Remote Medicare Enrollment Specialist (Contractor)

RemoteJobsOne; New York (NY); Remote; USD 55,000 - 83,000; Part time

Job summary

RemoteJobsOne is seeking a Medicare Enrollment Specialist for a fully remote contractor role in the United States. The position offers 20-30 hours per week on a short-term project, with pay in the $40-$60 per hour range.

You will review Medicare enrollment questions, write rubrics for enrollment scenarios, and evaluate AI-generated answers against established standards. Prior SSA Medicare enrollment or employer benefits guidance is required, with clear, precise writing.

Qualifications

• Former SSA Medicare enrollment experience or employer benefits/HR Medicare guidance.
• 1+ years advising on enrollment, SEPs, Part B penalties, Medigap vs MA, and Part D.
• US-based and available to start quickly, 20–30 hours/week.

Responsibilities

• Review sample questions about Medicare enrollment and flag inaccuracies.
• Write rubrics defining correct, complete enrollment answers for initial enrollment, SEPs, and Part B penalties.
• Cover Medigap vs Medicare Advantage and Part D in rubrics, including employer/ retiree coverage scenarios.
• Explain how employer coverage interacts with Medicare (size of employer, primary vs secondary, COBRA, creditable coverage).
• Evaluate AI-generated answers against rubrics, flag errors and omissions.
• Provide written feedback to the project team asynchronously.

Skills

Medicare enrollment knowledge

Clear, precise writing

Social Security knowledge

Job description

RemoteJobsOne is seeking a Medicare Enrollment Specialist for a fully remote contractor role in the United States. The position offers 20-30 hours per week on a short-term project, with pay in the $40-$60 per hour range.

You will review Medicare enrollment questions, write rubrics for enrollment scenarios, and evaluate AI-generated answers against established standards. Prior SSA Medicare enrollment or employer benefits guidance is required, with clear, precise writing.