My approach
How I work with clients
Translate first, recommend second. If you don't yet know what MOOP, IRMAA, or a formulary is, we're not comparing plans — we're building vocabulary.
Licensed Medicare Caddie
Kelsy Ensign
Licensed Insurance Agent
Tech-background agent who translates Medicare acronyms into plain English and makes clients feel confident, not confused.
Turning 65Medicare AdvantagePrescription Drug CoverageAnnual Reviews
- States licensed
- Multiple states — ask for current list
- Languages
- English
Biography
About Kelsy
Kelsy came into Medicare from a tech background, which means she's spent most of her career translating complicated systems into plain English. She noticed Medicare needed the same treatment — a lot of jargon protecting a fairly simple set of choices.
Her clients tend to say the same thing after their first call: I finally get it. That's the moment she's chasing every time.
In their own words
Why I became a Medicare Caddie
"Medicare shouldn't require a translator. I became a Caddie so people could stop nodding along and actually understand what they're choosing."
Who I love helping
The people I do my best work for
Anyone who feels like Medicare is written in a language they never learned, and adult kids trying to help a parent through the paperwork.
Favorite part of the job
What keeps me coming back
The 'oh — that's all it means?' moment when the acronyms finally click.
Fun fact
A little about Kelsy off the clock
Came from tech. I still geek out over new productivity apps and gadgets in my spare time.
🏌️ Kelsy's Caddie's Tip
"The Medicare acronyms are the hardest part. Once someone explains MOOP, PPO, HMO, and IRMAA once, the rest of the decision gets a lot easier."
Ready to work with Kelsy?
No pressure, no scripts — just a plain-English walkthrough of what fits your situation.
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.