School Principal

Location: Winsted

Position Type:

Administration/Principal

Date Posted:

1/29/2026

Location:

Pearson School

 Additional Information:
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Pearson School Principal (Grades 36)

About Our School & District

The Winchester Public Schools is an elementary school district serving approximately 600 students in a close-knit school community. We are deeply committed to high-quality teaching and learning, strong relationships, and a culture where students and adults feel known, valued, and supported. Our district values collaboration, continuous improvement, and shared responsibility for student success.

The Opportunity

We are seeking an elementary school principal who is a strong instructional leader, a relationship builder, and a thoughtful systems thinker. The ideal candidate believes that academic excellence and student well-being are inseparableand leads in ways that reflect both.

Key Responsibilities

Instructional Leadership

* Serve as the school's instructional leader, ensuring high-quality, standards-aligned teaching and learning in all classrooms.

* Support teachers through meaningful feedback, coaching, and professional learning.

* Use multiple sources of data to monitor student progress and guide instructional improvement.

* Promote inclusive, engaging, and developmentally responsive instructional practices for Grades 36 learners.

Culture, Climate, and Relationships

* Foster a positive, inclusive school culture grounded in trust, respect, and belonging.

* Build strong relationships with students, staff, families, and community partners.

* Support student behavior through proactive, relationship-centered, and developmentally appropriate approaches, relying heavily on restorative practices and positive behavioral supports.

* Model empathy, professionalism, and reflective practice.

Leadership & Management

* Lead and support a collaborative school leadership team.

* Recruit, retain, and develop high-quality staff.

* Manage school operations, schedules, and resources effectively, prioritizing safety and instruction.

* Communicate clearly and consistently with families and the broader school community.

* Collaborate as a member of the district leadership team.

Qualifications

* Connecticut certification as an Intermediate Administrator or Supervisor (092), or eligibility.

* Prior experience as a principal preferred.

* Successful teaching experience at the elementary level; experience in Grades 36 preferred.

* Demonstrated success as an instructional leader.

* Strong interpersonal, communication, and collaborative skills.

* Commitment to building strong relationships and a positive school culture.

* Experience leading or participating in school improvement efforts.

Preferred Attributes

* A leader who is visible, approachable, and student-centered.

* Deep belief in the potential of every child and adult.

* Experience supporting teachers through coaching and professional learning.

* Comfort navigating both instructional leadership and day-to-day school operations.

Salary & Benefits

Salary and benefits are competitive and commensurate with experience and qualifications, in accordance with the administrator contract.

Reports to:

Superintendent of Schools

Work Year: 260 work days, including days of the teacher work year

Application Procedure:
Apply Online in Applitrack, found on the district website

Selection Procedure:
Multi-Tiered Interview Process

Application Procedure

Please visit the Winchester Public Schools website to apply online chesterschools.org. Please be sure to attach your cover letter, resume, and three recent references.

The Winchester Board of Education, per its policy, does not make employment decisions on the basis of race, color, religion, age, sex, marital status, sexual orientation, national origin, alienage, ancestry, disability,

pregnancy, genetic information, veteran status, gender identity or expression, status as a victim of domestic violence, or any other basis prohibited by state or federal law ("Protected Class"), except in the case of a bona fide occupational qualification.