SHIP Medicare Counselor

10 Openings | Remote – United States | Independent Contractor

Compensation: Illustrative annualized equivalent of $57,600–$115,200 based on 1,920 hours per year.
Actual rate: $30–$60 per hour.

This is a short-term project requiring 20–30 hours per week. The annualized figures are for comparison only and do not represent guaranteed annual earnings.

About the Role

We are seeking experienced SHIP Medicare Counselors to help evaluate and improve AI systems that provide Medicare-related information. You will apply your Medicare counseling expertise to assess whether sample beneficiary questions reflect real-world concerns and whether AI-generated answers are accurate, complete, and useful.

Accuracy is the priority, with a strong emphasis on clear, practical guidance for beneficiaries from diverse backgrounds. Previous AI experience is not required; your Medicare counseling knowledge and ability to evaluate information critically are what matter most.

Key Responsibilities

• Review sample Medicare questions and identify those that do not reflect the questions beneficiaries commonly ask.

• Develop evaluation rubrics defining accurate, complete responses for Medicare enrollment scenarios, including Initial Enrollment Periods, Special Enrollment Periods, and Part B late enrollment penalties.

• Create criteria for comparing Medigap and Medicare Advantage, explaining their key differences and the circumstances in which each option may be appropriate.

• Develop rubrics for Medicare Part D prescription drug plan comparisons.

• Evaluate AI-generated answers against established criteria, identifying factual errors, missing information, and outdated guidance.

• Provide clear, precise written feedback to help the project team improve the accuracy and usefulness of AI-generated Medicare information.

• Work asynchronously to complete reviews and deliver feedback within project requirements.

Required Qualifications

• Active or recent State Health Insurance Assistance Program (SHIP) certification, or previous Social Security Administration (SSA) Medicare enrollment experience.

• At least one year of experience advising beneficiaries on:

  • Initial Medicare enrollment and Special Enrollment Periods.

  • Medicare Part B late enrollment penalties.

  • Medigap versus Medicare Advantage.

  • Medicare Part D prescription drug plan comparisons.

• Must be based in the United States.

• Ability to start quickly and commit 20–30 hours per week for a short-term project.

• Strong written communication skills, with the ability to explain Medicare rules accurately and clearly.

Preferred Qualifications

• Experience developing Medicare counseling guides, training materials, evaluation rubrics, or educational resources.

• Experience advising beneficiaries from diverse backgrounds, including rural communities and people who speak languages other than English.

Project Details

• Position type: Independent contractor

• Work arrangement: Fully remote

• Location requirement: United States

• Time commitment: 20–30 hours per week

• Duration: Short-term project

• Openings: 10

• Compensation: $30–$60 per hour

Who Should Apply?

This opportunity is suited to current or recently certified SHIP counselors and former SSA Medicare enrollment professionals who understand Medicare enrollment rules, plan comparisons, and common beneficiary concerns. If you can assess Medicare information carefully and communicate your findings in precise, practical written feedback, your expertise can help improve AI-generated guidance for Medicare beneficiaries.