Medicare Enrollment Specialist

Remotebridge; United States; Remote; USD 34,000 - 48,000; Full time

Job summary

Remotebridge is seeking a Medicare Enrollment Specialist for a short-term, remote project. You’ll use SSA Medicare enrollment or employer benefits experience to evaluate AI questions and ensure accurate, useful answers for real beneficiaries.

Responsibilities include writing rubrics for initial enrollment, special enrollment periods, and Part B penalties; covering Medigap vs Medicare Advantage and Part D; and analyzing how employer coverage interacts with Medicare.

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 coordination with employer coverage, including creditable coverage.
• US-based availability to start quickly and commit 20–30 hours/week.
• Clear, precise writing.

Responsibilities

• 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.
• 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.

Skills

Medicare enrollment knowledge

Benefits/HR advising

Clear writing

Job description

Role Title: Medicare Enrollment Specialist

Role Type: Contractor

Location: Remote

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

Our team 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