Remote Medicare Enrollment Specialist — Clinical AI Evaluation — LLM Alignment & Research

Are you a domain specialist skilled in Medicare, Enrollment, Coordination, Coverage? RemoteJob Staffing is seeking a remote Remote Medicare Enrollment Specialist — Clinical AI Evaluation — LLM Alignment & Research ($40 - $60/hour) to help train and validate frontier AI systems through structured problem authoring, rubric design, and analytical output auditing from anywhere in the US, UK, Canada, or Australia.

Day-to-Day Impact

• 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
• 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
• Review sample questions about signing up for Medicare and flag any that don’t sound like what real people ask.

Essential Background & Expertise

• 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
• Core Competencies: Medicare, Enrollment, Coordination, Coverage, COBRA
• Able to start quickly and commit 20-30 hours/week
• Clear, precise writing

Rate & Flexible Work Terms

• 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 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.