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 62 years ago.

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.

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

1984

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

1996

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 original Bailey Group team
The Bailey Group office located on Plantation Island Dr

2001

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

2003

 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 Health Group and Florida Blue
The Bailey Group 20th Anniversary logo

2016

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.

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.

Start Your Career With Us

Help us change the way people feel about their insurance and benefits.

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.

Work as a Team

Teamwork is an important part of who we are. We are always looking for new tools that can help us become a more efficient and informed team. For example: we began using Slack two years ago and it has transformed the way we work and made communicating with each other a lot more fun.

 "I love helping our associates grow, which in turn helps our clients and our business."

 Deborah Croft, Operations Officer

"I feel passionate about being part of a close-knit team that is constantly looking for ways that we can be better and serve our clients more effectively."

Sabrina Abare, Director of Group Benefits

"The Bailey Group has the best employees so coming to work allows me to spend time with great people and develop fulfilling relationships."

Becky Cromwell, Account Executive

"I love helping people embrace a healthier lifestyle; It is so rewarding to see people start over with a healthier mind, body and spirit."

Jaime Sanders, Director of Health Promotion

Current Career Opportunities

No opportunities available at this time.

Check back soon as we're always searching for qualified individuals to join our team.

Interested in working with us? Let us keep you up-to-date on new opportunities to join our team.

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Jacksonville Business Journal Best Place to Work emblem
American Heart Association Fit Friendly Worksite emblem
Best of St. Augustine trophy
2016 Healthiest Company in Northeast Florida

1200 Plantation Island Dr S #210 | St. Augustine, FL 32080 | Get Directions

© 2017 MFB Financial, Inc. dba The Bailey Group | All Rights Reserved. The information on our blog is not intended to be exhaustive nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel for legal advice. Some policies may have exclusions and limitations. For costs and complete details of coverage, call or write the insurance agent. The amount of benefits and premium will vary depending upon the plan selected.

The Bailey Group logo

1200 Plantation Island Dr S #210 | St. Augustine, FL 32080

© 2017 MFB Financial, Inc. dba The Bailey Group | All Rights Reserved. The information on our blog is not intended to be exhaustive nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel for legal advice. Some policies may have exclusions and limitations. For costs and complete details of coverage, call or write the insurance agent. The amount of benefits and premium will vary depending upon the plan selected.