Medicare Enrollment Specialist – Medicare Benefits, Enrollment Counseling & AI Evaluation

10 Openings | Remote | Independent Contractor | U.S.-Based

Compensation: $40–$60/hour
Estimated annualized equivalent: $76,800–$115,200/year

The annualized figures assume 40 hours per week for 48 working weeks. This is an illustrative equivalent, not guaranteed annual compensation. The project is short-term, with an expected commitment of 20–30 hours per week.

About the Opportunity

Do you have experience helping beneficiaries navigate Medicare enrollment or advising employees on Medicare-related benefits? This remote contract opportunity allows you to apply your expertise in Social Security, employer-sponsored coverage, and Medicare plan selection to improve the accuracy and usefulness of AI-generated guidance.

As a Medicare Enrollment Specialist, you will review beneficiary questions, develop evaluation criteria, and assess AI-generated answers against established Medicare enrollment and coverage rules. Your work will help ensure that responses address real-world beneficiary concerns accurately, clearly, and comprehensively.

This role is particularly suited to former Social Security Administration (SSA) Medicare enrollment professionals and employer benefits or HR specialists experienced in Medicare counseling.

Prior AI experience is not required. Your Medicare knowledge, practical counseling experience, and ability to communicate complex benefits information clearly are the primary qualifications.

Key Responsibilities

• Review beneficiary questions: Evaluate sample Medicare enrollment questions and flag those that are unrealistic, unclear, or inconsistent with common beneficiary concerns.

• Develop evaluation rubrics: Define the requirements for accurate, complete answers on initial enrollment, Special Enrollment Periods, Part B late-enrollment penalties, and coordination with Social Security benefits.

• Assess Medicare coverage options: Develop criteria covering Original Medicare, Medicare Advantage, Medigap, and Medicare Part D prescription drug coverage.

• Evaluate employer and retiree coverage: Address how employer size affects primary and secondary coverage, as well as the implications of COBRA, retiree coverage, and creditable coverage.

• Review AI-generated answers: Assess responses against established rubrics and identify inaccuracies, missing information, misleading statements, and common misconceptions.

• Provide structured feedback: Document findings clearly and explain how responses can be improved for accuracy, completeness, and practical usefulness.

• Support consistent evaluation: Help establish reliable standards for assessing Medicare-related AI responses across different beneficiary situations.

Required Qualifications

• Former SSA Medicare enrollment experience or employer benefits/HR experience advising employees on Medicare.

• At least one year of experience advising on:

  • Initial Medicare enrollment and Special Enrollment Periods.

  • Medicare Part B late-enrollment penalties.

  • Medigap versus Medicare Advantage.

  • Medicare Part D prescription drug coverage.

• Working knowledge of Social Security and employer coverage coordination, including creditable coverage.

• Understanding of how employer size can affect Medicare coordination and primary versus secondary coverage.

• Familiarity with COBRA and retiree coverage considerations.

• U.S.-based and able to begin promptly.

• Availability to commit 20–30 hours per week for the short-term project.

• Strong written communication skills, with the ability to explain complex enrollment rules precisely and clearly.

Preferred Qualifications

• Experience with income-related monthly adjustment amounts (IRMAA) and Medicare premium adjustments.

• Knowledge of Medicare rules for individuals who continue working, including Health Savings Account (HSA) considerations.

• Experience creating beneficiary guides, counseling scripts, educational materials, or training resources.

• Experience supporting diverse beneficiary populations, including rural communities and people with limited English proficiency.

Core Skills and Expertise

Medicare Parts A, B, C, and D; Medicare enrollment counseling; initial enrollment periods; Special Enrollment Periods; Part B late-enrollment penalties; Social Security and Medicare coordination; employer-sponsored insurance; primary and secondary coverage; COBRA; retiree coverage; creditable coverage; Medigap; Medicare Advantage; plan comparison and selection; beneficiary education; evaluation rubric development; and quality assurance.

Work Arrangement and Compensation

• Work arrangement: Remote, independent contractor.

• Location requirement: United States.

• Compensation: $40–$60 per hour.

• Time commitment: 20–30 hours per week.

• Project duration: Short-term.

• Start timeline: Candidates should be available to start quickly.

• Work style: Asynchronous, with written feedback delivered to the project team.

The annualized equivalent of $76,800–$115,200 is calculated using 1,920 hours per year. It is provided for comparison only and does not represent expected earnings from this short-term, part-time project.

Why Consider This Opportunity?

Use your Medicare enrollment and benefits expertise to help make AI-generated guidance more accurate, practical, and accessible. Your work can help beneficiaries receive clearer information about enrollment deadlines, coverage coordination, penalties, and plan choices while contributing to the development of more reliable AI systems.

Application Process

Qualified U.S.-based Medicare enrollment or employer benefits professionals can apply for consideration. Applicants should be prepared to demonstrate their practical Medicare counseling knowledge, written communication skills, and availability for the 20–30-hour weekly commitment.