Medicare Enrollment Specialist - Remote

YO AI Labs; New York (NY); Remote; USD 34,000 - 48,000; Part time

Job summary

YO AI Labs is seeking an experienced Medicare Enrollment Specialist for a remote, short-term project. The contractor will evaluate and improve AI-generated Medicare guidance, leveraging Social Security or employer benefits expertise.

The role requires 1+ year advising on Medicare enrollment and related areas, with strong written communication and attention to detail. Start quickly and commit to 20–30 hours per week from anywhere in the United States.

Qualifications

• Experience advising on Medicare enrollment, Special Enrollment Periods, Part B penalties, Medigap, Medicare Advantage, and Part D.
• Knowledge of Social Security and employer coverage coordination.
• Ability to work remotely and deliver clear feedback in writing.

Responsibilities

• Review Medicare enrollment questions for realism and relevance.
• Develop rubrics for initial enrollment, Special Enrollment Periods, and penalties.
• Evaluate Medicare scenarios involving employer or retiree coverage.
• Assess interactions between employer coverage and Medicare, including COBRA and creditable coverage.
• Evaluate AI-generated answers for errors and omissions.
• Provide clear written feedback to the project team.

Skills

Medicare enrollment experience

Social Security knowledge

HR/benefits advising

Written communication

Attention to detail

Remote coordination

Job description

Role Title: Medicare Enrollment Specialist

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.

Key Responsibilities

• 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.

Required Qualifications

• 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.

Preferred Qualifications

• 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.