Healthcare
Medicare Enrollment Specialist
- Posted
- Location
- Global
- Openings
- 10
Role Title: Medicare Enrollment Specialist
Role Type: Contractor
Location: Remote
Time Commitment: 20-30 hours/week, short-term project
The company is looking for Medicare Enrollment Specialists to help evaluate and improve AI systems on Medicare topics. You’ll use your Social Security or employer benefits experience to check that questions sound like real beneficiaries and that answers are correct and useful. Accuracy comes first. No AI experience is needed; your domain knowledge is what matters.
Scope of Work
- Review sample questions about signing up for Medicare and flag any that don’t sound like what real people ask.
- Write rubrics that define a correct, complete answer on initial enrollment, special enrollment periods, and Part B late penalties, including how enrollment ties to Social Security benefits.
- Cover Medigap vs. Medicare Advantage and Part D in your rubrics, with a focus on scenarios involving employer or retiree coverage.
- Cover how employer coverage interacts with Medicare, including employer size, primary vs. secondary coverage, COBRA, and creditable coverage.
- Evaluate AI-generated answers against your rubrics, flagging errors, omissions, and common misconceptions.
- Share clear written feedback with the project team, working asynchronously.
Required Qualifications
- Former SSA Medicare enrollment experience, or employer benefits/HR experience advising employees on Medicare
- 1+ years advising on initial enrollment, special enrollment periods, Part B late penalties, Medigap vs. Medicare Advantage, and Part D
- Working knowledge of Social Security and employer coverage coordination, including creditable coverage
- US-based
- Able to start quickly and commit 20-30 hours/week
- Clear, precise writing
Nice to Have
- Experience with premium adjustments (such as IRMAA), working while enrolled, or HSA rules alongside Medicare
- Experience creating guides, counseling scripts, or training materials
- Experience helping a diverse range of beneficiaries, including rural and non-English-speaking clients
Skills
- Medicare
- Enrollment
- Coordination
- Coverage
- COBRA
This role at a glance
At $40–$60/hr, the Medicare Enrollment Specialist role comes to about $3,470–$5,200 a month for 20 hours a week, or $6,930–$10,400 a month full time — roughly $83,000–$125,000 over a full year. These are estimates before tax; contract roles are paid for the hours you work. It was posted 3 days ago. Healthcare roles listed on RemoteJobsOne have stayed open a median of 14 days before closing, counted over the 32 that have closed so far. 7 people applied to this role through RemoteJobsOne in the last 30 days.
20 hours a week
$3,470–$5,200
a month, before tax
Full time
$6,930–$10,400
a month at 40 hours a week
A full year
$83,000–$125,000
full time, 52 weeks
Open for
3 days
Healthcare roles here close after about 14 days, counted over 32 that have closed. Apply while it is open.
How this pay compares
This role pays $40–$60/hr. Across the 35 hourly healthcare roles open on RemoteJobsOne right now, the median runs from $80 to $125 an hour, and published rates range from $20 to $285. Its top rate of $60 sits below the category's median floor.
This role
$40–$60/hr
Healthcare median
$80–$125/hr · full spread $20 to $285
Questions about this role
How much does the Medicare Enrollment Specialist role pay?
It pays $40–$60/hr, which is about $6,930–$10,400 a month full time before tax. The rate is set by the employer and shown exactly as published.
Compare pay across remote rolesIs this Medicare Enrollment Specialist job fully remote?
Yes. It is listed as a fully remote role, with the posting naming Global. You work from home, on your own equipment.
Is it full-time, part-time or contract work?
It is a contract role: you are paid for the hours you work, and you choose how many to take on within what the employer needs.
How remote contract work worksWhat skills does the Medicare Enrollment Specialist role ask for?
The posting asks for Medicare, Enrollment, Coordination, Coverage and COBRA. Naming them clearly in your application helps.
How do I apply for Medicare Enrollment Specialist?
Press Apply on this page and enter your name and email. We email you your personal application link straight away, and you can continue at once to the employer's hiring platform to finish. Most roles there ask for a short AI interview afterwards — voice or video, in your browser. Then watch your email: the next steps arrive there.
How to prepare for the AI interview
Before you apply
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