Medicare Enrollment AI Evaluation Specialist

OpenTrain AI, Inc.; Northern (KY); Hybrid; USD 69,000 - 207,000; Part time

Job summary

OpenTrain AI, Inc. is seeking a remote, part-time contractor to help improve AI systems that answer Medicare questions. You will assess the realism and accuracy of beneficiary questions and evaluate generated answers.

Responsibilities include writing clear evaluation standards, creating rubrics for enrollment-related topics, and delivering precise written feedback asynchronously.

Qualifications

• Former SSA Medicare enrollment experience or employer benefits or HR experience advising employees on Medicare.
• Experience with enrollment periods, Medigap, and Part D.
• Ability to write clear feedback and guidance.

Responsibilities

• Review questions about Medicare enrollment and identify unrealistic concerns or scenarios.
• Create rubrics for initial enrollment, special enrollment periods, Part B late-enrollment penalties, and Medicare and Social Security coordination.
• 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 and identify errors, omissions, and common misconceptions.
• Write clear expert feedback that can help improve future AI responses.

Skills

Medicare enrollment

HR advising

SSA knowledge

Written English

Job description

The Work

You will help improve AI systems that answer Medicare questions. You will assess whether beneficiary questions are realistic and whether generated answers are accurate, complete, and useful.

The work includes writing clear evaluation standards, reviewing AI responses, finding errors and missing information, and giving precise written feedback asynchronously.

• Review questions about Medicare enrollment and identify unrealistic concerns or scenarios.
• Create rubrics for initial enrollment, special enrollment periods, Part B late-enrollment penalties, and Medicare and Social Security coordination.
• 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 and identify errors, omissions, and common misconceptions.
• Write clear expert feedback that can help improve future AI responses.

What It Pays And Takes

This is a remote, part-time contractor opportunity for specialists based in the United States. The project is short term and completed asynchronously.

• Pay: $50 to $150 per hour.
• Time: 20+ hours per week.
• Location: Open to candidates in the United States.
• Work arrangement: Remote, part-time contract work.
• Required experience: Former SSA Medicare enrollment experience or employer benefits or HR experience advising employees on Medicare.
• Experience requirement: At least one year advising on initial enrollment, special enrollment periods, Part B late-enrollment penalties, Medigap, Medicare Advantage, and Part D.
• Knowledge: Social Security and employer coverage coordination, including creditable coverage.
• Communication: Clear and precise written English.
• Helpful experience: IRMAA, working while enrolled, HSA rules alongside Medicare, beneficiary education, or creating guides, counseling scripts, and training materials.
• Additional helpful background: Supporting diverse beneficiaries, including people in rural areas and people who do not speak English.

About AI Training Work

AI training is the human work behind systems that answer questions and generate text. Specialists review examples, write guidance, and rate model responses so AI systems become more accurate and useful; experienced professionals are paid for applying their subject knowledge to this work.