Small business & groups
Health Coverage for You and Your Team
You're running this without an HR department or a big-company budget, so 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.
Ryan Michalek, Licensed Health & Life Insurance Agent, NPN 21043091. Last updated November 8, 2026 · Read my Google reviews
What are the health coverage options for a small business?
A small business can offer a group health plan, or let each person buy their own individual plan. Which fits depends on your team size, budget, and how much administration you want to handle. There's no one-size answer, and the trade-offs 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. I really enjoy this work, because I've seen too many small business owners skip coverage altogether or pay for a plan sized for a company ten times theirs.
If it's really just you right now, with 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.
What a small team needs is the right coverage for the people actually on payroll, set up without a mountain of paperwork. That's the part I handle for small business owners.
Covering yourself vs. covering a team
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, and for your own coverage (just you, or you and your family) you're typically on an individual or private under-65 plan (the guide to health insurance for small business owners covers that side), and how the premium is handled depends on whether you're a sole proprietor, an LLC, or an S-corp (here’s how the self-employed health insurance deduction generally works; your CPA confirms the details). For a team, you're looking at a group plan, or each person buying their own plan. Over time, plenty of owners end up doing both.
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 each person buying their own plan. 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.
Small business health insurance, by who's on the payroll
Most small business owners asking about health insurance want to know one thing first: what can a business my size actually do? The answer starts with headcount, and with who counts. Under HealthCare.gov's SHOP rules (checked November 8, 2026), only employees who aren't business owners, partners, or family members count toward the 1 to 50 full-time-equivalent employees a small employer needs. Carriers' small-group rules off the federal marketplace sometimes draw the line differently, so I confirm yours, but here is how it usually breaks down:
- Just you, or you and family. Usually individual coverage in your own name, not a group plan. How owners cover themselves, by entity
- One to three employees who aren't family. A small-group plan may be possible, and you can join it as long as at least one of them enrolls too. Helping each person get their own individual plan can fit better at this size.
- Four to fifty. A group plan is the usual starting point. The renewal packet each year is your comparison window, and a team spread across states changes the math (see below).
- Fifty or more full-time equivalents. The federal employer requirement applies, and the decision involves your CPA and benefits counsel, not just a broker. If that's outside what I do, I'll tell you plainly.
How I help
I keep it simple: explain your options clearly, handle the setup, and stay available as your team grows or changes, so you deal with one licensed advisor and 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, set up for a team your size.
- I handle the setup myself, so it stays simple on your end.
- I set up coverage for small and growing teams, and I stay with them as they hire and change.
A real one: A family-run small business right here in Tampa (the owner, his wife, and a few relatives on the payroll) came to me through my website when their group plan's renewal rates were set to jump sharply. We went through it together: the public marketplace, the private market, and a hard look at that renewal. For him, a private plan turned out to be the better fit, and once he saw how the numbers worked, he moved each of his people onto their own individual plans and put money toward helping them cover it, which penciled out better for everyone than renewing the old group plan. I didn't pitch him anything, I just laid the math out plainly until he could pull the trigger with confidence.
Another one, from this fall: A young business owner near Chicago got his own plan with me. Within a day, three of the people who work for him came to me too, and each one ended up with a plan in his own name. No group plan and no paperwork for the business, just each person set up directly with me. If your people are asking you what to do about health insurance, send them my way.
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's cleaner to help each person enroll in their own state's individual market. 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.
Most owners don't think to ask about this, but 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'm 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'm not licensed, I'll 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.
Small-group options by state: North Carolina chamber plans.
Selling the business: what happens to the group plan
When you sell, the group plan often ends at closing unless the buyer agrees to keep it, and if the company stops offering any group plan, COBRA ends with it. Federal law ends COBRA on the date the employer stops providing any group health plan to any employee (29 U.S.C. 1162, checked November 8, 2026). So "everyone can just take COBRA" may not hold after a sale, and your team deserves to hear that early.
Who owes continuation coverage after an asset sale or a stock sale, and whether the buyer's plan picks your people up, is settled by the purchase agreement and federal benefits rules. That's a question for your deal attorney or a benefits advisor, and it's worth asking before the letter of intent is signed, not the week of closing. Federal COBRA also applies only to employers with 20 or more employees in the prior year (U.S. Department of Labor), so a smaller group should ask its carrier what continuation, if any, applies.
What your employees do
- Get the end date early. Losing job-based coverage opens a special enrollment window, and HealthCare.gov lets people apply up to 60 days before coverage ends, so a date two months out is worth far more than one two weeks out.
- A spouse's plan is the quickest landing for some. Federal rules only require a spouse's employer plan to allow 30 days after coverage ends to ask to join (29 CFR 2590.701-6).
- Everyone else compares the marketplace and private plans. My marketplace partners enroll the ACA plans; I help with private under-65 plans and ACA-supplemental coverage. For anyone 65 or older, I'll connect you with my Medicare partner.
What you, the owner, do
Your own coverage ends with the group plan too, unless the buyer keeps you on as an employee with benefits. Line up an individual plan in your own name that starts the day after the group plan ends, so the earn-out or consulting period after closing doesn't leave you uninsured. If the sale also makes this a big income year, the subsidy side is on the LLC and S-corp owner page, and if the proceeds are funding retirement before 65, see the early retiree guide.
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.
Built around the team you have
Real coverage that helps you take care of your people, sized for the team you actually have.
I handle the setup
I handle the details so you can stay focused on running your business, and you don't need an HR department for any of it.
Here as your team grows
One licensed advisor who stays available as you hire or things change, with 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.
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, since 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, so 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.
Am I required to offer my small team health insurance?
Generally no. Businesses under 50 full-time-equivalent employees aren't 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 helping each person get their own plan. 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, since 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, though 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. Which fits depends on where your people live and how many are in each place. I'm licensed in 31 states, so a multi-state team usually doesn't mean handing you off.
Should a small business owner buy their own plan or set up a group plan?
Start with who you’re covering. If it’s just you, or you and your family, an individual private or marketplace plan is usually the simpler fit, and the guide for LLC and S-corp owners walks through how the premium is handled for each business structure. A group plan, or each person buying their own plan, comes into play once you have employees you want to cover. Many owners start with their own plan and add a team option later. I’ll help you sort out which applies, at no cost, and coordinate with your CPA on the tax side.
Who can help a small business set up health coverage?
An independent broker who works with small employers, someone who can walk you through a group plan versus each person buying their own plan, and compare what actually fits a team your size and budget. The right one isn’t tied to one carrier, costs you nothing to work with, and is straight about trade-offs. Check reviews and verify the license. That’s how I work: an independent Tampa broker who helps owners cover themselves and small teams, five-star reviewed, licensed in 31 states (NPN 21043091), no fee to you.
Can the owner join the small group plan with their employees?
Usually yes. Under HealthCare.gov's SHOP rules, an owner can enroll in the same group coverage offered to employees as long as at least one employee who isn't a business owner, partner, or family member also enrolls. If the only people on payroll are you and your family, the owner's coverage is usually an individual plan instead. Off-marketplace group carriers set their own participation terms, so I confirm eligibility for your group before you count on it.
What happens to my employees' health insurance if I sell my business?
The group plan often ends at closing unless the buyer keeps it, and if the company stops offering any group plan, COBRA ends too (29 U.S.C. 1162). Losing that coverage opens a special enrollment window, and employees can apply up to 60 days before it ends, so give them the date early. Who owes continuation coverage after the sale is set by the purchase agreement, so ask your deal attorney before you sign.
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-employedFamilies & individuals
Buying your own coverage for your household instead of through a job.
Explore family coverageSelling or retiring before 65
Sold the business before Medicare? Bridge the gap to 65.
See bridge optionsCOBRA & coverage gaps
COBRA ending, between jobs, or losing a plan? Line up your next plan so there's no gap.
See gap optionsChurches & ministry staff
A small congregation is a small employer. Pastors and church staff have their own rules to work through.
Coverage for pastorsSkilled trades & contractors
Electricians, plumbers, HVAC, and trades buying their own coverage.
Explore trades coverageNot 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 you keep me as your broker either way. 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. What day and time works best for a 15-minute call?
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.