Job Description: Medicare Enrollment Specialist

Role Type: Contractor
Location: Remote, United States
Time Commitment: 20–30 hours per week, short-term project

About the Role

We are seeking experienced Medicare Enrollment Specialists to help evaluate and improve AI systems focused on Medicare. You will use your Social Security or employer benefits expertise to review questions and ensure AI-generated answers are accurate, clear, and useful. No prior AI experience is required.

Key Responsibilities

1. Review Medicare enrollment questions for accuracy and real-world relevance.

2. Create evaluation guidelines covering initial enrollment, Special Enrollment Periods, Part B late penalties, and Social Security benefits.

3. Assess Medigap, Medicare Advantage, Part D, and employer or retiree coverage scenarios.

4. Evaluate employer coverage rules, including COBRA, creditable coverage, and primary versus secondary insurance.

5. Review AI-generated answers and identify errors, omissions, and misconceptions.

6. Provide clear written feedback to improve AI response quality.

Required Qualifications

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

2. At least 1 year of experience with Medicare enrollment, coverage options, and Part B penalties.

3. Knowledge of Social Security benefits and employer coverage coordination.

4. Must be based in the United States.

5. Available for 20–30 hours per week and able to start quickly.

6. Strong written communication and attention to detail.

Nice to Have

• Knowledge of IRMAA, HSA rules, and working while enrolled in Medicare.

• Experience creating guides, counseling scripts, or training materials.

• Experience assisting diverse beneficiaries, including rural and non-English-speaking individuals.