Overview

Thomas Jefferson School (TJ) seeks a seasoned, relationship-driven development leader to support  the school’s philanthropic priorities with a clear and sustained focus on major and leadership gifts. Reporting directly to the Head of School, the Director of Development is a member of the senior leadership team and serves as the school’s lead strategist and relationship manager for transformational philanthropy.

This role is centered on cultivating deep, trust-based relationships with alumni, parents, trustees, and friends of the school; personally managing a portfolio of major gift prospects; and partnering closely with the Head of School and Board of Trustees to secure significant philanthropic investments aligned with TJ’s strategic priorities.

The successful candidate will be an experienced major gift fundraiser who excels in one-on-one engagement, understands how to guide donors toward meaningful commitments, and is energized by developing a high-impact program within a close-knit school community.

The Opportunity

TJ is entering a period of focused philanthropic growth. With strong leadership, an engaged Board of Trustees, and a deeply loyal alumni community, the school is well positioned to convert engagement and readiness into significant major and leadership gifts. 

Sustaining the Annual Fund is also foundational to TJ’s philanthropic success. The Director of Development will provide strategic leadership for the Annual Fund, ensuring it reflects TJ’s values, strengthens donor loyalty, and serves as a meaningful entry point to deeper engagement and future major giving. While execution may be shared with colleagues and partners, the Director will be responsible for aligning Annual Fund strategy with broader development goals and long-term relationship building.

As a small institution with an outsized reputation, TJ offers the Director of Development the opportunity to:

• Focus primarily on high-value donor relationships and solicitations
• Partner directly with the Head of School on leadership-level philanthropy
• Engage trustees as active partners in major gift cultivation and asking
• Help shape the philanthropic future of a school whose impact extends far beyond its size
• This role is ideal for a development leader who prefers relationship-centered fundraising over transactional volume and thrives in an environment where credibility, trust, and long-term partnership matter most.

Key Responsibilities

Major & Leadership Giving

• Personally manage and grow a portfolio of major and leadership gift prospects
• Design and execute individualized cultivation, solicitation, and stewardship strategies
• Partner closely with the Head of School on top-tier donor relationships and solicitations
• Secure leadership and transformational gifts aligned with institutional priorities

Annual Fund Strategy & Integration

• Provide strategic oversight of the Annual Fund, ensuring it supports donor retention, engagement, and pipeline development
• Align Annual Fund messaging and timing with institutional priorities and leadership giving goals
• Use Annual Fund participation and giving patterns to identify, qualify, and advance future major gift prospects
• Collaborate with colleagues and external partners to ensure consistent, donor-centered execution

Donor Strategy & Stewardship

• Ensure personalized, high-touch stewardship for major and leadership donors
• Collaborate with colleagues and external partners to deliver thoughtful donor communications and recognition
• Maintain long-term donor relationships that encourage sustained and increased philanthropic investment

Board & Volunteer Engagement

• Serve as staff liaison to development-related committees of the Board of Trustees
• Effectively engage trustees as active partners in donor cultivation, solicitation, and stewardship through clear strategy, guidance, and sustained support
• Provide strategic updates and insights to support leadership-level fundraising decisions

Institutional Storytelling and Representation

• Articulate TJ’s mission, impact, and priorities with clarity and authenticity
• Represent the school confidently with donors, alumni, parents, and external stakeholders
• Ensure donor-facing messaging supports leadership giving and long-term engagement

Strategy, Metrics, and Accountability

• Use data and prospect insights to inform donor strategy and prioritization
• Track progress toward major and leadership gift goals
• Collaborate with leadership to assess outcomes and refine philanthropic priorities
• Facility with relevant technologies (e.g., Google Workspace, Blackbaud) and willingness to learn new systems

About Thomas Jefferson School

Thomas Jefferson School (TJ) is an intentionally small, coeducational boarding and day school for students in grades 7–12. With an established reputation as an intellectual greenhouse for high-ability students, TJ offers a rigorous liberal arts curriculum within a close-knit, international community. TJ is consistently ranked among the top boarding schools and recognized by Niche as a top college-prep high school in Missouri. Learn more at www.TJS.org.

Application Process

This is a year-round position with competitive salary and benefits for a school of our size and type. Please submit a résumé and cover letter to jobs@wizenow.com with “Director of Development” in the subject line. Cover letters should be addressed to Jane Roth, Head of School. Review of applications will begin immediately and continue until the position is filled.

Thomas Jefferson School is an equal opportunity employer and does not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national or ethnic origin, age, marital status, veteran status, or disability.

Necessary Skills and Qualities

Proven Major Gift Experience

• Demonstrated success securing major and leadership-level gifts
• Comfort managing complex donor relationships and significant solicitations

Relationship-Centered Fundraising

• Skilled listener who builds trust and guides donors toward meaningful commitments
• Confidence in partnering with senior leaders and trustees

Focused, Collaborative Leadership

• Thrives in a role emphasizing prioritization, accountability, and follow-through
• Comfortable working independently while collaborating closely with senior leadership
• Collegial spirit, positive outlook, integrity, and sense of humor

Strong Communicator and Ambassador

• Clear, persuasive communicator in both written and verbal contexts
• Able to represent the school with confidence and professionalism
• Cultural fluency, empathy, and sensitivity to linguistic and cultural differences

Community Engagement and Curiosity

• Engages fully in the life of the school to authentically represent its culture
• Values continuous learning and professional growth

About Thomas Jefferson School

Thomas Jefferson School is a small, coed boarding and day school for high-ability students in grades 7-12. We are known for our strong liberal-arts focus and close-knit, international community. TJ is consistently ranked among the top boarding schools in the nation and is rated by Niche as a top college-prep private high school in Missouri. As a boarding and day school, on-campus life is a major part of our program. All administrative faculty members shape and contribute to the culture of our close-knit community by engaging with students both in and out of the classroom. For more information about our school, visit www.TJS.org and refer to our Statement of Faculty Excellence and Statement of Mission and Philosophy.

Connections working at Thomas Jefferson School