Executive Assistant to the President & Head of School

About Gulliver Preparatory School

Gulliver is a leading school of distinction, founded in 1926 and rooted in a century of educational excellence. To this day, our mission remains unchanged: to create an academic community devoted to educational excellence, with a personal touch, that fulfills each student’s potential. Our dedicated educators are at the heart of this mission, as they empower our students to think, create, and grow with purpose, connecting the classroom to the real world, and preparing them for what’s next. At Gulliver, we believe that success is not just what students achieve, but also who they become, and the role they play in shaping the future.

Rooted in the spirit of Miami, Gulliver embodies the city’s energy and innovation to create a learning environment that’s dynamic and future-facing. We aspire to be a national model for teaching and learning, where the intellectual curiosity of educators and students drives creativity, discovery, and the highest levels of achievement in the classroom, in our community, and beyond. 

Working at Gulliver

Gulliver is a trusted guide for families, and our faculty and staff are core to building powerful relationships that ensure every child thrives. Our compassionate, inspired educators nurture individuality and character, fostering a culture of collaboration that challenges students to meet their full potential and prepare for a future full of possibility.

Join a community where passionate educators elevate their craft, inspire future-ready learners, and take teaching and learning to the next level!

Position Overview

The Gulliver Preparatory Executive Assistant (EA) to the Senior Leadership Team (SLT) is a trusted strategic partner to the school’s most senior leaders. This highly visible role requires a professional of the utmost discretion, judgment, organizational ability, and interpersonal sophistication who can operate effectively in a fast-paced and mission-driven independent school environment.

The EA serves as an extension of the SLT, helping to advance institutional priorities through exceptional communication, coordination, anticipation, and execution. The EA possesses not only outstanding administrative and operational skills, but also the strategic awareness and professional presence to “see the game” before it unfolds—proactively identifying needs, anticipating challenges and opportunities, managing sensitive communications, and ensuring the smooth coordination of leadership initiatives across the school community.

The EA is a poised, energetic, and deeply professional individual who thrives in dynamic environments, demonstrates excellent judgment under pressure, and is committed to supporting the mission and values of Gulliver Preparatory School.

Essential Responsibilities

Executive Leadership Support

• Manage and prioritize the dynamic calendars of the President, Head of School, and CFO/COO, ensuring strategic alignment of time, priorities, meetings, and institutional commitments.
• Prepare briefing materials, agendas, correspondence, talking points, and background information in advance of meetings, events, and decision-making opportunities.
• Document key decisions, action items, and next steps emerging from meetings and leadership discussions, and ensure timely, clear, and professional follow-up communication to appropriate stakeholders to support accountability, alignment, and execution.
• Anticipate emerging needs and proactively identify areas requiring preparation, follow-up, communication, or strategic attention.
• Support the SLT in maintaining effective communication and alignment across the leadership team and broader school community.
• Exercise exceptional discretion and confidentiality in all matters related to school operations, personnel, students, families, and governance.

 Board of Trustees Coordination

• Coordinate all logistics and communications related to the board and committee meetings.
• Prepare and distribute board materials, agendas, presentations, minutes, and supporting documents in a timely and polished manner.
• Assist in managing board communications and follow-up items while maintaining professionalism, responsiveness, and confidentiality.
• Support trustee engagement efforts and help ensure a high-quality experience for board members and distinguished guests.

 Communications

• Draft, edit, and manage high-level correspondence on behalf of the President and Head of School with careful attention to tone, audience, and institutional voice.
• Prepare polished presentations, reports, speeches, and communications suitable for trustees, faculty, parents, donors, and community stakeholders.
• Serve as a professional and welcoming representative of the SLT in interactions with all constituents.
• Ensure clear and consistent communication flow across leadership teams and institutional initiatives.

 Leadership Team Coordination

• Coordinate leadership meetings, retreats, agendas, and follow-up action items.
• Assist in managing strategic projects and institutional initiatives across departments.
• Monitor timelines, deliverables, and communication workflows to support organizational effectiveness and accountability.
• Help identify communication gaps, political sensitivities, and emerging opportunities requiring leadership attention.

 Event Leadership and Institutional Presence

• Assist in planning and executing key institutional events, meetings, ceremonies, and community functions involving the SLT.
• Ensure that members of the SLT are clear on speaking expectations and runs of show for school events and activities.
• Demonstrate flexibility and stamina in supporting evening and weekend events, urgent school matters, and time-sensitive situations.

Qualifications

• Bachelor’s Degree required. 
• Outstanding organizational skills and attention to detail.
• Exceptional written, verbal, and interpersonal communication skills.
• Strong judgment, emotional intelligence, and political acumen.
• The ability to anticipate needs, think strategically, and proactively solve problems.
• Professional presence, maturity, discretion, and confidentiality.
• The ability to thrive in a fast-paced environment requiring adaptability, stamina, and responsiveness.
• Advanced proficiency with productivity, presentation, and communication platforms.

The EA is a proactive and trusted professional who can “see around corners,” extend the effectiveness and reach of senior leadership, and contribute meaningfully to the culture and operational excellence of the school.

Pre-Employment Requirements

Criminal Background Check, Level II Fingerprint Screening(s), and Drug screen. 

Gulliver is deeply committed to the principles of equity and diversity and seeks to create an inclusive community for all faculty and staff. Gulliver is an Affirmative Action/Equal Opportunity employer and a Drug Free Workplace.