SHIP Medicare Counselor

confidential; United States; Remote; USD 34,000 - 55,000; Part time

Job summary

Zekai is seeking a SHIP Medicare Counselor for a 100% remote, short-term contract. You will evaluate AI-generated Medicare guidance using your counseling experience to ensure answers are accurate and useful to real beneficiaries.

You will develop rubrics for enrollment scenarios, compare Medigap vs Medicare Advantage and Part D, and provide clear feedback to the project team. This role requires 20-30 hours per week and can start quickly.

Qualifications

• Active SHIP certification or recent SSA Medicare enrollment experience.
• 1+ years advising on enrollment periods, Part B 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 from remote locations.

Responsibilities

• Review sample Medicare questions and flag any non-representative queries.
• Write rubrics defining correct, complete enrollment scenarios (initial enrollment, special enrollment periods, Part B late penalties).
• Cover Medigap vs Medicare Advantage and Part D plan differences in rubrics and guidance.
• Evaluate AI-generated answers against rubrics, flag errors and outdated guidance.
• Provide clear written feedback to the project team asynchronously.

Skills

SHIP certification

Medicare counseling

Policy interpretation

Clear writing

Remote collaboration

Job description

Role Title: SHIP Medicare Counselor

Role Type: Contractor

Location: Remote

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

our partner 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• Evaluate AI-generated answers against your rubrics, flagging errors, omissions, and outdated guidance.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

This is a 100% remote contract role, open to applicants worldwide in the countries the employer accepts.