Remote | Medicare Enrollment Specialist — $40–$60/hour

24-Mag•New York, NY

20h•Remote

About The Position

A remote freelance consulting opportunity for experienced Medicare Enrollment Specialists, Social Security Administration professionals, and employee benefits advisors. The specialist will use practical Medicare counseling and coverage-coordination experience to review realistic enrollment inquiries, develop structured evaluation criteria, and assess AI-generated responses for accuracy, completeness, relevance, and usefulness to beneficiaries. Prior AI training project experience is not required. The work covers Medicare eligibility and enrollment procedures, enrollment periods and penalties, Social Security coordination, Medicare coverage options, and interactions with employer-sponsored and retiree coverage. The consultant will document findings and recommendations, complete assigned reviews independently, and collaborate asynchronously with the project team. The engagement is short-term, fully remote, limited to candidates based in the United States, and expected to require 20–30 hours per week. Candidates should be prepared to begin promptly. There are 10 openings, with compensation of $40–$60 per hour.

Requirements

At least 1 year of relevant experience advising on Medicare enrollment and coverage counseling.
Former Social Security Administration experience involving Medicare enrollment, or professional HR/employee benefits experience advising employees on Medicare.
Strong working knowledge of Medicare eligibility, enrollment procedures, Initial Enrollment Periods, and Special Enrollment Period requirements.
Familiarity with Medicare Part B late enrollment penalties and related enrollment considerations.
Experience explaining Original Medicare, Medigap, Medicare Advantage, and Part D.
Working knowledge of the relationship between Social Security benefits and Medicare enrollment.
Understanding of employer-sponsored health insurance and its interaction with Medicare coverage.
Familiarity with coordination of benefits, primary and secondary payer considerations, and how employer size may affect coverage coordination.
Practical understanding of COBRA and creditable coverage considerations.
Ability to identify inaccurate, incomplete, or outdated Medicare enrollment information.
Experience advising beneficiaries or employees about transitioning between employer coverage and Medicare.
Strong understanding of common Medicare enrollment questions and beneficiary concerns.
Excellent written communication, with emphasis on clarity, precision, and practical usefulness.
Strong analytical reasoning, attention to detail, and structured problem-solving capabilities.
Ability to apply structured evaluation criteria consistently and provide actionable written feedback.
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 with Medicare premium adjustments, including IRMAA.
Familiarity with Medicare coverage while working or Health Savings Account (HSA) considerations.
Experience preparing informational guides, beneficiary counseling scripts, or training materials.
Experience assisting diverse beneficiary populations, including rural and non-English-speaking individuals.
Prior experience with AI model training or evaluation projects is not required.

Responsibilities

Review sample questions about Medicare eligibility, enrollment procedures, and healthcare coverage options.
Assess whether sample inquiries reflect common and realistic questions from beneficiaries and prospective enrollees; identify unclear requests, unrealistic scenarios, and missing information.
Recommend improvements to make sample questions reflect realistic enrollment circumstances and coverage concerns.
Develop criteria for accurate explanations of initial enrollment, enrollment deadlines, Special Enrollment Periods, and Part B late enrollment penalties.
Evaluate Medicare enrollment guidance involving Social Security benefits and eligibility circumstances; identify incomplete, inaccurate, or misleading information about timelines and procedures.
Review information about Original Medicare, Medigap, Medicare Advantage, and Part D, including comparisons and beneficiary considerations.
Assess guidance on employer-sponsored health insurance, retiree coverage, employer size, and primary versus secondary coverage coordination.
Identify inaccuracies involving COBRA, creditable coverage, and interactions between Medicare and employer health plans.
Develop structured rubrics for evaluating the correctness, completeness, and usefulness of answers to Medicare enrollment questions.
Evaluate AI-generated responses for accuracy, completeness, relevance, and practical usefulness; identify factual errors, omissions, misconceptions, and outdated guidance.
Document evaluation criteria, findings, enrollment considerations, and coverage-coordination procedures in clear written feedback.
Recommend specific corrections and improvements to AI-generated Medicare guidance.
Apply direct professional experience to provide practical insights and complete assigned review activities independently in an asynchronous project environment.
Maintain accuracy, consistency, and professional written communication throughout deliverables.