Job Description

Overview

Nativity Preparatory School is a tuition-free, Jesuit middle school serving boys from under-resourced communities. In a structured, academically challenging environment, students develop a love for learning and a sense of responsibility to their community.

Why This Role Matters: This is a rare opportunity to lead the next chapter of a small but mission-driven school transforming outcomes for boys in Boston. We seek an experienced advancement leader to build a major gifts program, grow an energized donor base, and lead strategy from the front lines, working closely with the President and the Board of Trustees to support long-term sustainability and growth.

Position Overview

The Chief Advancement Officer (CAO) will lead all aspects of fundraising and donor engagement at Nativity Prep. With a strong foundation in place, this is an ideal moment to reimagine and elevate our advancement strategy, with a focus on major gifts. The CAO will manage a small team and collaborate with the President and Board to drive major philanthropic initiatives, including a future capital campaign.

Responsibilities

• Design and implement a comprehensive fundraising plan centered on major gifts, annual giving, planned giving, and institutional partnerships
• Build and manage a portfolio of high-net-worth donors and prospects capable of giving $25,000+
• Collaborate with the President and Board to identify, cultivate, and solicit transformational gifts
• Bring creativity and an entrepreneurial mindset to long-term planning and day-to-day challenges

Leadership & Team Development

• Supervise and mentor advancement team staff
• Set clear goals and foster a collaborative, accountable culture focused on results
• Foster an inclusive, supportive, and empowering culture for staff and stakeholders

Campaign Planning

• Develop strategy and build capacity within the school for a future comprehensive capital campaign

Board & Donor Engagement

• Equip and engage Board members in fundraising strategy and outreach
• Build deep, authentic relationships with supporters who believe in the Nativity mission
• Serve as a natural relationship builder who ensures long-term donor engagement and satisfaction

Events & Stewardship

• Oversee execution of high-impact fundraising events (e.g. Promise Dinner, Golf Tournament)
• Ensure donors are thanked, informed, and inspired to stay engaged
• Use data to inform strategy, measure progress, and continuously improve performance
• Provide regular progress reports to the President and Board

Who Were Looking For

• Were seeking a confident, mission-driven fundraiser with:
• 710+ years of experience in development, with at least 5 in a leadership role
• Proven success soliciting and closing major gifts ($25K+), including working with high-net-worth individuals, foundations, and corporate partners
• Experience leading and mentoring staff
• Excellent communication and relationship-building skills
• Deeply aligned with and committed to Nativity Preps mission as a Jesuit Catholic school
• A self-starter mindset with the ability to build, execute, and adapt strategy

Working Conditions & Compensation

• Occasional evenings and weekends required for events and donor engagement
• Some local and national travel
• Competitive salary commensurate with experience
• Full benefits: health, dental, disability, and retirement plans

To Apply: Please submit your resume and cover letter to Luc Benjamin, Director of Admissions & Recruitment, at lbenjamin@nativityboston.org. Applications will be reviewed as they are received.

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