Vice President of Programs in South Boston, Massachusetts at CATHLEEN STONE ISLAND OUTWARD BOUND SCHOOL

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.

Our 2025-2030 Strategic Plan work is well underway with new curriculum design for our Connections (grades 7-9) and Green Ambassadors (grades 10-13) students. Deeply embedded in our service model, we hold that practicing hands-on science in our ecosystems enhances students’ ability to question, observe, and spark their curiosity about the natural world. Tapping into our challenge structures and participating in outdoor education courses helps them build confidence, resilience, and a greater sense of possibility. This unique combination of field science and dynamic challenges profoundly impact students' academic and social-emotional growth. In partnership with Stone Living Lab, Manomet Conservation Sciences, Boston Public Schools, and the Stone Foundation, CSIOBS has created a new learning sequence that integrates Outward Bound experiential and social emotional learning practices: Students.Harbor.Outdoors.Resilience.Environment (SHORE). It is our goal for our students to become outdoor enthusiasts and environmentally conscious champions and advocates.

The Opportunity

CSIOBS seeks a dynamic, student- and people-centered Vice President (VP) of Programs to lead the strategic and operational goals for all program education areas. This position will be part of the senior management team that drives the organization's overall strategy. With a program budget of $2.3 million and a current of 28 persons (year-round, eight to nine months, and seasonal employees), the VP will focus on the following areas: program leadership and management, external relationships, and knowledge management. This position reports to the Chief Executive Officer and President.

What's Exciting about this role?

• Lead transformational outdoor learning on a 204-acre island in Boston Harbor, where forests, salt marshes, wetlands, classrooms, challenge courses, and climbing towers become part of the student learning experience.
• Bring the Outward Bound pedagogy to life by helping students build resilience, confidence, environmental responsibility, leadership, and a stronger sense of possibility through hands-on, challenge-based learning.
• Shape innovative programming at the intersection of experiential education, field science, social-emotional learning, workforce development, and climate resilience.
• Join a mission-driven senior leadership team with the opportunity to expand CSIOBS’ impact across Greater Boston, deepen partnerships with schools and community organizations, and influence the next chapter of youth development on the island.

What will you do?

The VP will drive the overall program strategy, strengthen the core program model and performance, lead and advance innovation initiatives designed to deepen CSIOBS’ reach and impact, work with OBUSA staff on learning and evaluation, and carry out the duties as prescribed in our 2025 - 2030 strategic plan.

Leadership & Management:

Manage direct reports for up to 5 persons.

• Attract, develop, coach, and retain the program team; oversee the entire Program Team function and activities (e.g., program design, systems management, data collection, reporting, and evaluation).
• Enhance, oversee, and implement the design, development, and delivery of a program strategy that maximizes the outcomes of CSIOBS program elements (Connections, Discovery, Summer Expeditions, and Green Ambassadors.)
• Work with education partners to develop the SHORE learning sequence for 7 – 9 graders consistent with Massachusetts. In addition, explore the possibilities of a new curriculum for 10 to 12 graders.
• Lead the administration of the current Green Ambassadors program and expand resources to strengthen the elements of a career exploration to a workforce development program. In addition, supervise the redesign of the Green Ambassadors program with support of external contractors, including a pitch plan competition, and recruit 50-100 volunteers to serve as mentors, judges, coaches, and investors.
• Collaborate with Stone Foundation, UMass Boston, and Stone Living Lab to launch this expanded Green Ambassador program. This program could include micro credential badging and/or pre-college credit for high school students.
• Ensure that the organizational vision for equity, diversity, inclusion, and belonging (EDIB) is incorporated into all facets of the program.
• Be creative and innovative in raising government agency partnerships with the CEO and President and Chief Advancement Officer to fund program requirements.
• Strong emotional intelligence, including a demonstrated ability to manage confidential, sensitive, or proprietary information discreetly and professionally.

External Relationships:

• Present to the board at quarterly meetings, in-person and virtual meetings, and on committee calls.
• Support Chair and Co-Chair of the Board of Trustees Education Committee through meetings and lead 3-4 sessions per year with the whole committee.
• In partnership with other leaders, initiate, develop, and manage relationships with school leaders locally and meet/visit with school leaders regularly.
• Cultivate Boston Public Schools district relationships to become strategic partners.

Knowledge and Relationship Management:

• Establish and nurture relationships with site staff to understand regional perspectives and needs, build trust, and facilitate program design, implementation, and evaluation informed by those closest to program participants.
• Seek and create innovative opportunities to invest in staff through support, training, coaching, and observation.
• Build strong collaborative relationships with senior management team members1 and their direct reports to integrate cross-program activities.
• Develop the necessary systems, processes, and tools to better support the facilitation, collection, and sharing of knowledge generated by the programs.
• Partner with the Senior Management Team to ensure program growth and expansion goals; with the Advancement Department to ensure impact data is identified and collected for fundraising purposes.
• Collaborate and develop essential partnerships that will further our mission and ensure that our students have a firm plan for participating in our scope and sequence with graduating from high school and pursuing a post-secondary pathway.
• Champion a data, quality, and evaluation culture that aligns with programmatic strategic outcomes.
• The ideal candidate for this role is comfortable leading through changing priorities and holding exacting standards for a team’s high-stakes work. The risks and potential of experimentation energize you as a path to breakthrough strategies in outdoor spaces, and you know how to inspire teams to achieve ambitious goals.

Reporting to the CEO and President of CSIOBS:

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. Her approach is guided by four closely intertwined principles: people, focus, passion, and place. She is 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. 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 communication on all projects.

Compensation and Benefits

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 20 personal days, 13 company-wide holidays and up to 17 vacations days.
• Individual, local, regional, and national training.
• A commitment to developing leaders 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.

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.

Who are you?

All CSIOBS staff bring a commitment to our mission of unleashing students to be challenged via discovery, as well as the ability to thrive in an environment that values excellence, gratitude, well-being, diversity, authenticity, and collaboration. All candidates should demonstrate leadership, coaching, relationship management experience, and substantial success in managing funder relationships. Specifically, the VP will bring:

Qualifications Needed: At least ten years of management experience, with preference given to those with an advanced degree.

Program Leadership and Management: The ideal candidate will have a hands-on approach to leading various initiatives and a background in outdoor and wilderness programs, career readiness, and post-secondary programming.

Exceptional Communication and Influencing Skills: The VP must have strong written and verbal communication skills, be a persuasive, credible, and polished communicator, and have excellent interpersonal and multidisciplinary project skills.

Relationship Management & Interpersonal Skills: A “people-first” mindset, strong ability to

build trusting relationships and convey empathy in all interactions.

Cultural Competence: An understanding of systemic and institutionalized racism facing communities of color and the historical context of privilege and power in America, with sensitivity and humility in engaging colleagues around these topics.

Systems Management and Improvement: Skill in creating and maintaining transparent, well-defined systems and processes, with an eye on continuous improvement.

A Resource to Our Network of Partners: Help amplify partner successes, make connections between partners, facilitate learning sharing, and offer your expertise to partners in our networks wherever it makes sense.

An Entrepreneurial Approach to the Work and Learn New Skills: In our fast-paced, unstructured environment, we encourage staff to figure things out independently and ask for help if they’re stuck.

Adaptability: You should prefer working in a fast-paced environment and be invigorated and motivated by new opportunities and challenges.

Accountability: Personal responsibility for work product and results; excellent organizational skills to juggle multiple projects and ad hoc requests. Work closely with the Finance Department to budget and monitor programmatic work funding and ensure we promptly report on outcomes. Guide and coach team members on proactively strategizing to improve program delivery for progressively increasing effectiveness and accountability.

Location Requirements

This hire must reside in the Boston area and be willing to work on our island in Boston Harbor for eight months of the year. During the off-season, the hire will work at our local office in Seaport Boston.

Work Conditions and Physical Requirements

The New England coast experiences various weather conditions, which can be challenging to adapt to. You will be required to work on the island 4+ or more times a week from April to October. Ferry transportation is available. 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.

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.

How to Apply?

Please submit your resume and a cover letter addressed to Sylvia Watts McKinney, CEO and President to the link below by 2 pm EST on Friday October 2nd, 2026.

If you should be selected for an interview, here are a few resources to help you as you get ready to apply for this opportunity:

• Good Company by Arthur M. Blank, “You’re Only as Good as Your People”, pp. 45 – 62
• No One Left Alone by Liz Walker, “The Inequity of Grief” , pp. 57 – 70
• 5 Easy Theses: Commonsense Solutions to America’s Greatest Economic Challenges by James M. Stone, “Education”, pp. 99 -134
• Climate Change and Youth: Turning Grief and Anxiety into Activism by Linda Goldman, “Youth Activists for the Environment”, pp. 195 - 218