Welcome to Cool Insurance Group!

Offering Life | Medicare | Health (Individual, Dental, and Vision)

Welcome! We are here to serve you. Cool Insurance Group, LLC was founded by John Bird, a Lexington, Kentucky native and veteran insurance industry executive. John has been in the business 30+ years including more than 20 years at he highest level with Blue Cross and Blue Shield plans in Kentucky and Louisiana and ten years working with Humana.

Today Cool Insurance Group, LLC is led by Claudia Bird and Timothy Chancellor. Our organization is comprised of experienced, trained, and licensed professional agents who are EXPERTS in all matters of financial services. We currently have access to and represent more than 70 insurers, including our top partners (listed above).

Our COVID-19 Solutions

Each year, Cool Insurance Group, LLC, through it’s 30+ licensed and appointed agents, serves thousands of Kentucky and West Virginia clients age 65+. This is our family. We love them as such. Sadly, our nation is currently at war with a deadly virus and none of us know what is going to be the long term outlook of this war. Because we care your safety, we have made some COVID accommodations to connect with our clients.

We offer Virtual Meetings, Telephone Call Solutions, and In-Person Visits (where we will wear masks and gloves). Let us know how we can best serve you!

It is a pleasure working at Cool Insurance Group. It truly is like a family with Claudia and Timothy. J I would tell anyone that is interested in selling Health Insurance to Seniors they should join Cool.

– Willy Fogle

Herman Miller

Joining CIG was the BEST DECISION of my life, professionally. Every year my income has grown at a healthy rate, John, Claudia, and Timothy have followed through on every promise they ever made to me.
– Michael Todd Oldfield

Emma Swenson

Join Our Team

Become an Agent

Top Compensation in the Industry

Expert Support Team

Reputable Organization

Agent Independence (team members are not micromanaged).

Question? Give us a call or fill out the contact form.


2808 Palumbo Dr.
Lexington, KY 40509