Medicare Enrollment Specialist

Posted 12 Oct 2026

$50–150/hr

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Work

Remote · Contract

Experience

1+ years

Eligibility

Open to United States

Field

Medicine & healthcare

Skills

Medicare Parts A, B, C, and DMedicare Enrollment CounselingInitial Enrollment PeriodsSpecial Enrollment PeriodsPart B Late Enrollment PenaltiesSocial Security and Medicare CoordinationEmployer and Retiree Coverage CoordinationPrimary and Secondary CoverageCOBRACreditable CoverageMedigapMedicare AdvantagePlan Comparison and SelectionBeneficiary EducationIRMAA Premium AdjustmentsHSA Rules with MedicareAI Answer EvaluationRubric DevelopmentCounseling Scripts and Training Materials

About this role

Role Title: Medicare Enrollment Specialist

Role Type: Contractor

Location: Remote

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.

Scope of Work

  1. Review sample questions about signing up for Medicare and flag any that don’t sound like what real people ask.
  2. 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.
  3. Cover Medigap vs. Medicare Advantage and Part D in your rubrics, with a focus on scenarios involving employer or retiree coverage.
  4. Cover how employer coverage interacts with Medicare, including employer size, primary vs. secondary coverage, COBRA, and creditable coverage.
  5. Evaluate AI-generated answers against your rubrics, flagging errors, omissions, and common misconceptions.
  6. Share clear written feedback with the project team, working asynchronously.

Required Qualifications

  1. Former SSA Medicare enrollment experience, or employer benefits/HR experience advising employees on Medicare
  2. 1+ years advising on initial enrollment, special enrollment periods, Part B late penalties, Medigap vs. Medicare Advantage, and Part D
  3. Working knowledge of Social Security and employer coverage coordination, including creditable coverage
  4. US-based
  5. Able to start quickly and commit 20-30 hours/week
  6. Clear, precise writing

Nice to Have

  1. Experience with premium adjustments (such as IRMAA), working while enrolled, or HSA rules alongside Medicare
  2. Experience creating guides, counseling scripts, or training materials
  3. Experience helping a diverse range of beneficiaries, including rural and non-English-speaking clients

Disclosure: Skillora is independent of micro1. The apply button carries our referral code, and if you are placed, micro1 pays Skillora a fee. It does not change what you are paid, our ranking does not know which listings pay us, and selection is decided by micro1’s own vetting.

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