Medicare Enrollment Specialist – Remote (US)

RemoteJobsOne; New York (NY); Remote; USD 55,000 - 83,000; Part time

Job summary

RemoteJobsOne is seeking a Medicare Enrollment Specialist for a fully remote contractor role in the United States. The position offers 20-30 hours per week on a short-term project, with pay in the $40-$60 per hour range.

You will review Medicare enrollment questions, write rubrics for enrollment scenarios, and evaluate AI-generated answers against established standards. Prior SSA Medicare enrollment or employer benefits guidance is required, with clear, precise writing.

Qualifications

• Former SSA Medicare enrollment experience or employer benefits/HR Medicare guidance.
• 1+ years advising on enrollment, SEPs, Part B penalties, Medigap vs MA, and Part D.
• US-based and available to start quickly, 20–30 hours/week.

Responsibilities

• Review sample questions about Medicare enrollment and flag inaccuracies.
• Write rubrics defining correct, complete enrollment answers for initial enrollment, SEPs, and Part B penalties.
• Cover Medigap vs Medicare Advantage and Part D in rubrics, including employer/ retiree coverage scenarios.
• Explain how employer coverage interacts with Medicare (size of employer, primary vs secondary, COBRA, creditable coverage).
• Evaluate AI-generated answers against rubrics, flag errors and omissions.
• Provide written feedback to the project team asynchronously.

Skills

Medicare enrollment knowledge

Clear, precise writing

Social Security knowledge

Job description

IMPORTANT: after you apply, please check your email. We send you a link to complete your application — it is not considered until that last step is done. If you do not see it, check your spam folder.

This is a fully remote position, open to candidates based in United States.

Pay: $40–$60/hr

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