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Posted August 05, 2026

COBRA Specialist - Compliance

Diversified Benefit Services, Inc.
Oconomowoc, WI, US Full Time
23USD - 25USD per hour

Job Description

Job Description

Please note; this role is based in Hartland, WI!

Job Title:
COBRA Specialist

Company Overview:
We are a fast-growing Third Party Administrator (TPA) specializing in tax-advantaged benefit plans such as Flexible Spending Accounts (FSAs), Health Reimbursement Arrangements (HRAs), Health Savings Accounts (HSAs), COBRA, and Individual Coverage HRAs (ICHRAs). Our mission is to help employers and participants maximize their benefits with confidence, clarity, and compliance.

Job Description:
We are seeking a COBRA Specialist to join our dynamic and detail-focused team. The COBRA Specialist is responsible for the day-to-day administration of an assigned group of client accounts, ensuring COBRA plans are administered accurately and in accordance with applicable regulations and mandates. This role serves as a trusted resource to clients, providing education and guidance on COBRA requirements while delivering a high level of responsive, knowledgeable service to both clients and COBRA members.

Responsibilities:

  • Responsible for overall administration of COBRA benefits for assigned clients.
  • Maintain a strong working knowledge of COBRA and stay current with legislative and regulatory changes.
  • Ensure compliance with COBRA regulations.
  • Communicate directly with clients, beneficiaries, and brokers by phone and through email regarding COBRA, including enrollments, notices, coverages, terminations, reporting and premium payments.
  • Provide a high level of customer service to all clients and members, including timely, knowledgeable and professional responses to all inquiries via phone, mail and e-mail.
  • Maintain a strong working knowledge of software systems.
  • Responsible for new client set-ups, annual renewals, timely processing of qualifying events and coverage changes as they occur.
  • Generate accurate and timely client reports.
  • Serve as back-up for other COBRA Specialists.
  • Maintain strong working relationships with all departments within the company to ensure client requests are met and a high level of service is consistently provided.
  • Maintain strong working relationships with all departments within the company to ensure client requests are met and a high level of service is consistently provided.
  • Be an active participant in department meetings and provide input on process improvements.
  • Meet established quality standards within the department.

Qualifications:

  • Previous experience in benefits, insurance or human resource environment. Prior COBRA experience
  • Professional written and verbal communication skills.
  • Computer competency and ability to quickly learn various software programs.
  • Strong time management, problem solving and organizational skills in a deadline driven environment.
  • Demonstrate meticulous attention to detail.
  • Ability to handle multiple assignments efficiently and accurately while meeting strict deadlines.
  • Able to handle information on a confidential business appropriate need to know basis.
  • Possess basic match/accounting competencies required within position.
  • Assertive in obtaining information needed to perform job functions in a timely manner.
  • Able to work in a varied, fast-paced, changing environment and accept change positively.

Job Type:
Full-time

Schedule:

  • Monday to Friday
  • Flexible start time (8:00 or 8:30 a.m.)
  • Onsite fulltime for six months / transitions to hybrid (1 day remote/4 in office thereafter)

Compensation:

  • Competitive salary
  • Annual performance bonus opportunities

Benefits:

  • Health, dental, and vision insurance
  • Disability insurance – company paid
  • Life Insurance – company paid
  • FSA, HSA, and HRA benefits with employer funding (of course!)
  • 401(k) with employer match
  • Paid time off and holidays
  • Employee Referral bonus program
  • Paid training program and professional development
  • Opportunities for advancement within a growing organization

Location:

  • Hartland, WI

Ready to Apply?
Whether you come from a healthcare background, employee benefits, human resources, an insurance environment, or just passionate about making work more meaningful and directly navigating consumers through the benefits waters– we want to meet you!

APPLY NOW OR TAG SOMEONE WHO’S READY FOR THEIR NEXT GREAT OPPORTUNITY! https://www.dbsbenefits.com/careers/

\nCompany Description

Who we are:

For nearly 40 years, Diversified Benefit Services, Inc. (DBS), continues to be a leading third party administrator (TPA) of FSA’s, ICHRA's, HRA’s, HSA’s, COBRA, and other customized benefit plans. At DBS we believe that good people are the key to our success, and we understand the importance of finding qualified, motivated and positive professionals who thrive on challenge and seek opportunities to utilize their skills and talents. DBS provides a well-rounded training program that gives our employees the best innovative tools and support they will build upon to be engaged and successful.

Company Description

Who we are:\r\n\r\nFor nearly 40 years, Diversified Benefit Services, Inc. (DBS), continues to be a leading third party administrator (TPA) of FSA’s, ICHRA's, HRA’s, HSA’s, COBRA, and other customized benefit plans. At DBS we believe that good people are the key to our success, and we understand the importance of finding qualified, motivated and positive professionals who thrive on challenge and seek opportunities to utilize their skills and talents. DBS provides a well-rounded training program that gives our employees the best innovative tools and support they will build upon to be engaged and successful.

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