Meet Our Leadership Team

Doug Wiles, CPCU, AAI
President

Doug is a graduate of the University of Florida and has been a licensed Property and Casualty and Life Insurance agent since 1979. He has been chairman and a member of several insurance company advisory boards during his career. Doug has earned the Chartered Property and Casualty Underwriter (CPCU) and Accredited Advisor in Insurance (AAI) designations.

In 2004, Doug completed eight years as a member of the Florida House of Representatives, District 20, serving Clay, Flagler, St. Johns, and Volusia Counties. He is a retired lieutenant colonel, having served in the US Army and the Florida Army National Guard for 25 years. Doug has worked with a number of local public service organizations, including the Kiwanis Club of Historic St. Augustine, the St. Augustine-St. Johns County Chamber of Commerce, the Flagler Hospital Board of Trustees, Catholic Charities and the United Way of St. Johns County. He is an Elder at Memorial Presbyterian Church.

Wayne E. Howell, Jr., CPCU, AAI
Vice President

A Jacksonville native, Wayne graduated from the University of Florida in 1983 with a BS degree in Business Administration. Following graduation, he joined Herbie Wiles Insurance as a Member of the Commercial Insurance Department, where he later served as department manager. Wayne is a minority owner of the agency and presently serves the as the Vice President of Marketing. He has earned the Chartered Property and Casualty Underwriter (CPCU) and Accredited Advisor in Insurance (AAI) designation.

A father of two, Wayne is past president of the Historic St. Johns County Police Athletic League and the Kiwanis Club of St. Augustine. He is a past member of the board of directors of the St. Augustine Humane Society and the Betty Griffin House. He is a 2002 graduate of Leadership St. Johns, a senior Ambassador for the St. Augustine Chamber of Commerce and serves as a member of the board of directors for the St. Augustine City Employees Retirement System.

Letha O’Neil-Wiseman
Vice President

Letha is responsible for insuring that each Herbie Wiles client receives exceptional service. A graduate of Tallahassee Community College with a paralegal degree, Letha has an extensive background in law, including mediation, loss control and products liability. Before coming to Herbie Wiles, she was a senior paralegal and managed a law firm with three locations.

Letha is married and the mother of two. She is a board member of the St. Augustine High School Baseball, Softball and Golf Boosters and volunteers with the Police Athletic League and St. Augustine Little League. Letha has received many awards for her legal work, including three-time Dispute Resolution Manager of the Year Awards. Most recently she was recognized as a National High Achiever by the Travelers Insurance Company for her work in providing exceptional service to customers.

Jim Gallo, AAI
Senior Agent

Jim has been a licensed Property and Casualty and Life and Health Insurance Agent since 1986. He has earned the Accredited Advisor in Insurance (AAI) designation. Since 1999, Jim’s career with Herbie Wiles has been in sales and service.

A native Floridian and Rotary member, Jim grew up in Palm Beach County. He started a family business and moved to San Mateo in 1998. Jim enjoys boating and fishing with his family.

Ralph Klein, CIC
Senior Agent

Ralph is a licensed Property & Casualty and Life & Health Insurance Agent. As an Account Executive, he has successfully developed target market programs for habitation and church risks as well as restaurants. Ralph works with specialty programs for condominiums, medical malpractice and aviation. He is a member of the Society of Certified Insurance Counselors, and joined Herbie Wiles Insurance in April 1988.

A 1981 graduate of the University of Florida, Ralph has been active in the St. Augustine community. He is a past Chairman of the St. Augustine-St. Johns County Chamber of Commerce and a past president of the Sunrise Rotary Club of St. Augustine. He is currently a coach for the U11 Select soccer team of the Ancient City Soccer Club. Ralph enjoys cooking, golf, racquetball and spending time with his wife and three children.

Herbie Wiles
Founder & Chief Executive Officer

Herbie Wiles is a father, grandfather, Navy Veteran of WWII, lifetime resident of St. Augustine, and CEO of Herbie Wiles Insurance.

A 1952 graduate of Florida State University, he obtained his BA in business and, with his mind set on an insurance career, went to work with his father as a State Farm agent. In 1961 he founded Herbie Wiles Insurance. Over the years, Herbie grew his independent insurance group, and now his son, Doug, manages the daily operations. Herbie still maintains an office and helps guide the business as needed.

An active member of the community, Herbie dedicates much of his time to the St. Augustine Historical Society, Flagler Hospital Advisory Board, Betty Griffin House, and the Presidents Council of Flagler College. Herbie also enjoys getting together with his good friends, his coffee club, golf, and traveling.

Steve Jones, CPCU,AAI,ARM,CIC,CPIA
Vice President of Sales & Marketing

Steve is a graduate of Virginia Tech and has been employed in the insurance industry since 1980. After a successful career in marketing and risk management consulting in the mid-Atlantic region, Steve moved to Florida in 1999 as the Director of Marketing for the country’s largest municipal self-insurance fund, protecting the local governments in Florida. More recently Steve spent three years with the Liberty Mutual organization managing part of their Florida sales production.

During his career Steve has earned five professional insurance designations and a number of sales achievement awards. He has worked with many of the insurance markets serving Florida and brought his expertise to Herbie Wiles Insurance in 2009. He is married with three daughters and they enjoy volunteering at Give Kids the World in Orlando.

THE HOUSE that TRUST BUILT