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About Samsil & Holland

Our Story

Who We Are

“When I was in high school, I debated between financial planning, and a career in teaching. While I was in my teaching career, I lost both of my grandfathers within 13 days of each other. One of them was financially prepared for his passing and the other one wasn’t. I saw the emotional and financial burden that family members had to go through. I got licensed, got some guidance from Jeff whom I’ve known for 40 years, and I resigned at the end of that following school year.” 

Cory Samsil, Founder


“My father was in the insurance business as I grew up, and I was attracted to that industry because of the control he had of his time and his ability to set his own schedule. But the rewards that I draw now are watching the successes of my clients like being able to retire, buying retirement homes and condos, travelling, and knowing I played a small part in guiding them to this point and watching them succeed and enjoy it.”

Jeff Holland, Founder


The Team

Jeff Holland, Founder

Licensed Agent

Jeff Holland is a licensed agent for annuities, life insurance, disability income insurance, and medical insurance. He held a license in securities and investments until December of 2022. He graduated from Delta State University with a Bachelor’s in Business Administration in 1978. From the American College, he earned CLU (Chartered Life Underwriter™) designation in 1983, and ChFC (Chartered Financial Consultant™) designation in 1987. Jeff is not affiliated with The O.N. Equity Sales Company or O.N. Investment Management Company.

Jeff is also an active member of several organizations and committees in the Paducah, Kentucky, area, such as the National Association of Insurance and Financial Advisors, the Million Dollar Round Table, Baptist Health-Paducah Foundation Board, and Rosebower Baptist Church to name just a few. He has been married to his wife, Terri, for over 40 years. They share a daughter, Kelsey, a son-in-law, Mitchell, and two grandchildren, Bennett and Kate.

Cory Samsil, Founder

Licensed Agent

Cory Samsil is a licensed agent for annuities, life insurance, disability income insurance, medical insurance, securities, and investments. He is licensed to sell health and life insurance in Kentucky, and to sell securities in Kentucky, Tennessee, Missouri, Illinois, and Florida. He graduated from Murray State University as a teacher, and taught in Mayfield schools until 2004, when he transitioned to the insurance and investment industry. He is a Chartered Retirement Plans Specialist℠ (CRPS) through the College for Financial Planning.

Cory is also a faith-driven family man. As a member of Lone Oak Baptist Church, he’s a teacher and Finance Committee Chair. He’s also Executive Committee Emeritus Member of Sunrise Children’s Services, Inc., the largest faith-based childcare provider in Kentucky. In his spare time, he enjoys delving deeper into Scripture, as well as spending time with his wife, Niki, and their two children, Lexi and Cooper, riding ATVs or at sporting events.

Ashley Watts

Executive Assistant

Ashley is our Executive Assistant. She started as a temp receptionist in the fall of 2006 with an Associate’s Degree in Business Administration, and became a full-time assistant to Jeff and Cory in May of 2007. This Southwestern Indiana native has been married to her high school sweetheart since June of 2007, sharing two beautiful children.

Kristina Merritt

Client Services Manager

Kristina is our Client Services Manager. Before the end of her first year working with Jeff and Cory, she became licensed in Life and Health insurance in January of 2023. She moved to Kentucky in November of 2018 with a background in banking and shares one son with her husband.

Ronnie Reil


Ronnie is the first face you see when you step in to Samsil & Holland. She has been in the insurance business for over 40 years in multiple settings, with a Life & Health Insurance License for 36 years. She has two children, and four grandchildren.