Payroll and Benefits Specialist

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At Pomfret School, our mission is to empower students to pursue lives of meaning and purpose. Grounded in our core values of Community , Growth , and Integrity , we cultivate a collaborative and innovative environment where every employee is valued and supported. As a key member of the Business Office team, the Payroll and Benefits Specialist plays an essential role in sustaining our institutional vitality by ensuring our faculty and staff are cared for with precision and equity so they can focus on inspiring the next generation of change makers and problem solvers.

Responsible for preparing and producing timely and accurate payrolls, executing benefits and retirement administration, ensuring compliance with non-profit audit and regulatory filings, and performing general business office duties. Reports to the Director of Human Resources.

• Accuracy and attention to detail
• Confidentiality and discretion
• Timeliness
• Problem analysis and resolution
• Audit readiness and regulatory compliance knowledge

Essential Job Duties and Responsibilities

Payroll Operations & Financial Compliance

• Prepare and process biweekly and monthly payrolls for over 170 employees.
• Review and ensure the accuracy and timeliness of approved timesheets.
• Enter, track, and deduct all garnishments, rate changes, voluntary contributions, and tax withholdings.
• Prepare payroll journal entries and perform account reconciliations.
• Issue annual W-2 and 1095-C forms to employees and file corresponding year-end returns.
• Prepare payroll schedules and support materials for the school's annual external CPA financial audit and IRS Form 990 preparation (including Schedule J executive compensation tracking).
• Manage payroll records and classifications for the annual Workers’ Compensation insurance audit.
• Complete quarterly and annual statutory filings, including Form 941, CT Paid Leave (CTPL) remittances and supplemental compensation calculations, CT Unemployment (UC-2), and CT withholding reconciliations.

Benefits & ERISA Plan Administration

• Administer day-to-day employee benefits programs, including health, dental, vision, life, short/long-term disability, and 403(b) retirement plans.
• Lead annual open enrollment, employee onboarding benefit orientations, and qualifying life event status changes.
• Coordinate the annual 403(b) retirement plan audit with independent auditors and process the annual Form 5500 filing with the Department of Labor.
• Reconcile monthly benefit invoices against payroll deductions and process vendor payments.
• Track and manage leave administration (FMLA, CT Paid Leave, workers' compensation, and PTO balances).

HRIS, Analytics & Mandatory Reporting

• Maintain HRIS employee database integrity, processing status changes, salary adjustments, and terminations.
• Complete mandatory federal and regional reporting, including EEO-1 demographic filings and independent school staffing census surveys.
• Generate routine and custom payroll, benefit, and demographic reports for internal budgeting and leadership review.

Requirements

Qualifications & Experience

• Education: Associate or bachelor’s degree in Accounting, Business, Human Resources, or related field preferred (or equivalent practical experience).
• Experience: 3–5 y Direct experience supporting annual financial audits, workers' comp audits, and Form 5500/403(b) plan audits. Non-profit experience strongly preferred.
• Audit Experience: Direct experience supporting annual financial audits, workers' comp audits, and Form 5500/403(b) plan audits.
• Technical Skills: Proficiency in payroll/HRIS platforms (e.g., Paylocity, Veracross, ADP) and advanced proficiency in Microsoft Excel.
• Knowledge: Deep understanding of federal and Connecticut state payroll laws, wage regulations, ERISA rules, and non-profit compliance standards.

Benefits Package:

Medical, dental, and vision insurance; 403(b) retirement plan with generous employer matching; paid time off (vacation, personal, sick, and school holidays); life and disability insurance; professional development opportunities; and tuition remission.