COBRA Customer Service Representative

Position Summary

Flexible Benefit Service LLC (Flex) is seeking a detail-oriented, service-driven COBRA Customer Service Representative to support our brokers, employer clients, and qualified beneficiaries with health plan continuation administration.

This role is accountable for the timely and accurate processing of COBRA qualifying events, eligibility updates, EDI and lockbox file processing, carrier coordination, and high-touch customer support. The ideal candidate thrives in a compliance-driven environment, communicates complex benefit information clearly, and delivers exceptional service under tight timelines.

What You Will Do

COBRA Administration & Eligibility Management

• Process qualifying events accurately and within regulatory timeframes
• Maintain employer eligibility records, including new hires and terminations
• Manage annual COBRA renewals, including: Collecting renewal data from employers and brokers, Updating plan designs, rates, and open enrollment parameters
• Ensuring Qualified Beneficiaries are updated post-enrollment

Client & Participant Support

• Respond promptly to calls and emails from COBRA participants, brokers, and plan administrators
• Explain benefit plan details, COBRA regulations, and required notices
• Support employers with remittance questions, invoice inquiries, and compliance guidance
• Provide website overviews and functionality support to employers and participants

Carrier & Vendor Coordination

• Work directly with insurance carriers on:
• Reinstatements
• Termination confirmations
• Eligibility discrepancies

Cross-Training & CDHP Support

• Cross-train to support CDHP plans, including:
• HRA, FSA, HSA, Commuter, and Lifestyle Spending Accounts
• Claims support
• Participant website navigation and functionality

Flex operates in a dynamic, compliance-driven environment. Responsibilities may evolve based on business needs.

Qualifications

Education

• Preferred: Associate degree

Required Experience

• 2-3 years customer service and call center experience in a corporate, fast-paced environment
• Strong attention to detail and accurate data entry skills
• Clear, professional verbal and written communication
• Ability to explain complex benefit regulations in a client-friendly manner
• Proficiency in Microsoft Word, Excel, Outlook, and database systems
• Organized, deadline-driven, and process-focused
• Professional, service-oriented demeanor
• Ability to work independently and collaboratively
• COBRA administration experience preferred

Why Join Flex?

Flexible Benefit Service LLC is a leading third-party administrator serving brokers and employers nationwide. We specialize in COBRA, consumer-directed health plans (HRA, FSA, HSA), and related compliance services.

At Flex, you’ll join a team that values:

• Precision and compliance excellence
• Client partnership and responsiveness
• Continuous improvement
• Professional growth in the employee benefits industry

Location & Work Structure

• Chicago-based organization
• Hybrid work environment

If you are passionate about benefits administration, thrive in a structured yet fast-paced environment, and take pride in delivering exceptional service with regulatory precision, we encourage you to apply.

Apply today and grow your career with Flex.

Flex is committed to fostering an inclusive workplace where people across all dimensions of diversity and intersectionality, including, but not limited to race, ethnicity, religion, sexual orientation, age, marital status, disability, gender identity, gender expression, sex, or country of origin are welcomed, valued, and celebrated! We have an opportunity to increase representation at all levels and need your unique talents, background, and perspectives. We look forward to your contributions.

Job Type: Full-time

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Flexible schedule
• Health insurance
• On-the-job training
• Paid time off
• Vision insurance

Experience:

• Group Health Insurance: 2 years (Preferred)
• customer service in a corporate office setting: 2 years (Required)

Work Location: Hybrid remote in Chicago, IL 60631