Medicare Enrollment Specialist

micro1; United States; Remote; USD 34,000 - 55,000; Full time

Job summary

micro1 is seeking Medicare Enrollment Specialists to support a short-term, remote project. You will evaluate AI-generated Medicare questions for realism and accuracy, using your SSA Medicare enrollment or employer benefits experience.

No AI experience needed; strong domain knowledge and precise writing are essential. Expect 20-30 hours per week, contractor engagement, with clear feedback to the project team.

Qualifications

• Former SSA Medicare enrollment experience or employer benefits/HR advising on Medicare.
• 1+ year advising on initial enrollment, special enrollment periods, and Part B penalties.
• Knowledge of Medigap, Medicare Advantage, and Part D.

Responsibilities

• Review sample Medicare enrollment questions and flag non-realistic queries.
• Write rubrics defining correct answers for initial enrollment, special enrollment periods, and penalties.
• Cover interactions between employer coverage and Medicare, including COBRA and creditable coverage.
• Evaluate AI-generated answers against rubrics and flag errors.
• Provide written feedback to the project team.

Skills

Medicare enrollment experience

Social Security knowledge

Written communication

Remote work capability

Job description

Role Title: Medicare Enrollment Specialist Role Type: Contractor Location: Remote Time Commitment: 20-30 hours/week, short-term project micro1 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

Originally posted on Himalayas