Payroll & Benefits Manager

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

This is a great opportunity for an HR professional who is ready to take the next step in their career and grow their knowledge of employee benefits, payroll, and HR compliance.

We’re looking for someone who is highly organized, detail-oriented, self-motivated, comfortable working independently, and exceptionally strong in Microsoft Excel. You don’t need to walk in knowing every aspect of benefits, payroll, or compliance, we’re willing to train the right person. What matters most is your ability to take initiative, learn, research, solve problems, work accurately, and provide great support to our employees and managers.

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 employee communications.
• Assist employees with benefit questions and help them understand their coverage and eligibility.
• Work with benefit carriers, brokers, third-party administrators, and vendors.
• Support annual benefit renewals and Open Enrollment.
• Learn and apply requirements related to ACA, ERISA, COBRA, 401(k), and other benefit regulations.
• Maintain required benefit documentation, notices, and compliance records.
• Research regulatory changes and work with the HR Director to help ensure benefit and payroll practices remain compliant.
• Prepare, review, and process biweekly payroll through Paycom.
• Maintain accurate employee payroll and benefit information.
• Assist employees and managers with payroll and benefit questions.
• Use Microsoft Excel for reporting, audits, data analysis.
• Maintain and organize the inter-office SharePoint platform to communicate HR information, documents, and resources.
• Assist with HR reporting, audits, compliance requirements, and special projects.

What We’re Looking For

We’re looking for someone who is dependable, curious, resourceful, and ready to learn. You should be comfortable digging into information, researching a question when you don’t know the answer, and following an issue through to resolution.

Our Must-Haves

• Must be a self-starter with the ability to work independently, take initiative, prioritize responsibilities, and follow tasks through to completion with minimal supervision.
• Strong Microsoft Excel skills, including formulas, lookups, pivot tables, reporting, and working confidently with data.
• Working knowledge of Microsoft SharePoint.
• Previous Human Resources or related professional experience.
• Strong analytical, research, and problem-solving skills.
• Excellent attention to detail, organization, and follow-through.
• Ability and willingness to learn new systems, processes, and regulatory requirements.
• Strong written and verbal communication skills.
• Ability to communicate clearly and provide professional, employee-focused service.
• Sound judgment and the ability to maintain strict confidentiality.

Experience That’s a Plus

Experience with employee benefits or payroll is preferred but not required. Experience with Paycom and familiarity with ACA, ERISA, COBRA, or 401(k) administration are also a plus.

Training will be provided to the right candidate.

Previous experience in hospitality, a high-volume workplace, or a seasonal workforce environment is also a plus.

Why Wintergreen?

This isn’t your typical office setting.

Wintergreen Resort is a four-season mountain resort in Virginia’s beautiful Blue Ridge Mountains, offering skiing, golf, racquet sports, lodging, dining, recreation, and more. Our HR team supports a diverse workforce across the resort, which means 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.

Come build your HR career somewhere with a pretty incredible view.

Wintergreen Resort is an Equal Opportunity Employer.