Health Coverage for You and Your Team
Taking care of your people matters to you — but you're running this without an HR department or a big-company budget, and you shouldn't have to pretend otherwise. I help owners and small teams find coverage that actually fits: real benefits, without the paperwork or price tag built for a much bigger business.
What are the health coverage options for a small business?
A small business can offer a group health plan, set up a reimbursement arrangement like a QSEHRA or ICHRA that funds employees' own coverage tax-efficiently, or point employees to the individual market. Which fits depends on your team size, budget, and how much administration you want to handle. There is no one-size answer, and the tradeoffs are real. An independent broker can walk the options with you at no cost, and coordinate with your CPA on the tax side.
Benefits that work for small teams
Whether you're covering just yourself as the owner or a handful of employees, I'll walk through private group and individual options and help you understand what makes sense for your size, budget, and goals. It's work I genuinely enjoy, because I've seen too many small business owners either skip coverage altogether or end up overpaying for a plan sized for a company ten times theirs.
If it's really just you right now — no employees yet — your own coverage works differently than a group plan, and how the premium is handled depends on whether you're an LLC, S-corp, or sole proprietor. The health insurance guide for LLC & S-corp owners walks through the owner's individual coverage structure by structure.
You don't need an enterprise benefits package — you need the right coverage for the team you actually have, set up without a mountain of paperwork. That's the gap I fill for small business owners.
Health insurance for small business owners
As a small business owner, you're really weighing two decisions at once: coverage for yourself, and whether to offer something to a team. They're separate paths. For your own coverage — just you, or you and your family — you're typically on an individual or private under-65 plan, and how the premium is handled depends on whether you're a sole proprietor, an LLC, or an S-corp. For a team, you're looking at a group plan or a reimbursement arrangement that funds employees' own coverage. Plenty of owners do both over time, starting with their own plan and adding a team option as they grow — I'll help you sort out which applies to you, at no cost.
What health insurance can a small business owner get for themselves?
As the owner, your own coverage is usually a separate decision from anything you set up for a team. If it's just you — or you and your family — you're typically looking at an individual or private plan, and how the premium is handled often depends on whether you're a sole proprietor, LLC, or S-corp. Covering employees is a different path — a group plan, or a reimbursement arrangement that funds their own coverage. Plenty of owners do both, starting with their own plan and adding a team option as they grow. I'll help you sort out which applies to you, at no cost, and coordinate with your CPA on the tax side.
How I help
I keep it simple: explain your options clearly, handle the setup, and stay available as your team grows or changes. One licensed advisor, no runaround.
- I'll walk you through group and owner-coverage options side by side, so you can see what actually fits your team.
- You get real benefits, without the enterprise-level cost or complexity that comes with them elsewhere.
- I handle the setup myself, so it stays simple on your end.
- Everything here is built around small and growing teams, not giant ones.
When your team is in more than one state
This is the wall most owners hit the moment they hire outside their own state. A small-group plan is generally issued in the state where your business sits, so how well it actually serves someone two states away comes down to that plan's network — not to what the brochure says. Sometimes a group plan still makes sense. Sometimes it is cleaner to help each person enroll in their own state's individual market, funded tax-efficiently through a reimbursement arrangement like a QSEHRA or ICHRA. Which way it goes depends on where your people actually live, how many are in each place, and what care they need close to home.
Here is the part most owners do not think to ask about: your broker has to be licensed in each state where coverage is written. Plenty of local brokers hold one or two licenses, which is why a multi-state team so often turns into a hand-off. I am licensed in 31 states, so in most cases I can handle both sides of a two-state team myself. If one of your people lands somewhere I am not licensed, I will tell you plainly and connect you with someone I trust rather than leave you sorting it out.
Worth knowing on timing: group plans usually renew on a set anniversary, and the renewal packet is when the real numbers show up. That packet is the right moment to compare — not the week it takes effect.
Real benefits, sized for a small team.
Group & Owner Options
Whether it's just you as the owner or a handful of employees, I'll walk through the private group and individual options that fit.
Priced for a Small Team
Real coverage that helps you take care of your people, sized and priced for the team you actually have — not the one a big company built its plan for.
Simple Setup, Handled
I handle the details so you can stay focused on running your business — no HR department required.
Grows With Your Team
One licensed advisor who stays available as you hire, change, or scale — no runaround when things shift.
Quick answers for small businesses.
What are health insurance options for a small business with a few employees?
You have more options than most owners realize — from a true small-group plan to helping your team get individual coverage. I'll lay out what makes sense for your size, budget, and goals, without the enterprise-level cost.
How does a small business owner set up group health insurance?
I handle it end to end: comparing carriers, sizing the plan to your team and budget, and walking you and your employees through enrollment. You don't need an HR department — that's my job.
How many employees do I need to offer group coverage?
Often as few as one or two, though the rules vary by state. If a formal group plan isn't the right fit, I'll show you other ways to cover yourself and your team.
What does small business health insurance cost?
It depends on your team's size, ages, and the level of coverage — there's no single number. I'll get you real quotes to compare instead of guesses, at no cost to you.
Is there a fee to work with you?
No — my help is free. I'm compensated by the carrier when you enroll, so it doesn't add to your cost.
If I set up an ICHRA or QSEHRA, does that open an enrollment window for my team?
Generally yes, and it's the part owners are most often surprised by. Being offered an individual coverage HRA or a QSEHRA is itself a qualifying event on the official federal list — your employees typically get about 60 days to enroll in their own plan, whether or not it's Open Enrollment. One practical wrinkle: the marketplace generally can't complete that enrollment online, so it takes a phone call. That's usually where I come in — I'll walk each person through their own options so the benefit you funded actually lands. For how the reimbursement is treated on your return, your CPA is the right call.
Can I reimburse employees for their own coverage instead of a group plan?
Often, yes. Arrangements like a QSEHRA or an ICHRA let a small employer reimburse employees on a tax-advantaged basis for coverage they buy themselves, instead of sponsoring a single group plan — which can be simpler for a small or spread-out team. The rules and contribution limits matter, so it's worth mapping to your headcount and budget before you decide. I'll explain how it compares to a traditional group plan for your business.
Am I required to offer my small team health insurance?
Generally no. Businesses under 50 full-time-equivalent employees are not required to offer coverage, so offering it is a choice about recruiting and retention rather than a mandate. If you do want to help, options range from a group plan to a reimbursement arrangement that funds employees' own plans. An independent broker can walk the choices with you, and coordinate with your CPA on the tax side, at no cost.
Can a small business owner write off health insurance premiums?
There can be a tax advantage to how an owner's premiums are handled, and it often depends on your business structure — sole proprietor, LLC, or S-corp. That part is your CPA's call, not mine — I don't give tax advice. What I do is make sure the coverage itself is set up right for you, and I'm glad to coordinate with your accountant so the two line up.
Can I get coverage mid-year, or only during open enrollment?
It depends on the type of plan. Marketplace coverage generally opens during Open Enrollment or after a qualifying life event, but private, medically underwritten plans can often be applied for year-round — approval isn't guaranteed and timing can vary. If you've got a gap now or a change coming, it's worth a quick call so we can look at your options and the timing together.
What if my employees are in different states?
A small-group plan is generally issued in the state where your business is located, so how well it covers an out-of-state employee depends on that plan's network. The alternative is helping each person enroll in their own state's individual market, sometimes funded through a QSEHRA or ICHRA. Which fits depends on where your people live and how many are in each place. I am licensed in 31 states, so a multi-state team usually does not mean handing you off.
Official sources: for the government rules referenced above, see HealthCare.gov — coverage for small businesses & the self-employed and CMS — Small Business Health Options Program (SHOP). Michalek Health Solutions is an independent broker and is not affiliated with these agencies.
Just covering yourself or your family?
Self-employed & 1099
Buying your own coverage as a freelancer, contractor, or solo business owner.
Explore self-employed →Families & individuals
Buying your own coverage for your household instead of through a job.
Explore family coverage →COBRA & coverage gaps
COBRA ending, between jobs, or losing a plan? Move fast and avoid a gap.
See gap options →Churches & ministry staff
A small congregation is a small employer. Pastors and church staff have their own wrinkles.
Coverage for pastors →Skilled trades & contractors
Electricians, plumbers, HVAC, and trades buying their own coverage.
Explore trades coverage →Not sure this is your lane? If group or small-business coverage turns out to be your better path, you're not on your own — I'll connect you to a partner I trust who does exactly that, and I stay in your corner either way. One honest starting point, whatever fits your family. Meet the partners I trust →
In their words
“Ryan did a great job in getting us updated insurance options. Very informative and followed up to be sure we got exactly what we needed.”
— A Tampa business owner
“Incredibly helpful with sorting out which plans made the most sense for my current situation. His responses to questions were quick, educational and actually felt like an interaction with someone who wanted to help.”
— Matt P.
“Ryan was very helpful walking me through the various options and asked the right questions to land me in the right plan for me and my family.”
— Dave L.
Let's set your team up right.
I'll lay out group and owner options in plain English and handle the setup once you decide.
Want numbers before a conversation? You can run the free estimator → for your own coverage, or check if you can enroll now → if a qualifying life event just changed things for you or an employee.