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. 

Education/Experience

The most competitive candidates for LHP will offer most or all of the following qualifications and qualities:

• Bachelor’s degree required; master’s preferred.
• Commitment to the mission and values of Lake Highland Prep and the ability to support and communicate effectively.
• Outstanding relationship-building and collaboration skills to work with a diverse community.
• Ten or more years of progressively successful advancement experience with a record of accomplishment of building comprehensive fundraising programs and plans that achieve excellent results.
• Proven experience leading successful capital campaigns and building a coordinated fundraising program that integrates annual giving (Highlander Fund), major, and planned gifts.
• Partner with the President and Chief Financial Officer to align fundraising goals and financial planning, ensuring transparency and the strategic use of philanthropic resources to advance institutional priorities.
• An understanding of independent school financial models and the integral role of advancement in achieving financial goals.
• Success in identifying, soliciting, securing, and stewarding a portfolio of donors. 
• Knowledge of best practices in fundraising and the ability to apply them in innovative ways.
• A self-starter with a flexible and adaptable style who can construct, articulate, and implement an annual advancement plan while building and inspiring a collaborative team. 
• Patience and persistence, with an ability to set ambitious, challenging, and tangible goals. 
• Strong supervisory experience that demonstrates the ability to lead, mentor, and develop an advancement team to achieve the institutional goals of LHP’s mission and strategic plan.
• Inclusive, ethical, and mission-driven professional who models integrity and respect
• Sophisticated communication skills, both oral and written, and the capacity to tailor messaging to the needs and interests of all audiences.
• Willingness to travel extensively to cultivate and solicit prospects and to steward donors.
• Experience working in an independent school or private college environment is preferable.
• Experience working with advancement database systems, analytics to inform strategy, measure progress, and enhance donor cultivation, solicitation, and stewardship efforts. 
• Visionary, collaborative leader with high emotional intelligence.
• Demonstrate financial acumen and the ability to align fundraising and enrollment strategies with long-term fiscal sustainability.
• Strategic thinker who values the expertise and contributions of others.
• Passionate advocate for education, community engagement, and student success.
• A joyful spirit and a fine sense of humor.

To Apply:

Interested and qualified candidates are invited to contact the consultants in confidence. Candidates will ultimately need to submit the following materials as separate PDF documents:

• A cover letter expressing their interest in this particular position;

• A current and comprehensive résumé of no more than four pages showing all positions and dates as well as responsibilities and accomplishments

• A list of five professional references with name, relationship, phone number, and email address of each (references will not be contacted without the candidate’s permission) to: 

Jonathan Ball, Managing Associate - jball@carneysandoe.com

Sara Shulman, Practice Leader - sara.shulman@carneysandoe.com

About Lake Highland Preparatory School

Lake Highland Preparatory School (LHP), a PreK-12 independent school in Orlando, Florida, was founded in 1970. The school strives to offer its students an unparalleled education with long-lasting life lessons rooted in integrity, grit, and grace. In spite of its size as one of the ten largest independent schools in the U.S., Lake Highland’s approach ensures that every child is known and nurtured. Students learn within an academically challenging and supportive environment, with teachers who are actively committed to the academic and social-emotional development of every child. This powerful combination results in joyful learning that prepares students exceptionally well for college and life beyond.

Connections working at Lake Highland Preparatory School