Benefits Manager Jobs in Virginia

Wintergreen Resort is seeking an experienced Payroll & Benefits Manager to join our Human Resources team.

This is a key HR role responsible for the administration and compliance of our employee benefit programs, along with bi-weekly payroll. We're looking for someone with a strong benefits background who understands that benefits administration goes well beyond enrollment — including eligibility, employee communications, regulatory requirements, COBRA, 401(k), carrier relationships, and compliance.

The right person will be knowledgeable, organized, detail-oriented, and comfortable serving as a resource to employees and managers while working closely with the HR Director.

What You'll Do

• Administer employee benefit programs, including medical, dental, vision, life, disability, COBRA, and 401(k).
• Manage benefit eligibility, enrollments, qualifying life events, terminations, deductions, and required employee communications.
• Maintain working knowledge of ACA, ERISA, COBRA, 401(k), and applicable federal and state benefit requirements.
• Monitor ACA eligibility and support required benefit compliance, documentation, and reporting.
• Work closely with benefit carriers, brokers, third-party administrators, and vendors.
• Support annual benefit renewals and Open Enrollment, including employee communications, system setup, and enrollment support.
• Serve as a knowledgeable resource to employees and managers regarding benefits and payroll.
• Complete required employer reporting and records, including EEO-1 and OSHA 300 reporting.
• Stay current on federal and state laws and regulatory changes affecting employee benefits and payroll and communicate potential compliance impacts to the HR Director.
• Prepare, review, and process bi-weekly payroll through Paycom.
• Ensure payroll practices comply with applicable federal and state wage and hour requirements.
• Maintain required payroll, benefit, and compliance records and reporting.
• Assist with regulatory reporting, audits, and compliance requirements

What We're Looking For

Strong employee benefits administration and compliance experience is essential for this position.

• Hands-on experience administering employee benefit programs.
• Working knowledge of ACA, ERISA, COBRA, 401(k), and benefit compliance requirements.
• Payroll processing experience and knowledge of wage and hour requirements.
• Strong Microsoft Excel skills, including formulas, lookups, pivot tables, and reporting.
• Strong working knowledge of Microsoft SharePoint.
• Strong research, problem-solving, organizational, and communication skills.
• Excellent attention to detail and ability to manage multiple deadlines.
• Ability to explain benefit and payroll information clearly to employees and managers.
• Sound judgment and the ability to maintain strict confidentiality.
• Paycom experience preferred

Previous HR, benefits, and payroll experience is a must. Hospitality, high-volume, or seasonal workforce environment is a plus.

Why Wintergreen?

Wintergreen Resort is a four-season mountain resort offering skiing, golf, racquet sports, lodging, dining, recreation, and more. Our HR team supports a diverse workforce, so no two days are exactly alike.

Eligible full-time employees receive a comprehensive benefits package including medical, dental, vision, life insurance, short- and long-term disability, paid time off, 401(k), and unique resort recreational benefits and discounts.

Salary: $60,000–$64,000 annually

Wintergreen Resort is an Equal Opportunity Employer.