Drew Cunningham

As we welcome March, a month of growth and renewal, I’m reminded of the exciting possibilities ahead. Just like the season blossoms, this is a perfect time to nurture your dreams and plans. Whether it’s safeguarding your family or building a brighter future, I’m here to guide and support you every step of the way. Wishing you a month filled with fresh beginnings, hope, and success. Let’s embrace this season of change together!

As a lifetime resident of Owensboro, KY, I take great pride in serving and protecting our community from the unexpected. Helping individuals, families, and local businesses feel confident about what they are preparing for has always been important to me, and I’m grateful for the opportunity to guide customers through important decisions that support their future and the people they care about most. I attended Daviess County High School and graduated from Murray State University before becoming a State Farm Agent in 2018. Since then, I’ve been honored to serve Owensboro, KY, Western Kentucky, and Daviess County by providing Auto Insurance, Car Insurance, Home Insurance, Renters Insurance, Life Insurance, Motorcycle Insurance, Business Insurance, and Property Insurance. My team and I have been recognized with company and industry awards for our commitment to quality service, including Top 100 New Agent awards, Ambassador Club Travel two times, and Honors Club three times.

I was also voted Owensboro, KY’s Greatest Gold Agent in 2024 and 2025, an honor that truly reflects the belief this community has placed in my team and me. Staying involved locally matters to me, and I enjoy supporting the growth of our area by working alongside other small business owners. I am a member of the Owensboro, KY Chamber of Commerce, the Chamber of Young Professionals, and serve on several local boards, including Fellowship of Christian Athletes and the River City Pickleball Club.

Outside the office, I enjoy spending time with my wife Kaitlyn, our two daughters Claire and Libby, and our family and friends. We love traveling, discovering new places, and staying connected to everything our Owensboro, KY community has to offer.

My team of insurance professionals and I are excited to help customers prepare for life’s unexpected events through Auto Insurance, Home Insurance, Life Insurance, Renters Insurance, Business Insurance, and more. Because we live and work in Owensboro, KY and Daviess County, we are proud to serve customers throughout Kentucky and Indiana, including Evansville, IN, Newburgh, IN, and all of Tennessee. We look forward to connecting with you and helping you find the right coverage for your needs, so feel free to call, text, or stop by our office when you’re ready to get a personalized quote.

Frequently Asked Questions

Do you offer auto insurance in Kentucky? Yes! We provide personalized auto insurance coverage for Kentucky, Tennessee and Indiana and help take the confusion out of the process.

Do you provide home and condo insurance? Absolutely. We make home and condo insurance easy to understand.

Can you help with renter's insurance? Yes, we simplify renter's insurance so you can protect your belongings with confidence.

Do you offer life insurance? We provide term, whole, and final expense life insurance, explained clearly for every customer.