[Hiring] Medicare Enrollment Specialist @24-MAG

Role Description

We are sharing a specialised remote consulting opportunity for experienced Medicare Enrollment Specialists, Social Security Administration Professionals, and Employee Benefits Advisors with strong expertise in:

• Medicare enrollment
• Social Security coordination
• Employer-sponsored health coverage
• Medicare plan options

Selected professionals will:

• Review realistic Medicare enrollment inquiries
• Develop structured evaluation criteria
• Assess AI-generated responses for accuracy, completeness, and practical usefulness

The work combines hands-on Medicare counseling experience with healthcare coverage coordination, enrollment procedures, and written evaluation to improve how AI systems respond to questions from Medicare beneficiaries and individuals approaching eligibility. Prior experience with AI training projects is not required.

Qualifications

• Former Social Security Administration experience involving Medicare enrollment, or professional HR/employee benefits experience advising employees on Medicare
• At least 1 year of experience advising on Medicare initial enrollment, Special Enrollment Periods, Part B late penalties, Medigap versus Medicare Advantage, and Part D
• Strong working knowledge of Medicare eligibility and enrollment procedures
• Practical understanding of Medicare initial enrollment periods and Special Enrollment Period requirements
• Familiarity with Medicare Part B late enrollment penalties and relevant enrollment considerations
• Experience explaining Medicare coverage options, including 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 Medicare coordination of benefits, including primary and secondary payer considerations
• Knowledge of how employer size may affect Medicare 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• Ability to identify inaccurate, incomplete, or outdated Medicare enrollment information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 skills, with an emphasis on clarity, precision, and practical usefulness
• Strong analytical reasoning, attention to detail, and structured problem-solving capabilities
• Experience with Medicare premium adjustments, including IRMAA, is advantageous
• Familiarity with Medicare coverage while working or Health Savings Account (HSA) considerations is beneficial
• Experience preparing informational guides, beneficiary counseling scripts, or training materials is preferred
• Experience assisting diverse beneficiary populations, including rural and non-English-speaking individuals, is advantageous
• Ability to apply structured evaluation criteria consistently and provide actionable written feedback
• 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

Requirements

• Freelance / contract engagement
• Fully remote — United States only
• Compensation: $40–$60/hour
• Expected Commitment: 20–30 hours per week
• Project Duration: Short-term engagement
• 10 available openings
• Candidates should be prepared to begin promptly

Engagement Details

• Professional Background: Former SSA Medicare enrollment professional or HR/employee benefits specialist with direct Medicare advisory experience
• Experience Requirement: At least 1 year of relevant Medicare enrollment and coverage counseling experience
• Professional Focus: Medicare enrollment, Social Security coordination, employer-sponsored coverage, and beneficiary assistance
• Technical Focus: Initial Enrollment Periods, Special Enrollment Periods, Part B penalties, Medigap, Medicare Advantage, Part D, COBRA, and creditable coverage
• Responsibilities will include reviewing realistic Medicare questions, developing evaluation rubrics, and assessing AI-generated enrollment guidance
• Assignments will focus on factual accuracy, enrollment requirements, coverage coordination, 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 with IRMAA, working while enrolled in Medicare, HSA considerations, or beneficiary education materials 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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