Director of Advancement

Chesterton Academy is searching for its next Director of Advancement.

The mission of Chesterton Academy is to help parents raise up a new generation of joyful leaders and saints, educated in the classical tradition and the truths of the Catholic faith. Our rigorous, integrated curriculum unlocks student’s potential and prepares students to succeed in college and professional life, and to excel in service of family, of country, and of Christ our Lord. Chesterton Academy offers: a well-rounded education that develops strong intellectual habits; a supportive community growing in virtue and holiness; and a culture for promoting character and leadership. We are a joyfully Catholic, classical high school.

The Director of Advancement reports to the Headmaster and, as a member of the Chesterton Academy leadership team, directs the school’s fundraising and public engagement efforts. The Director is responsible for:

Working closely with the Headmaster and Board of Directors to develop a comprehensive fundraising plan to meet the Academy’s annual fundraising goals and to develop advancement strategies and objectives;

Managing a portfolio of major donors, practicing a moves management strategy that guides prospective donors from identification, qualification, cultivation, solicitation, and stewardship;

Assist the Headmaster in donor assessment and portfolio assignments;

Implementing a comprehensive 12-month calendar cycle of fundraising and donor engagement events, including the planning and execution of these special events

Acquisition of new donors that offer strategic advantage in expanding the donor base by identifying new sources of donors and converting prospective donors into active donors;

Establishing giving levels and implementing action plans for each level;

Supporting the planning and execution of the annual Chesterton Gala, especially by seeking principal sponsors and major gifts for the matching Pre-Gala Fund, obtaining table sponsorships for prospective parents/students, and securing vendor and other outside institutional/corporate sponsorships;

Securing foundation gifts and grants and leading efforts to expand the same; researching, writing, and submitting grant proposals to obtain foundation support, cultivating relationships with foundations that support the Academy, and forming relationships with new potential supporting foundations;

Collaborating with the Communications team and the Headmaster to develop, oversee, and execute effective donor communications and marketing materials;

Drafting and managing all branding and documentation for appeals, campaigns, and fundraisers to compellingly convey the Academy’s mission, impact, and needs across the community in an authentic way that honors our students and their families;

Working closely with Headmaster and the Academy’s Directors of Operations and Finance to identify funding needs to maintain and enhance the Academy’s Catholic mission and culture;

Coordinating all donor recognition and appreciation programs and all gratitude efforts (e.g., thank you cards, phone-a-thons, in-person meetings, events, gifts, etc.);

Assisting the Headmaster in creating quarterly reports for the Board; serving as staff liaison and resource for the Development Committee of the Board, meeting monthly with committee members.

Optimizing the use of wealth assessment and other relevant software (e.g., Raiser’s Edge) to discover, cultivate, and track donors;

Diligently improving relevant knowledge, skills, and experience (e.g., professional development classes, working with a mentor, etc.) to achieve ever greater excellence in the field;

Identifying, recruiting, coordinating, and engaging volunteers, including prospects, parents, alumni, grandparents, students, faculty, administrative staff, as appropriate;

Maintaining thorough and current documentation of all relevant activities;
Other duties as assigned.

Experience and Qualifications

Demonstrates passion, commitment, and behavior that are consistent with Chesterton Academy’s Mission, Model of Formation, and Catholic Identity.

3+ years of fundraising, sales, or marketing experience, or the equivalent.

Demonstrates leadership qualities such as maintaining vision, expectations, and energy for positive improvement and results.

Exercises good judgment in using and/or keeping information regarding donors, employees, and Chesterton Academy confidential.

Works well independently and as a team member.

Capacity to manage multiple projects simultaneously and flexibility to accommodate rapidly changing priorities.

Strong interpersonal, verbal communication, and presentation skills

Attention to detail, project management, and ability to organize tasks.

Proven track record of meeting sales/development goals.

Excellent written and verbal communication skills.

Follows instructions completely and asks for help and/or guidance from supervisors when needed.

Experience measuring data and outcomes of events to determine effectiveness.

Strong computer skills including demonstrated experience with appropriate software (Microsoft, Google Workspace, etc.) and experience with Raiser’s Edge or a similar customer relationship management system preferred.

Experience in a Catholic school or nonprofit organization strongly preferred.

Contact

Applicants should send a cover letter and resume to Mr. Brad Mitchell, Director of Finance at bmitchell@chestertonacademy.org.