Medicare Enrollment Specialist – Remote

RemoteJobsOne; New York (NY); Remote; USD 69,000 - 207,000; Part time

Job summary

RemoteJobsOne is seeking Medicare Enrollment Specialists for a fully remote contract based in the United States. You will use your SSA Medicare enrollment or employer benefits experience to validate the accuracy and usefulness of AI-generated Medicare guidance, ensuring responses sound like real beneficiaries.

This contract role requires 20-30 hours per week with a quick start, and you will develop rubrics for initial enrollment, SEPs, and Part B late penalties, including how enrollment ties to

Qualifications

• Experience with Medicare enrollment or employer benefits advising employees on Medicare.
• 1+ years advising on initial enrollment, SEPs, Part B penalties, Medigap vs MA, and Part D.
• Ability to coordinate with Social Security and employer coverage, including creditable coverage.

Responsibilities

• Review sample questions about Medicare enrollment and flag non-representative queries.
• Write rubrics for correct, complete answers on enrollment, SEPs, and Part B penalties, including SS benefits ties.
• Cover Medigap vs Medicare Advantage and Part D, focusing on employer/retiree coverage scenarios.
• Explain how employer coverage interacts with Medicare, including employer size, primary vs secondary coverage, COBRA, and creditable coverage.
• Evaluate AI-generated answers against rubrics, flag errors and misconceptions.
• Share written feedback with the project team asynchronously.

Skills

Medicare enrollment

Policy counseling

Written communication

Job description

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

Pay: $50–$150/hr

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