Director of DevelopmentSociety of Gilbert Keith Chesterton

DIRECTOR OF DEVELOPMENT
Reports to Vice President, Advancement

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.

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.

Your Responsibilities Include

• 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

Knowledge and Skills You Bring to the Organization

• 5 plus 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

• The candidate must exhibit faithfulness to the Magisterium of the Catholic Church in accord with our canonical status as a private association of the Christian faithful.

Standout Candidates May Also Bring

• 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

The Society of Gilbert Keith ChestertoThe Society of Gilbert Keith Chesterton

The Society of Gilbert Keith Chesterton is a 501(c)(3) non-profit organization established as a canonically recognized private association of the Christian faithful in the Archdiocese of Saint Paul and Minneapolis. Our mission is to evangelize through education, inspiring people to live joyful, holy lives, with G.K. Chesterton as a model of lay spirituality. We advance this mission through conferences, publications, and local societies that cultivate serious engagement with Chesterton’s thought and the Catholic intellectual tradition.

The Chesterton Schools Network

Through the Society’s educational initiative, the Chesterton Schools Network (CSN), we are leading one of the most significant expansions of Catholic secondary education in modern times, forming a new generation of joyful leaders and saints to build up the Kingdom of God and advance the Culture of Life envisioned by the great Pope Saint John Paul II.

In just over a decade, the CSN has grown to over 100 schools, serving more than 4,400 students across 88 dioceses, 32 states, and 10 countries. With demand for affordable faithful high school options in communities everywhere, we follow God's lead as we see the realistic capacity to grow to 1,000 schools serving 100,000 students annually by 2040.

The Chesterton Schools Network was the 2025 awardee of the $1 million Yass Prize, one of the nation’s most prestigious honors for education innovation.

Our Team

Are you running at the pace of an energetic start-up? As growth accelerates across the Chesterton Society and the Chesterton Schools Network, we are seeking talented individuals who are energized by our growth and want their work to help spark the future of Catholic, classical education. Devote working time to the mission of evangelization that is the Society of G. K. Chesterton, including daily prayer and personal advancement of those particularly Chestertonian virtues of charity, joy, learning and continuous conversion. We invite you to explore new ground with our opportunities.

• Full-Time, Exempt, Salaried

• Base salary range $60,000 to $90,000, based on experience and demonstrated capability. This role offers significant growth potential in scope, responsibility, and compensation as results are delivered and the organization expands.

• Medical health benefit stipend and a generous package of discretionary paid time off plus staff holidays.

• Remote with frequent travel to cultivate and steward donors