Operations Specialist - Employee Benefits

Benbase • Bartlett, IL

2d • $72 • Remote

About The Position

We’re hiring an Operations Specialist to support high-volume, high-accuracy benefits administration across carriers, benefit platforms, and internal systems.

This role focuses on execution, data integrity, and operational follow-through. You’ll handle enrollment and eligibility activity, validate billing and documentation, and help ensure that benefits data is accurate and consistent across systems, including AI-enabled automations.

The Operations Specialist works closely with Implementation Managers and Account Managers, playing a critical role in turning clean intake and strategy into reliable downstream execution. This is a great role for someone who enjoys detail-oriented work, problem-solving, and keeping complex processes running smoothly.

Requirements

• Experience in HR operations, benefits administration, insurance operations, payroll, accounting, or other detail-oriented operational roles.
• Familiarity with benefit administration platforms, carrier portals, or payroll systems is a plus.
• Associate’s or Bachelor’s degree in a business-related field (or equivalent experience).
• Strong attention to detail and commitment to data accuracy
• Analytical and critical-thinking skills with the ability to identify patterns and root causes
• Comfortable managing multiple tasks and priorities in a deadline-driven environment
• Clear written and verbal communication skills
• Comfortable using Google Workspace (Gmail, Docs, Sheets) and web-based tools
• Self-directed and productive in a remote work environment
• Interested in learning and applying automation and AI-enabled tools to improve operational efficiency
• Dependable, team-oriented, and committed to doing work the right way

Responsibilities

• Process enrollment and eligibility activity across benefit administration platforms, carrier portals, and internal systems
• Evaluate and resolve complex eligibility events (life events, additions, terminations, corrections), identifying discrepancies and determining appropriate resolution paths
• Validate and organize carrier invoices, enrollment confirmations, ID cards, and reporting materials to support accurate billing and compliance
• Perform ongoing data quality checks across AI-enabled and other systems, identifying root causes of errors and preventing recurring issues
• Monitor and validate digital or automated workflows that intersect with human operational work, ensuring output quality and exception handling
• Investigate invoice discrepancies requiring human review, including root-cause analysis and coordination with carriers or vendors
• Support accurate and timely billing by identifying errors early and escalating issues appropriately
• Apply judgment to determine when issues can be resolved independently versus when escalation or cross-functional involvement is needed
• Partner with Implementation and Account Management teams to review intake materials for completeness and clarity
• Supply accurate data and documentation to support compliance, reporting, and client deliverables
• Maintain clear internal documentation and system notes to support transparency and smooth handoffs across teams

Benefits

• Financial: Competitive pay starting at $72K, stock options, 401(k) with employer matching and live financial advisor support, FSA, HSA tax-saving options, company-paid life and disability.
• Health & Wellness: Medical insurance, Dental, Vision, $0 Telehealth, enhanced Employee Assistance Program (EAP), company-paid accident and critical illness for individuals, company contribution to your Health FSA.
• Work-Life: Flexible PTO, paid parental leave, home office stipend, monthly connectivity reimbursement, company contribution to your Dependent Care FSA to help with day care.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: Associate degree