SHIP Medicare Counselor

$30–60/hr

rate as listed

Workload: 20–30 hrs/week
Engagement: Project-based
Location: Worldwide
Field: Medical

Review Medicare questions and AI-generated answers for accuracy, completeness, and relevance to real beneficiaries. This remote, short-term contract requires current or recent SHIP certification or former SSA Medicare enrollment experience, plus at least one year of advising on core Medicare enrollment and coverage topics.

Day-to-day work

You will review sample Medicare questions, identify prompts that do not resemble real beneficiary concerns, and write scoring rubrics for correct and complete answers. The subject matter includes initial enrollment, special enrollment periods, Part B late penalties, Medigap versus Medicare Advantage, and Part D plan comparison. You will then evaluate AI-generated responses against those rubrics and document errors, omissions, or outdated guidance.

What the screening assesses

The platform will look for verifiable SHIP or SSA Medicare enrollment experience and at least one year of advising across the Medicare topics named above. Expect follow-up questions that test how you handle enrollment scenarios, distinguish coverage options, verify time-sensitive guidance, and translate counseling knowledge into precise evaluation criteria. Experience creating guides, training materials, or rubrics is preferred, as is experience counseling diverse beneficiaries, including rural and non-English-speaking clients.

Practical details

This is a remote contractor role for a short-term project, with work completed asynchronously. Candidates must be based in the US, able to start quickly, and available for 20-30 hours/week. The platform reports an observed pay band, not a guaranteed rate or volume of work.

Pay band: $30–60/hr

What they look for

SHIP certification
Medicare enrollment
Special enrollment periods
Part B late enrollment penalties
Medigap vs. Medicare Advantage
Part D plan comparison

Included with this listing

Interview prep — 10 questions

Matched to what this platform's screening actually measures. Answer each out loud in 60–90 seconds: claim → concrete example → implication.

What it tests: This verifies which of the role's two qualifying backgrounds you meet, how recent it is, and whether it involved direct Medicare enrollment work.
A strong answer: State the credential or SSA role, dates, organization or office type, and the Medicare counseling or enrollment duties performed. Include an approximate counseling volume or case mix if you can verify it.
Where people lose it: Candidates lose points by saying only that they are Medicare knowledgeable without naming their SHIP status, SSA role, dates, or direct responsibilities.

Summary, eligibility guidance and screening preparation are prepared by Sidequest from the platform's posting. Check the source listing before applying.

MEDICINE on Sidequest

What medicine AI work pays

Rates by specialty, the platforms hiring, and every open role in this field.