Remote Medicare Enrollment Specialist — AI Research & Domain Evaluation

Join ZR Talent Group's remote specialist network as a Remote Medicare Enrollment Specialist — AI Research & Domain Evaluation earning $40 - $60/hour. Working asynchronously from anywhere in the US, UK, Canada, Australia, New Zealand, Ireland, or South Africa, you will apply your practical background in Medicare, Enrollment, Coordination, Coverage to benchmark frontier artificial intelligence models, identify failure modes, and elevate domain-specific accuracy.

Prior experience building machine learning systems is not required—our research partners value authentic practitioner judgment, domain rigor, and clear analytical writing.

Key Responsibilities & Deliverables

• 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.

Required Qualifications & Technical Criteria

• 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

Preferred Experience & Bonus Attributes

• 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, Remote Eligibility & Schedule

• Compensation Band: $40 - $60/hour
• Work Model: 100% Remote / Work From Home with flexible asynchronous scheduling
• Eligible Remote Locations: United States, Canada, United Kingdom, Australia, New Zealand, Ireland, and South Africa
• Current Openings: 10 active specialist positions
• Hiring Organization: ZR Talent Group
• Core Skills & Technologies: Medicare, Enrollment, Coordination, Coverage, COBRA