Director of Development

Join our Advancement team as Director of Development to drive philanthropic revenue and fuel the fastest-growing network of joyfully and faithfully Catholic, classical high schools in the world. Now with 106 schools globally, the Chesterton Schools Network is on the move. The director supports our mission to evangelize through education, not only through high-quality high schools, but also publications, conferences, pilgrimages, and related initiatives, ensuring donor investment keeps pace with expansion, strengthening capacity and sustaining long-term mission impact.

About the role

The role requires a strategic closer with entrepreneurial drive who, with deep mission conviction, loves G.K. Chesterton and his common sense, joyful approach to life. The Director of Development is a leader who owns revenue outcomes, manages a disciplined portfolio, and converts qualified prospects into sustained donor investment through structured pipeline management and confident solicitation.

Responsibilities

• Build and manage a qualified portfolio of major gift prospects with clear revenue targets
• Conduct disciplined cultivation, solicitation, and stewardship cadence for assigned donors
• Close major gifts aligned with campaign priorities and annual goal
• Develop and grow the Knights of the Apostolate recurring giving society
• Increase donor retention and lifetime value through structured stewardship
• Partner with Development Operations to maintain accurate pipeline tracking and forecasting
• Support strategic fundraising events tied to major cultivation moments
• Collaborate with Marketing to align messaging, campaigns, and donor communications
• Provide regular reporting on pipeline health, gift projections, and revenue performance
• Identify new donor segments and growth opportunities aligned with our mission
• Serve as a joyful, credible ambassador for the Society and the Chesterton Schools Network

Requirements

• 5+ years of experience in major gifts, advancement, or mission-driven fundraising
• Proven track record of closing five- and six-figure gifts
• Strong portfolio management discipline with clear movement of prospects through stages
• Comfort making direct, confident gift asks
• Experience building recurring revenue programs
• Familiarity with donor CRM systems and pipeline reporting
• Strong written and verbal communication skills
• Ability to connect mission impact to donor passion
• Entrepreneurial mindset with bias toward measurable outcomes
• Deep alignment with the Catholic faith and the mission of evangelization through education
• Faithfulness to the Magisterium of the Catholic Church in accord with our canonical status as a private association of the Christian faithful

Preferred Qualifications

• Experience fundraising for education or Catholic apostolates
• Background managing giving societies or campaign initiatives
• Experience working within a rapidly scaling nonprofit
• Familiarity with education freedom policy environments
• Advanced training in fundraising strategy or nonprofit leadership