Remote Medicare Enrollment Specialist — Clinical AI Evaluation (Flexible AI Training Role)

Pinnacle AI Evaluation Partners invites qualified professionals to apply for our remote Remote Medicare Enrollment Specialist — Clinical AI Evaluation (Flexible AI Training Role) opportunity ($40 - $60/hour). You will leverage hands-on experience in Medicare, Enrollment, Coordination, Coverage to audit AI-generated solutions, pinpoint reasoning gaps, and construct authoritative reference responses.

Core Project Workflow

• 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.
• 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.

Required Technical & Domain Mastery

• 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
• 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 Summary

• Compensation Rate: $40 - $60/hour (contract specialist remuneration)
• Work Arrangement: 100% Remote / Work From Anywhere
• Core Competencies: Medicare, Enrollment, Coordination, Coverage, COBRA
• Hiring Organization: Pinnacle AI Evaluation Partners

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.