Medicare Enrollment AI Evaluation Specialist

The Work

You will help improve AI systems that answer Medicare questions. Your work will focus on whether beneficiary questions sound realistic and whether AI responses are accurate, complete, and useful.

You will work asynchronously and provide clear written feedback. The project covers Medicare enrollment guidance, Social Security coordination, employer and retiree coverage, and common benefits questions.

• Review sample questions about signing up for Medicare.
• Identify questions or concerns that do not reflect realistic beneficiary experiences.
• Create rubrics for initial enrollment, special enrollment periods, and Part B late-enrollment penalties.
• Develop guidance on Medigap, Medicare Advantage, Part D, employer size, primary and secondary coverage, COBRA, and creditable coverage.
• Evaluate AI-generated answers against the rubrics.
• Identify errors, missing information, and common misconceptions.
• Share precise written feedback asynchronously.

What It Pays and Takes

This is a remote, part-time contractor opportunity for specialists based in the United States. The work is intended for people with practical experience advising on Medicare enrollment or employee benefits.

• $40 to $60 per hour.
• 20 or more hours per week.
• Remote work for candidates in the United States.
• Professional fluency in English.
• Former SSA Medicare enrollment experience or employer benefits or HR experience advising employees on Medicare.
• At least one year advising on initial enrollment, special enrollment periods, Part B late-enrollment penalties, Medigap, Medicare Advantage, and Part D.
• Working knowledge of Social Security and employer coverage coordination, including creditable coverage.
• Clear and precise written communication.
• Helpful experience includes IRMAA, working while enrolled, HSA rules alongside Medicare, beneficiary education, or creating guides, counseling scripts, and training materials.
• Experience supporting diverse beneficiaries, including rural and non-English-speaking clients, is valued.

How It Works

Apply on OpenTrain with your resume, then complete the application on the hiring site.

About AI Training Work

AI training work is the human side of building artificial intelligence. Specialists review examples, write guidance, and rate model answers so AI systems learn to give more accurate and useful responses.

People with experience in fields such as Medicare enrollment and benefits advising are paid for the practical knowledge they bring to these evaluations.