COBRA Account Manager - Hybrid Remote and In-Office Chicago, IL



Position Purpose

The COBRA Account Manager is responsible for a high level of support for clients, including primary contact for implementation, on-going support and developing relationships, ensuring an exceptional customer experience for new and existing clients. Focuses on growing and developing existing clients in addition to serving as knowledgeable support for COBRA and all Flex products including FSAs, HRAs, HSAs and Commuter.


Key Responsibilities:

Relationships – Builds and maintains strong, long-lasting relationships with clients and their producers. Assists with providing COBRA product knowledge and service support to enhance client experience. Identifies potential additional product offerings and development to enhance benefits and services provided by Flex. Guides clients through benefit strategies and plan changes, including regulatory requirements. Provides service support at a broker, employer, or employee level as needed to offer an excellent service experience.

New Business Implementation – Handles the initial introduction to Flex for new assigned clients and sets the expectations for a successful implementation. Primary point of contact for assigned clients. Develops materials, including guides, presentations, and forms, to maximize the onboarding experience. Conducts new business implementation and renewal process to provide a successful client experience.

Service – Manages day-to-day service activities of new and existing Flex clients, which includes:

  • Key interface between assigned clients and other departments to ensure most current status and information is available to both the client and all areas within Flex.
  • Primary point of contact for questions, escalation, and problem resolution throughout the plan year.
  • Provides service levels that maximize retention for assigned clients and other Flex clients as needed
  • Trains and educates clients on system processes when needed.
  • Provides communications on system/procedural changes to clients.
  • Handles COBRA service support, including eligibility updates, emails, remittance details, invoicing and more.
  • Schedules and completes a minimum of bi-weekly follow-ups to ensure exceptional level of service is provided.
  • Proactively provides Employer performance statistics and conducts annual assessment meetings with assigned clients to maintain relationships.

Provides email and call center support to the service and new business teams as needed

Assessment – Reviews and provides feedback regarding department procedures and documentation in order to improve the customer experience. Utilizes client suggestions, product requests and analyzes trends to provide recommendation for procedural and product enhancements. Maintains and tracks customer feedback and experience, reporting on overall customer satisfaction.

Education – Provides clients with knowledgeable support related to COBRA all current and future Flex products and available services. Provides assistance with registration, training on websites, including eligibility updates, reports and other website tools and features. Coordinates presentations and webinars with marketing team for FSA, HRA, Commuter and HSA enrollment, including education meetings for both assigned clients and other Flex clients. Conducts enrollment meetings and Benefit fairs for existing clients.

Support – Stays abreast of all department and COBRA processes, especially CDHP sales, new business implementation, customer service and renewal procedures in order to provide back-up support when needed.  Conducts website demonstrations or finalist presentations as needed for prospective Flex clients in support of the CDHP sales team.


We are a dynamic company in a rapidly changing environment.  Accordingly, the responsibilities associated with this position will change in accordance with the company’s business needs.  More specifically, the incumbent may be required to perform additional and/or different responsibilities from those set forth above.




  • Bachelor’s degree in Communication, Business or related field


  • 3 to 5 years experience in an account management role, preferably with 2 to 3 years in the health insurance industry.
  • Knowledge of group health marketplace and in-depth expertise of account based, consumer-driven programs, including COBRA, FSAs, HRAs & HSAs.
  • Proficient with Microsoft applications (Word, Excel, PowerPoint, Outlook).

Performance Skills:

  • Excellent time management and organizational skills.
  • Strong written and verbal communication skills.  Ability to be assertive in a tactful manner.
  • Ability to work successfully in a fast-paced environment while remaining professional, courteous and helpful.
  • Willingness to be flexible to accommodate and meet customer needs; must be service oriented.
  • Ability to create presentations and conduct enrollment meetings for large or small audiences
  • Effective problem-solving and decision-making skills.
  • Bilingual English and Spanish a plus.

Physical Requirements:

  • Some local travel required (10% to 20%) to conduct key account and enrollment meetings.
  • Professional attire required for business meetings and appointments with key accounts.



Problem Solving and Decision Making

Must be very responsive to clients. Must be able to work autonomously to identify the urgency of various issues, determine how these get prioritized and be resourceful to bring matters to resolution.  However, must be able to identify if requests are beyond the scope of the service that this position is intended to provide, handle this tactfully and escalate as appropriate.  

Position and Risk Designation

This position has a Tier 2 Risk Designation. Please refer to the associated Position Access and Risk Designation document.


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