Director of Leadership Giving and Annual Gifts

Latin School of Chicago provides its students with a rigorous and innovative educational program in a community that embraces diversity of people, cultures and ideas. Latin inspires its students to pursue their passions and lead lives of purpose and excellence. This is an exciting opportunity for someone who has a passion for fundraising in an outstanding academic environment.

Latin School of Chicago seeks a strategic, relationship-driven fundraiser to serve as Director of Development, Leadership & Annual Gifts, a key leadership role responsible for generating over $2.5 million annually from individual donors through gifts of $1–$25,000.

This role leads Latin’s individual giving strategy for parents, parents of alumni, grandparents, and friends of the School, utilizing a full range of engagement and solicitation methods—including the Latin Fund (annual fund), leadership-level individual gifts under $25,000, targeted appeals, and donor stewardship. They will work collaboratively with the Director of Development and Alumni Engagement and the Director of Operations & Major Gifts to develop and implement this strategy.

In addition to managing a personal portfolio of individual donors, the Director, Individual Giving supervises the Annual Giving Manager, who is responsible for the day-to-day execution of the Latin Fund and related annual giving initiatives. Together, they ensure a cohesive, donor-centered individual giving program that balances scale, strategy, and meaningful engagement.

The Director of Leadership and Annual Gifts works in close partnership with the Director Development and Alumni Engagement and the Interim Director of Major Gifts and Operations. Together, these roles ensure a coordinated approach across constituencies, with clear accountability and a seamless donor experience.

Reporting to the Chief Development Officer and collaborating across Development and Alumni Relations, this position plays a central role in fostering and sustaining a strong culture of philanthropy at Latin.

The salary range for this position is $100,000 to $110,000, not including an outstanding insurance and benefits package.

PRIMARY RESPONSIBILITIES:

Individual Giving Strategy & Revenue

• Lead and execute a comprehensive individual giving strategy focused on individual donors giving between $1 and $25,000, generating over $2.5 million annually.
• Provide strategic oversight of the Latin Fund, ensuring strong participation, consistent growth, and alignment with broader individual giving goals.
• Develop and implement strategies to increase donor acquisition, retention, and upgrades across all individual giving audiences within scope.
• Partner with the Chief Development Officer to align individual giving efforts with institutional priorities and long-term fundraising goals.

Portfolio & Relationship Management

• Manage a personal portfolio of approximately 150 individual donors and prospects, primarily composed of:
  • Current parents and guardians
  • Parents of alumni
  • Grandparents
  • Friends and supporters of the School
• Engage donors through consistent, personalized outreach, achieving approximately 400 meaningful contact points annually.
• Support and organize volunteer leadership and parent volunteers in coordinated solicitation efforts.
• Maintain accurate, timely records of donor interactions, strategies, and outcomes in Raiser’s Edge.

Team Leadership & Annual Giving Oversight

• Supervise and provide strategic direction to the Annual Giving Manager, who leads execution of the Latin Fund and related annual giving campaigns.
• Set annual goals, metrics, and priorities for the Latin Fund in partnership with the Chief Development Officer and Annual Giving Manager.
• Ensure alignment between annual giving efforts and broader individual giving strategies, including leadership-level gifts under $25,000 and donor upgrades.
• Coach and support the Annual Giving Manager’s professional development, fostering strong project management, donor-centric communications, and cross-departmental collaboration.
• Collaborate with Development Operations to ensure accurate reporting, segmentation, and analysis of annual giving performance.

Alumni Partnership & Coordination

• Work side by side with the Director of Development and Alumni Engagement to support alumni giving efforts, ensuring coordination of messaging, strategy, and donor experience.
• Collaborate on outreach and stewardship for constituents with overlapping relationships (e.g., alumni who are also parents or grandparents).
• Share prospect insights and coordinate strategies while maintaining clear portfolio ownership and fundraising accountability.

Donor Engagement, Stewardship & Appeals

• Design and implement stewardship strategies that reinforce donor impact and strengthen long-term donor relationships.
• Collaborate on multi-channel appeals—including mail, email, and digital campaigns—targeting parents, families, and community supporters.
• Ensure timely and thoughtful acknowledgment and recognition of gifts in partnership with the Development Operations Manager.
• Attend and support donor cultivation and stewardship events, including some evenings and weekends during the school year.

Messaging & Case for Support

• Articulate Latin’s mission, values, and funding priorities clearly and compellingly to individual donors. Provide messaging to other members of the team for use in their fundraising efforts.
• Prepare donor-facing materials, including solicitation letters, leadership giving pieces, one-pagers, briefing documents, and stewardship communications.
• Maintain strong fluency in school priorities so donors can connect their philanthropy to impact.

Collaboration & Institutional Leadership

• Work closely with the Chief Development Officer, Director of Development and Alumni Engagement, and Development Operations to ensure coordinated outreach and a seamless donor journey.
• Partner with the Head of School, as appropriate, to support donor engagement and select solicitations.
• Contribute to planning for future capital and endowment campaigns, as directed.

Qualifications

Education & Experience

• Bachelor’s degree required; CFRE a plus
• 6+ years of fundraising experience, preferably in independent schools, higher education, or mission-driven nonprofits
• Demonstrated success managing an individual donor portfolio and driving revenue through gifts up to $25,000
• Experience with annual funds, individual giving programs, and donor stewardship strategies
• Experience supervising or mentoring fundraising staff, or demonstrated readiness to step into a people-management role
• Campaign experience a plus, but not required

Skills & Attributes

• Relationship-oriented, donor-centered approach
• Strong understanding of individual giving best practices
• Excellent written, verbal, and interpersonal communication skills
• Highly organized, strategic, and detail-oriented
• Comfortable collaborating across teams with shared constituencies
• Proficiency with Raiser’s Edge and standard productivity tools

Work Environment

This is a full-time, in-person role requiring some evening and weekend work during the school year, local travel, and limited regional travel (1–2 trips annually).

FOR ADDITIONAL CONSIDERATION:

Latin School of Chicago is committed to bringing together a diverse faculty, staff, and student body. We encourage candidates who represent the broad, diverse community to which we aspire. Latin School of Chicago is an Equal Opportunity Employer committed to an inclusive school experience for all.

High quality, comprehensive benefits package highlighted by a 200% match for a 3% withholding in your 403(b).