MICHELLE CRAWFORD

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. 

In 2018, she partnered with Cunningham Insurance, Inc to be able to fully service her clients and referrals with all lines of coverage.

As an individual, Michelle has a blended family with four grown sons, a daughter, four beautiful daughters-in-law and seven beautiful grandsons, Callahan, Lennon, Casen, Will, Wesley, Iszac & Oliver. She loves her family and the Lord. She is an active member of Pierce Chapel Global Methodist Church in Midland, GA where she led local missions for over 7 years and continues to serve on this team today.

KENNY CUNNINGHAM

Crawford Benefits partners with Kenny Cunningham and Cunningham Insurance, Inc to offer our clients the opportunity to meet all their insurance needs in one office. 

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.

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 to Melissa and they have a precious little boy, JT. He lives on a centennial family farm in Marion County along with a wide assortment of pets. 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 working around in the yard.

TAYLOR MASON

Taylor Mason joined the team in July 2023 as back office support and compliance. She is currently engaged to her Fiancé, Logan and planning her 2024 wedding. She has 3 dogs, a Chihuahua, Roxy, and 2 mini dachshunds, George, and Jerry. She is a proud Colorado Native. In her spare time enjoys traveling, concerts, and hanging out at home with her little family. She is currently a member of Zeal Church in Colorado and travels home often to attend in person. She is a joyful, witty, old soul who is excited for her future with Crawford Benefits. 

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.

Teresa Wimberly

Teresa joined our team in August 2024 as our front office coordinator. She is a long-time resident of Columbus, GA. She has been married to her husband, Rick, for 46 years and they have three grown sons who are all married. She has 3 pets currently, a black lab named Bo, a Maltese named Bailey, and a cat named Chipper Jones. She loves to cook and do a little gardening. She loves the beach and the mountains, but most of all spending time with family. Teresa spent 23 years working with an insurance company which she retired from at the end of 2023. She looks forward to applying her experience to the success of 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.