Director of Advancement

Job Description

Chesterton Academy of The Holy Family seeks a mission-driven and visionary Advancement Director to lead all development efforts, including major gifts, annual giving, alumni relations, planned giving, advancement events, and campaign strategy. The Director of Advancement plays a vital role on the leadership team and works closely with the Head of School, Board of Directors, parents, and benefactors to build a sustainable culture of philanthropy rooted in the school's Catholic identity. This self-starter will lead all fundraising efforts, cultivating and stewarding relationships with various constituents, and providing consistent communications throughout the year to our stakeholders.

Key Responsibilities
Serve as the chief fundraiser and ambassador for the school's advancement initiatives, dedicating 50% of time to external relationship-building.
Follow and implement the comprehensive development strategy to meet both short- and long-term fundraising goals.
Cultivate and steward relationships with major donors, alumni, foundations, and corporate partners.
Manage and grow annual and major gift programs, as well as planned giving and endowed funds.
Collaborate with the Head of School and Board to align advancement efforts with institutional priorities.
Lead and mentor advancement staff, ensuring clear objectives and professional development.
Direct all advancement-related events, including the annual gala, alumni reunions, and donor recognition gatherings.
Maintain accurate and confidential donor records using database software (Bloomerang).
Partner with the Business Office to ensure sound fiscal operations and accurate gift acknowledgment.
Evaluate the effectiveness of advancement strategies using key performance indicators and reporting systems.
Support the Board in its development responsibilities and provide regular performance updates.
Build a culture of philanthropy throughout the Chesterton Academy community.
Attend key school events and other events, as deemed necessary by the Head of Business Operations.

Knowledge, Skills, and Abilities
Outstanding written and verbal communication skills, with the ability to articulate the school's mission to diverse audiences.
Strategic thinker with strong leadership and administrative abilities.
Proven success in cultivating major gifts and donor relationships.
Attention to detail and a commitment to data-driven decisions.
Proficiency in fundraising software, especially Bloomerang or similar CRM platforms.
Deep understanding of development best practices, donor segmentation, and stewardship.

Education & Experience
Bachelor's degree required; Master's degree preferred.
Minimum of five years of progressive experience in fundraising or development.
At least five years in a leadership role, preferably with direct interaction with a board of directors.

Compensation & Benefits
Competitive salary, commensurate with experience
Health Benefits & 401(k) retirement savings plan
Generous paid time off, including approximately 26 PTO days for school holidays
Paid sick leave included in PTO policy
Annual professional development opportunity at the Chesterton Schools Network Summit Conference
Additional stipends available for coaching and extracurricular responsibilities

Special Qualities & Characteristics
Deeply committed to the mission of Chesterton Academy and the Catholic Church.
Practicing Catholic in good standing who is willing to sign the Oath of Fidelity to the Magisterium.
Strong ethical reputation and ability to lead by example.
Collaborative, adaptable, and enthusiastic about working in a small-school environment.

Qualifications:
A practicing Catholic in good standing with the Catholic Church
Please note that all faculty and staff will be required to take an Oath of Fidelity to the Magisterium of the Roman Catholic Church.

Reports To: Head of School Job Status: Full-time, 12-month, Exempt
Salary: Commensurate with experience

Apply @ www.chestertonacademyoftheholyfamily.com/careers

About the Employer

The purpose of Chesterton Academy of The Holy Family is to nurture the minds and the souls of our children through a well-defined and academically rigorous classical education and to develop complete thinkers who learn to draw on faith and reason for the purpose of building the culture of life. We desire to pursue TRUTH, GOODNESS, and BEAUTY, as revealed by God, throughout the school day.

Students at Chesterton Academy of The Holy Family enjoy a cohesive, content-rich education. A broad exposure to many different disciplines helps students avoid the pitfalls of specializing too early, which can lead to limited interests and narrow thinking.