1

Flexible Cobra Insurance Jobs (NOW HIRING)

Be Seen First

... Flexible Spending Accounts (FSAs), Health Reimbursement Arrangements (HRAs), Health Savings ... Previous experience in benefits, insurance or human resource environment. Prior COBRA experience

Accounts Receivable Specialist

Wheeling, IL

$21 - $27.75/hr

Flexible and adaptable with a positive attitude Why Join Cobra * Stable and growing organization ... Short and longterm disability insurance fully paid by the employer * $50,000 life insurance policy ...

Human Resources Assistant

Salem, OR · On-site

$21.32 - $27.36/hr

Life and Long-Term Disability Insurance * Paid Time Off and Holiday Pay * Flexible Spending Account ... COBRA insurance; retirement plans; pre-tax and health reimbursement account programs; and other ...

Human Resources Assistant

Salem, OR · On-site

$37K - $48K/yr

Life and Long-Term Disability Insurance * Paid Time Off and Holiday Pay * Flexible Spending Account ... COBRA insurance; retirement plans; pre-tax and health reimbursement account programs; and other ...

Be Seen First

Prior COBRA, health insurance or employee benefits compliance/research experience a plus. Job Type: Full-time Schedule: * Monday to Friday * Flexible start time (8:00 or 8:30 a.m.) * Onsite fulltime ...

Insurance Coordinator

Seattle, WA · On-site

$22.08 - $33.77/hr

Handle interactions with insurance carriers, employers, COBRA Administrators, and other vendors ... Flexible spending accounts * Life insurance options * Long term disability * Mass transit subsidy ...

Insurance Coordinator

Seattle, WA · On-site

$22.08 - $33.77/hr

Handle interactions with insurance carriers, employers, COBRA Administrators, and other vendors ... Flexible spending accounts * Life insurance options * Long term disability * Mass transit subsidy ...

next page

Showing results 1-20

Flexible Cobra Insurance information

See salary details

$26K

$67.1K

$144.5K

How much do flexible cobra insurance jobs pay per year?

As of Aug 24, 2026, the average yearly pay for flexible cobra insurance in the United States is $67,113.00, according to ZipRecruiter salary data. Most workers in this role earn between $36,000.00 and $78,000.00 per year, depending on experience, location, and employer.

What is the difference between Flexible Cobra Insurance vs Dental Hygienist?

AspectFlexible Cobra InsuranceDental Hygienist
CredentialsTypically no specific credentials required, but knowledge of insurance plans helpfulDental hygiene license and certification
Work EnvironmentInsurance providers, HR departments, or benefits administrationDental offices, clinics, or healthcare facilities
Industry UsageInsurance and benefits industryHealthcare and dental industry
Common Search IntentUnderstanding insurance options after employmentLearning about dental hygiene roles and responsibilities

Flexible Cobra Insurance involves managing health insurance continuation options after employment, often requiring knowledge of insurance plans. Dental Hygienists focus on providing dental care and require specific healthcare credentials. While both are related to health and benefits, they serve different roles within their industries.

More about Flexible Cobra Insurance jobs

What cities are hiring for Flexible Cobra Insurance jobs?

Cities with the most Flexible Cobra Insurance job openings:

What are the most commonly searched types of Cobra Insurance jobs?

The most popular types of Cobra Insurance jobs are:

What states have the most Flexible Cobra Insurance jobs?

States with the most job openings for Flexible Cobra Insurance jobs include:

Infographic showing various Flexible Cobra Insurance job openings in the United States as of August 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution, with an average salary of $67,113 per year, or $32.3 per hour.

COBRA Specialist - Compliance

Diversified Benefit Services, Inc.

Oconomowoc, WI • On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 18 days ago

Be Seen First

After you apply to this job, you can share why you’re interested to jump to the top of the candidate list.


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/

Company 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.