Remote Medicare Enrollment Specialist — AnyHired Specialist Network

As a Remote Medicare Enrollment Specialist — AnyHired Specialist Network with AnyHired ($40 - $60/hour, 100% remote), you will play a direct role in shaping how next-generation AI systems reason through complex problems in Medicare, Enrollment, Coordination, Coverage. This contract offers flexible remote scheduling for qualified professionals across the US, UK, Canada, Australia, New Zealand, and Ireland.

Role Deliverables

• 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.
• Cover Medigap vs. Medicare Advantage and Part D in your rubrics, with a focus on scenarios involving employer or retiree coverage.

Professional Qualifications

• 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
• Experience creating guides, counseling scripts, or training materials

Hourly Compensation & Flexibility

• 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: AnyHired

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.