HR Benefit & Payroll Spec

Location: Westport, CT (in office) 
Reports To: HRIS Director

Join Out Team!

At Maplewood Senior Living, our associates make a difference every day by supporting the people who care for our residents. We're looking for a detail-oriented, customer-focused HR Benefits & Payroll Specialist who enjoys solving problems, improving processes, and delivering exceptional service.

If you're passionate about benefits administration, payroll, HR technology, and helping employees navigate important moments in their careers, we'd love to meet you.

What You'll Do! 

As our HR Benefits & Payroll Specialist, you'll play a key role in ensuring associates are paid accurately, enrolled in the right benefits, and supported through every stage of their employment. You'll collaborate with HR, Payroll, Accounting, Operations, and our community leaders while helping maintain the integrity of our HR systems.

Benefits Administration

• Administer medical, dental, vision, life, disability, and voluntary benefit programs.


• Process new enrollments, qualifying life events, benefit changes, and terminations.


• Reconcile monthly benefit invoices and resolve vendor billing discrepancies.


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


• Assist with annual Open Enrollment planning, testing, and employee communications.


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


• Partner with benefit vendors to resolve enrollment and coverage issues.


• Audit benefit elections, payroll deductions, and HRIS data for accuracy.


• Process court-ordered benefit garnishments. 

Payroll Administration 

• Support the processing of weekly and bi-weekly multi-state payroll.


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


• Analyze payroll reports to identify and resolve discrepancies before payroll processing.


• Prepare payroll, PTO accrual, and month-end reporting.


• Process payroll deductions and vendor payment files.


• Ensure final pay is issued in compliance with state wage payment laws.


• Stay current on payroll regulations and system enhancements. 

HRIS & Employee Support

• Maintain accurate employee records within UKG.


• Troubleshoot HRIS integrations and payroll data issues.


• Manage UKG Pro Learning assignments and course completions.


• Respond to associate inquiries through shared HR mailboxes.


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


• Create training materials and process documentation.


• Partner with internal teams to improve HR and payroll processes and deliver an outstanding associate experience.

What You Bring 

• 2–5 years of experience in Human Resources, Benefits Administration, Payroll, or a related field.


• Experience processing payroll and administering employee benefits.


• Experience with HRIS and payroll systems, preferably UKG Pro (UltiPro) and/or UKG Workforce Management (Kronos).


• Strong analytical, organizational, and problem-solving skills.


• Excellent customer service and communication abilities.


• Advanced attention to detail with the ability to manage multiple priorities.


• Strong Microsoft Excel skills.


• Ability to handle confidential information with professionalism and discretion.


• Ability to work independently while collaborating effectively with a team.

Why Maplewood? 

At Maplewood Senior Living, you'll be part of a collaborative HR team that values innovation, continuous improvement, and exceptional service. You'll have the opportunity to expand your expertise in benefits, payroll, HRIS, compliance, and process improvement while making a meaningful impact on the associate experience across a growing senior living organization.

If you're looking for a career where your work truly matters, we encourage you to apply today!