ABOUT US

Our Mission

Since 2000, our Agency has been committed to simplifying Medicare for individuals in the Somerset, Kentucky community with integrity, compassion, and faith-based values—building lasting relationships centered on trust and focused on delivering personalized health and financial insurance solutions that safeguard retirement years with clarity, confidence, and peace of mind.

Hours of Operation

Monday - Friday: 9 AM to 5 PM
Closed Saturday and Sunday

Location

408 South Main Street

Somerset, KY 42501

Telephone:

(606) 677-1759

Randall Whitehead Jr. is passionate about helping Medicare retirees make informed decisions regarding their Medicare health and Long-Term financial coverages. Serving the Somerset-Pulaski County community, he is committed to building lasting relationships and providing clear, customized solutions tailored to each client’s unique needs. His work is grounded in Christian principles and a genuine desire to serve others with integrity, honesty, and compassion. Randall remains active in the community through his church and involvement in various local organizations.

A 2002 graduate of Southwestern High School in Pulaski County.

Randall went on to earn his Bachelor’s Degree in Business from Morehead State University in 2007. In 2008, he joined the agency formerly known as Garry Greer and Associates Inc. Through dedication, hard work, and an unwavering commitment to his clients, Randall was named agency partner in 2017 by founder Garry Greer, forming Greer, Whitehead and Associates, Inc.

Following Mr. Greer’s retirement, Randall assumed full operational leadership of the agency in 2019.

Continuing the agency’s legacy of trusted service, he officially rebranded the firm in 2026 as Randall Whitehead Jr Insurance Services Inc., reflecting both its continued growth and his long-term vision of relationship-driven, solutions-based service for the community.

Meet Randall Whitehead Jr.

Testimonials

"Randall treats you like family. He checks in regularly, keeps me informed about any changes, and is always just a phone call away when I have questions. It gives me great peace of mind knowing someone I trust is looking out for my health coverage needs."

-Delmer

"What means the most to us is that Randall doesn’t just treat you like a policy number—he treats you like family. He listens carefully, makes thoughtful recommendations based on our needs, and always follows up to make sure we’re comfortable with our coverage. We feel confident knowing we have someone we trust looking out for both our health insurance well-being."

-Catherine and Don

“I have trusted Randall with my insurance needs for over 14 years, and I truly couldn’t ask for better service. He has always taken the time to explain my Medicare and Financial options clearly and make sure I understand what works best for my situation. I never feel rushed or pressured—just cared for. "

-Sharon

“My husband and I have been so grateful for the guidance and support we’ve received from Randall. Choosing the right Medicare coverage felt overwhelming at first, but he took the time to sit down with us, answer every question, and explain our options in a way we could truly understand."

-Phyllis and Gene