Chief Advancement Officer

Cathleen Stone Island Outward Bound School (CSIOBS), formerly known as Thompson Island Outward Bound Education Center, seeks a strategic, innovative, entrepreneurial, and results-oriented Chief Advancement Officer (CAO). A local and national treasure, CSIOBS is a beacon for experiential education with a mission to build stronger, more equitable school communities by delivering free programs that boost academic success and foster personal growth, empowering young people through outdoor education and exploration. CSIOBS   is one of the nine Outward Bound USA schools dedicated to changing lives through challenge and discovery.

CSIOBS is a not-for-profit organization providing adventurous and challenging experiential learning programs that inspire character development, compassion, community service, environmental responsibility, and academic achievement. The organization serves adolescents from all economic and social communities of greater metropolitan Boston and the institutions and adults who support them. Many of the students CSIOBS serves attend Boston Public Schools, and CSIOBS has been associated with Boston Public Schools for over 50 years. CSIOBS firmly believes that access to green spaces and natural environments positively impacts children's mental health and well-being, laying a solid foundation for them to become lifelong learners. 

Deeply embedded in CSIOBS’s service model is the belief that practicing hands-on science in the Island’s ecosystems enhances students’ ability to question, observe, and spark their curiosity about the natural world. Tapping into challenge structures and participating in outdoor education courses help them build confidence, resilience, and a greater sense of possibility. This unique combination of field science and dynamic challenge profoundly impacts students' academic and social-emotional growth. CSIOBS intentionally includes STEM initiatives in its programming and takes responsibility for stewarding students to become environmentally conscious champions and advocates. 

The 204-acre nature preserve is one of 34 islands and peninsulas that comprise the Boston Harbor Islands National and State Park. This one-of-a-kind outdoor classroom is a mere 25 minutes by a CSIOBS ferry from downtown Boston, and serves as an urban oasis to thousands of young people from Boston’s Public Schools (BPS) and to guests who choose to host their special events on the grounds. See the Island and hear from students in this short video highlighting CSIOBS from WCVB Boston’s Chronicle. 

The next Chief Advancement Officer will have the opportunity to partner with an inspirational CEO and President as the organization embarks on its new strategic plan. (To learn more about the CEO and President, this IM podcast interview shares her background and vision.) In alignment with the organization’s strategic plan, they will design and execute a comprehensive development strategy to propel CSIOBS into the future, fostering sustainable growth and impactful outcomes for Boston’s youth. This will include assessing current development activities as well as team capacity and needs, and charting a course to grow the development operation to meet CSIOBS’s ambitious goals. 

As well as a top-notch strategist and team leader, the CAO will be a proven producer who will build and personally manage a portfolio of high-net-worth individual and institutional funders, clearly articulating and prioritizing the case for supporting CSIOBS’s unique mission. Importantly, this individual will play a key role in galvanizing a new generation of funders while maintaining deep and meaningful ties with the organization’s long-standing and most generous benefactors. 

Compensation for this position will be competitive and negotiated in good faith, with the range beginning at $200,000. CSIOBS’s main campus is on the Island. Year-round and seasonal workers are also co-located on the mainland (in offices in Boston’s Waterfront District) and/or remotely. This hire will reside in the Boston area and work on the Island for eight months of the year; during the off-season, they will work at the local office in Boston’s Seaport neighborhood.

Cathleen Stone Island Outward Bound School’s staff and board care deeply about social justice, equity, and diverse perspectives and backgrounds, creating a rich work environment and enhancing their ability to pursue their mission. They hope you will join them as they continue to grow a diverse organization that fosters a work environment where people from all backgrounds are welcomed and valued. 

Screening of complete applications will begin immediately and continue until the completion of the search process. Confidential inquiries, nominations, referrals, and applications (including resumes and two- to three-page letters of interest responding to the opportunities and challenges outlined above) should be submitted electronically below.

Kennedy Kearney-Fischer is leading this search with Karson Freeman and Rachel Banderob.

Cathleen Stone Island Outward Bound School is an equal opportunity employer and actively seeks staff that are as diverse as the communities they serve. 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 their minor students against abuse and neglect is of the highest priority.