Medicare Enrollment Specialist - Remote

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

We are seeking experienced Medicare Enrollment Specialists to evaluate and improve AI-generated Medicare guidance. You'll use your Social Security or employer benefits expertise to ensure questions reflect real beneficiary concerns and answers are accurate, complete, and practical. No prior AI experience is required.

• Review Medicare enrollment questions for realism and relevance.
• Develop rubrics covering initial enrollment, Special Enrollment Periods, Part B late enrollment penalties, and enrollment coordination with Social Security benefits.
• Evaluate Medigap, Medicare Advantage, and Part D scenarios involving employer or retiree coverage.
• Assess how employer coverage interacts with Medicare, including employer size, primary versus secondary coverage, COBRA, and creditable coverage.
• Evaluate AI-generated answers for errors, omissions, and common misconceptions.
• Provide clear, actionable written feedback to the project team asynchronously.

• Previous SSA Medicare enrollment experience or employer benefits/HR experience advising employees on Medicare.
• At least 1 year of experience advising on Medicare enrollment, Special Enrollment Periods, Part B penalties, Medigap, Medicare Advantage, and Part
  
  D.
• Working knowledge of Social Security, employer coverage coordination, and creditable coverage.
• Based in the United States.
• Ability to start quickly and commit 20–30 hours per week.
• Strong written communication skills and attention to detail.

• Experience with IRMAA premium adjustments, working while enrolled in Medicare, or HSA rules.
• Experience creating guides, counseling scripts, or training materials.
• Experience assisting diverse beneficiaries, including rural and non-English-speaking communities.