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COBRA Specialist


Job Location:

Hartland, WI - USA

Monthly Salary: Not provided by the employer
Posted: 21 August 2026 (13 days ago)
Application Deadline: 18 November 2026
Vacancies: 1 Vacancy

Job Summary

Are you detail-oriented customer-focused and passionate about helping people navigate employee benefits

Were looking for a COBRA Specialist to join our growing Benefits Administration this role youll be the trusted resource for an assigned portfolio of clients ensuring their COBRA benefits are administered accurately compliantly and with exceptional service.
If you thrive in a fast-paced environment enjoy solving problems and take pride in delivering a seamless client experience wed love to hear from you.

What Youll Do
As a COBRA Specialist youll play a key role in supporting employers brokers and plan participants by:
  • Managing the day-to-day administration of COBRA benefits for an assigned client portfolio.
  • Processing qualifying events enrollments coverage changes terminations and premium payments accurately and on time.
  • Preparing and distributing required COBRA notices while ensuring compliance with federal regulations.
  • Serving as the primary point of contact for clients beneficiaries and brokers via phone and email.
  • Providing timely knowledgeable and professional customer service while resolving questions and issues.
  • Maintaining accurate records and generating client reports using our benefits administration systems.
  • Partnering with internal teams to ensure client needs are met and service expectations are exceeded.
  • Staying current on COBRA regulations and legislative updates.
  • Supporting teammates by providing backup coverage and contributing ideas for process improvements.
What You Bring
Were looking for someone who is organized dependable and committed to providing outstanding service. The ideal candidate will have:
  • Experience in a benefits administration insurance or human resources environment.
  • Prior COBRA administration experience (preferred but not required).
  • Excellent written and verbal communication skills.
  • Strong computer skills with the ability to quickly learn new software applications.
  • Exceptional time management and organizational abilities in a deadline-driven environment.
  • Outstanding attention to detail and a commitment to accuracy.
  • The ability to manage multiple priorities while maintaining quality and meeting deadlines.
  • Strong problem-solving skills and the confidence to proactively obtain information needed to complete tasks.
  • The ability to handle confidential information with professionalism and discretion.
  • Basic math and accounting skills related to premium payments reconciliations and reporting.
Why Youll Love Working Here
Were a collaborative team that believes great service starts with great people. We value accuracy accountability continuous learning and supporting one another. Youll have the opportunity to build meaningful client relationships while growing your knowledge of employee benefits and compliance in a rewarding career.
If youre ready to put your organizational skills customer service mindset and attention to detail to work in a role where youll make a real impact wed love to hear from you. Apply today! this role sounds like a fit wed love to hear from you. Apply now.

Diversified Benefit Services Terms and Conditions:

1. Diversified Benefits Services uses SMS in efforts to contact candidates in a timely manner in order to request more information or keep candidate informed regarding the status of their application.

2. You can cancel the SMS service at any time. Just text STOP to the short code. After you send the SMS message STOP to us we will send you an SMS message to confirm that you have been unsubscribed. After this you will no longer receive SMS messages from us. If you want to join again just sign up as you did the first time and we will start sending SMS messages to you again.

3. If you are experiencing issues with the messaging program you can reply with the keyword HELP for more assistance or you can get help directly at

4. Carriers are not liable for delayed or undelivered messages.

5. As always message and data rates may apply for any messages sent to you from us and to us from you. You will receive occasionally. If you have any questions about your text plan or data plan it is best to contact your wireless provider.

6. If you have any questions regarding privacy please read our privacy policy below.

Privacy Policy: We collect your mobile number and related opt-in data for the delivery of SMS messages. Your mobile opt-in data and consent will not be shared with third parties or affiliates for marketing or promotional purposes.




Required Experience:

Senior IC


About Company

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An experienced and cutting-edge TPA Diversified Benefit Services, Inc. (DBS) is a leading third party administrator (TPA) providing excellence in benefit management solutions for nearly thirty years. DBS is fully devoted to designing, enrolling, administering and servicing account bas ... View more

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