Medicare Enrollment Specialist

Confidential; United States; Remote; USD 55,000 - 83,000; Part time

Job summary

Zekai seeks a Medicare Enrollment Specialist for a remote contractor role. You will review AI-generated Medicare questions and answers, ensuring accuracy and usefulness for real beneficiaries.

Your domain knowledge in SSA Medicare enrollment or employer benefits will drive rubric creation and quality checks. You’ll write precise rubrics for initial enrollment, special enrollment periods, and Part B penalties, addressing Medigap vs Medicare Advantage and Part D, with emphasis on employer/retiree

Qualifications

• Former SSA Medicare enrollment experience, or employer benefits/HR advising on Medicare.
• 1+ years advising on initial enrollment, special enrollment periods, Part B late penalties, Medigap vs Medicare Advantage, and Part D.
• Working knowledge of Social Security and employer coverage coordination, including creditable coverage.

Responsibilities

• Review sample questions about signing up for Medicare and flag any that don’t sound like real questions.
• Write rubrics defining correct, complete answers on enrollment topics and penalties.
• Cover Medigap vs Medicare Advantage and Part D in rubrics, focusing on employer/retiree coverage scenarios.
• Evaluate AI-generated answers against rubrics, flag errors and omissions.
• Share clear written feedback with the project team remotely.

Skills

Medicare enrollment experience

Clear writing

Remote work readiness

Benefits/HR advisory

Job description

Role Title: Medicare Enrollment Specialist

Role Type: Contractor

Location: Remote

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

our partner is looking for Medicare Enrollment Specialists to help evaluate and improve AI systems on Medicare topics. You’ll use your Social Security or employer benefits experience to check that questions sound like real beneficiaries and that answers are correct and useful. Accuracy comes first. No AI experience is needed; your domain knowledge is what matters.

Scope of Work

• Review sample questions about signing up for Medicare and flag any that don’t sound like what real people ask.
• Write rubrics that define a correct, complete answer on initial enrollment, special enrollment periods, and Part B late penalties, including how enrollment ties to Social Security benefits.
• Cover Medigap vs. Medicare Advantage and Part D in your rubrics, with a focus on scenarios involving employer or retiree coverage.
• Cover how employer coverage interacts with Medicare, including employer size, primary vs. secondary coverage, COBRA, and creditable coverage.
• Evaluate AI-generated answers against your rubrics, flagging errors, omissions, and common misconceptions.
• Share clear written feedback with the project team, working asynchronously.

Required Qualifications

• Former SSA Medicare enrollment experience, or employer benefits/HR experience advising employees on Medicare
• 1+ years advising on initial enrollment, special enrollment periods, Part B late penalties, Medigap vs. Medicare Advantage, and Part D
• Working knowledge of Social Security and employer coverage coordination, including creditable coverage
• US-based
• Able to start quickly and commit 20-30 hours/week
• Clear, precise writing

Nice to Have

• Experience with premium adjustments (such as IRMAA), working while enrolled, or HSA rules alongside Medicare
• Experience creating guides, counseling scripts, or training materials
• Experience helping 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.