Most of my work is with people buying their own coverage. But a good share of those people run something, and once you have a second or third W-2 on payroll the question changes from "what plan do I pick" to "what am I supposed to offer, and what does it cost me." That question has four real answers, and the wrong one is expensive in a way you do not notice for about eleven months.
I am licensed in Florida and eighteen other states, so a group with people spread across state lines is not a problem. You can verify my license before we talk.
The first number that matters is 50
Everything about your obligations turns on one question: did you average 50 or more full-time and full-time-equivalent employees during the prior calendar year? At 50 and above you are an applicable large employer and the employer shared responsibility rules apply. Below 50, there is no federal requirement to offer coverage at all.
Full-time means 30 hours a week, or 130 hours in a month. Part-timers do not each count as one person, but their hours add up into equivalents, which is how businesses that feel small on paper cross the line without realizing it. If you are anywhere near the number, count it properly before you assume either way.
Most Tampa employers I talk to are well under 50. That is good news: it means you get to choose what makes sense rather than what is required. That holds across the county, and the Brandon and Hillsborough County page covers what individual coverage looks like out there for the people those employers are trying to help.
Your four real options, in the order I usually walk through them
1. QSEHRA, and for most small employers this is where I start
Instead of buying a plan, you reimburse employees tax-free for coverage they buy themselves. For 2026 the IRS caps this at $6,450 a year for self-only and $13,100 for family, which works out to roughly $537 and $1,092 a month.
Three reasons I lead with it. The reimbursements are a deductible business expense to you and tax-free to the employee, as long as that employee has qualifying coverage, so the same dollar goes further than a raise would. You never have to pick a plan on someone else's behalf, which means you are not the person they come to when their doctor is out of network. And you set the number, so your cost is a line item you control instead of a renewal letter you open in September and hope about.
It fits small teams especially well, because those are the companies where picking one plan for everybody is guaranteed to fit somebody badly. Two catches: you have to be under 50 full-time equivalents, and you cannot run a QSEHRA alongside a group plan. It is one or the other.
Here is the part owners find out too late. If you are a sole proprietor, a partner, or you own more than 2 percent of an S corp, you cannot reimburse yourself through the QSEHRA. The IRS treats you as self-employed rather than an employee for this. You can still set one up for your staff, and you take the self-employed health insurance deduction for your own premium instead. Owners on W-2 payroll at a C corp can participate like any other employee. Confirm your own situation with your CPA before you set an allowance, because the answer turns entirely on how the business is structured.
2. ICHRA, at any size
Same idea, no size limit and no contribution cap. You decide the allowance, employees buy their own individual plans, and you can set different allowances for different classes of employee, such as full-time versus part-time. If you are over the QSEHRA cap or over 50 employees, this is the version of the same approach that still works.
The catch that matters: an employee who takes your ICHRA money generally gives up their premium tax credit. For a lower-income employee who would have qualified for a large subsidy, that can leave them worse off than if you offered nothing. You also cannot offer the same class of employee a choice between a group plan and an ICHRA. This is the option with the most upside and the most ways to get it wrong, and the math is entirely dependent on what your people earn.
3. Group health plans, the fully insured kind
The traditional route. You pick a plan, you pay a fixed premium, the carrier takes all the claims risk. Rates are set by your census and renew annually, and a bad claims year is the carrier's problem, not yours. It is the easiest thing for employees to understand, and for some companies it is still the right answer, usually when people expect a group plan or when the census prices well.
The tradeoff is that you are paying for that predictability, you own the plan choice and everything that comes with it, and if your group is young and healthy you are subsidizing everyone else in the pool.
4. Level-funded
You pay a steady monthly amount that covers expected claims plus stop-loss protection. If your group runs healthier than projected, you can get money back at the end of the year. If it runs worse, the stop-loss absorbs it.
Level-funded usually prices better for younger, healthier groups and worse for older ones. It also brings extra reporting, including PCORI fees, which is the kind of thing nobody mentions until you are already in it. It is worth quoting alongside fully insured, not instead of it.
The tax credit most small employers never claim
If you have fewer than 25 full-time equivalent employees, your average employee wage is around $65,000 or less, and you cover at least half of employee-only premiums, you may qualify for a credit worth up to 50 percent of what you contribute. Nonprofits can get up to 35 percent. The credit is largest for the smallest, lowest-wage employers, and it scales down from there.
The step people miss is that claiming it generally requires enrolling through the SHOP marketplace. Buy the same coverage outside SHOP and the credit is off the table. If you are in that range and nobody has mentioned this to you, that is worth a conversation on its own.
What I need to quote it
Nobody can price a group off a headcount. To bring back real numbers rather than a range, I need a census: ages, zip codes, and who is taking employee-only versus adding a spouse or kids. Plus your current plan if you have one, your renewal date, and whether you want dental and vision quoted alongside.
That is usually a single spreadsheet, and once I have it the quotes take days, not weeks.
Timing, and why renewal date is the real deadline
The HRA routes depend on employees buying individual plans, so they run on individual open enrollment, which starts November 1 for 2027 coverage. That makes right now the window to set one up for January. My open enrollment guide covers those dates and what changed this year, and the subsidy changes in it matter a great deal if you are weighing an ICHRA.
Group coverage is different. It runs on your renewal date, not the January calendar. If your plan renews October 1, the decision window is August and September. Start 60 to 90 days out and you have room to compare; start three weeks out and you are re-signing whatever you already have.
Questions Tampa employers actually ask
Do I have to offer health insurance to my employees?
Only if you averaged 50 or more full-time and full-time-equivalent employees during the prior calendar year. That threshold makes you an applicable large employer, and the employer shared responsibility rules kick in. Full-time counts as 30 hours a week, or 130 hours in a month. Below 50 there is no federal requirement to offer anything, which surprises a lot of owners who assume they are already out of compliance.
How many employees do I need to get a group plan?
In Florida a group plan generally starts at one enrolled employee besides the owner, though carriers set participation and contribution minimums that matter more than the headcount. The practical floor is usually whether enough of your people will actually enroll rather than stay on a spouse's plan.
What is the difference between fully insured and level-funded?
Fully insured means you pay a fixed premium and the carrier takes all the claims risk. Level-funded means you pay a steady monthly amount that covers expected claims plus stop-loss protection, and if your group runs healthy you can get money back at the end of the year. Level-funded usually prices better for younger, healthier groups and worse for older ones, and it comes with extra reporting.
Can I just give employees money to buy their own plans?
Yes, through an HRA, and for a small employer that is usually where I start. A QSEHRA lets you reimburse employees up to an IRS cap. The reimbursements are a deductible business expense to you and tax-free to the employee as long as they carry qualifying coverage, and you never have to pick a plan for anyone. You have to be under 50 full-time equivalents and you cannot run it alongside a group plan. An ICHRA has no size limit and no contribution cap, but employees generally give up their premium tax credit to use it. Which one wins depends on what your people earn, and that math is worth running before you commit.
Can I reimburse myself as the owner?
Usually not through the HRA itself. If you are a sole proprietor, a partner in a partnership, or own more than 2 percent of an S corporation, the IRS treats you as self-employed rather than an employee, so QSEHRA and ICHRA reimbursements to yourself are not tax-free. You can still set up the arrangement for your employees and take the self-employed health insurance deduction for your own premium. An owner who is a W-2 employee of a C corporation can participate normally. Structure decides this, so confirm yours with your CPA.
What does small business health insurance cost in Tampa?
There is no useful average. Group pricing turns on the ages of your census, your zip code, the plan design you pick, and how much of the premium you cover. Two companies with the same headcount can be thousands of dollars apart per month. Send me a census and I will bring back real numbers instead of a range.
Is there a tax credit for offering coverage?
There is, and most small employers never claim it. If you have fewer than 25 full-time equivalent employees, your average employee wage is roughly $65,000 or less, and you pay at least half of employee-only premiums, the credit can be worth up to 50 percent of what you contribute, or 35 percent for nonprofits. It generally requires enrolling through the SHOP marketplace, which is the step people miss.
Send me a census and I will price it properly
The HRA math, fully insured, and level-funded side by side, with the tax credit checked. No cost to you, and no pressure to move if what you have is already right.
Get my options →The bottom line
Under 50 employees you are choosing, not complying. That is a better position than most owners think they are in. For a lot of the companies I work with a QSEHRA ends up being the answer, because it is deductible, it caps your cost at a number you set, and it takes you out of the business of picking plans. But a group plan still wins for some, and the deciding factor is usually what your people earn rather than what you would prefer. Text or call and we can sort which one you are in a single conversation.