Director of Major Gifts

Cathleen Stone Island Outward Bound School is dedicated to transforming lives through challenge and discovery within the inspiring setting of the Boston Harbor Islands National and State Park. The organization provides experiential learning and outdoor education programs that foster personal growth, leadership, and teamwork. Through unique curricula and immersive experiences, students are encouraged to confront their strengths and push their limits in a supportive environment.

Cathleen Stone Island Outward Bound School is committed to equipping individuals with the confidence and skills to thrive in their personal and professional lives.

The Director of Major Gifts will develop and manage a strategic fundraising program to build strong relationships with donors and generate significant support for the organization's mission. This full-time remote role includes leading efforts in major gift solicitations, overseeing planned and annual giving campaigns, and cultivating relationships with top contributors and alumni. The Director will also implement stewardship programs, conduct prospect research, and collaborate with cross-functional teams to achieve annual fundraising goals.

The role requires strong organizational and leadership skills to promote the financial sustainability of the school.

• Experience with Planned Giving and Annual Giving, including crafting and managing effective campaigns
• Proficiency in Alumni Relations and Stewardship to foster and maintain long-term donor relationships
• Expertise in Prospect Research to identify and engage potential major donors
• Strong written and verbal communication skills with an emphasis on relationship-building
• Demonstrated ability to work independently in a remote environment
• Bachelor's degree in a relevant field; advanced degree or certifications are a plus
• Experience in the nonprofit sector or with outdoor education organizations is beneficial
• Collaborative mindset and proven ability to lead and inspire teams