Senior Benefits Specialist

FourLeaf Career•Bethpage, NY

About The Position

The Senior Benefits Specialist is a key member of FourLeaf’s Human Resources team, responsible for administering, ensuring compliance of, optimizing, and delivering employee benefits, leave management, and retirement programs. The role serves as a subject matter expert and primary resource for employees, managers, vendors, and internal partners on benefits matters. It supports daily operations while identifying improvements to processes and the employee experience and ensuring regulatory compliance. The position also provides backup support for multi-state payroll and contributes to process improvement, vendor management, and compliance activities. The specialist administers health, welfare, retirement, and wellbeing programs; supports employee enrollment, education, and inquiries; coordinates leave programs and ADA accommodations; and assists with retirement plan administration, education, and compliance. The role monitors vendor service and contractual obligations, supports audits and regulatory filings, reconciles invoices and data, and maintains benefits procedures and documentation. It also supports payroll processing, audits, reconciliations, tax compliance, reporting, and accurate benefits and payroll data in UKG and related systems, partnering with teams across HR, Payroll, HCMS, Compensation, Employee Relations, Employee Experience, and Finance.

Requirements

Five or more years of progressive HR experience, with a strong focus on benefits, leave management, retirement plans, and compliance.
Deep knowledge of benefits, retirement plans, employment laws, and HR compliance requirements.
Experience collaborating with Legal, Risk, and cross-functional teams.
Demonstrated experience administering FMLA, ADA, disability, and leave programs.
Experience managing external vendors, brokers, carriers, and third-party administrators.
Experience supporting retirement and pension plans.
Experience participating in compliance audits and regulatory filings.
Proficiency in HRIS systems and Microsoft Office Suite, including Excel, Outlook, Word, PowerPoint, and Teams.

Nice To Haves

Bachelor’s degree in Human Resources, Business Administration, or a related field, or comparable experience.
Experience supporting or processing payroll in a multi-state environment.
Experience within a highly regulated, multi-location organization.

Responsibilities

Administer company-sponsored health, welfare, retirement, and wellbeing programs accurately, on time, and in compliance with applicable requirements.
Serve as the primary contact for employee and manager questions about benefits, enrollment, eligibility, claims, and plan provisions; resolve issues and provide clear, timely communication.
Facilitate benefits-related new-hire onboarding and employee education.
Support annual Open Enrollment planning, system configuration, testing, communications, employee support, and post-enrollment audits.
Analyze program utilization, enrollment trends, and employee feedback to identify improvements to benefits, processes, communications, and engagement.
Manage relationships with benefit carriers, brokers, third-party administrators, retirement plan providers, and leave-management vendors; monitor performance, service levels, issue resolution, and contractual obligations.
Administer and coordinate FMLA, ADA accommodations, state-specific leave, short- and long-term disability, paid family leave, and military leave.
Coordinate leave administration with employees, leaders, Employee Relations, Payroll, and third-party administrators, including the interactive accommodation process and ADA compliance support.
Monitor leave trends and identify opportunities to improve consistency, effectiveness, and employee support.
Support administration of 401(k), pension, and other retirement programs, including eligibility, enrollments, contribution changes, communications, and participant support.
Coordinate with retirement providers, recordkeepers, Payroll, and internal stakeholders to ensure accurate plan administration, reporting, and issue resolution.
Support retirement compliance activities, annual audits, nondiscrimination testing, Form 5500 preparation, participant disclosures, and fiduciary governance requirements.
Support retirement education and financial wellness initiatives.
Ensure compliance with applicable federal, state, and local benefits and leave regulations, including ERISA, COBRA, FMLA, ADA, HIPAA, ACA, and Section 125.
Support regulatory filings, audits, reporting, nondiscrimination testing, Form 5500 preparation, and compliance reviews.
Conduct audits and reconciliations to maintain data integrity, plan accuracy, and process effectiveness.
Support Enterprise Risk Management, First Line of Defense, and vendor risk assessment activities as applicable.
Review and reconcile vendor invoices and billing statements, resolving discrepancies with Payroll and Finance.
Identify operational improvements that increase efficiency, reduce risk, and improve the employee experience.
Develop, maintain, and improve benefits-related standard operating procedures and documentation.
Serve as a backup resource for multi-state payroll processing; support payroll audits, reconciliations, tax compliance, reporting, inquiries, and issue resolution.
Ensure accurate integration and maintenance of benefits and payroll data within UKG and related systems.
Partner with HR, Payroll, HCMS, Compensation, Employee Relations, Employee Experience, and Finance to optimize service delivery and operational effectiveness.
Recommend solutions that improve programs, policies, and employee outcomes.