Meet The Bailey Group

Our Story

Our journey to become one of the largest insurance and benefits firms in the State of Florida began over  60 years ago.

John D. Bailey, Sr. at his desk in 1954


The firm of Thompson Bailey Baker, established 75 years ago, was founded by John Thompson and Harold Ryman in St. Augustine, Florida. In 1954, John Bailey becomes a partner in the business.

Mark Bailey, Sr. out of college.


John's son, Mark, joins the firm after graduating from Vanderbilt University with a double-major in economics and business.

John D. Bailey, Sr. and Mark Bailey, Sr.


Mark Bailey, Sr. subsequently buys Thompson Bailey Baker's principal lines of business associated with health, life, annuities, retirement benefits, estate conservation, and financial products. Shortly after, The Bailey Group is founded.

The Bailey Group office located on Plantation Island Dr


The Bailey Group moves into their new office located on Plantation Island Drive just off of the 312 bridge heading east.

The Bailey Health Group and Florida Blue


 The Bailey Health Group is founded and partners with BlueCross and BlueShield of Florida (now known as Florida Blue) to offer individual health insurance products.

The Bailey Group 20th Anniversary logo


The Bailey Group celebrates their 20th year serving the Northeast Florida community.

Meet Our Team

Learn more about the incredible team of people behind The Bailey Group.

Deborah Croft
Tommy Delany
Tiney Rahilly
Natalie Braddock
Mark Bailey, Jr.
Kaylah Cox
Cory Olsen
Beth Toy
Price Wheeler
Joanie Thornton - Administrative Assistant

We're Not Co-Workers. We're Family.

The key to our culture? We treat each other as family, not co-workers. Through all of our growth, we have never lost sight of our roots as a family owned business.

Deborah Croft and Becky Cromwell work outside of our offices on a beautiful, sunny day.
Hanna Chester, Madison Cofield and Jaime Sanders at a conference
Sabrina Abare and Sandra Combariza dressed up as Santa Claus at the Santa Suits on the Loose 5K
Our team together on the beach in St. Augustine after a sunrise yoga session sponsored by our wellness team.
Our team at the Character Counts! in St. Johns County 6K
Our team stuffing backpacks for the St. Johns County School District.
Sabrina Abare, Bailey Mullin, Jaime Sanders, Hanna Chester and Deborah Croft accept our First Coast Worksite Wellness Healthiest Company Award.
Our team stops to take a picture during our daily wellness walk around the building.
The Bailey Group takes the ALS Ice Bucket Challenge
Our Health Promotion team accepts Healthiest Company award.