Medicare / Health Insurance Virtual Assistant for AEP

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: TYPE OF WORK

Part Time

: SALARY

$5/hr

: HOURS PER WEEK

20

: DATE UPDATED

Sep 1, 2026

JOB OVERVIEW

Seeking Part-Time Medicare / Health Insurance Virtual Assistant for AEP

We are a U.S.-based Medicare and health insurance agency looking for a detail-oriented Virtual Assistant to help during the busy Medicare Annual Enrollment Period.

This role is ideal for someone with experience in health insurance, Medicare quoting, CRM work, data entry, client follow-up, and administrative support. Accuracy is very important because we work with sensitive client information and insurance plan details. Good English speaking and writing required.

The position will start part-time, with the possibility of growing into more hours depending on performance and business needs.

Main Duties:

• Preparing Medicare drug plan / PDP quote information

• Entering client-provided drug lists, doctors, and pharmacies into quoting tools

• Helping organize Medicare Advantage and drug plan comparison information

• Updating client profiles in the CRM

• Tracking client responses, missing information, and follow-up status

• Calling or messaging clients to collect missing doctors, drugs, pharmacy, or Medicare details

• Uploading and organizing documents, call recordings, notes, and screenshots

• Updating spreadsheets used for sales tracking, enrollment tracking, and client status

• Checking whether clients have submitted needed information

• Helping with data cleanup and importing/exporting CSV files between systems

• Researching phone numbers, addresses, or missing client details when needed

• Using ChatGPT and other tools to help organize information, summarize notes, or improve workflows

Preferred Experience

Strong preference will be given to applicants who have experience with:

• Medicare drug plan quoting or Medicare Advantage quoting

• Health insurance admin support

• GoHighLevel / GHL

• CRM data entry and pipeline management

• Excel or Google Sheets

• Client follow-up by phone, text, or email

• Healthcare, insurance, benefits, or BPO experience

• Strong English communication for client calls or follow-up messages

What We Are Looking For:

• Very detail-oriented

• Careful with sensitive client information

• Comfortable following instructions and checklists

• Able to communicate clearly when something is missing or unclear

• Reliable and responsive during working hours

• Willing to learn our process through Loom videos, training notes, and live check-ins

• Comfortable doing repetitive admin work during a busy season

• Able to ask questions instead of guessing

Schedule and Pay:

• Part-time to start

• Around 4 hours per day to begin

• Schedule will be based around U.S. Eastern Time business hours

• More hours may be available

• Weekly payout through PayPal

• Rate is $5/h

What to Expect:

This is not just a general VA role. You will be helping with real Medicare client support during a busy season, so accuracy matters. You should expect:

• Training through Loom videos and written instructions

• A weekly check-in call or short Zoom meeting

• Daily task updates

• Put the word banana somewhere in your reply so I know you read it

• Work involving client records, plan details, drug lists, doctor lists, spreadsheets, and CRM updates

• A fast-moving environment during AEP

• Feedback and corrections as you learn the process

Hiring Process:

To apply, please complete the short test below. Applicants who do not answer the test may not be considered. After reviewing your answers, we will choose candidates for:

1. A short first interview with our current VA / operations assistant

2. A final interview with the agency owner / licensed agent

3. A paid test task or trial period if needed

Please answer these questions when applying:

1. Have you worked with Medicare, health insurance, benefits, or medical data before? Briefly explain your experience.

2. Have you used GoHighLevel, another CRM, Excel, Google Sheets, or any quoting tools? List the tools you have used.

3. A client sends a medication list but one drug name looks misspelled and the dosage is unclear. What would you do before entering it into a quote?

4. Write a short client message for this situation: “We still need your updated drug list and preferred pharmacy before we can prepare your plan comparison.”

5. Are you comfortable working with sensitive client information and following strict instructions for accuracy?

6. Are you available 12-4 EST?

Short Test:
To apply for this position, please follow the instructions below:

- Include a two to three sentence introduction explaining your specific experience with Health Insurance and drug related quotes.

- Change the subject line of your application response to "Yes-Health Insurance Experience - [number of years experince]"

- A link to your bio and/or resume

- A screenshot off your upload/download speed

- Speech sample

SKILL REQUIREMENT

Customer Support Phone Support Healthcare

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Medicare / Health Insurance Virtual Assistant for AEP

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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