HR Benefits & Payroll Specialist

Location: Westport, CT (On-Site)
Compensation: $70,000–$80,000 annually

What You’ll Do

Benefits Administration

• Administer medical, dental, vision, life, disability, and voluntary benefit programs throughout the associate lifecycle.

• Manage benefit enrollments, qualifying life events, coverage changes, and terminations.

• Reconcile monthly benefit invoices, investigate billing discrepancies, and partner with vendors to resolve enrollment and coverage issues.

• Support Affordable Care Act (ACA) tracking, compliance, and reporting.

• Coordinate annual Open Enrollment activities, including system testing, data validation, and associate communications.

• Audit benefit elections, payroll deductions, eligibility, and HRIS data to ensure accuracy.

• Respond to associate questions about benefits, eligibility, payroll deductions, and claims.

• Process court-ordered benefit garnishments and related changes.

Payroll Administration

• Support accurate, timely weekly and biweekly payroll processing across multiple states.

• Review employee changes, benefit deductions, taxes, garnishments, and payroll adjustments.

• Analyze payroll reports, identify discrepancies, and resolve issues before payroll is finalized.

• Prepare payroll, paid time off (PTO) accrual, and month-end reports.

• Process payroll deductions and vendor payment files.

• Help ensure final pay is issued in accordance with applicable state wage payment requirements.

• Monitor payroll processes, identify opportunities for improvement, and stay current on regulatory and system changes.

Leave Administration & Workers’ Compensation

• Coordinate leave administration, including Family and Medical Leave Act (FMLA), applicable state leave programs, and other company-approved leaves of absence.

• Track leave requests, eligibility, required documentation, deadlines, and return-to-work dates.

• Communicate leave requirements, next steps, and status updates to associates, HR partners, and community leaders while maintaining confidentiality.

• Partner with associates, managers, HR, benefits providers, and other stakeholders to support a smooth and compliant leave process.

• Oversee workers’ compensation claim coordination, including incident documentation, claim submissions, follow-up, and communication with carriers and relevant internal partners.

• Monitor claim status and support the coordination of work restrictions, return-to-work arrangements, and required documentation.

• Maintain accurate records and reporting to support compliance, timely follow-up, and effective case management.

• Identify recurring issues and opportunities to improve leave and workers’ compensation processes.

HRIS, Reporting & Associate Support

• Maintain accurate employee and employment-related data in UKG Pro and related HR systems.

• Research and troubleshoot HRIS, payroll, benefits, and system integration discrepancies.

• Manage UKG Pro Learning assignments, completion tracking, and related administrative support.

• Monitor and respond to inquiries through shared HR mailboxes, providing timely, helpful, and solutions-focused service.

• Support audits, employment verifications, compliance reporting, and special HR projects.

• Develop clear training materials, process guides, and standard operating procedures to promote consistency across communities.

• Partner with HR and cross-functional teams to streamline workflows, strengthen data accuracy, and improve the overall associate experience.

What You Bring

• 2–5 years of experience in benefits administration, payroll, leave administration, workers’ compensation, or a related HR operations role.

• Hands-on experience supporting payroll processing and employee benefits administration.

• Familiarity with FMLA, state leave requirements, workers’ compensation processes, and related documentation is preferred.

• Experience with HRIS and payroll systems; UKG experience is a plus.

• Strong analytical skills and the ability to investigate issues, identify root causes, and recommend practical solutions.

• Excellent organizational skills and attention to detail, with the ability to manage multiple priorities and deadlines.

• Strong Microsoft Excel skills and comfort working with reports and employee data.

• Clear, professional communication skills and a customer-focused approach to associate support.

• The ability to handle confidential and sensitive information with discretion.

• A proactive mindset, a commitment to continuous improvement, and the ability to work independently while collaborating effectively with others.

Why Join Maplewood Senior Living?

At Maplewood Senior Living, your work supports the people who make a difference in our residents’ lives. You’ll join a collaborative HR team where accuracy, accountability, service, and continuous improvement matter.

In this role, you’ll have the opportunity to:

• Lead with Integrity
• Invest in People 

• Value Accountability

• Engage & Communicate 

Ready to Make a Difference?

If you’re a detail-oriented HR professional who enjoys bringing order to complex processes, helping people find solutions, and making HR operations work better for everyone, we encourage you to apply.

Join Maplewood Senior Living and help support the people who make our communities feel like home.

Salary : $70,000 - $80,000