Medicare Enrollment Specialist (AI Evaluation)

You will help evaluate AI systems that answer Medicare questions. The work is focused on realistic enrollment guidance, accurate benefits information, and clear written feedback completed asynchronously.

You will review sample beneficiary questions, create evaluation rubrics, assess AI-generated answers, and identify errors, missing information, and common misconceptions.

• Review questions about initial Medicare enrollment and identify concerns that do not reflect realistic beneficiary experiences.
• Create rubrics for initial enrollment, special enrollment periods, Part B late-enrollment penalties, and Medicare and Social Security coordination.
• Develop guidance covering Medigap, Medicare Advantage, Part D, employer size, primary and secondary coverage, COBRA, and creditable coverage.
• Evaluate AI answers against the rubrics and provide precise written feedback.
• Address topics such as IRMAA, working while enrolled, HSA rules alongside Medicare, beneficiary education, and counseling or training materials when relevant.

This is a remote, short-term contractor project for specialists based in the United States. Work is part time, asynchronous, and requires at least 20 hours per week.

• Pay: $40 to $60 per hour.
• Location: Open to candidates in the United States.
• Language: Professional fluency in English.
• Experience: Former SSA Medicare enrollment experience or employer benefits or HR experience advising employees about 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 background includes experience supporting rural and non-English-speaking beneficiaries, as well as creating guides, counseling scripts, or training materials.

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

AI training is the human work behind systems that answer questions and generate text. People with subject expertise review model outputs, create examples, and explain what accurate and useful answers should contain. OpenTrain helps people find these projects, build a profile, and apply in one place.