Associate Head of School for Advancement (SY 2027-2028)

Lake Highland Preparatory School Inc•Orlando, FL

54d•Onsite

About The Position

Lake Highland Preparatory School (LHP), a Prekindergarten through 12th grade school in Orlando, Florida, seeks a strategic and relational leader to serve as Associate Head of School for Advancement. This is a unique opportunity to join a thriving institution at a moment of exciting transformation, with bold strategic planning, a major capital campaign underway, and a deep commitment to both community and tradition. Reporting directly to President Jim McIntyre and serving as a key member of the President's Leadership Team, the Associate Head of School for Advancement will lead the school's philanthropy and advancement program in its entirety, encompassing annual giving, major and planned gifts, and campaign fundraising. This leader will partner closely with the Directors of Communications and Marketing and of Enrollment Management, ensuring that Lake Highland's advancement work, storytelling, and family recruitment are well aligned in service of the school's mission. With a solid foundation in place, including a successful fundraising track record, an endowment poised for growth, and the transformational Elevate Campaign, LHP is well positioned to support the incoming Advancement leader. The school seeks a seasoned and relational fundraising professional who will honor the school's rich history and family-centered culture while bringing fresh eyes, strategic clarity, and collaborative energy to strengthen a comprehensive philanthropy program.

Requirements

Bachelor's degree required; master's preferred.
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.
Experience working with advancement database systems. analytics to inform strategy, measure progress, and enhance donor cultivation, solicitation, and stewardship efforts.
Commitment to the mission and values of Lake Highland Prep and the ability to support and communicate them effectively.
Outstanding relationship-building and collaboration skills to work with a diverse community.
Proven experience leading successful capital campaigns and building a coordinated fundraising program that integrates annual giving (Highlander Fund), major, and planned gifts.
Ability to partner with the President, Associate Head of School, 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.
Deep experience with volunteer management.
Lead with compassion and high expectations, providing the challenge and support needed for others to grow in confidence, competence, and character.
Build and maintain trust through integrity, reliability, accountability, confidentiality, generosity, and mutual respect.
Establish consistent systems and processes that strengthen the mission, support people, and sustain excellence.
Lead with honesty, humility, and empathy.
Foster collaborative and inclusive communities where people feel valued, contribute meaningfully, question respectfully, and grow together.
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 to cultivate and solicit prospects and to steward donors.
Experience working with advancement database systems and analytics to inform strategy, measure progress, and enhance donor cultivation, solicitation, and stewardship efforts.
Visionary, collaborative leader with high emotional intelligence.
Demonstrated financial acumen and the ability to align fundraising strategy with long-term fiscal sustainability.
Strategic thinker who values the expertise and contributions of others.
Passionate advocate for education, community engagement, and student success.
Alignment with Lake Highland’s mission and values.
A joyful spirit and a fine sense of humor.

Nice To Haves

Experience working in an independent school or private college environment is preferable.

Responsibilities

Serve as the President's senior advisor and thought partner on all areas of institutional philanthropy and advancement.
Develop and implement a comprehensive, data-informed advancement strategy that supports Lake Highland's strategic vision, The Future Is Here.
Advance the school's philanthropic priorities and long-term fundraising capacity in partnership with senior leadership and the Board of Trustees.
Work closely and collaboratively with the Directors of Communications and Marketing and of Enrollment Management to ensure that advancement efforts are well coordinated and resources are leveraged with the school's broader storytelling and family-recruitment work.
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.
Lead all fundraising initiatives, including the Highlander Fund (annual giving), capital campaigns, planned giving, corporate and foundation support, and endowed funds.
Design and implement systems for identifying, cultivating, soliciting, and stewarding donors to strengthen the culture of philanthropy across the Lake Highland community.
Personally manage a portfolio of major donors and prospects, building meaningful, mission-aligned relationships with them.
Oversee stewardship and donor recognition events, including the Founders Circle, President's Dinner, and annual giving reports.
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, including helping to identify and support the President's own portfolio of prospects and donors.
Clarify and strengthen the partnership with the Lake Highland Parent Association and support alumni engagement through volunteer opportunities, events, and philanthropy.
Serve as the primary liaison to the Development Committee and Committee on Trustees, ensuring active Board engagement in philanthropy and governance.
Ensure accuracy in financial reporting, gift processing, and compliance with ethical fundraising standards in collaboration with the Business Office.
Oversee Advancement operations to ensure the integrity, security, and strategic use of data, integrating analytics and donor intelligence into all advancement strategies.
Build strong, collaborative working relationships with the Directors of Communications and Marketing and of Enrollment Management.
Help ensure that donor- and campaign-facing storytelling, publications, and digital content are consistent with the school's broader brand and messaging in partnership with the Director of Communications and Marketing.
Help align advancement priorities and family relationships with the school's recruitment and retention efforts, contributing strategic input and advancement expertise to both areas in partnership with the Director of Enrollment Management.
Build, lead, and mentor a high-performing Advancement team, setting clear goals, establishing success metrics, and promoting professional growth across annual giving, major and planned gifts, alumni relations, and advancement operations.
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.