SHIP Medicare Counselor - Remote at YO AI Labs | GlassEver Jobs

SHIP Medicare Counselor - Remote at YO AI Labs | GlassEver Jobs

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SHIP Medicare Counselor - Remote

United States Nov 07, 2026
Medicaid-Counselor Benefits-Counselor Medicare-Advisor

Job Description

Role Title: SHIP Medicare Counselor

Role Type: Contractor
Location: Remote, United States
Time Commitment: 20–30 hours per week, short-term project

We are seeking experienced SHIP Medicare Counselors to evaluate and improve AI-generated Medicare guidance. You'll use your counseling expertise to ensure questions reflect real beneficiary needs and answers are accurate, relevant, and easy to understand. No prior AI experience is required.

Key Responsibilities

  • Review sample Medicare questions for realism and relevance to beneficiary needs.
  • Develop rubrics for enrollment scenarios, including initial enrollment, Special Enrollment Periods, and Part B late enrollment penalties.
  • Create evaluation criteria covering Medigap, Medicare Advantage, and Part D plan comparisons.
  • Assess AI-generated answers for accuracy, completeness, and outdated guidance.
  • Identify errors and omissions and provide clear, actionable written feedback.
  • Collaborate asynchronously with the project team.

Required Qualifications

  • Active or recent SHIP certification, or previous SSA Medicare enrollment experience.
  • At least 1 year of experience advising beneficiaries on Medicare enrollment, penalties, Medigap, Medicare Advantage, and Part D.
  • Based in the United States.
  • Availability to start quickly and commit 20–30 hours per week.
  • Strong written communication and attention to detail.

Preferred Qualifications

  • Experience creating Medicare counseling guides, training materials, or evaluation rubrics.
  • Experience advising diverse beneficiaries, including rural and non-English-speaking communities.
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