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Benefits and Leave Specialist, HR (Full Time

Job in Williamsburg, James City County, Virginia, 23187, USA
Listing for: WILLIAMSBURG LANDING INC
Full Time position
Listed on 2026-08-04
Job specializations:
  • HR/Recruitment
    Regulatory Compliance Specialist, HRIS Specialist, HR Generalist / Talent Management, Recruiter / Talent Acquisition
Salary/Wage Range or Industry Benchmark: 65000 - 90000 USD Yearly USD 65000.00 90000.00 YEAR
Job Description & How to Apply Below
Position: Benefits and Leave Specialist, HR (Full Time)

Benefits and Leave Specialist, HR (Full Time)

Williamsburg Landing Williamsburg, Virginia, United States

About this position

Description:

JOB SUMMARY

Reporting to the Chief Talent Officer, as a member of the Talent Management team, the Benefits & Leave Specialist administers Williamsburg Landing's health and welfare plans, retirement programs, and leave of absence processes, ensuring accuracy and regulatory compliance. Key duties include managing statutory compliance for FMLA and short-term disability, coordinating the ADA interactive process, administering the workers' compensation program, and executing mandatory regulatory filings.

Additionally, the role administers position and compensation workflows, including processing pay and position classification changes in the HRIS. The ideal candidate will combine a strong compliance and analytical focus—including routine internal data audits, strong HRIS database management, and utilization of Excel for premium reconciliation, with a professional, service-oriented approach to supporting team members with their compensation, benefits and leave inquiries.

ESSENTIAL JOB FUNCTIONS

  • Administers health and welfare plans, including enrollments, changes and terminations; processes required documents through payroll and insurance providers to ensure accurate record-keeping and proper deductions
  • Reviews and approves billing statements, notifies carriers of changes, and ensures timely approval of invoices for payment by Finance & Accounting
  • Conducts routine internal audits of health and welfare plan enrollments against carrier billing to prevent compliance leakage
  • Maintains a thorough understanding of health plan benefits and coverage offerings, deductibles, employer contributions, and employee premiums; explains coverages to team members during new hire orientation and upon request
  • Ensures all plan administration strictly aligns with ACA, COBRA, HIPAA, Section 125, and relevant state mandates
  • Provides compliance oversight and administration for retirement plans (e.g., 403b), ensuring adherence to ERISA, IRS, and DOL regulations. Manages the execution of mandatory annual filings (Form 5500), non-discrimination testing, required participant disclosures, and serves as the primary point of contact for annual plan audits.
  • Manages the end-to-end statutory compliance of FMLA, short-term/long-term disability, and unpaid leaves of absence. Ensures precise tracking of job-protected leave, accurate designation notices, timely medical certifications, and coordinates with TM Business Partners to facilitate the ADA interactive process for return-to-work accommodations.
  • Administers the workers' compensation program in strict accordance with state regulations and OSHA recording criteria, mitigating organizational risk by analyzing injury trends, filing timely First Report of Injury (
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