Meet The Bailey Group

Learn about our story, culture and career opportunities.

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
Tim Olson
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.

What It's Like to Work With Us

Great Benefits (Naturally!)

We currently provide benefits to over 300 group clients, so we understand how important benefits are when it comes to finding (and keeping) top talent. We provide medical, dental, vision, 401(k), life insurance and more to all of our full-time employees.

Growth Opportunities

We encourage every member of our team to make learning and personal growth a priority, whether that's through attending industry conferences or taking part in our in-house training sessions.

Flex Fridays

This is without a doubt our team's favorite perk. Every other Friday, as long as all work has been taken care of, we get to take a (paid) half-day to be with our family and friends and enjoy St. Augustine's beautiful weather.

Wellness Walks

Sitting is literally killing us. Well, we're not just going to sit around and watch that happen to us. We go out as a team every day and take a few laps around our building. It's a great opportunity for us to share ideas and think on our feet.

Current Career Opportunities

No opportunities available at this time. Check back soon!

Let us keep you up-to-date on new opportunities to join our team.

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2018 Healthiest Company in Northeast Florida Gold Award
Best of St. Augustine trophy
Jacksonville Business Journal Best Place to Work emblem
American Heart Association Fit Friendly Worksite emblem