Medicare Enrollment Specialist

You will help evaluate and improve AI systems that answer Medicare questions. The work involves reviewing sample beneficiary questions, defining what accurate answers should include, rating AI responses, and giving clear written feedback asynchronously.

• Review Medicare enrollment questions and flag examples that do not sound like real beneficiary inquiries.
• Write rubrics for accurate answers about initial enrollment, special enrollment periods, Part B late penalties, Medigap and Medicare Advantage, Part D, and employer coverage coordination.
• Evaluate AI-generated answers against your rubrics and identify errors, missing information, and common misconceptions.
• Provide clear written feedback to the project team asynchronously.

What it pays and takes

This is a remote, short-term, part-time project for a Medicare enrollment specialist. Candidates must be based in the United States and able to start quickly.

• Pay: $40 to $60 per hour.
• Time: 20 to 30 hours per week.
• Location: Open to candidates in the United States.
• Language: Professional fluency in English and clear, precise writing skills.
• Experience: Former SSA Medicare enrollment experience, or employer benefits or HR experience advising employees about Medicare.
• Experience: At least one year advising on initial enrollment, special enrollment periods, Part B late penalties, Medigap and Medicare Advantage, and Part D.
• Knowledge: Social Security and employer coverage coordination, including creditable coverage.
• Helpful background: Knowledge of IRMAA premium adjustments, working while enrolled, or HSA rules alongside Medicare.
• Helpful background: Creating guides, counseling scripts, or training materials.
• Helpful background: Supporting rural and non-English-speaking beneficiaries.

How it works

You apply here in about two minutes and finish on the hiring platform. The next step is a short AI interview (technical roles include a coding challenge). Passing it is how you qualify for paid tasks, so take it soon after you are invited.

The hiring platform's application for this job asks for your resume, your LinkedIn profile, your phone number, your location and answers to 4 screening questions.

About AI training work

AI training is the human work behind systems that answer questions and generate text. People with specialist knowledge review model responses, define accurate standards, and explain mistakes so AI systems can provide more useful and reliable answers; OpenTrain is where people find these projects and start applications.