Medicare Annual Enrollment runs from Oct 15 to Dec 7. For those eight weeks, seniors compare plans, sort through a pile of mailers, and start calling agents. When a caller reaches voicemail, they usually don’t leave a message. They call the next agent in the pile.
Your Medicare annual enrollment marketing only works if someone answers when the phone rings. Here’s how to get your phone ready before Oct 15.
What changes during enrollment
Three things happen at once:
- Your call volume jumps in the same weeks your calendar fills with appointments.
- Most calls are simple: “Can I book a time?” “What should I bring?” “Are you open Saturday?”
- You can’t answer any of them while you’re sitting with a client.
Before you promote more appointments, decide who answers the phone while you’re in them. Write down the answers to the questions you hear every day, like your hours, address, parking, and how to book. Keep that list where whoever answers can find it without knocking on your door.
Tailor the “what to bring” answer to the appointment. A new client may need their Medicare card, current plan documents, and a list of their doctors and prescriptions. A returning client may only need to bring what’s changed. Give each caller the list for their visit, not one long checklist.
Get a number people remember
Most enrollment marketing is offline: mailers, TV, newspaper ads, and seminars. Wherever your number appears, it has to be easy to find and easy to remember.
- Mailers: Put the number right next to “Call to book,” big enough to read at arm’s length. Print a proof at actual size before you approve it.
- TV and radio: Say the number twice, slowly. Leave it on screen long enough for someone to write it down.
- Newspaper: Give it enough contrast to stand out from the copy around it.
- Seminars: Put it on the handout people take home.
A vanity number from 800.com turns your digits into a word people can recall after the mailer is in the recycling. Pick wording that’s easy to understand when it’s spoken, not just when it’s read.
One quick test before you print: hand the mailer to someone outside your agency and ask how they’d book an appointment. If they hesitate, simplify the instructions, and keep any required disclosures visible while you do.
Answer every call, even when you’re with a client
An 800.com AI agent picks up the calls you can’t. It answers common questions, books appointments on your calendar, and transfers callers who need you right now.
Set three rules before you turn it on:
- It never recommends a plan. It sticks to approved office information and booking help. Any coverage question goes to a licensed agent.
- Every transfer has a name and a backup. Decide who gets transferred calls and what happens if they don’t pick up. Then test the backup.
- Compliance reviews the whole script. Add any required disclaimers to the greeting. Then have your compliance reviewer check the full caller experience against current CMS marketing rules, including the greeting, booking language, and transfers.
Then make two test calls. On the first, ask “Which plan should I pick?” The agent should explain that it can’t recommend a plan and offer to book a time with you. On the second, book a routine appointment. It should handle that without any friction.
Track which mailer pulled
If you send two versions of a mailer, give each one its own phone number. Do the same for TV, newspaper, and seminars. 800.com call tracking ties every call to its source and records it so you can review it later.
To get answers you can use:
- Change one thing at a time. Test the offer or the audience, not both, or you won’t know which change made the difference.
- Label every number. Save a copy of the exact piece each number ran on.
- Count bookings, not just calls. Note whether each caller booked or needed something you don’t offer. A busy line doesn’t prove the mailer reached the right people.
- Listen for gaps. Before you review recordings, confirm consent and handling requirements with compliance. If callers keep misunderstanding what the appointment is for, fix that wording before the next drop.
Plan your Dec 7 finish
The last week of enrollment gets crowded, so plan it now.
- Make reminder calls for booked appointments. Confirm the time, the place, and what to bring, and use your agency’s approved contact process. If someone needs to reschedule, offer them a specific open time.
- Keep your calendar accurate. Remove slots as they fill so no one books a time that’s already gone.
- Book next year’s review before every client leaves. Agree on the date together so you both know what comes next.
Planning outreach beyond enrollment? See 35 holiday phone campaign ideas for small businesses.
Your pre-enrollment checklist
- Mark the times you’ll need phone coverage during appointments.
- Print your mailer at actual size and test the booking instructions on someone outside your agency.
- Send your greeting and call script to compliance.
- Assign a separate number to each mailer version and channel.
- Block time for reminder calls in the first week of December.
Enrollment is eight weeks long. An 800.com AI agent answers every call and books appointments, so you don’t lose callers to the next agent.
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