Department: The Winston School

Reports to: Head of School

Full/Part-time: Full-time (11 months)

Date Posted: May 2026

Start Date: July 15, 2026

About The Winston School
The Winston School is a small college preparatory school designed to maximize the potential of bright students who learn differently. Through individualized learning strategies, our students are empowered to confidently meet the challenges of tomorrow. 

At the Winston School, students gain the learning skills and self-reliance to succeed in college and throughout life. Serving children in grades K-12, Winston challenges its students to achieve in an environment that not only supports but also celebrates their individuality and creativity.

Position Description
The executive assistant provides consistent, confidential, and professional administrative support for the head of school and admissions office, as well as serving as the front desk coordinator. This position is integral in welcoming our community to the campus, and plays an integral role in the day-to-day goings on of both the faculty and the student body. The ideal candidate will be the first line of communication between the head of school and the wider community.

Primary Responsibilities

• Promote the school’s mission, making it the center of all decisions and actions.
• Support an atmosphere of trust and openness among teachers, students, and parents.
• Maintain professional relationships with all faculty, staff, students and parents.
• Uphold a high standard of customer service and confidentiality related to school business and student issues.  
• Provide a warm, helpful, and informed welcome for all who enter the building.
• Work collaboratively with other staff to complete daily tasks, including but not limited to, taking attendance, managing phone calls and visitors, welcoming prospective families, and connecting with students.
• Organize and review daily priorities with the head of school and director of enrollment management.
• Work with the head of school to organize and coordinate faculty support, board meetings, and campus activities.
• Assist the head of school with work and events related to the board of trustees.
• Manage all arrangements for faculty/staff meetings and employee events.
• Record all meeting minutes, including board of trustee meetings.
• Attend the main phone line, gate access to campus, and coordinate with other support staff, as needed.
• Provide general clerical duties and administrative support to the school.
• Assist with managing and maintaining teaching/administrative supplies and materials.
• Maintain family, faculty, and student databases in collaboration with the senior leadership team.
• Prepare and manage the school calendar and other scheduled events.
• Serve on administrative and academic committees, as needed.
• Open and deliver the school’s mail, greet delivery drivers, and coordinate deliveries.
• Complete occasional errands.
• Assist in planning and executing campus-wide events.
• Work with the head of school and leadership team to prepare new-staff and faculty orientation for the start of the school year.
• Compile information as requested, formatting reports, graphs, tables, records, and presentations.
• Assume responsibility for other projects as assigned by the head of school.

 Qualifications / Experience

• Bachelor’s degree
• 5+ years' prior experience in education or as an executive assistant to a high-level school administrator or corporate executive
• Outstanding interpersonal skills
• Dedication to a high level of confidentiality
• Professional maturity and discretion
• Exceptionally capable in both written and oral communication
• Excellent organizational skills while still exhibiting a high degree of flexibility
• Technologically savvy, and willing to learn new programs and platforms
• Proven success at working collaboratively and efficiently on a creative and goal-oriented team
• Able to make quick decisions, take initiative, and prioritize tasks in a fast-paced environment
• Passionate about the mission and vision of The Winston School
• Warm and personable with a good sense of humor and considerable patience
• High-energy and enthusiastic about working in an academic atmosphere
• Familiarity with managing GOOGLE suite and other software

Please submit a cover letter addressing your interest and qualifications for the position, a current resume, and contact information for at least three (3) professional references to: jmilam@winston-school.org. 

Information about our school can be found at https://www.winston-school.org/. 

Priority review of applications will begin immediately, and will continue until the position is filled. 

About The Winston School

THE WINSTON SCHOOL IS A SMALL COLLEGE PREPARATORY SCHOOL DESIGNED TO MAXIMIZE THE POTENTIAL OF BRIGHT STUDENTS WHO LEARN DIFFERENTLY®. THROUGH INDIVIDUALIZED LEARNING STRATEGIES, OUR STUDENTS ARE EMPOWERED TO CONFIDENTLY MEET THE CHALLENGES OF TOMORROW. AT THE WINSTON SCHOOL, STUDENTS GAIN THE LEARNING SKILLS AND SELF-RELIANCE TO SUCCEED IN COLLEGE AND THROUGHOUT LIFE. SERVING CHILDREN IN GRADES K-12, WINSTON CHALLENGES ITS STUDENTS TO ACHIEVE IN AN ENVIRONMENT THAT NOT ONLY SUPPORTS BUT ALSO CELEBRATES THEIR INDIVIDUALITY AND CREATIVITY.

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