About Medicare Caddies
Medicare Caddies is an independent insurance agency built on a simple idea: you shouldn't have to navigate Medicare alone, and you shouldn't have to explain your story to a new voice every time you have a question.
Education first. Enrollment when you're ready.
We built the Medicare Knowledge Center, the Medicare Caddie AI, and the Compare Plans tool so you can learn at your own pace. When you're ready, you can enroll online yourself — or ask a licensed insurance agent to walk the course with you. Both paths lead to the same place.
The Caddie relationship doesn't end at enrollment
One of the biggest reasons people choose Medicare Caddies isn't the enrollment. It's what comes after. Every member is paired with a dedicated Medicare Caddie who's available year-round — for plan questions, network changes, prescription changes, notices from your carrier, or anything else Medicare throws at you.
When possible, you'll work with the same Medicare Caddie who already knows your situation. Our goal is to give members a consistent point of contact.
We're here for more than enrollment.We're here for the entire round.
Most Medicare websites help you choose a plan. Medicare Caddies stays with you after you've enrolled.
Whether you enroll online or with one of our licensed insurance agents, you'll always know who to reach out to when Medicare questions come up. When possible, you'll work with the same Medicare Caddie who already knows your situation — no call center, no starting over, no explaining your story to someone new every time.
Our goal is to give members a consistent point of contact whenever possible. Ongoing support is provided by our team of Medicare Caddies.
- Understanding your plan
- Annual Election Period reviews
- Moving to another state
- Doctor network questions
- Pharmacy & prescription changes
- Life changes affecting coverage
- Understanding notices from your carrier
- General Medicare guidance year-round
Medicare Caddies is an independent insurance agency. We are not affiliated with, endorsed by, or connected to the U.S. government, the federal Medicare program, or the Centers for Medicare & Medicaid Services (CMS). We help compare Medicare Advantage plans from the insurance companies we represent, and we don't offer every plan available in your area.