Assistant to the Head of the Westchester Lower School
Job Details
Westchester Lower School - White Plains, NY


Westchester Lower School


The Windward School is currently seeking an Assistant to the Head of the Westchester Lower School.


This position works closely with the Head of Westchester Lower School. The ideal candidate will require strong communication, interpersonal and organizational skills, the ability to work proactively to support day-to-day operations at Westchester Lower School, a keen attention to detail, a positive team-oriented approach, and flexibility.


Qualified candidates should not only have the experience and expertise listed but also should:

  • Have a deep understanding of and a passion to support The Windward School’s mission
  • Display a proven commitment to diversity work and fostering an inclusive culturally competent school environment


Duties and Responsibilities

  • Supplies daily administrative support to the Head of the Westchester Lower School
  • Coordinates communication between the Head of Westchester Lower School’s office and families, faculty, and staff, as well as other Windward departments and divisions
  • Manages multiple schedules and calendars
  • Creates and regularly updates documents, reports, and letters
  • Maintains divisional and student files and provides, distributes, and tracks student-related documents
  • Drafts and distributes divisional communications utilizing School’s message notification system  
  • Manages parent-teacher conference scheduling and progress report distribution

Specific Requirements

  • Bachelor’s degree
  • 3-5 years of mid level administrative support experience
  • Essential computer and database skills including a strong working knowledge of, but not limited to, Microsoft Office (Outlook, Excel, Word, Teams, PowerPoint), as well as Adobe Pro and online scheduling tools. Experience with project management software a plus.
  • Excellent verbal and written communication skills
  • The ability to prioritize tasks and assignments while maintaining a welcoming, supportive office in a busy school setting
  • The ability to maintain a high degree of confidentiality and discretion at all times

About Us

The Windward School is the preeminent school for the remediation of language-based learning disabilities for students in Grades 1-9.  Through a multisensory, direct instruction curriculum, Windward helps students thrive academically, while enabling them to understand their learning styles, build confidence, and develop self-advocacy skills. 


The Windward School's vision is a world where every child with a language-based learning disability is empowered to achieve unlimited success. 


Windward currently employs more than 450 faculty and staff members across four divisions and three campuses, giving employees a small, tight-knit community at their campus while feeling part of a larger organization. Two Westchester campuses are located in White Plains, NY, and the Manhattan campus is located on the Upper East Side. 


The Windward School also has two divisions that support its mission — The Windward Teaching Training Program and The Windward Institute.

  • The renowned Windward Teacher Training Program recruits, hires, trains, mentors, and retains teachers at The Windward School. 
  • The Windward Institute offers professional development to all educators, forms partnerships with research and educational institutions, and advocates for students with language-based learning disabilities.


The Windward School truly transforms students' lives, and our faculty and staff all contribute daily to the School's mission. The friendly, hard-working, and collegial Windward community provides a supportive professional environment in which all members are encouraged to develop into outstanding educational professionals. 


Our Mission

The School is an independent, coeducational day school dedicated to providing an excellent instructional program for children with language-based learning disabilities.  The multisensory curriculum is designed for students of average to superior intelligence who can benefit from the unique educational experience provided.  Through direct instruction in small class settings, a trained staff assists students to improve their language skills.  Academic success, combined with opportunities for social and emotional growth, enables students to understand their learning styles, build confidence, and develop self-advocacy skills. Windward is committed to helping students achieve their full potential in preparation for a successful return to the mainstream educational environment.  To meet these goals, the School provides ongoing training to its faculty based on the most current research and also shares its expertise with the parent body, other educators, and the broader community.