Meet Our Team

Becki Jennings is the owner of Jennings Insurance Group. The agency opened in June 2011, after she returned to Missouri from Boise, Id, where she lived for 20 years and raised her two daughters.

Becki began her career in the insurance industry in 2007. She remains focused on senior benefits, including Medicare Health Plans, Annuities, Life Insurance, and Employee benefits.

Becki is passionate about her clients and works to introduce legislation to help Medicare beneficiaries and clients in the State of Missouri. She is a member of the National Association of Benefits and Insurance Professionals, where she serves as Legislative Chair for the Central Missouri Chapter. Becki joins them while they remain on the front lines, lobbying in Washington DC for brokers and their clients.

Ashley Wall serves as Agency Manager.  She graduated from Western Illinois University with a bachelor’s degree in Agriculture Business.  After graduation, she spent the next ten years working in many leadership roles including Safety Specialist, Colleague Development Manager, and Territory Operations Manager for one of the world’s largest agricultural food processing companies. Ashley has a great deal of experience with Human Resources and Employee Benefits.  She has a rooted agriculture background and strong passion for the business industry.

She is a member of the National Association of Health Underwriters. NAHU is the largest association for Health Insurance Brokers. Since moving to the lake area, she has become involved in Day Break Rotary, Young Professionals of the Lake and is a member of the Lake Ozark Marine Dealer’s Association. Ashley appreciates and is truly passionate about getting involved and giving back to the communities in which she lives and works.

Having strong ties to the Lake area, Ashley and her family moved from Central Illinois following her husband, Scott’s career advancement.  Scott and Ashley are the proud parents of two little girls. Ashley is excited to live and work at the Lake of the Ozarks and enjoys the opportunity to work with so many great businesses.

Dennis performs the role of Legacy Planning Coordinator. He has obtained the unique certification of Certified Estate Planner from the National Institute of Certified Estate Planners and is 1 of 8 Certified Estate Planners in Missouri. He will work with you through the Estate Planning process and help you design a trust that will protect your legacy for future generations. He is skilled in the administration of trust documents and is always willing to answer any questions you may have about Estate Planning.

In his personal time, you will find Dennis with his wife, ReAnn, enjoying life on Lake of the Ozarks. Being a farm kid at heart, Dennis enjoys working with his hands, designing and building projected and making them come to life.

Chelsea Witt specializes in employee benefits and individual health coverage. Chelsea graduated from Central Methodist University with an Associates Degree. She also has Business Management and Marketing education from William Woods University and State Fair community college. Prior to joining Jennings, Chelsea held administrative management positions. Chelsea’s desire is to create lifelong clients and plans to expand her skills as she continues to gain experience in the insurance industry.

Chelsea has two passions, her family and her music. She stays busy with her husband, and her little boy and baby girl; along with her music. Chelsea is the agency “ROCKSTAR”. She is a member of the band Old Soul Savage and can be found performing most weekends at local venues.

Amy Churchwell supports the Agency’s financial planning and will & trust business. Prior to joining the Agency, she held positions in client service, finance and portfolio management for 36 years, with Russell Investments and most recently, Bank of America Private Bank. Amy and her husband moved to Lake of the Ozarks in 2022 after living in San Diego for 29 years. She is loving lake life and has no regrets about leaving city life behind.

Keely Gaherty specializes in individual and group health insurance, including Medicare, the Marketplace, health sharing options and employee benefits.

Prior to joining the Jennings team, Keely was the Admissions Coordinator at a senior living community in Dubuque, IA. During her tenure at the senior living community, she met many people who did not have the proper insurance coverage when they suffered a catastrophic event. Knowing she is able to find the best possible coverage at an affordable price is what drives her.

In her free time she enjoys her dogs and boating on Lake of the Ozarks with her husband, Jason and their friends.

Kylene specializes in Individual Health Insurance, specifically Medicare and the Marketplace, as well as specializing in Estate, Life, and Retirement Planning.

She is a Certified Estate Planner which has given her valuable skills to help you with your Estate Planning documents. Kylene has over 15 years of valuable customer service skills. She will walk you through the process of your Estate Planning and Medicare, as well as Life and Retirement Planning to help make the process as simple and smooth as possible for you.