Employee Benefits Solutions

From The Bailey Group

For the last 20 years we have been helping organizations like yours protect and retain your most important asset – your employees. Here's how we do it:

Laser-Like Focus on Benefits

We made the decision nearly 20 years ago to make employee benefits our core focus. And in hindsight, that was the best decision we could have made. The Affordable Care Act is a compliance nightmare waiting to happen for your organization – and you need a partner that is dedicated to helping you take on that challenge.

Local Firm With a National Presence

While our roots are firmly set in the Nation's Oldest City, we have earned the opportunity to provide benefits to over 300 group clients covering more than 61,000 employees located across the United States.

Sky-High Client Retention

There is no customer satisfaction metric more important than client retention. We are proud of the fact that our client retention has remained high through all of the turmoil and change the Affordable Care Act has created.

Our Incredible Team

We employ some of the best and brightest talent in the business. Almost all of our associates are licensed. And those that aren't typically get their license within the first 6 months of working at The Bailey Group.

Trusted By Over 300+ Organizations


"Over the last couple of weeks I have relied on your staff to assist me with a number of projects, and as usual, their performance and responsiveness has been outstanding. I am sure you are aware of the quality of people you have."

Ron Roy, Ring Power

"The Bailey Group is a value added partner in our business. As a not-for-profit healthcare and charitable service organization, we employ a workforce of more than 260 people. The products and services provided by The Bailey Group are outstanding."

Dr. Larry Lake, Bayview

"I wanted to make sure you knew of the valuable asset you have in Andrea. I just became aware of the extraordinary level of customer service she provided to one of our employees. It is obvious that Andrea truly cares for the people she supports and her commitment and dedication to her job is apparent."

Dan, HR Director

"We researched and chose The Bailey Group when we moved our headquarters and manufacturing facility to St. Augustine 12 years ago. We have continued with them every year as they have the best service and rates you could find. Not just local but nationwide. Rulon loves the service that The Bailey Group provides."

Matthew Robison, Rulon

"I am always amazed each year by the outstanding work & dedication of The Bailey Group family. I must call you family because the term 'consultant group' does not apply to you. Every year, each of you dedicates more time, money, and awesome customer service to our staff. I could not accomplish any of this without all of you."

Margot, HR Director

All The Ways We Can Help

Keep scrolling or click a specific section to learn more.

All The Ways We Can Help

Keep scrolling or click a specific section to learn more.

All The Ways We Can Help

Keep scrolling or click a specific section to learn more.

Health Care Reform

The Affordable Care Act fundamentally changed the way organizations like yours manage benefits.

Group Analysis & Compliance Checklist

We'll work diligently to make sure your program is on the right track to comply with the Affordable Care Act (ACA) using our compliance checklists.

Vendor Review & Guidance

There are literally hundreds of vendors offering products and services geared towards helping you comply with the ACA. Our team will help you review each one and choose the best option for your organization.

6055/6056 Reporting

IRS Sections 6055 and 6056 reporting requirements will be a hot topic in regards to your benefits for years to come. We can offer your organization personalized guidance on how to properly comply and avoid penalties.

Articles, White Papers, Newsletters and More

Through our partnership with Broker Briefcase, we're able to provide you with the most up-to-date articles, white papers, newsletters and more.

Employee Transition to Individual Plan

Our Individual & Family Insurance team can assist your employees transition off of your group plan and on to an individual plan through the Health Insurance Marketplace.

HCR Extravaganza Meetings

Our Group Team meets on a bi-weekly basis to discuss the latest happenings with the Affordable Care Act so that we can keep you properly informed. We lovingly call them our Health Care Reform Extravaganza meetings. 

Compliance Assistance

There are countless rules and regulations governing employee benefit plans, many of which are complex. We can help you meet your compliance obligations and keep you up-to-date on laws and regulations that affect your employee benefits program.

All of these services are provided at no extra cost.

5500 Filings

Is your plan subject to ERISA? If so, you should be filing a Form 5500 annually to the Department of Labor (DOL). We do everything from completing the form to filing it for you. The only thing we need from you is your electronic signature at the end.

WRAP Document & Section 125 Creation

Unfortunately, most employers are not in compliance with either the SPD or Plan Document requirements. Leave the creation of your WRAP and Section 125 documents to us.

Unlimited Legal Consultation

Have a burning question about anything related to your benefits? Send them our way. Through our partnership with NFP, we have access to a team of lawyers exclusively focused on employee benefits law.

Data Analytics

We can help you understand where to adjust your plan design to maximize the cost effectiveness of your benefits for your organization and employees.

Cost Utilization Reports

Our cost utilization report gives you the ability to drill down into your claims data to take a granular look at your benefits and how they're being used by your employees.

Benchmark Reports

Ever wondered how your benefits stack up to other organizations in your industry and location? Our detailed benchmark reports will help you keep your benefits competitive, and in turn, increase employee retention.

Actuarial Renewal Tool

Concerned that your renewal is much higher than it should be? Our in-house actuarial renewal tool allows us to plug your data in to see where your renewal really should be coming in at, which gives us negotiating power to reduce your rate.

Provider Network Analysis & Disruption Report

Contemplating changing your plan? We'll take a look at top 50 providers for your group to make sure the most utilized providers are in your new plan's network.

Plan Design Evaluation

We're constantly evaluating your plan to ensure you're getting the most possible out of your benefits, while saving money at the same time.

Human Resources Support

Think of us as a true extension of your HR department. We are here to help make your job (and life!) easier.

Strategic Guidance & Strategy Development

The key to achieving meaningful change within your organization is to set SMART goals and build a solid strategy around those goals. We'll help you map out a 3 – 5 year strategy to achieve your organization's most ambitious goals.


Through HR Helpline, you'll have direct access to employment law attorneys to receive confidential, documented responses to your organization’s specific questions

HR 360

We have partnered with HR360 to provide our clients with an award-winning online library that delivers comprehensive, easy-to-navigate human resources and benefits news, content, tools and forms to companies nationwide.

Webinars & Education

We'll provide you and your team monthly education/development opportunities on the latest HR, compliance and health care reform topics.

Well-Being & Engagement

In partnership with your Wellness Champions, our Well-Being & Engagement team will walk your organization through these seven steps to building a successful and sustainable wellness program.

Step 1
Capture Senior-level Support

We'll help you present the business case for workplace wellness in your organization and hone in on your senior-level champions.

Step 2
Create a Wellness Committee

We'll provide you with a comprehensive toolkit that will help in your committee's development. We can also be there to chair and facilitate committee meetings.

Step 3
Data Collection

This is a critical step in order to ensure your program has maximum employee participation and is tailored to your population's wants and needs.

Step 4
Develop Operating Plan

Want to know the key to your wellness program's success? Strategy. We'll help you develop a 3 – 5 year strategy so that it's crystal clear where your program has been and where it's going in the future.

Step 5
Effective Interventions

This is the fun part. We'll help you initiate effective interventions with your employees through disease management education, interactive health promotion programming and corporate weight management programs.

Step 6
Develop a Healthy Culture

We will help your organization develop a healthy culture by reviewing and identifying policies that may be serious stressors to your employee population.

Step 7

This is the stage where we find out what your return on investment has been. We'll also continue to track and supervise your program to make sure we are meeting the goals established during step 4.

Communications & Enrollment

Understanding the complexity of benefits plans is a challenge even for experienced benefits managers. With strategic planning, we provide custom communication materials that will help both you and your employees understand your plans and the issues influencing your benefits decisions.

Narrated Enrollment / New Hire Presentations

Who better to teach the ins and outs of your benefits than your Account Executive. We'll record a detailed video all about your benefits that your current and new employees can watch anytime, anywhere.


Employee Benefit Surveys

We'll work with you to develop a comprehensive benefit survey that will help you understand what's resonating with your employees and what might need to be adjusted.

Example of an employee benefits survey

Custom Benefits at a Glance Booklets

Everything related to your benefits, all in one place, in a beautifully printed booklet. Our team puts these together and prints them in-house. You'll wonder how you ever communicated your benefits without them.

On-Site Open Enrollment Meetings

Open Enrollment is obviously a critical time for your benefits program. Our team will work with you to schedule as many on-site meetings as necessary to make sure your employees fully understand their benefits.

Custom Enrollment Forms

For groups that still use paper enrollment as their method of choice, we make it incredibly easy for your employees to enroll using our customized enrollment forms. 

Comprehensive Benefits Solutions


  • Group Medical
  • Group Ancillary (Life, AD&D, STD and LTD)
  • Group Dental & Vision
  • Voluntary Benefits
  • Disability
  • Long-term Care (LTC)
  • Consumer Driven Health Plans (HSAs/HRAs)
  • Flexible Spending Accounts (FSAs)
  • Pharmacy Benefit Management
  • Stop Loss
  • Employee Assistance Programs (EAPs)
  • Third Party Administrators (TPAs)
  • International Benefits
  • Health Advocacy Services
  • Integrated Benefits Administration Solutions
  • Professional Employer Organization Services

Retirement & Executive

  • 401(k)
  • 403(b)
  • Defined Benefit Plan
  • Savings Incentive Plan
  • Executive Life Carve-Out
  • Profit Sharing
  • SEP, SIMPLE, Solo(k)
  • 409A Deferred Compensation
  • Executive Bonus Plan
  • Executive carve-out plans and services
  • Executive compensation consulting
  • Non-qualified plans

Voluntary Worksite

  • Accident
  • Critical Illness
  • Hospital Indemnity
  • Disability
  • Legal
  • Identity Theft Protection
  • Telehealth
  • New Benefits

Workplace Wellness

  • Strategy, goal and budget development
  • Committee toolkit
  • Wellness challenges
  • Wellness branding
  • Committee involvement
  • Tobacco free policy development
  • Needs & interest survey
  • Newsletters
  • Program evaluation
  • Health fair coordination
  • Compliance checks

Strong Carrier Relationships

  • Florida Blue (Blue Diamond status)
  • United Healthcare (Platinum agency)
  • Aetna
  • Sun Life
  • Lincoln
  • Humana
  • Plus, over 70 insurance carriers
Florida Blue Blue Diamond Agent
UnitedHealthcare Platinum Agency
Aetna Premiere Producer

Let's Talk About Your Benefits

Want to have a conversation about your benefits and how we can help? Fill out the short form below and a member of our Group Benefits team will get back to you shortly.