Remote job · Office and administration
Medicare Enrollment Specialist (Remote Contract)
- Remote, worldwide
- A company building AI training data
- Posted 13 Oct 2026
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Apply with Keywordise AIAbout the role
A short term remote contract reviewing sample Medicare questions and writing rubrics so AI answers on enrollment and coverage can be checked for accuracy.
What you will do
- Cover how enrollment links to Social Security benefits in the rubrics
- Address Medigap versus Medicare Advantage and Part D, especially scenarios involving employer or retiree coverage
- Assess AI generated answers against the rubrics and flag errors, gaps and common misconceptions, then share written feedback asynchronously
What they look for
- Former Social Security Administration Medicare enrollment experience, or employer benefits or HR experience advising staff on Medicare
- Based in the United States and able to start quickly with 20 to 30 hours a week
- Clear and precise writing
Nice to have
- Experience writing guides, counseling scripts or training materials
- Experience helping diverse beneficiaries, including rural and non English speaking clients
How it works
- 1Upload your CVSign up with Google or your email and add your CV. It takes about a minute.
- 2We tailor your applicationKeywordise writes a CV and a cover letter for this job from your real experience.
- 3We apply for youYour application goes to the employer and you follow it in your dashboard.
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