Remote Medicare Enrollment Specialist (Direct Contract Placement)

Work 100% remotely as a Remote Medicare Enrollment Specialist (Direct Contract Placement) with RemoteJob USA Staffing, earning $40 - $60/hour. You will design challenging domain prompts, grade complex model outputs, and refine reasoning trajectories using your background in Medicare, Enrollment, Coordination, Coverage.

Position 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, 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.
• Assess and benchmark model-generated answers against your rubrics, flagging errors, omissions, and common misconceptions.
• Share clear written feedback with the project team, working asynchronously.
• Former SSA Medicare enrollment experience, or employer benefits/HR experience advising employees on Medicare

Required Competencies

• Clear, precise writing
• Practical background using 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
• Compensation Band: $40 - $60/hour
• Work Location: Remote (100% Remote / Asynchronous Flexibility)
• Available Openings: 10 open positions

Earnings & Remote Work Details

• Compensation Rate: $40 - $60/hour (contract specialist remuneration)
• Work Arrangement: 100% Remote / Work From Home
• Eligible Remote Countries: United States, United Kingdom, Canada, Australia, New Zealand, Ireland, and South Africa
• Core Competencies: Medicare, Enrollment, Coordination, Coverage, COBRA
• Hiring Agency: RemoteJob USA Staffing

Direct Application Process: Click the Apply button on this page to proceed directly to our partner application portal and submit your profile for immediate consideration.