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Medicare Enrollment Specialist

micro1 Micro1 Part-timeRemote
Posted Oct 13, 2026 · ✓ Still open — checked 4 hours ago

Quick facts

Type
Part-time
Location
Remote
Hours
20–30 hours / week
Platform
Micro1 — 260 open jobs
Typical pay at Micro1
$25–150/hour · median $90 (17 jobs on our site)
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Required Skills
Medicare Parts A B C D
Medicare enrollment counseling
Social Security and Medicare coordination
Employer coverage and creditable coverage
Plan comparison and selection
Beneficiary education
About micro1
micro1 is a data lab that helps AI labs & Enterprises train foundational models and agents. We provide frontier evaluations and reinforcement learning environments to improve LLM capabilities, as well as contextual evaluations to monitor and improve AI agents in enterprise settings.

Our AI recruiting agent sources and vets domain experts for our data platform that enables rapid production of high-quality training data. Our research spans high-value, specialized domains (legal, medical, finance, coding, etc.), where expert-level data is the hardest to produce and most valuable for advanced model performance. Our pipeline performance system ensures both quality and velocity.

Role Title: Medicare Enrollment Specialist

Role Type: Contractor

Location: Remote

Time Commitment: 20-30 hours/week, short-term project

micro1 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. 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.

Required Qualifications

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
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About Micro1

micro1 recruits engineers and domain experts for AI labs using its AI interviewer. Once vetted, contractors work on human-data projects such as writing and checking model outputs or building coding evaluations.