Owensboro, Kentucky

Medicare and insurance in Owensboro, explained before you decide.

I’m Mike Webb. I was born and raised in Owensboro, and I have spent more than 16 years in the insurance industry. I compare your options, explain how each one works in everyday language, and then the decision is yours.

A review costs you nothing and never obligates you to buy.

Mike Webb, owner of Webb Insurance Group, in a navy suit
Mike WebbOwner and licensed insurance agent
  • 16+years in the insurance industry
  • 1agent, and the same person every time you call
  • 4license lines in Kentucky: life, health, property and casualty

What I help with

Medicare first. The rest of your coverage, too.

Medicare Supplements are the center of my practice. I also help with life, health, supplemental, group and auto coverage, so one local agent can look at the whole picture.

The center of my practice

Medicare Supplements

Original Medicare covers a lot, but not everything. A Medicare Supplement, also called Medigap, helps pay the deductibles and coinsurance Medicare leaves to you. A plan with the same letter has the same benefits from every company, so the real differences are the monthly price and how each company has handled rate increases. Comparing those is my job.

Explore Medicare Supplements

A Kentucky rule worth knowing

Your birthday opens a 60-day window every year.

Since January 1, 2024, Kentucky has let anyone who already has a Medicare Supplement switch to the same plan with a different insurance company once a year, without answering health questions. Outside that window, a new company can usually ask about your health and decline you or charge more.

If your premium has gone up, your birthday window is the easiest time to see whether the same coverage costs less with another company. Call me a few weeks before your birthday and I will have the comparison ready.

How the birthday rule works
  1. 1You already have a Medicare Supplement.
  2. 2You apply during the 60 days that start on your birthday.
  3. 3You keep the same plan letter, for example Plan G to Plan G.
  4. 4You move to a different insurance company.

“The guaranteed issue period shall begin annually on the insured’s birthday and shall end sixty (60) days after their birth date.”

806 KAR 17:570, Section 14. Kentucky Department of Insurance regulation, in effect since January 1, 2024.

How it works

What happens when you call

No pressure and no jargon. This is what a review with me looks like, start to finish.

  1. You call, or ask me to call you

    Tell me what is going on: turning 65, a premium that went up, a new job, a new baby. A few minutes is enough to know what we should look at.

  2. We go over your situation

    For Medicare, have your Medicare card, your list of prescriptions and the names of your doctors handy. For anything else, your current policy or declarations page helps.

  3. I compare plans from the companies I represent

    You see the options side by side with the trade-offs spelled out: the monthly cost, what you pay when you use care, and whether your doctors and prescriptions are covered.

  4. You decide

    If something fits, I help with the application. If nothing beats what you already have, I will tell you that too.

  5. I am still here next year

    Plans and prices change. You keep the same agent and the same phone number, and I can recheck your coverage before Annual Enrollment and before your birthday window.

Mike Webb smiling, headshot

Meet Mike

“We take pride in providing education and integrity with every person that we encounter.”

Mike Webb, owner, Webb Insurance Group

Insurance runs in my family. My dad and stepmom retired from MetLife, and my wife’s dad and grandparents retired from Commonwealth and Transamerica. My wife and I also own Joys Cooking Classes and More and Joy-Full Java+Juice here in Owensboro.

More about Mike

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Questions

Questions people ask me first

Something else on your mind? Call (270) 302-0524.

Do you charge for a review?

No. Insurance companies pay agents when a policy is placed, so my help costs you nothing extra, and a review never obligates you to buy anything.

Which insurance companies do you work with?

I am an independent agent, so I can compare plans from more than one company. Before we look at a single quote, I will tell you which companies I represent for your kind of coverage.

Can I change my Medicare Supplement if my premium keeps going up?

Often, yes. In Kentucky, the birthday rule lets you move to the same plan with a different insurance company during the 60 days that start on your birthday, with no health questions. Outside that window a new company can usually ask about your health, so timing matters.

When should I call if I am turning 65?

Three to six months before your 65th birthday is a good time. Your Initial Enrollment Period for Medicare starts three months before the month you turn 65, and your six-month Medigap open enrollment period starts once you are 65 and enrolled in Part B.

Will other agents call me if I fill out your form?

No. Your information comes to me, and I do not sell or share it with other agents or call centers.

Do you only work with people on Medicare?

No. I also help families with life insurance, people under 65 with health insurance, local employers with group benefits, and drivers with auto insurance.

Free, no-obligation review

Call me, or tell me when to call you.

A phone call is the fastest way to get answers. If now is not a good time, send the form and I will call you back when you say.

(270) 302-0524

Mike’s direct line

Good to have handy

  • Your Medicare card, if you have one
  • A list of your prescriptions and doctors
  • Your current policy or declarations page

Request a call back

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