SHIP Medicare Counselor – Remote

IMPORTANT: after you apply, please check your email. We send you a link to complete your application — it is not considered until that last step is done. If you do not see it, check your spam folder.

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

Pay: $30–$60/hr

Role Title: SHIP Medicare Counselor

Role Type: Contractor

Location: Remote

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

the company is looking for SHIP Medicare Counselors to help evaluate and improve AI systems on Medicare topics. You’ll use your counseling experience to check that questions sound like real beneficiaries and that answers are correct and useful. Accuracy comes first, then usefulness to people from all walks of life. No AI experience is required; your counseling expertise is what matters.

Scope of Work

1. Review sample Medicare questions and flag any that don’t reflect what real beneficiaries ask.
2. Write rubrics defining a correct, complete answer for enrollment scenarios, including initial enrollment, special enrollment periods, and Part B late penalties.
3. Cover Medigap vs. Medicare Advantage and Part D plan comparison in your rubrics, including key differences and when each option fits.
4. Evaluate AI-generated answers against your rubrics, flagging errors, omissions, and outdated guidance.
5. Give clear written feedback to the project team, working asynchronously.
6. 
   

Required Qualifications

1. Active or recent SHIP certification, or former SSA Medicare enrollment experience
2. 1+ years advising on initial enrollment, special enrollment periods, Part B late penalties, Medigap vs. Medicare Advantage, and Part D
3. Based in the US
4. Able to start quickly and commit 20-30 hours/week
5. Clear, precise writing
6. 
   

Nice to Have

1. Experience creating guides, training materials, or rubrics for Medicare counseling
2. Experience counseling a diverse range of beneficiaries, including rural and non-English-speaking clients

How to apply

Apply here with your profile. We will then email you a link to complete your application on the hiring platform — your application is only considered once that final step is done.