Close ×

The Bailey Group

The Bailey Group


Company Representatives

Charles Bailey, President

813.207.7512 ext. 105




Phillip Crawford, Regional VP




Industry Memberships and Accreditations 



Mission Statement

Our Mission is to provide the most trusted, fast and dependable life insurance for SBA borrowers. We show business owners how to FastTrak life insurance through our three platform offerings: Instant Issue, Issue Today and FastTrak®.



Over 20 years in business, The Bailey Group is an expert in placing and assigning life insurance policies that meet the SBA requirements.

The Bailey Group saves borrowers time, worries and money by leveraging our relationships with national life insurance leaders for the best product and pricing. It’s our superpower.

Our current record of providing a new policy with recorded collateral assignments is less than 1 hour– the latest by 7 business days.

Over the past two decades, as our own small business has grown, we have first-hand experience of some of the challenges that business owners face. To operate a successful business, owners and key talent dedicate valuable time to operating the business and managing vendor relationships.

Whether it’s renewing Property & Casualty Insurance, workers’ compensation policies or handling payroll, disability and employee benefits, business owners and their office managers are often distracted from what they do best.. .growing their businesses.

In 2022, we created a separate and unaffiliated company, Bailey Enterprise Holdings (BEH). Through due diligence, BEH identified providers who are dedicated to serving the needs of small and medium-sized businesses. Access to these insurance and support services will further empower borrowers to grow and protect their businesses and retain their best talent.

The Bailey Group works together with Bailey Enterprise Holdings and Brier Grieves Insurance to address all insurance needs in one place. A strategic partner of The Bailey Group, Brier Grieves Insurance specializes in helping lenders and borrowers with Property and Casualty Insurance needs required by the SBA.