SHIP Medicare Counselor – Remote

RemoteJobsOne; Philadelphia (Philadelphia County); Remote; USD 14,000 - 207,000; Full time

Job summary

RemoteJobsOne is seeking SHIP-certified Medicare counselors to help evaluate and improve AI systems on Medicare topics. This fully remote contractor role emphasizes accuracy and usefulness for diverse beneficiaries. No AI experience required; counseling expertise matters and rapid start is possible.

You will review questions, develop rubrics for enrollment scenarios, compare Medigap vs Medicare Advantage and Part D, and provide clear feedback to the project team, working asynchronously.

Qualifications

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

Responsibilities

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• Evaluate AI-generated answers against your rubrics, flagging errors, omissions, and outdated guidance.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

Skills

SHIP certification

Strong writing

Job description

• Philadelphia, Pennsylvania, United States

IMPORTANT: after you apply, please check your email. We sendyou a link to complete your application — it is not considered until that laststep 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: $10–$150/hr

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

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• Evaluate AI-generated answers against your rubrics, flagging errors, omissions, and outdated guidance.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

Required Qualifications

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

Nice to Have

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