R- Work from
- United States
- Contract
- Contract
- Salary
- $40 – $60 / hour
- Posted
- 12 November 2026
- Apply by
- 11 January 2027
the company 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.
IMPORTANT: after you apply, please check your email. We sendyou a link to complete your application — it is not considered until that laststep is done. If you do not see it, check your spam folder.
Pay: $40–$60/hr
Role Title: Medicare Enrollment Specialist
Role Type: Contractor
Location: Remote
Time Commitment: 20-30 hours/week, short-term project
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.
Requirements
- 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
Eligibility
- This is a fully remote position, open to candidates based in United States.
How to apply
Apply here with your profile. We will then email you a link to complete yourapplication on the hiring platform — your application is only considered oncethat final step is done.
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