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

This full-time position in Middle School Mathematics requires an individual who is skilled in teaching students with ADHD, dyslexia, and other high-incidence, related learning differences through multisensory and differentiated instruction. The classroom teacher is highly collaborative and committed to designing and adapting instruction to meet a range of student learning needs and interests. They are skilled in establishing strong relationships with students and provide effective and consistent communication with parents regarding students’ behaviors, academic concerns, and progress. The classroom teacher is responsible for organizing and implementing a rigorous and differentiated instructional program in seventh and eighth grades. The Middle School Math teacher is responsible for teaching numeracy, computation, problem solving, and complex mathematics while being attentive to the integration of social-emotional learning and sensory regulation. 

Primary Responsibilities

• Provide direct, differentiated instruction for students, focusing on the development of mathematical understanding alongside collaboration, critical thinking, and problem solving. 
• Accommodate and meet the needs of a range of neurodivergent students with dyslexia, dysgraphia, dyscalculia, ADD/ADHD, and other executive functioning and processing challenges. 
• Identify, select, modify, and create instructional resources to meet the needs of students with varying backgrounds, learning styles, and learning needs, in collaboration with middle school teammates. 
• Serve as Middle School advisor and assist with field trips, clubs, activities, and other extracurricular opportunities
• Design, plan and implement curriculum that is grounded in research-based practices and responsive to students with diverse learning profiles. 
• Integrate technology into the curriculum following best practices.
• Use classroom management systems that are focused on students’ social emotional needs and self-regulation.
• Create and cultivate a positive environment that encourages students to actively participate in their own learning.
• Provide effective and consistent communication with parents and the school’s Student Support Team regarding students’ behaviors, academic progress, and social-emotional development.
• Model professional and ethical standards when working with students, families, colleagues, and the community. 
• Perform supervisory duties as assigned, attend and participate in professional learning opportunities, and/or engage in other school-related duties as appropriate.

 Qualifications / Experience

• Bachelor’s Degree in Mathematics, middle grades education, special education, or related field required. 
• Teaching certification preferred with certification in teaching Mathematics (grades 5-12) or coursework/professional learning toward certification
• Graduate degree or extensive graduate work in the field of Math Education, Special Education, or learning differences/neurodiversity is preferred. 
• Minimum of 3-5 years classroom teaching experience.\
• Experience teaching students with Learning Differences, and demonstrated ability to provide classroom-based accommodations that support the development of mathematical proficiency and understanding. 
• Proficiency with instructional technology, especially Google Suite and cloud based network solutions.
• Strong work ethic, sense of humor, and commitment to continuous improvement and learning
• Multi-sensory math training or familiarity is ideal!

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.