City of Chesapeake Header

Payroll Analyst - Benefits

Chesapeake, VA

Job Description

The Finance Department is looking for a qualified Payroll Analyst to complete the timely and accurate enrollment and reconciliation of the employee/retiree health related benefits; to include medical, dental and vision plans in compliance with all federal, state and city mandates.

Other responsibilities of the Payroll Analyst include:
  • Reconciliation of the General Ledger Liability Accounts related to all health-related benefits each month. Maintain a current knowledge of the payroll system, payroll related laws and regulations and City personnel and payroll policies and procedures.

  • Administers health related benefits in the payroll system for all eligible City employees.

  • Oversees benefit enrollments for all new hires, employees with qualifying life events and Consolidated Omnibus Budget Reconciliation Act (COBRA) participants.

  • Serves as primary contact for plan vendors and third-party administrators to resolve eligibility, enrollment, and vendor billing discrepancies. Ensures accurate and timely remittance and payments to vendors.

  • Creates invoices and maintains EZ Pay for Retiree over 20 years premiums and Cobra participants.

  • Processes annual open enrollment updates and benefit reconciliation audits; balances and reconciles monthly benefit enrollment; ensures accurate collection of employee benefit premiums.

  • Collaborates with employees and the Department of Human Resources to resolve and address benefit related issues and questions.

  • Manages the transmission of benefit files to vendors to include verification of file delivery and benefit enrollments.

  • Generates reports for the annual audit.

Performs other related duties as assigned.

The City of Chesapeake offers an exceptional range of benefits. Please browse our Benefits Brochure, for a full list of benefits and employee perks.

#Payroll
#PayrollAnalyst

PDN-a1ac0a85-24e9-4f61-abe4-776006575756
The Finance Department is looking for a qualified Payroll Analyst to complete the timely and accurate enrollment and reconciliation of the employee/retiree health related benefits; to include medical, dental and vision plans in compliance with all federal, state and city mandates.

Other responsibilities of the Payroll Analyst include:
  • Reconciliation of the General Ledger Liability Accounts related to all health-related benefits each month. Maintain a current knowledge of the payroll system, payroll related laws and regulations and City personnel and payroll policies and procedures.

  • Administers health related benefits in the payroll system for all eligible City employees.

  • Oversees benefit enrollments for all new hires, employees with qualifying life events and Consolidated Omnibus Budget Reconciliation Act (COBRA) participants.

  • Serves as primary contact for plan vendors and third-party administrators to resolve eligibility, enrollment, and vendor billing discrepancies. Ensures accurate and timely remittance and payments to vendors.

  • Creates invoices and maintains EZ Pay for Retiree over 20 years premiums and Cobra participants.

  • Processes annual open enrollment updates and benefit reconciliation audits; balances and reconciles monthly benefit enrollment; ensures accurate collection of employee benefit premiums.

  • Collaborates with employees and the Department of Human Resources to resolve and address benefit related issues and questions.

  • Manages the transmission of benefit files to vendors to include verification of file delivery and benefit enrollments.

  • Generates reports for the annual audit.

Performs other related duties as assigned.

The City of Chesapeake offers an exceptional range of benefits. Please browse our Benefits Brochure, for a full list of benefits and employee perks.

#Payroll
#PayrollAnalyst

PDN-a1ac0a85-24e9-4f61-abe4-776006575756

About City of Chesapeake

Chesapeake, Virginia is a vibrant community that enjoys the best of two worlds, one of urban variety, culture, and excitement, and another of rural landscapes and relaxed living. 

Located 20 minutes from the oceanfront, 15 minutes from downtown Norfolk, and 45 minutes from Colonial Williamsburg and the Outer Banks of North Carolina, Chesapeake is the perfect place in which to live, work, and raise a family. 

Home to beautiful parks, lakes, and rivers, Chesapeake has more miles of deepwater canals (part of the Intracoastal Waterway) than any other city in the country! 

The City of Chesapeake was formed through the merger of the City of South Norfolk and Norfolk County in 1963. It’s a community of communities, with each having its own distinctive history. 

Over the last decade, many national and international companies have taken advantage of the City’s ports, atmosphere, and highly qualified labor market by relocating to Chesapeake. 

Chesapeake’s neighborhoods offer a variety of comfortable housing alternatives, from apartments and town homes, to single-family residences and executive homes. The City is consistently ranked by the FBI as one of the safest U.S. cities (with populations over 150,000), which lends to the safe, community atmosphere that residents enjoy.

Related Jobs

Continue to Apply

City of Chesapeake would like you to finish the application on their website.

Apply For This Job
City of Chesapeake
Payroll Analyst - Benefits
City of Chesapeake
Chesapeake, VA
May 1, 2026
Your Information
First Name *
Last Name *
Email Address *
This email belongs to another account. Please use a diferent email address or Sign In.
Zip Code *
Password *
Confirm Password *
Create your Profile from your Resume
By clicking the Apply button, you agree to the terms of use and privacy policy and consent to receive emails from us about job opportunities, career resources, and other relevant updates. You can unsubscribe at any time.
Continue to Apply

City of Chesapeake would like you to finish the application on their website.

©2026 International Association of Women.
Powered by TalentAlly.