Employment Opportunities

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: [email protected]. 

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.

Position Description
The Winston School seeks a dynamic and experienced College Counselor and International Baccalaureate (IB) Programme Coordinator. This individual will be instrumental in fostering a supportive, engaging, and challenging environment for students, helping them to identify strengths and opportunities, and navigate the college application process. Additionally, as Winston pursues IB Programme authorization in both the Middle Years and Diploma Programs, our ideal candidate has experience working with learning different students in a high-challenge, high-support environment to support academic excellence. As a key member of the student support team, the College Counselor partners closely with students and families to guide them through a thoughtful, individualized college search and application process.  

Central to this position is building meaningful, trusting relationships with students and families. The College Counselor helps students make intentional choices in academic planning, extracurricular involvement, and personal growth, ensuring they take full advantage of the many opportunities available at Winston and beyond. Grounded in the belief that well-rounded engagement in academics, athletics, service, and extracurriculars leads to meaningful postsecondary paths and lifelong success, the College Counselor plays a key role in preparing students for life after Winston. 

This position also includes direct academic advising, collaboration with faculty and administrators, and ongoing engagement with college admission professionals. Summer work is expected in coordination with the Head of Upper School and the Head of School. The College Counselor also supports related programming such as coordinating accommodation on standardized tests, admissions-focused workshops, and IB Programme related support. 

Key Responsibilities and Essential Functions

Student Advising & Academic Planning

• Serves as the College Counselor and IB Programme Coordinator
• Guides students in developing and annually reviewing a thoughtful four-year academic plan aligned with their college or career goals, alongside the Head of Upper School
• Counsels students on course selection, academic rigor, senior projects proposals, athletic eligibility requirements, performing and visual arts auditions/portfolio requirements, and summer enrichment opportunities
• Manages course selection and add/drop processes for Grades 9–12
• Monitors and supports students’ academic progress in collaboration with the Center for Teaching and Learning, division leadership, and faculty.
• Maintains cooperative relationships with local and regional college providers of Dual Credit courses

College Counseling & Application Support

• Guides students and families through all aspects of the college search and application process
• Recommends colleges aligned with each student’s academic profile, interests, and family priorities
• Counsels families through merit scholarship, honors program, financial aid, athletic recruitment, performing arts auditions, and service academy application processes
• Provides guidance and support throughout all aspects of the application process, including application platform workshops; review and feedback on all application materials; writing a highly personalized counselor recommendation; and review of teacher recommendations
• Maintains accurate matriculation records and documentation of post-secondary school achievement
• Serves as a student advocate throughout the admission process
• Stays informed about evolving trends in college admission and communicates updates effectively to students and parents

Program Development & Leadership

• Develops, plans, and implements advising programs and educational events for students and families in collaboration with the Head of Upper School
• Presents to students and parents at key junctures in the academic planning and college process.
• Assists in coordinating and hosting college representative visits.
• Builds and maintains professional relationships with college admission officers through visits, fly-in programs, webinars, and ongoing research.

International Baccalaureate Programme 

• Program Leadership & Compliance: Ensuring the school adheres to IB regulations, managing authorization processes, and overseeing school-wide implementation of the curriculum
• Administration & Assessment: Coordinating internal assessments, mock exams, and final exams; submitting grades to the IBO and managing the IB calendar
• Teacher Support & Development: Facilitating professional development, organizing staff training, and ensuring teachers are familiar with IB publications and resources
• Student & Parent Liaison: Advising students on subject choices, managing program components, and communicating program requirements to parents
• Resource Management: Managing the IB program budget and procuring necessary materials.

Qualifications/Experience:

• Bachelor’s degree required; Master’s degree preferred.
• Minimum of three years of experience in selective college admissions (preferred) and/or college counseling.
• Understanding of the unique needs of college bound students with learning differences
• Strong understanding of the college admission landscape across institution types, selectivity levels, and student support services and programs
• Excellent writing, communication, organizational, and time-management skills
• Demonstrated ability to work effectively in a high-stakes, deadline-driven environment
• High ethical standards and commitment to student advocacy and student privacy
• Sensitivity to and experience working with students from diverse backgrounds
• Proficiency with Google Workspace (Gmail and Google Drive); experience with Naviance, YouScience, or similar college counseling platforms preferred
• Strong public speaking, listening, and interpersonal skills

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 the Head of School, Dr. Jenn Milam, [email protected]. 

Priority review of applications will begin April 2026, and will continue until the position is filled.