Payroll Supervisor

Payroll Supervisor / Cheshire Public Schools

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The Payroll Supervisor is a highly visible and critical position within the Office of School District Operations, responsible for the accurate, timely, and compliant administration of all district payroll functions. This role carries significant financial, operational, and regulatory responsibility and works collaboratively with Human Resources, Finance, and district leadership.

• Plan, coordinate, and manage all aspects of the district’s payroll operations.
• Ensure the accurate and timely processing of bi‑weekly payroll through Munis, including employee compensation, payroll and benefit deductions, balancing, reconciliation, reporting, and recordkeeping.
• Serve as the system administrator and subject‑matter expert for payroll‑related systems, including Munis, Frontline Absence Management, Frontline Time & Attendance, PSST, and related platforms.
• Process and review wage, stipend, and benefit changes in Munis, ensuring all actions are properly authorized and compliant with established procedures, collective bargaining agreements, and Board of Education policies.
• Prepare, file, and maintain all required federal, state, and agency payroll reports and filings in a timely and accurate manner.
• Provide oversight, training, and supervision to the Benefits Specialist supporting payroll and benefits administration.
• Develop detailed annual payroll budget projections, including calculations for contractual step movements, general wage increases, stipends, and other payroll‑related costs.
• Participate in internal budget development and review meetings; prepare payroll cost analyses; and provide payroll and financial documentation in support of the Town’s annual audit.
• Respond professionally and confidentially to employee inquiries related to payroll, compensation, and benefit deductions.
• Maintain accurate employee payroll records and work schedules within Frontline and related systems.
• Coordinate and communicate with payroll‑related vendors and external partners, as necessary.
• Monitor changes in payroll, tax, and benefits laws and regulations, and assist in implementing procedural updates to ensure continued compliance.
• Participate in and/or lead special projects and related duties in payroll, benefits, and human resources as assigned by the Human Resources Manager, Chief Operating Officer, or Superintendent of Schools.

Chief Operating Officer

• Demonstrated working knowledge of payroll, benefits, and applicable human resources laws and regulations.
• Strong knowledge of accounting and bookkeeping principles, with excellent mathematical, analytical, and technology skills.
• Ability to independently manage special projects and programs, exercise sound judgment within assigned areas of responsibility, and appropriately identify when guidance or approval is required from the Human Resources Manager or other administrators.
• Excellent interpersonal and teamwork skills, with strong verbal and written communication abilities.

• Experience in a school district and/or municipal environment.
• Experience working with Tyler Technologies products, including Munis and/or Infinite Visions.
• Associate’s Degree or higher from an accredited institution.
• Five (5) or more years of progressively responsible experience in payroll administration, including a strong understanding of payroll and benefits administration.

In accordance with the Agreement Between Cheshire Board of Education and the Cheshire Educational Secretaries and Technicians Union. Grade 6 Position, Starting Salary $37.34/hour (effective School Year 25‑26). Full Benefits Provided including excellent Medical, Dental and Retirement Plans.

Please apply online at

Cheshire Public Schools reserves the right to close the posting when a suitable applicant is found before the closing date.

Mid‑Senior level

Full‑time

Human Resources