Associate Head of School for Advancement (2026-2027)

Job Summary

Lake Highland Preparatory School seeks an Associate Head of School for Advancement to begin July 1, 2026.

The Associate Head of School for Advancement will serve as the President’s senior advisor and thought partner on all areas of institutional advancement, communication, and enrollment. This leader will provide strategic guidance and management support to the Directors of Communications and Enrollment Management, shaping and executing school-wide initiatives that align with institutional goals.

They will develop and implement a comprehensive, data-informed strategic plan that unifies philanthropy, marketing, and admissions objectives within Lake Highland’s strategic vision, The Future is Here. In partnership with senior leadership and the Board of Trustees, the Associate Head will advance the school’s philanthropic priorities, market position, and long-term sustainability.

Fostering a culture of collaboration, innovation, and trust, the Associate Head will ensure each leader has the autonomy and authority to lead their teams effectively while maintaining strategic alignment across departments. They will also engage with the Orlando community to extend Lake Highland’s mission through strategic partnerships, civic involvement, and leadership engagement that generate opportunities and resources for the school.

ADVANCEMENT & PHILANTHROPY

The Associate Head will lead all fundraising initiatives, including the Highlander Fund (annual giving), capital campaigns, planned giving, corporate and foundation support, and endowed funds. They will design and implement systems for identifying, cultivating, soliciting, and stewarding donors to strengthen the culture of philanthropy across the Lake Highland community.

This leader will personally manage a portfolio of major donors and prospects, building meaningful, mission-aligned relationships with them. They will oversee stewardship and donor recognition events, including the Founders Circle, President’s Dinner, and annual giving reports. Additionally, the Associate Head will partner closely with the President to implement strategic fundraising initiatives that strengthen key donor relationships and secure financial resources to advance the school’s mission and long-term vision. This includes helping to identify and support the President’s own portfolio of prospects and donors.

The development of meaningful partnerships with all constituencies is paramount. The Associate Head will clarify and strengthen the partnership with the Lake Highland Parent Association and support alumni engagement through volunteer opportunities, events, and philanthropy. They will serve as the primary liaison to the Development Committee and Committee on Trustees, ensuring active Board engagement in philanthropy and governance.

In collaboration with the Business Office, they will ensure accuracy in financial reporting, gift processing, and compliance with ethical fundraising standards. The Associate Head will oversee Advancement operations to ensure the integrity, security, and strategic use of data, integrating analytics and donor intelligence into all advancement strategies.

MARKETING & COMMUNICATIONS

Partnering with the Director of Communications and Marketing, the Associate Head will guide a comprehensive communications program that advances the school’s mission, enhances brand identity, and deepens community engagement. They will ensure consistency in messaging, tone, and visual identity across all platforms.

This includes supporting storytelling initiatives that celebrate Lake Highland’s mission, people, and impact; coordinating the production of strategic publications, annual reports, campaign materials, and digital content; and utilizing data analytics and market research to assess communication effectiveness and refine marketing and outreach strategies.

ADMISSIONS & ENROLLMENT MANAGEMENT

The Associate Head will partner with the Director of Enrollment Management to guide strategic initiatives for student recruitment, retention, and community engagement, supporting the development of longterm strategies informed by data analysis, demographic trends, and market segmentation.

Ensuring that the admissions experience reflects the mission and values of Lake Highland, the Associate Head will promote an inclusive, personalized journey for every family. They will facilitate integration of enrollment messaging into broader marketing and advancement efforts and review key metrics such as yield, retention, and diversity to guide decision-making.

LEADERSHIP AND TEAM DEVELOPMENT

The Associate Head will empower the Directors of Communications and Marketing and Enrollment Management to lead their teams with autonomy, creativity, and accountability. They will set clear institutional goals, establish success metrics, and promote professional growth across all departments.

This leader will build a culture of transparency, collaboration, and mission-driven excellence, serving as a mentor and modeling ethical leadership, humility, and professionalism consistent with Lake Highland’s values.