We are sharing a specialised remote consulting opportunity for experienced SHIP Medicare Counselors and Medicare Enrollment Professionals with strong expertise in Medicare enrollment, beneficiary counseling, Medigap, Medicare Advantage, Part D, and healthcare coverage guidance to contribute their professional knowledge to advanced AI training and evaluation initiatives.
Selected professionals will review realistic Medicare beneficiary questions, develop structured evaluation criteria, and assess AI-generated responses for accuracy, completeness, clarity, and practical usefulness. The work combines firsthand Medicare counseling experience with enrollment guidance, health plan comparisons, and written evaluation to improve how AI systems assist individuals navigating Medicare coverage and enrollment decisions. Prior experience with AI training projects is not required.
Key Responsibilities
Medicare Beneficiary Inquiry Review
- Review sample questions concerning Medicare enrollment, healthcare coverage, and beneficiary assistance.
- Evaluate whether inquiries accurately reflect questions commonly received from Medicare beneficiaries.
- Identify unrealistic scenarios, unclear requests, and missing information in sample Medicare questions.
- Apply practical counseling experience to assess the relevance and authenticity of beneficiary inquiries.
- Recommend improvements to ensure questions reflect realistic Medicare enrollment and coverage situations.
Medicare Enrollment & Eligibility Evaluation
- Develop evaluation criteria for accurate guidance concerning Medicare initial enrollment procedures.
- Assess AI-generated explanations of Special Enrollment Periods and relevant enrollment circumstances.
- Review information concerning Medicare Part B late enrollment penalties and associated requirements.
- Identify incomplete, inaccurate, or outdated information relating to enrollment timing and eligibility.
- Evaluate whether suggested next steps appropriately address the beneficiary's circumstances and coverage needs.
Medigap, Medicare Advantage & Part D Plan Comparison
- Review guidance comparing Original Medicare with Medicare Advantage and Medigap coverage arrangements.
- Assess explanations of Medicare Part D prescription drug coverage and relevant plan considerations.
- Evaluate whether AI-generated comparisons accurately describe important differences between available coverage options.
- Develop criteria for assessing how well responses address beneficiaries' individual healthcare and coverage priorities.
- Identify misleading comparisons, missing considerations, and unclear explanations of Medicare plan features.
AI Response Evaluation & Quality Standards
- Develop structured rubrics defining correct, complete, and useful answers to Medicare questions.
- Evaluate AI-generated responses against established accuracy, completeness, and relevance criteria.
- Identify factual errors, omitted information, outdated guidance, and common Medicare misconceptions.
- Assess whether responses provide clear, actionable information suitable for diverse beneficiary populations.
- Document evaluation findings and recommend specific improvements to response quality.
Technical Documentation & Project Collaboration
- Prepare clear written feedback explaining identified errors, missing information, and recommended corrections.
- Document evaluation criteria, Medicare counseling considerations, and relevant enrollment procedures.
- Communicate practical insights based on direct experience assisting Medicare beneficiaries.
- Complete assigned review activities independently within an asynchronous project environment.
- Maintain high standards of accuracy, consistency, and professional written communication throughout project deliverables.
Ideal Profile
- Active or recent State Health Insurance Assistance Program (SHIP) certification, or previous Social Security Administration (SSA) Medicare enrollment experience.
- At least 1 year of experience advising beneficiaries on initial enrollment, Special Enrollment Periods, Medicare Part B late penalties, Medigap versus Medicare Advantage, and Part D.
- Strong working knowledge of Medicare enrollment procedures and relevant eligibility considerations.
- Practical experience counseling individuals about Medicare coverage and enrollment decisions.
- Familiarity with Medicare Initial Enrollment Periods and Special Enrollment Period requirements.
- Understanding of Medicare Part B late enrollment penalties and related enrollment guidance.
- Strong knowledge of Original Medicare, Medigap, Medicare Advantage, and Part D.
- Experience explaining differences between Medicare coverage options to beneficiaries.
- Ability to evaluate whether plan comparisons accurately reflect important coverage considerations.
- Demonstrated understanding of common Medicare beneficiary questions and counseling scenarios.
- Ability to identify inaccurate, incomplete, misleading, or outdated Medicare information.
- Experience communicating complex healthcare coverage concepts clearly to individuals with varying levels of Medicare knowledge.
- Excellent written communication skills, with an emphasis on clarity, precision, and practical usefulness.
- Strong analytical reasoning, attention to detail, and structured problem-solving capabilities.
- Demonstrated ability to apply consistent evaluation criteria to Medicare counseling scenarios.
- Experience preparing Medicare counseling guides, educational resources, training materials, or evaluation rubrics is advantageous.
- Experience supporting diverse beneficiary populations, including rural communities and non-English-speaking individuals, is beneficial.
- Ability to provide constructive written feedback based on professional Medicare counseling experience.
- Strong organisational skills and the ability to work independently within a remote project environment.
- Must be based in the United States.
- Availability to begin promptly and commit 20–30 hours per week.
- Prior experience with AI model training or evaluation projects is not required.
Engagement Details
- Freelance / contract engagement
- Fully remote — United States only
- Compensation: $30–$60/hour
- Expected Commitment: 20–30 hours per week
- Project Duration: Short-term engagement
- 10 available openings
- Availability: Candidates should be prepared to begin promptly.
- Certification / Background Requirement: Active or recent SHIP certification, or former SSA Medicare enrollment experience.
- Experience Requirement: At least 1 year of relevant Medicare enrollment and coverage counseling experience.
- Professional Focus: Medicare beneficiary counseling, initial enrollment, Special Enrollment Periods, and health plan comparisons.
- Technical Focus: Medicare Part B late enrollment penalties, Medigap, Medicare Advantage, Part D, and AI response evaluation.
- Responsibilities will include reviewing realistic beneficiary questions, developing evaluation rubrics, and assessing AI-generated Medicare guidance.
- Assignments will focus on factual accuracy, enrollment requirements, coverage comparisons, and practical usefulness to beneficiaries.
- Deliverables will include structured evaluation criteria, written response assessments, and actionable feedback.
- Work will be conducted remotely through asynchronous collaboration with the project team.
- Experience preparing Medicare counseling materials or assisting diverse beneficiary populations is particularly relevant.
- Previous experience with AI training projects is not required.
About the Platform
This opportunity is available through 24-MAG LLC. We connect experienced professionals with remote consulting opportunities across technical, evaluation, and project-based workstreams.
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