Director of Finance and Operations

Position Type:Administration/Director of Business ServicesDate Posted:5/1/2026Location:Central OfficeDate Available:07/01/2026DIRECTOR OF FINANCE & OPERATIONSThe 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 ROLEThe 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 RESPONSIBILITIESLead the development and management of the district's budget and long-term financial plansOversee all accounting, financial reporting, and internal controlsSupervise operations including facilities, maintenance, transportation, food services, and safetyOversee business and personnel functions, including benefits, contracts, and complianceManage purchasing, procurement systems, and vendor relationshipsSupport and participate in collective bargaining and labor relationsCoordinate grant applications, management, and reportingOversee risk management, insurance, and regulatory complianceServe as a strategic advisor and key thought partner to the Superintendent and Board of EducationThe 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.QUALIFICATIONSDemonstrated leadership in managing complex operations or organizationsStrong understanding of budgeting, accounting, and financial systemsSound judgment and the ability to solve problems independentlyExcellent communication and interpersonal skillsSomeone who is organized, reliable, and follows throughAbility to think strategically while attending to operational detailsREQUIREMENTSValid motor vehicle operator's licenseMust be eligible for bonding in accordance with Connecticut State StatutesDegree in Accounting, Finance, Business, or Public Administration from an accredited college or universityExperience in school finance, municipal finance, or a related field preferredConnecticut certification as a School Business Administrator (085 or 092)* Related and provable experience or an equivalent combination of education, training, and experience will be consideredSALARY & TERMSThis 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 yearGenerous benefits package including health, vision, and life insurances, and sick, personal and vacation leaves.Competitive salary commensurate with experience: Range $130,000-$150,000APPLICATION PROCEDUREPlease visit the Winchester Public Schools website to apply online at www.winchesterschools.org. Please be sure to attach your cover letter, resume, and three recent references.