions

• Expected ongoing coordination and collaboration with all CDs and Program Managers 
• Courses are dynamic, and demand sound decision making within the scope of CSIOBS methodology 
• CDs must be able to manage their course(s) with appropriate autonomy 
• Environmental fluctuations are typical of the New England coast, and can including 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  
• Must be available for course support 24 hours a day for duration of course 
• Must respond to course delivery needs and/or behavioral/medical needs
• This position requires a criminal background check 

Physical Requirements

• Must be currently vaccinated against COVID-19 up to CDC guidance  
• 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 and down ramps 
• Must be able to be on feet an average of 3+ hours per day 
• Able to work though inclement weather conditions that include heat, rain, snow, or cold. 

Compensation and Benefits  

Salary Range: $24.76-$24.76/hour

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.