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Vice President of Asset Management

Cathleen Stone Island Outward Bound is one of the largest Outbound Bound Schools in the United States. It is located on one of the largest and most ecologically diverse islands among the 34 islands and peninsulas that comprise the Boston Harbor Islands National Park. Covering 204 acres, this island features mature forests, meadows, freshwater and marine wetlands, salt marshes, and critical geological features. In addition to its natural beauty, the island offers amenities such as a formal school campus with dormitories, a dining hall, classrooms, lab space, auditoriums, a gymnasium, outdoor challenge courses, and climbing towers. 



Cathleen Stone Island Outward Bound School (CSIOBS) is a not-for-profit organization that primarily provides adventurous and challenging experiential learning programs that inspire character development, compassion, community service, environmental responsibility, and academic achievement. Our organization serves adolescents from all economic and social communities of greater metropolitan Boston and the institutions and adults who support them.  


This is an exciting time to be our Vice President (VP) of Asset Management. This role presents a unique chance to oversee the management of all leases and island operations for our diverse assets. These include Cathleen Stone Island, the EDIC/BPRA Berth 10 dock, our headquarters at 21 Drydock in the Seaport area, and a potential urban campus in the Roxbury/Dorchester/Jamaica Plains neighborhoods of Boston.  The Vice President of Asset Management will work closely with our Program team to ensure our students have transportation, food service, lodging, classrooms, and meeting spaces.


A new CEO and President started in April 2023. She is leading CSIOBS in adopting a new strategic plan, advancing a new campus plan, and enhancing our business model based upon over 125 participants, including student parents, staff, board members, donors, BPS administrators, and many more.   Thanks to generous gifts from philanthropists, CSIOBS can transition programs to prioritize climate resiliency, sustainability, and entrepreneurship as part of our outdoor program based on Outward Bound principles and practices.  As an additional resource, this is a great article to review:    Thompson Island to receive a $12 million gift from Stone Foundation - The Bay State Banner




We seek a dynamic and creative professional dedicated to enhancing our housing, grounds and facilities, operations, events, and water transportation services. Specifically, the role will involve collaborating with the Executive Chef of our island kitchen, the Director of Special Events for events contracted by external companies, the Development Chief for development and fundraising activities, the Senior Director of Outward Bound Professionals for the training of adult leaders, the Safety Director for the implementation of safety initiatives, and our Director of Island Operations, who is responsible for waterfront operations, overall maintenance, and upkeep of our 204-acre island.

This role also includes managing the mainland office and potential real estate opportunities. The position will be a part of the senior management team and report directly to the CEO and President. Direct reports to the VP include the Director of Event Sales, the Director of Waterfront and Operations, and the Executive Chef. The VP will also support the Asset Management Committee of the Board of Trustees. The VP will oversee the strategy for and support rentals that generate approximately $2.8 million or more in annual event and conference sales.



  • Provide leadership in managing our assets—this includes all buildings (about 14), land, and equipment on the island, our main office space in the Seaport area, a dock as part of the EDIC/BPRA division of the City of Boston, and the proposal of an urban site in the Roxbury/Dorchester/Jamaica Plan.
  • Working with our insurance broker and financial consultants to manage our insurance contracts, including Property, Liability, Executive, Flood, Maritime, Cyber, and Worker’s Compensation Insurance, and all requirements as required by CSIOBS and OBUSA.
  • Oversee all vendors and maintain a competitive and consistent procurement process for all contracts.
  • Develop and manage housing equity strategies for employees.
  • Serves as or appoints a duty responsibility.
  • Managed and supervised the Unescorted Access Program in coordination with the National Park Service.
  • Oversee hospitality service for all island visitors (students, trustees/donors, volunteers, event/conference clients), including all food and beverage services.
  • Supervise the maintenance of facilities, fleet, and grounds and engage with senior staff members in developing more sustainable practices that minimize the organization’s carbon footprint.
  • Build and maintain a robust and collaborative relationship with the VP of Climate Resiliency, Sustainability and Entrepreneurship to support the success of all island education programs.
  • Guide the sales activities for the island’s fee-for-service education programs.
  • Build and maintain strong relationships with the Chief Development Officer, Director of Events, Director of Island Management, and the Executive Chef.
  • Serve as CSIOBS’s representative to the organization's key partners, such as the Boston Harbor Islands National Park Area, the National Park Service, and the Department of Conservation and Recreation.
  • Serve as the staff person to the Assets Management Committee of the Board of Trustees.



  • Excellent leadership and management skills, including a strong ability to set short-term and long-term priorities, balancing vision with changing circumstances and effectively managing seasonal, year-round, part-time, and full-time staff.
  • 7-10+ years of experience with progressively increasing management/leadership responsibilities. Candidates strongly encouraged from the real estate or hospitality industry with expertise in multiple disciplines (Negotiations, Procurement, Maintenance, Housekeeping, Security, and Transportation)
  • Minimum of 4-year degree required; advanced degree preferred.
  • Willingness and ability to work, as needed, to manage an island-based operation open seven days a week, 24 hours a day for 7-9 months of the year, while staffing operations appropriately to maintain a healthy work environment for self and all employees.
  • Excellent written and oral presentation and communication skills. 
  • Strong emotional intelligence, including a demonstrated ability to manage confidential, sensitive, or proprietary information discreetly and professionally.
  • Ability to navigate/build relationships and collaborate at all organizational levels.  Ability to build consensus, find common ground, and influence outcomes.
  • Flexible and comfortable navigating through ambiguity or shifting priorities.
  • Highly experienced in customer satisfaction, internally and externally, including the use of longstanding and new tools to consistently gauge and improve customer experience. Developing a net promoter score based on the customer experience is particularly interesting.
  • Strong fiscal understanding of budget, expenses, and costs; ability to forecast revenue and manage budget.
  • Solid computer skills: MS Word, Excel, and PowerPoint; familiarity with Tripleseat.



The CEO and President of CSIOBS is deeply committed to developing innovative solutions for complex challenges and advocating for social justice, especially for the young students supported by CSIOBS.  She is a natural problem-solver who thrives on tackling significant obstacles.   She is inherently entrepreneurial and unwavering in her pursuit of resources. Her approach is guided by four closely intertwined principles:  people, focus, passion, and place. She is currently dedicated to expanding CSIOBS's vision to better cater to our students' needs and empower them to become advocates for climate action, armed with the knowledge and drive to seek solutions.   The CEO and President will collaborate with architectural teams to support staff in creating climate-resilient programs and enhancing the island’s facilities and systems to minimize our carbon footprint. Please listen to this podcast to hear her initial thoughts.  Should you join our team, expect to work closely with a dynamic individual who prioritizes regular communications on all projects. 



The New England coast experiences various weather conditions. You will be required to work on the island 4+ or more times a week from March to November. CSIOBS will take care of your ferry transportation and onsite housing if needed. As a valuable team member, you will be asked to assist in loading and unloading cargo from the boat, which can be physically demanding. The work involves lifting and carrying packages weighing up to 25 pounds on and off moving docks and ramps. Every challenge presents an opportunity for growth and development. A criminal background check is required for this position.



This hire must reside in the Metropolitan Boston area and be willing to work on our island in Boston Harbor for nine-ten months of the year. When the island is closed to the public, there is the potential to work remotely or in person at our local office in Seaport, Boston.


We are committed to staff learning, growth, and development. Our holistic investment includes the following: 

  • Competitive salaries. This is an exempt position with a starting salary of $125,000 to $155,000. 
  • Medical insurance with up to 80% employer contribution. 
  • Dental, vision, FSA, life, and disability insurance plans. 
  • 401 (K) and Employer Match
  • Generous paid time off, including 17 vacation days, 20 personal days, and 13 company-wide holidays. 
  • Individual, local, regional, and national training. 
  • A commitment to developing leaders from within the organization. 
  • An organizational culture that supports staff well-being and holistic self-care. 
  • Ample opportunities to connect with the students and communities we serve. 



With a staff that cares deeply about social justice and equity, 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 and as a team. We hope you will join us as we continue to make a diverse organization that fosters a work environment where people from all backgrounds are welcomed and valued. 



Select "Apply for this Position" below to submit a resume and targeted cover letter addressed to Sylvia Watts McKinney, CEO and President.  Your entire application (resume and cover letter are both required for this role) is due on July 19, 2024, at or before 2 pm.



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. Cathleen Stone Island Outward Bound School 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.