Benefits Specialist

Winston Water Cooler is seeking a dynamic and highly experienced Benefits Specialist to lead the strategic management of our employees’ benefits programs across 70+ branch locations within a multi-state environment.

The Benefits Specialist is responsible for the administration, maintenance, and communication of employee benefit programs, including health, dental, vision, life insurance, short-term disability, long-term disability, 401k retirement plans, safe harbor, FMLA leave programs, COBRA, and wellness initiatives. This role serves as the primary point of contact for employee benefits inquiries and leverages Paycom to manage benefits enrollment, reporting, compliance, and employee data accuracy. Responsibilities commonly include benefits administration, open enrollment, compliance monitoring, employee support, vendor coordination and negotiation, market analysis, and HRIS management.

Key Responsibilities:

Administer employee benefit programs, including medical, dental, vision, life, short-term disability, long-term disability, HSA/FSA, 401k retirement plans, safe harbor, FMLA leave programs, COBRA, and wellness initiatives.

Own open enrollment processes and employee benefit elections via Paycom, including communication, strategy, compliance, documents, education and wellness initiatives.

Maintain accurate employee benefits records and HRIS data within Paycom.

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

Reconcile benefit invoices and payroll deductions.

Partner with insurance carriers, brokers, TPA’s, and vendors to resolve benefits-related issues not limited to renewals, audits, and transitions.

Ensure compliance with ACA, ERISA, COBRA, HIPAA, FMLA, SPD, SAR, WRAP, Form 5500 filings, and other applicable regulations.

Generate benefits reports, conduct audits, and analyze benefits utilization data.

Support payroll and HR teams with benefits deductions and reporting.

Required Qualifications:

Bachelor’s degree in human resources, business administration, or related field preferred.

5-8+ years of progressive benefits administration experience.

Fully-insured, self-insured, level-funded experience.

HIPPA certified.

Expert knowledge of employee benefits regulations and compliance requirements.

Ability to lead with empathy and compassion for others.

Excellent communication, organizational, and problem-solving skills.

A solution seeker.

Expert benefit invoicing and payroll deductions reconciliation experience.

Advanced Microsoft Excel (Pivot Tables, Reporting).

Preferred Qualifications:

Certified Employee Benefits Specialist (CEBS).

HR, PHR or SHRM certifications.

Experience with Paycom system administration, workflow configuration, reporting, and audits.

Bilingual English/Spanish