Kenny Cunningham
Kenny is President of Cunningham Insurance, Inc and has over 30 years’ experience in the sales and service of Life and Health Insurance. Kenny received is Bachelor of Business Administration degree in Risk Management and Insurance from the University of Georgia. He has also satisfied the educational requirements necessary to earn the Registered Health Underwriter (RHI) and the Registered Employee Benefits Consultant (REBC) designations from the American College.
Michelle Crawford
Cunningham Insurance, Inc. partners with Michelle Crawford and Crawford Benefits to offer our clients the opportunity to meet all their insurance needs in one office.
Michelle Crawford has been in the insurance business since 1995 and began her insurance career with State Farm Insurance. After six years with the company, she went to work for Chemical Financial Corporation and ran their insurance agency. During that time of managing the agency, she became licensed with AFLAC and traded in her corporate career for a self-employed one. With a very successful career with AFLAC as a District Sales Coordinator over the Big Rapids, Michigan area, she moved south to Columbus, GA where AFLAC corporate offices are located. She maintained a career as an independent agent and, over the years, expanded her business to include and focus on individual and group health insurance and Medicare products.
As an individual, Michelle has three grown sons, three beautiful daughters-in-law and a three beautiful grandsons, Callahan, Lennon and Casen with another grand on the way. She loves her family and the Lord. She is an active member of Pierce Chapel United Methodist Church in Midland, GA where she has led local missions for over 7 years and continues to serve on this team today as well as serve on the conference Board of Pensions and Benefits. Her strong desire to serve others fuels her passion for ministry and her business.
Jaime Meredith
Jaime Meredith joined our team in 2022 as an agent serving our Medicare and individual health insurance clients. Jaime Started his insurance career at State Farm in 2020 as a Licensed Agent and has been in the Customer Service industry for the last ten years. He is married (Melissa) with a baby boy due this July. He lives on a family farm in Marion County along with his dog Roxie, cats Dinah and Meeko, and 16 chickens. Jaime and Melissa are both active members of the New Providence Baptist Church in Buena Vista, working with and teaching the Youth group there. When Jaime is not working he enjoys sports, hunting, camping, and pretty much anything else outdoors.
Tere’se Winters
Tere’se (pronounced Tuh-race) Winters serves as our office manager and administrator. She comes with a background in customer service in the Insurance Industry. She is married with 3 children(and their spouses) and 7 grandchildren. In her spare time, Tere’se enjoys spending time with family & friends, cooking, sewing and riding the motorcycle and is a member of Addereth Christian Center.
Lisa Ashcraft
Lisa Ashcraft serves as our back office support. She handles client intake, customer service resolutions and commission issues. Lisa, with her husband Andy, are active members of Pierce Chapel UMC. They have three children and four grandsons. In her spare time she enjoys gardening, traveling, outdoor concerts and spending time with family.
Ricky Dupree
Ricky DuPree serves our team as Strategic Organizer. She has been Michelle’s right hand since she started with us. She is great at making sure projects are organized and executed efficiently and effectively. Ricky is a member of Gentian Baptist Church. She is married with two daughters and 4 beautiful grandchildren. Ricky is at her best when helping others which is what makes her a perfect fit for Crawford Benefits.
Ellie Mae & Kona
If you drop by our office there is a good chance you will be greeted by these two. Ellie Mae and Kona love to be in the office with us, but you will always know they are there by the sign outside our door. We know not everyone loves four legged friends like we do, so when we have in office client meetings, these girls are usually put up in an office as a courtesy.
