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Medicare Enrollment Specialist

$60
per hour
Contractor Remote Last verified 21 Jul 2026
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About the Role

Time Commitment: 20-30 hours/week, short-term project micro1 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.

What You'll Do

  • 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.

You're a Good Fit If You

  • Required skills: Medicare Parts A B C D, Medicare enrollment counseling, Social Security and Medicare coordination, Employer coverage and creditable coverage, Plan comparison and selection, Beneficiary education
  • 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
  • Experience with premium adjustments (such as IRMAA), working while enrolled, or HSA rules alongside Medicare
  • Experience creating guides, counseling scripts, or training materials

Role Highlights

Pay
$40-$60/h
Contract
Contractor
Location
Remote
Category
Model evaluation
Posted
3 days ago
Job ID
WE-7415

Pay & Payout

Engaged directly through micro1. Apply via the link below - micro1 handles onboarding and payment.

Common Questions

micro1 has a reliability rating of reliable based on the listings we track, with an onboarding time of 1-3 days. See our full micro1 review for the details behind that rating.

Applying takes you to micro1's own website, where the application is completed. We are not a recruiter or employer and do not process applications directly - we may be recorded as the referring source.

$40-$60/h - Engaged directly through micro1. Apply via the link below - micro1 handles onboarding and payment.

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.

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