About Cindy

Why I Started Eligry

In her own words — what Medicare almost cost her, and why she made it her mission to make sure it doesn’t happen to you.

Cindy Kowalski — Founder, Eligry Medicare Solutions

Honest Guidance in an Industry That Needs It

My name is Cindy Kowalski, and I founded Eligry LLC on a simple but powerful principle: providing honest answers about Medicare. Not sales pitches. Not the plans that pay the highest commissions. Just honest, transparent guidance focused entirely on your needs.

I am carrier-independent. That means I’m not tied to any single insurance company. I’m licensed to present plans from most major carriers, which allows me to show you all your options and help you find the right fit — not just push a specific product. This independence is critical because it means your interests come first, every single time.

I split my time between Highland, Indiana and Sarasota, Florida — which means I live the same reality as many of my clients. I know what it’s like to manage healthcare in two states. I know which plans travel with you and which ones leave you stranded the moment you cross a state line. That firsthand experience shapes the advice I give, because I’m not just studying the snowbird problem in a textbook — I’m living it.

Finding other insurance professionals who share this philosophy is hard. After all, it’s human nature to push the product that puts more money in your pocket. But when I do come across another honest soul who truly puts clients first, I do my best to bring them on board. My vision is to grow Eligry into a team of advisors who all share the same commitment to integrity over commissions.

My Medicare Wake-Up Call

My passion for Medicare education began when I turned 65 a few years ago. I was completely lost. Despite my extensive business background — 23 years as Sales Director at AT&T and 16 years running my own IT consulting company — the complexity of Medicare felt overwhelming.

I was already receiving Social Security, so Medicare enrolled me automatically — without me knowing about it. My card showed up in the mail and I had no idea what to do next. I didn’t understand the difference between Parts A, B, C, and D. I didn’t know what a Medicare Supplement was. And I certainly didn’t realize that the choices I was about to make could lock me into a plan that might not work once I started spending half the year in Florida.

By God’s grace alone, I avoided making irreversible mistakes that could have affected my health and financial security for the rest of my life. That close call changed everything.

I realized that if someone like me — with decades of business experience — could nearly make critical errors, countless others must be facing the same challenges. So I did something about it.

Why So Many People End Up in the Wrong Plan

Here’s the uncomfortable truth: it’s nearly impossible for the average person to understand everything they need to know to make the best Medicare decisions. The rules are complex. The options are overwhelming. And the consequences of a wrong choice can follow you for years.

What makes this worse is how the industry operates. Too many Medicare agents sell plans based on what earns them the highest commission — not what’s truly right for their clients.

That’s exactly why I became carrier-independent. I can review plans from most major carriers and recommend the one that makes sense for your situation — not the one that pays me the most.