More Than a Business—A Responsibility
The idea behind Sheepdog Insurance Group comes from a simple belief: some people are called to protect, guide, and stand in the gap for others.
In a world where insurance decisions can feel overwhelming and disconnected, our role is to help bring clarity, protection, and confidence to the people we serve.
What That Means for Our Clients
Helping you make informed, confident decisions
Making complex topics simple and clear
Being available when you need help—not just at signup
Building long-term relationships, not quick transactions
Our Roots
In Sheepdog Insurance Group, we all live here in Webster County, MO. We grew up here. We want to see our communities thrive. We believe in this area and know the potential we have. We have deep roots here, with family in Seymour and Webster County for 100+ years. We love the Ozarks and look to bring the best of the Ozarks to the forefront, the people.
Meet Kevin Plain, founder & Owner
Kevin started Sheepdog Insurance Group to build something different—something focused on people, not just policies. After working in the insurance and financial industry over 15 years combined, he saw how disconnected and transactional things often were and wanted to create a better experience for clients. So, he created a "people first" experience in Sheepdog.
Often times It is normal for someone to have their home & auto insurance agent, their separate financial advisor, their separate tax preparer, their seperate health insurance agent, etc. That isn't easy to navigate, and definitely doesn't feel like it is built for you or tailored to you. Often times these different plans, processes and products can compete with one another. In Sheepdog, all of that happens under one roof. No disjointed plans, no competing conflicts. We prioritize making your life easier.
Today, we work with individuals, families, and businesses to help them guard what matters most and make informed decisions regarding their future whether their needs are in insurance, finance or taxes.
Meet The Team
Meet Garrett Little, Producer/Agent
Garrett is our newest team member and is licensed in Property & Casualty, along with Life & Health Insurance. His primary focus is helping farm and business owners protect what they’ve worked hard to build. He understands that not everything fits into a nice little box—especially when your property, livelihood, and day-to-day operations are closely connected.
Garrett takes the time to understand your situation, ask questions, and help you make sense of your coverage options. Whether you’re protecting a family farm, running a business, or navigating a more complicated insurance need, his goal is to provide clear guidance and coverage that fits your circumstances.
He is also happy to help individuals and families with their personal insurance needs, including home, auto, and life insurance. Whatever brings you to Sheepdog, Garrett is here to help you guard what matters most.
Meet Lacey B, Account Manager/Tax Preparer/Bookkeeping
If you call the Sheepdog office, you will likely hear Lacey on the line. She is often times your first point of contact when making policy updates, requesting quotes, scheduling appointments and more.
She wears many hats in Sheepdog but her primary roles are tax preparation, bookkeeping and insurance account management. Her role is ensuring our clients have the best possible experience. Prompt service, fast and accurate quotes, and great customer service.
Lacey is not a licensed agent and cannot inform you on what coverages you should have, but she can tell you what the 'Sheepdog Standard' is as a guiding principle.
