Director of Finance and Operations

Location: Winsted

Position Type:
Administration/Director of Business Services

Date Posted:
5/13/2026

Location:
Central Office

Date Available:
07/01/2026
DIRECTOR OF FINANCE & OPERATIONS

The Winchester Public Schools is seeking a dynamic and strategic Director of Finance & Operations to serve as a key member of the district's leadership team. This position functions as a true partner to the Superintendent helping to shape, manage, and sustain all non-instructional systems that support student success.

This is an exceptional opportunity for a collaborative, solutions-oriented leader who thrives in a hands-on environment and is energized by the breadth and complexity of district operations.

THE ROLE

The Director of Finance & Operations oversees the financial health and operational effectiveness of the district. This includes leadership of budgeting and long-range financial planning, facilities and capital projects, transportation, food services, safety and security, and a range of business and personnel functions.

The successful candidate will bring both strategic insight and day-to-day execution ensuring that systems run smoothly, resources are aligned to priorities, and the district operates efficiently, transparently, and in compliance with all applicable regulations.

KEY RESPONSIBILITIES

• Lead the development and management of the district's budget and long-term financial plans
• Oversee all accounting, financial reporting, and internal controls
• Supervise operations including facilities, maintenance, transportation, food services, and safety
• Oversee business and personnel functions, including benefits, contracts, and compliance
• Manage purchasing, procurement systems, and vendor relationships
• Support and participate in collective bargaining and labor relations
• Coordinate grant applications, management, and reporting
• Oversee risk management, insurance, and regulatory compliance
• Serve as a strategic advisor and key thought partner to the Superintendent and Board of Education

The Winchester Public Schools is a close-knit, student-centered district where relationships matter and leadership is collaborative. The Director of Finance & Operations plays a critical role in shaping the district's future and ensuring that resources are aligned to support all students.

This position offers the opportunity to make a meaningful impact across all facets of district operations while working in close partnership with the Superintendent and a dedicated team of educators and staff.

QUALIFICATIONS

• Demonstrated leadership in managing complex operations or organizations
• Strong understanding of budgeting, accounting, and financial systems
• Sound judgment and the ability to solve problems independently
• Excellent communication and interpersonal skills
• Someone who is organized, reliable, and follows through
• Ability to think strategically while attending to operational details

REQUIREMENTS

• Valid motor vehicle operator's license
• Must be eligible for bonding in accordance with Connecticut State Statutes
• Degree in Accounting, Finance, Business, or Public Administration from an accredited college or university
• Experience in school finance, municipal finance, or a related field preferred
• Connecticut certification as a School Business Administrator (085 or 092)

* Related and provable experience or an equivalent combination of education, training, and experience will be considered

SALARY & TERMS

This is a non-union, full-time, non-remote forty (40) hour work week position with benefits. This position occasionally requires hours beyond the regular schedule, including evening Board meetings.

• 12 month work year
• Generous benefits package including health, vision, and life insurances, and sick, personal and vacation leaves.
• Competitive salary commensurate with experience:
  Range $130,000-$150,000

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.