Benefits Analyst

What You Will Do as a Benefits Analyst:

The Benefits Analyst is responsible for the day-to-day administration and operational execution of Workwear Outfitters' benefit and leave programs. This role partners closely with third‑party administrators (TPAs), vendors, payroll, local HR teams, and employees to ensure accurate enrollment, leave tracking, payroll alignment, compliance, and issue resolution across U.S. and Canadian benefit programs.

This position plays a critical role in ensuring benefits are administered accurately, timely, and in compliance with applicable regulations, with a strong focus on leave management, eligibility tracking, payroll reconciliation, and employee support.

• Administer leave management programs by partnering with the leave TPA and coordinating with associates, managers, and local HR.
• Enter and maintain leave data in Workday to ensure time is paid and tracked accurately.

• Manage life event communications, documentation, and approvals.
• Process Qualified Medical Child Support Orders (QMCSOs) within the benefits platform and Workday.
• Track new hires to ensure benefit enrollment within required eligibility windows; send reminders and follow up as needed.
• Conduct dependent verification activities and follow up on outstanding documentation.
• Process death‑related benefits, including life insurance paperwork and system updates.
• Respond to employee and local HR inquiries related to benefit and leave programs; research and resolve issues of varying complexity.
• Assist with benefit platform case management and other benefits‑related operational tasks as needed.
• Review weekly payroll files to ensure benefit deductions and leave pay are applied accurately; investigate and resolve discrepancies with Payroll and vendors.
• Administer and troubleshoot cases in Benefit solver (enrollment platform).
• Support Canadian benefits administration, including Medavie and Desjardins system administration and issue resolution.
• Review and reconcile benefit invoices; validate accuracy and submit for payment.
• Review and approve ACA eligibility data and support annual ACA filing processes.
• Assist with benefits‑related compliance activities and filings as needed (e.g., audits, documentation requests, regulatory reporting).
• Travel to site locations as needed to support Open Enrollment activities.
• Perform other benefits‑related duties as assigned to support the overall benefits function.

• Bachelor's degree required
• 2+ years of experience administering employee benefits and/or leave programs
• Strong attention to detail and analytical skills
• Strong organizational, communication, and problem‑solving skills
• Experience with Benefit solver and/or Workday preferred but not required