Our History

Herbie Wiles Insurance was founded in 1961 by Herbert L. Wiles. The agency's first home was a small office on Cordova Street, employing only a secretary. Herbie was initially successful in securing contracts with two major insurance companies in 1962, the Aetna Life & Casualty and Auto Owners Insurance Company.

Specializing in all forms of insurance, the agency quickly outgrew its initial office building and moved to its present location in 1966. The dwelling at 400 N. Ponce de Leon Blvd. was in a state of complete disrepair and significant renovation was required prior to occupancy. While converting old dwellings into businesses had been commonplace in St. Augustine, Herbie was the first businessman in the Saragossa Street area to complete such extensive renovation, turning an eye sore into a local landmark. Many other businesses in the area have since followed suit in converting older homes into offices.

While the majority of the agency's growth has come from new business sales, Herbie Wiles Insurance has acquired two other agencies: The Carl D. Langston Agency in 1974 and the T.R. Weathersby Agency in 1976.

Douglass F. Wiles joined his father in the agency in 1979. Continued growth meant an expansion in the facilities and in 1980, the dwelling next door, 76 Saragossa Street, was acquired. The two buildings were again renovated and moved together, creating more than 3,500 square feet of office space and a large parking lot, critical to a business in downtown St. Augustine.

The agency's first computer was purchased in 1981 and within a year, all customer files, accounting and claims information was available to customer service representatives. By 1984, computers were used to rate the majority of personal and commercial policies sold. Today, every employee has access to the agency's customer database, including customer information, accounting, word processing, claims and rating information. In fact, the agency uses a computer interface to “talk” with all its major insurance carriers, streamlining requests for policies and endorsements.

The agency appointed Wayne Howell as Vice President with responsibilities for agency marketing and development. Wayne has been with Herbie Wiles Insurance since 1983.

From its meager beginnings, Herbie Wiles Insurance has grown to 32 employees serving more than 8,500 accounts. We pride ourselves in our relationship with both our customers and our companies. While experiencing remarkable growth during both sides of the business cycle, our loss ratio with each carrier remains below industry standards. All employees are carefully screened prior to hiring and a management consultant regularly visits the office to confer with each employee on their personal goals and objectives.

Training and education is a hallmark for the agency. There are 17 licensed insurance agents on our staff. All employees receive regular in-house training on our computers and insurance issues. Management personnel and other key staff regularly attend formal classes sponsored by groups such as the Florida Association of Insurance Agents. In fact, most employees hold at least one professional insurance designation including Chartered Property and Casualty Underwriter, Accredited Advisor in Insurance and Certified Insurance Counselor.

Let us earn your trust.

THE HOUSE that TRUST BUILT