Director of Major Gifts

ABOUT THE OPPORTUNITY

Cathleen Stone Island Outward Bound is on the move!  Located in the heart of the Seaport District in Boston, MA on Drydock Ave, we are one of Boston’s longest standing youth development organizations, serving more than 1,700 students a year from Boston Public Schools. We are at an exciting point of momentum and growth as we prepare for the first phase of our five-year strategic plan implementation. In just four months we have built a fully staffed Advancement Team and now all we need is YOU. The Director of Major Gifts will round out our team to ensure we are well positioned to meet our aggressive major giving goals for 2026 and beyond.

The Director of Major Gifts will manage and grow a portfolio focused on gifts of $5,000 through six-figures, with responsibility for advancing donors through the full lifecycle from discovery and qualification to solicitation and long-term stewardship. Working closely with the Chief Advancement Officer, President & CEO, and members of the Board, the Director will be integral to the team’s goal of $3 million in major gifts this year. This position offers the opportunity to build and deepen meaningful relationships with donors who are passionate about educational equity, outdoor experiential learning, and youth development. The Director will bring an entrepreneurial mindset to growing the major gifts program strengthening systems, refining strategy, and shaping processes that support long-term fundraising success.

This is not a traditional Major Gifts Officer role with a static, inherited portfolio. Instead, it is an opportunity for a relationship-driven fundraiser who enjoys prospecting, building pipelines, and helping an organization evolve thoughtfully and sustainably. The Director of Major Gifts will prospect, qualify, solicit, and steward donors while also serving as a strategic partner to the Chief Advancement Officer, President & CEO, and Board members supporting their engagement with donors and helping to foster a strong, organization-wide culture of philanthropy.

WHAT SUCCESS LOOKS LIKE IN YEAR ONE

• A qualified, actively moving major gift portfolio
• Overall portfolio management
• A strong and growing donor pipeline
• New major gifts closed through proactive prospecting
• Effective moves management systems in place
• Successful partnership with CEO, CAO, and Board
• Clear reporting and revenue forecasting
• Strengthen engagements with personal relationships and building and stewarding prospects at events.

STRATEGIC LEADERSHIP, SCOPE AND INFLUENCE  

• Serves as the primary strategic thought partner for the organization’s major gifts strategy
• Independently develops and recommends prospect assignments and solicitation strategies in alignment with organizational priorities
• Leads the annual major gifts planning process, incorporating input from leadership and fundraising partners

ESSENTIAL FUNCTIONS

Strategic Leadership & Program Development

• Serve as a strategic partner to the Chief of Advancement, President & CEO, and senior leadership, contributing to organization-wide strategy beyond fundraising.
• Lead the evolution and scaling of a sustainable major gifts strategy that balances near-term revenue goals with long-term donor pipeline growth.
• Establish clear goals, benchmarks, and performance indicators for major gifts success; adapt strategy based on results and learning while tracking and reporting metrics using Raiser’s Edge.
• Leverage prospect research, data, and analytics to prioritize outreach, refine strategy, and strengthen the donor pipeline.
• Build the systems, discipline, and culture necessary to support future growth, including potential campaign readiness and team expansion.
• Build infrastructure for future campaign efforts
• Ability and expectation to serve as a strategic thought partner for overall campaign strategy.
• Utilize and optimize fundraising systems to support effective portfolio management and strategic decision-making.
• Track and analyze donor activity and pledges to inform strategy and forecasting.
• Report on pipeline health, donor retention, and revenue performance.

Major Gifts Fundraising & Donor Relationship Management

• Manage a dynamic portfolio of approximately 100–125 major gift donors and prospects, focused on gifts of $5,000 through six-figures and above, including both qualified donors and discovery prospects.
• Identify, qualify, and advance major and principal gift prospects through proactive prospecting, referrals, research, events, and relationship-building.
• Develop and execute individualized cultivation, solicitation, and stewardship strategies for donors and prospects, including proposal development, coordinated ask teams, and follow-up.
• Make direct solicitations and close gifts; maintain a high level of donor and prospect engagement, including regular in-person and virtual meetings (typically 15–25 substantive interactions per month).
• Ensure high-quality donor stewardship through personalized recognition, timely impact reporting, and ongoing engagement that supports long-term retention and growth.
• Coordinate donor visits, site tours on Cathleen Stone Island, and personalized donor experiences that deepen connection to mission and impact.

Organizational Leadership, Board Engagement & Collaboration

• Champion a donor-centered, relationship-driven fundraising philosophy that engages donors as partners in mission and impact.
• Represent the organization externally with confidence and credibility among donors, community leaders, and philanthropic partners.
• Strengthen a culture of philanthropy by coaching and supporting Board members in their roles as ambassadors and fundraisers; prepare and support the CEO and Board in donor cultivation and solicitation efforts.
• Prepare donor strategies, briefing materials, and talking points for leadership and Board members in advance of donor meetings and solicitations.
• Partner closely with program staff and the Director of Marketing to translate program outcomes, student impact, and organizational priorities into compelling donor narratives and funding opportunities.
• Coordinate with Advancement colleagues to ensure alignment across major gifts, events, annual giving, and donor communications.
• Play a strategic role in major fundraising events, including event planning, donor experience, and programmatic content with a focus on major donor engagement.
• Collaborate with program teams and stakeholders across the organization to build a deep understanding of CSIOBS’ work and communicate its mission with clarity, confidence, and impact.

QUALIFICATIONS

• Bachelor’s degree required.
• Five years in fundraising, including 3 years of successfully securing five- and six-figure major gifts.
• Proven success in developing and managing high-level donor relationships and solicitation success.
• 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 and SalesForce).
• Experience with prospect research, moves management systems, and data analytics.
• Knowledge of planned giving and campaign strategy is highly desirable.
• Ability to travel up across Greater Boston and the New England area; must be available for occasional evenings and weekends.
• A background check is required for this position.

WORK ENVIRONMENT

Please see full job description as attached, and on our careers page.

OUR BENEFITS

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

• Comprehensive Benefits package. Please see full job description as attached and on careers page.

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.