SHIP Medicare Counselor — 100% Remote Specialist

Work 100% remotely as a SHIP Medicare Counselor — 100% Remote Specialist with RemoteJob USA Staffing, earning $30 - $60/hour. You will design challenging domain prompts, grade complex model outputs, and refine reasoning trajectories using your background in Medicare, Medigap.

Position Responsibilities

• Write rubrics defining a correct, complete answer for enrollment scenarios, including initial enrollment, special enrollment periods, and Part B late penalties.
• Cover Medigap vs. Medicare Advantage and Part D plan comparison in your rubrics, including key differences and when each option fits.
• Assess and benchmark model-generated answers against your rubrics, flagging errors, omissions, and outdated guidance.
• Give clear written feedback to the project team, working asynchronously.
• Active or recent SHIP certification, or former SSA Medicare enrollment experience
• 1+ years advising on initial enrollment, special enrollment periods, Part B late penalties, Medigap vs. Medicare Advantage, and Part D
• Based in the US

Required Competencies

• Experience creating guides, training materials, or rubrics for Medicare counseling
• Experience counseling a diverse range of beneficiaries, including rural and non-English-speaking clients
• Compensation Band: $30 - $60/hour
• Work Location: Remote (100% Remote / Asynchronous Flexibility)
• Available Openings: 10 open positions
• Core Competencies: Medicare, Medigap
• Able to start quickly and commit 20-30 hours/week

Earnings & Remote Work Details

• Compensation Rate: $30 - $60/hour (contract specialist remuneration)
• Work Arrangement: 100% Remote / Work From Home
• Eligible Remote Countries: United States, United Kingdom, Canada, Australia, New Zealand, Ireland, and South Africa
• Core Competencies: Medicare, Medigap
• Hiring Agency: RemoteJob USA Staffing

Direct Application Process: Click the Apply button on this page to proceed directly to our partner application portal and submit your profile for immediate consideration.