Director of Major Gifts

Who are we?

Cathleen Stone Island Outward Bound School (CSIOBS) is in the heart of the Boston Harbor Islands. With a 200-year legacy of serving childing Boston, a 48-year partnership with the Boston Public Schools (BPS), and a 30-year affiliation with Outward Bound USA, 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 nine Outward Bound schools in the US, 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 partnering with public schools to deliver free experiential learning programs to students that will boost academic success and foster personal growth.

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.

Position Summary

Cathleen Stone Island Outward Bound School (CSIOBS) seeks a strategic and mission-driven Director of Major Gifts to lead and expand the school’s major gifts program. This role is central to supporting the organization’s strategic growth by managing a portfolio of individual donors and prospects contributing $5,000 or more annually. Reporting to the Chief Advancement Officer, the Director of Major Gifts will lead prospecting, cultivation, solicitation, and stewardship efforts while managing a growing portfolio and driving revenue goals. The Director of Major Gifts will also manage a part-time prospect manager to maintain a robust pipeline of new and early stage donors. This position is highly collaborative and will work closely with the Events and Marketing team as well as the President & CEO, Board of Trustees, and development leadership. It is an exciting opportunity to shape a high-performing major gifts program for a mission that transforms lives.

About You

You love frontline fundraising and bring a “hunter” mentality, actively connecting dots within the Greater Boston philanthropic landscape. Your persistence, optimism and energy for the Cathleen Stone Island Outward Bound mission is palpable and your ability to connect current and prospective donors to our programs and funding opportunities makes you a strategic fundraiser at heart. You are adept at working in Raisers Edge NXT and Salesforce and data-driven in your approach to managing your time and resources. You bring a collaborative mindset to the Development team at CSIOBS, partnering closely with leadership, Events and Marketing to ensure we are integrated in our donor cultivation and stewardship efforts. see opportunities for improving how we reach donors. You work well independently and enjoy being part of a high-performing team. You’re a quick study and can roll with change. You are passionate about outdoor exploration and experiential learning.

Key Responsibilities

• Donor Strategy & Relationship Management
  • Manage and grow a portfolio of 100–125 major gift donors and prospects.
  • Develop tailored strategies for donor cultivation, solicitation, and stewardship.
  • Conduct 15–25 meaningful donor/prospect interactions per month (in person or virtual).
  • Make direct, face-to-face solicitations, often in collaboration with senior leadership and board members.
  • Oversee development and execution of donor engagement plans using moves management tools.
• Prospect Identification & Campaign Support
  • Identify and qualify new major gift prospects through research, board engagement, and events.
  • Support and lead transformational giving opportunities, including campaign and legacy giving.
  • Coordinate donor visits, site tours (including on Cathleen Stone Island), and personalized experiences.
• Collaboration & Event Engagement
  • Work closely with the development, events, and communications teams to create compelling proposals, appeals, and stewardship materials.
  • Partner in planning and managing fundraising events, especially the annual gala (including content and seating strategy for major donors).
  • Assist in identifying and recruiting potential board and committee members.
• Data & Reporting
  • Maintain accurate and timely documentation in Raiser’s Edge CRM.
  • Produce and analyze reports tracking portfolio performance, donor pipeline, and revenue goals.
  • Use donor data to inform strategy and increase giving outcomes.

Qualifications

• Bachelor’s degree required; advanced degree preferred.
• Minimum 5 years of successful experience in major gifts, with a record of securing five- and six-figure gifts.
• Proven success in developing and managing high-level donor relationships.
• Excellent interpersonal and communication skills—written, verbal, and presentation.
• Strategic thinker with a collaborative mindset and high emotional intelligence.
• Strong organizational skills, with attention to detail and the ability to manage multiple priorities.
• Proficiency in Microsoft Office and donor databases (preferably Raiser’s Edge).
• Experience with prospect research, moves management systems, and data analytics.
• Knowledge of planned giving and campaign strategy is highly desirable.
• Ability to travel up to 40% across New England; must be available for occasional evenings and weekends.

Location & Other Requirements

This salaried position will require occasional night and weekend work. Administrative staff at CSIOBS work a hybrid schedule. Employees work out of our local office in Boston’s Seaport Neighborhood. Occasionally you will be required to go to our island in Boston Harbor for events, meetings, and trainings. Ferry transportation will be provided. A criminal background check is required for this position.

Compensation

This is a full-time, exempt position with a salary of $125,000.

Our Benefits:

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

• 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

How to Apply

Select “Apply for this Position” below to submit a resume and a compelling cover letter addressed to Jessica Thompson Somol, Chief Advancement Officer by September 5th.

Our Commitment to Equity, Diversity, Inclusion, and Belonging

Our staff and board care deeply about social justice, equity, and diverse perspectives and backgrounds, creating a rich environment and enhancing our ability to pursue our mission. We hope you will join us as we continue to make a diverse organization that fosters a work environment where people from all back grounds are welcomed and valued.

Equal Opportunity Employer

Cathleen Stone Island Outward Bound School is an equal opportunity employer and actively seeks staff that is 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.