Benefits Associate

Wonder • Chicago, IL

11d • $67,500 - $74,000 • Hybrid

About The Position

The Benefits Associate, reporting to the Sr Manager of Benefits, supports the day-to-day administration, accuracy, and compliance of Wonder’s benefit programs. This role is responsible for managing vendor file feeds, auditing benefits data across systems, resolving employee coverage issues, supporting claims and funding processes, and ensuring payroll and enrollment accuracy. The ideal candidate is highly detail-oriented, proactive in identifying discrepancies, and comfortable coordinating across HR, Payroll, Accounting, vendors, and employees.

Requirements

• 2+ years of experience in HR, Benefits Administration, or related operations roles.
• Experience working with HRIS systems (Workday preferred) and benefits vendors.
• Strong attention to detail and analytical mindset with experience auditing data and reconciling discrepancies
• Willingness to learn and cross-train with LOA specialist.
• Ability to manage recurring operational processes while responding to employee needs
• Strong communication and cross-functional coordination skills
• Proficiency in Excel and reporting tools

Responsibilities

• Benefits Administration & Data Integrity
• Monitor and reconcile benefit eligibility and enrollment data between Workday and vendor systems on a recurring basis, including medical, dental, vision, life, COBRA, HSA, and other benefit feeds.
• Review and investigate discrepancies in vendor file feeds; resolve issues and ensure corrections are processed accurately and promptly.
• Verify terminated employees are processed correctly in Workday and benefits systems.
• Closely review life events, new hire/rehire enrollments, and changes prior to approval for accuracy,
• Confirm 401(k) eligibility by validating work history across systems.
• COBRA Administration
• Review COBRA eligibility feeds and participant reports, including start dates and cancellations.
• Investigate cancellations to ensure individuals who require coverage remain active.
• Coordinate with COBRA vendors to correct eligibility or enrollment issues.
• HSA & Funding Oversight
• Audit HSA payroll deductions and employer funding to ensure amounts align with elections and payroll data.
• Run funding audits across systems to identify participants who have not yet received HSA funding and coordinate allocation.
• Partner with vendors to ensure HSA funds are applied correctly and resolve discrepancies.
• Payroll & Financial Coordination
• Review payroll reports and calculate arrears balances.
• Communicate arrears balances to employees and coordinate adjustments with Payroll.
• Track payroll adjustments and maintain documentation/logs prior to each pay period.
• Reconcile premium invoices for all benefit vendors and coordinate payments with Accounting.
• Vendor & Employee Support
• Serve as a primary contact for vendors to resolve escalated claims, eligibility corrections, funding issues, and administrative discrepancies.
• Partner with insurance carriers and administrators to resolve employee claims and coverage issues.
• Support employees and families through life insurance claim processes in coordination with carriers.
• Provide employees with guidance and next steps for Evidence of Insurability (EOI) submissions and other benefits requirements.

Benefits

• We offer a competitive salary package including equity and 401K.
• Additionally, we provide multiple medical, dental, and vision plans to meet all of our employees' needs as well as many benefits and perks that are not listed.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed