Small Business Insurance Solutions
Small Business Health Insurance That Actually Fits Your Business
Real options, clear guidance, and smarter coverage for business owners and growing teams.
Because your business deserves more than a generic plan and a call center.
K Simmons Insurance is based in Bradenton, Florida and helps small business owners, self-employed professionals, and growing teams compare health insurance options across 32 states. We work with multiple carriers to help you find plans that fit your team, your budget, and your goals — without the corporate runaround.
No pressure. No obligation. Just clear answers.
Independent agency. Based in Bradenton, Florida. Serving clients in 32 states.
Most Small Businesses Get This Wrong
Many business owners either overpay for coverage or choose plans that do not actually fit their team, budget, or long-term goals.
We help you compare real options so you can make a smarter decision from the start.
Who We Help
If this sounds like your business, you’re in the right place.
Small Teams
Businesses with 2–50 employees looking for practical group coverage options that fit real budgets.
Self-Employed Owners
Contractors, consultants, freelancers, and solo operators who need coverage built for how they actually work.
Growing Companies
Businesses ready to offer benefits that help attract, support, and retain quality employees.
What We Offer Small Businesses
Flexible coverage options built for real-world business needs.
Group Health Insurance
Compare group health plan options designed for smaller teams and real budgets.
Best for: Businesses with 2–50 employees that want to offer meaningful benefits.
Self-Employed Health Coverage
Coverage solutions for sole proprietors, freelancers, independent contractors, and owner-operators.
Best for: Solo owners and self-employed professionals.
Employee Benefits Packages
Health, dental, vision, and life insurance options that help you build a stronger benefits offering.
Best for: Businesses focused on retention and hiring.
Key Person Life Insurance
Protect your business if something happens to the people it depends on most.
Best for: Companies built around one or two critical leaders.
Why Business Owners Choose K Simmons Insurance
Business owners choose K Simmons Insurance for clarity, flexibility, and real options.
Independent Guidance
We are not tied to a single carrier, so our recommendations are based on fit — not pressure.
Built for Small Business
We understand businesses where the owner is also the HR department, operations manager, and decision-maker.
Local + Multi-State Support
Based in Bradenton, Florida, we help business owners compare coverage options across 32 states.
Multiple Carrier Access
We compare options across multiple carriers so you can make a more informed decision.
“I didn’t think we could afford coverage for our team. Kenroy helped us find an option that actually worked for our business.”
— Small Business Owner
How It Works
Tell Us About Your Business
We learn about your team, your current setup, your goals, and your budget.
We Compare Options
We review plans across multiple carriers and narrow things down to what actually fits.
You Choose with Confidence
We walk you through the options, answer your questions, and help you move forward.
Common Questions
How many employees do I need to qualify for group health insurance?
Many small businesses can qualify with as few as two eligible employees.
What if I’m self-employed?
There are coverage options built specifically for self-employed individuals and solo business owners.
Can benefits help me retain employees?
In many cases, yes. Offering benefits can improve retention and make your business more competitive.
Do you only work with businesses in Florida?
No. We are based in Bradenton, Florida and help business owners in 32 states compare coverage options.
Ready to Find the Right Coverage for Your Business?
Let’s simplify your options and help you make the right decision for your team.