Remote | SHIP Medicare Counselor — $30–$60/hour

24-Mag•New York, NY

21h•Remote

About The Position

This remote consulting role is for experienced SHIP Medicare Counselors and Medicare Enrollment Professionals contributing expertise to AI training and evaluation initiatives. The work involves reviewing realistic Medicare beneficiary questions, developing structured evaluation criteria, and assessing AI-generated responses for accuracy, completeness, clarity, relevance, and practical usefulness. The role draws on firsthand Medicare counseling experience, enrollment guidance, and knowledge of health plan comparisons to improve AI assistance for people navigating Medicare coverage and enrollment decisions. Prior AI training project experience is not required. The engagement is freelance/contract, fully remote, and limited to candidates based in the United States. The expected commitment is 20–30 hours per week for a short-term project, with candidates expected to begin promptly. Compensation is $30–$60 per hour. There are 10 openings. The opportunity is available through 24-MAG LLC, which connects professionals with remote consulting opportunities.

Requirements

Active or recent SHIP certification, or previous Social Security Administration (SSA) Medicare enrollment experience.
At least 1 year of relevant experience advising beneficiaries on initial enrollment, Special Enrollment Periods, Medicare Part B late enrollment penalties, Medigap versus Medicare Advantage, and Part D.
Strong working knowledge of Medicare enrollment procedures and 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 guidance.
Strong knowledge of Original Medicare, Medigap, Medicare Advantage, and Part D.
Experience explaining Medicare coverage options and evaluating whether comparisons address important coverage considerations.
Ability to recognize common beneficiary questions and counseling scenarios, and identify inaccurate, incomplete, misleading, or outdated information.
Ability to communicate complex healthcare coverage concepts clearly to people with varying levels of Medicare knowledge.
Excellent written communication, analytical reasoning, attention to detail, and structured problem-solving skills.
Ability to apply consistent evaluation criteria and provide constructive written feedback based on professional Medicare counseling experience.
Strong organizational skills and ability to work independently in a remote project environment.
Must be based in the United States.
Availability to begin promptly and commit 20–30 hours per week.

Nice To Haves

Experience preparing Medicare counseling guides, educational resources, training materials, or evaluation rubrics.
Experience supporting diverse beneficiary populations, including rural communities and non-English-speaking individuals.

Responsibilities

Review sample questions about Medicare enrollment, healthcare coverage, and beneficiary assistance; assess whether they reflect common beneficiary inquiries and identify unrealistic, unclear, or incomplete scenarios.
Recommend improvements to beneficiary questions so they reflect realistic enrollment and coverage situations.
Develop criteria for evaluating guidance about initial Medicare enrollment, Special Enrollment Periods, Part B late enrollment penalties, eligibility, and appropriate next steps.
Review and assess explanations comparing Original Medicare, Medicare Advantage, Medigap, and Part D, identifying misleading comparisons, omitted considerations, and unclear descriptions.
Develop structured rubrics defining correct, complete, relevant, and useful answers to Medicare questions.
Evaluate AI-generated responses for factual accuracy, completeness, relevance, clarity, and practical usefulness; identify errors, omissions, outdated guidance, and common misconceptions.
Prepare written feedback explaining identified issues and recommending corrections or improvements.
Document evaluation criteria, Medicare counseling considerations, and relevant enrollment procedures.
Communicate practical insights based on direct experience assisting Medicare beneficiaries.
Complete assigned reviews independently in an asynchronous remote project environment while maintaining accuracy, consistency, and professional written communication.