Online Medicare Enrollment Specialist — Remote Specialist

ActiveHired is expanding its remote specialist bench with a Online Medicare Enrollment Specialist — Remote Specialist at $40 - $60/hour. Contributors work asynchronously from home across major English-speaking countries, translating real-world workflows in Medicare, Enrollment, Coordination, Coverage into high-signal training examples and multi-step evaluation criteria for enterprise AI models.

Primary Responsibilities

• 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.
• 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.

Skills & Experience Needed

• 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
• Practical background using premium adjustments (such as IRMAA), working while enrolled, or HSA rules alongside Medicare

Remuneration & Remote Setup

• 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: ActiveHired

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.