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SHIP Medicare Counselor for AI Evaluation

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Job details

Pay

$30–$60 USD/hr

Engagement

Contract, part-time

Location

Remote

United States only

Posted

Oct 12, 2026

OpenTrain on Trustpilot

The work

You will help evaluate AI systems that answer Medicare questions. The work uses your counseling judgment to assess whether questions reflect real beneficiary concerns and whether answers are accurate, complete, useful, and current.

  • Review sample Medicare questions and identify prompts that do not reflect realistic beneficiary concerns.
  • Create rubrics for answers about initial enrollment, special enrollment periods, and Part B late enrollment penalties.
  • Write guidance for comparing Medigap, Medicare Advantage, and Part D plans, including key differences and appropriate use cases.
  • Evaluate AI-generated answers against your rubrics and flag errors, missing information, and outdated guidance.
  • Provide clear written feedback asynchronously.

Requirements

This is a remote, short-term contractor project for candidates in the United States. The project requires 20 to 30 hours per week.

  • Experience: Active or recent SHIP certification, or prior Medicare enrollment experience with the Social Security Administration.
  • Experience: At least one year advising on initial enrollment, special enrollment periods, Part B late enrollment penalties, Medigap versus Medicare Advantage, and Part D.
  • Skills: Clear, precise writing and the ability to explain Medicare guidance accurately.
  • Language: Professional fluency in English.
  • Skills: Medicare, Medigap

Open to applicants in

  • United States

Preferred

  • Helpful background: Creating Medicare counseling guides, training materials, or rubrics.
  • Helpful background: Serving diverse beneficiaries, including rural or non-English-speaking clients.

How to apply

  1. Press Apply now. You create a free OpenTrain account and add your resume.
  2. Finish your application on the hiring company's site. The company decides who it hires, so it runs its own form. It asks for your resume again, your LinkedIn profile, your phone number, your location and answers to 5 screening questions.
  3. Take a short AI interview.

Job ID: cmv5oo04g000506lcka547gix

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