Director of Annual Giving and Stewardship

OUR MISSION

Nativity Preparatory School is a tuition-free, Jesuit middle school in Boston, Massachusetts, offering a high-quality, comprehensive education to boys from under-resourced communities. Within an academically challenging and highly structured environment, students are accompanied as they develop a love for learning and sense of responsibility to their community. Our students grow to become men for others, READY to thrive in high school, college, and beyond.

POSITION OVERVIEW

The Director of Annual Giving and Stewardship plays a central role in Nativity Prep’s robust and growing Advancement efforts. Reporting to the Chief Advancement Officer, the director will serve as a leader in important elements of the Advancement Team’s work and collaborate daily to help the team achieve goals and sustain the school’s essential mission. 

The Director of Annual Giving and Stewardship is responsible for executing Nativity Prep’s annual fundraising strategy in close partnership with the Chief Advancement Officer. Working from an annual plan established with the CAO, the director will manage day-to-day implementation of annual giving, foundation grants, and the student sponsorship program. This includes coordinating timelines, tracking grant activity, supporting proposal development, managing donor relationships, and maintaining accurate reporting systems.

The director will ensure that advancement initiatives move forward in a disciplined and organized way, providing the CAO with clear visibility into progress and outcomes. This is a highly collaborative role that requires consistent communication, structured execution, and shared accountability for results.

WE WANT TO SPEAK WITH YOU IF

• You see building relationships and raising funds as a purposeful way to contribute to a Jesuit-sponsored school that accompanies boys and their families through Grades 5-8 and beyond.

• You thrive on direct interaction – especially through phone calls and in-person visits – with people who support Nativity’s people and cherish its mission.

• You enjoy asking members of a community for support, then finding creative ways to show gratitude for how they share their gifts.

• You feel comfortable working on a team that collaborates across the community, with opportunities to take leadership roles on key projects.KEY 

RESPONSIBILITIES

ANNUAL GIVING (70%)

• Collaborate on the design and execution of a multi-channel strategy that will help grow a $2.5M annual fundraising program.

• Co-create and manage an annual communications calendar to educate, solicit and thank Nativity Prep supporters who give to the school’s annual fund.

• Coordinate and manage the school’s foundation grant process, including tracking opportunities, supporting proposal development, maintaining submission timelines, and ensuring accurate reporting to the CAO.

• Manage the day-to-day coordination of Nativity's student sponsorship program by supporting donor engagement, ensuring timely communication and accurate track, and maintaining alignment with the school's advancement plan.

• Cultivate, solicit, and steward a portfolio of 25-50 prospects for gifts as high as $10,000 per year.

STEWARDSHIP (20%)

• Engage with foundations and organizations that support Nativity Prep through grants to complete impact reports, coordinate campus visits, and develop long-term relationships.

• Lead planning and execution of annual, on-campus events to show gratitude to Nativity Prep supporters, particularly those who direct gifts to the student sponsorship program.

ADVANCEMENT TEAM MEMBER (10%)

• Support various events and initiatives throughout the year, including the Nativity Promise Dinner, the Nativity Golf Classic, and the Nativity Dinner Program.

• Participate in professional and spiritual development opportunities, including retreats, presentations, and conferences available to Nativity Prep faculty and staff members.

• Represent the Advancement Team and/or Nativity Prep as assigned by the Chief Advancement Officer or School President.

WHO WE’RE LOOKING FOR

We’re seeking a mission-driven, relationship-oriented development professional who is energized by measurable goals and meaningful work. The ideal candidate will bring:

• At least 3 years of experience in fundraising, development, nonprofit management, or related fields.

• Experience managing annual giving campaigns, donor portfolios, or grant writing.

• Strong written and verbal communication skills, especially in persuasive and mission-centered storytelling.

• Comfort managing a portfolio of donors and confidently making direct solicitations.

• Ability to execute established plans with discipline and consistency.

• Strong organizational skills and attention to detail.

• Alignment with Nativity Prep’s Jesuit mission and commitment to serving boys and families from under-resourced communities.

ROLE EXPECTATIONS & CULTURE

• Full-time, in-office position based in Jamaica Plain (5 days per week).

• Direct, daily collaboration with the Chief Advancement Officer and school leadership.

• High visibility within a mission-driven school community.

• Measurable fundraising goals.

• Occasional evenings and weekends required for donor engagement and events.

• Opportunity to take meaningful ownership within a growing advancement program and

contribute to its continued expansion.

COMPENSATION

• Salary range: $70,000–$85,000, commensurate with experience

• Full benefits, including health, dental, disability, and retirement plans

HOW 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.