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Confidential

Medicare Enrollment Specialist

Dolton, IL

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Job description

Apply your Medicare enrollment and benefits expertise to help assess AI-generated guidance for accuracy, completeness, and real-world usefulness. This remote contract role focuses on the questions beneficiaries ask when navigating Medicare enrollment, Social Security coordination, employer coverage, and plan choices.

Key Responsibilities Review sample Medicare enrollment questions and identify prompts that do not reflect how beneficiaries communicate or what they need to know.

Create evaluation rubrics for correct, complete guidance on initial enrollment, special enrollment periods, Part B late-enrollment penalties, and connections between Medicare enrollment and Social Security benefits.

Address Medicare Parts A, B, C, and D, including Medigap versus Medicare Advantage and Part D considerations for people with employer or retiree coverage.

Evaluate how employer coverage coordinates with Medicare, including employer size, primary versus secondary coverage, COBRA, and creditable coverage.

Assess AI-generated answers against established rubrics, identifying errors, missing information, and common misconceptions.

Provide clear written feedback to the project team in an asynchronous work environment.

Qualifications Former Social Security Administration Medicare enrollment experience, or employer benefits or HR experience advising employees on Medicare.

At least 1 year of experience advising on initial enrollment, special enrollment periods, Part B late penalties, Medigap versus Medicare Advantage, and Part D.

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

Knowledge of Medicare enrollment counseling, plan comparison and selection, and beneficiary education.

Clear, precise writing skills.

Experience with premium adjustments such as IRMAA, working while enrolled, or HSA rules alongside Medicare is preferred.

Experience creating guides, counseling scripts, or training materials is preferred.

Experience supporting a diverse range of beneficiaries, including rural and non-English-speaking clients, is preferred.

Work Terms Remote, short-term independent contractor project.

Commit 20 to 30 hours per week and be available to begin promptly.

Compensation $50 to $150 per hour.

Eligibility Must be based in the United States.

Who can apply

Review the original listing for work authorization, qualifications and employer requirements.

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