Strategy

How to Get Health Insurance For a Small Business in Tampa

May 7, 2025

When Should a Small Business or Startup Get Health Insurance?

Finding affordable small business health insurance in Tampa doesn't have to be complicated. As a business owner, you need to know when it makes sense to offer health benefits and how to do it without breaking the bank. This guide walks you through everything you need to know about timing, options, and making health insurance work for your Tampa small business.

In this article:

  • Why health insurance matters for your Tampa small business
  • Signs your business is ready for health insurance
  • Legal requirements you need to know
  • How to make small business health insurance affordable in Tampa
  • Steps to implement a successful health insurance strategy
  • How using a PEO broker saves you time and money

Why does health insurance matter?

73% of employees would change jobs for better family benefits (Ovia Health)

Let's face it, you’re not ConnectWise or Reliaquest. Offering health insurance is a monumental decision for any small business owner in Tampa Here's why it might be worth considering sooner rather than later.

It helps you attract great employees. In Tampa's competitive job market, health benefits can be the difference between landing that perfect hire or watching them commit to your competitor. Good employees expect good benefits.

It keeps your team healthy and productive. When employees have access to healthcare, they take fewer sick days, they’re not putting off doctor visits because they can't afford them, and they’re generally more focused at work.

It creates loyalty. Employees who feel taken care of stick around longer. Lower turnover means less time, resources and money spent on recruiting and training new people.

It can actually save you money in the long run. Tax benefits, improved productivity, and higher retention can offset much of the cost of providing small business health insurance in Tampa.

Signs your business is ready for health insurance 

Not sure if it's the right time to offer health insurance? Here are some clear signs your Tampa small business might be ready:

You're having trouble attracting quality candidates. If good prospects are turning down your offers because of a lack of benefits, it's time to consider health insurance. 

Paying for Marketplace / ACA Plans. Many Tampa area companies offer a post-tax stipend for employees to obtain health insurance policies on their own. While this can be a good stop-gap measure, it’s generally not a long term or cost-effective strategy. Network options are often limited, premiums are high and there's often little tax advantage for the employer or employee.

Your team is growing. Many businesses start thinking about health benefits when they reach 5-10 employees. It becomes almost essential once you have 10-20 team members.

Your business is financially stable. You have predictable revenue and can afford to contribute at least 50% of the “employee only” tier for anyone enrolled in a plan. On average, this can be between $150-$400 per employee per month, depending on the network, and plan quality.

You're losing employees to companies that offer better benefits. If exit interviews reveal people are leaving for better benefits, that's a strong signal it’s time to receive an initial quote.

You're approaching 50 full-time employees. At this point, you'll need to prepare for the legal requirement to offer health insurance (more on that below).

Legal requirements you need to know

Let's keep this simple. Here's what Tampa small business owners need to know about health insurance requirements:

Under 50 employees: You're not legally required to offer health insurance. It's completely optional, though often recommended. 

50+ full-time employees: Once you hit this threshold, the Affordable Care Act (ACA) requires you to offer affordable health insurance that meets minimum standards. If you don't, you could face significant penalties.

If you're a growing Tampa business approaching 50 employees, it's time to start planning for health insurance before you're legally required to provide it.

Making health insurance affordable 

The cost of small business health insurance in Tampa doesn't have to be overwhelming. Here are practical ways to make it work for your budget:

Share costs with employees. Most small businesses in Tampa cover a percentage of the premium (typically 50-80%) while employees pay the rest.

Look into tax credits. Contributions towards group medical plans are tax-deductible for both employee and employer, reducing taxable income. Small businesses with fewer than 25 full-time employees may qualify for the Small Business Health Care Tax Credit, which can cover up to 50% of your premium costs.  

Consider a Professional Employer Organization (PEO). Tampa small businesses can partner with an online HR platform called a PEO to access better insurance rates typically reserved for larger companies. 

Start simple. Health insurance is the 2nd largest expense, behind salary, so launching a solid base plan and gradually expanding coverage as the business scales is often a smart financial play.

Compare several alternatives. Small business health insurance in Tampa varies widely in price and coverage. Taking the time to compare options can save you thousands, or, better yet, have a broker do the legwork for you. 

Implementation steps 

60% of employees say benefits are extremely or very important when deciding to stay with employers (Forbes)

Ready to move forward with small business health insurance for your Tampa company? 

We recommend a 60-day runway from the start of the evaluation to the first date of coverage. 

Here's the ultimate blueprint to follow:

1. Survey employees

How many of your full-time W2 employees are roughly interested in enrolling? Generally, insurance is reserved for employees, not 1099 contractors, who work on average 30 hours or more a week. Many carriers require 50% of FTE to enroll but this can be skirted with valid waivers.

Ask your team, anonymously, what matters most to them in health coverage. Would they prefer lower premiums or lower deductibles? How often do they anticipate using coverage? Do employees need specific doctors or hospitals in network? The more data, the better. Their input is a guidepost in deciding the plans to offer.

2. Quoting Process 

You’ll first need firm health insurance numbers to calculate how much your business can afford to contribute to group plans. Good news: it’s easy to initiate the insurance quoting process.

A majority of states require companies to work through an insurance broker, of your choice, to obtain group health insurance plans. You won’t be able to go directly to a carrier such as Blue Cross or United.

Connect with a reputable local health insurance specific broker, like Pro Health PEO Advisors, to submit an employee census so they can generate the 4 options available for a Tampa small business to review.

  1. Small group / Open Market health insurance
  2. Professional Employer Organization (PEO)
  3. Level funding insurance
  4. ICHRA / Marketplace Plans

3. Choose your package

Once you’ve received all quotes, you’ll meet with the broker to narrow down the field to 1-2 options. You'll decide whether you’d like to offer FSA or HSA at this time. Remember, there’s no right or wrong answers! Every company is unique; A good broker will provide their expertise and provide benchmarking analysis with how companies your size and in your industry are operating.

Many Tampa small businesses generally offer 2-3 plans and cover 50-75% of a single employee premium of the base plan. You have the ability to alter your strategy every year during renewals.

4. Communicate with your team

Once you've selected a solution, the broker will meet with employees to clearly communicate the benefit offerings; They’ll guide employees through what's covered under the plan, how to enroll dependents, general Q&A, and next steps.

5. Review annually

Small business health insurance in Tampa should be price checked annually to ensure you're continuing to receive the best value and coverage for your evolving needs. It’s important to have a responsive and knowledgeable broker in your corner who works for you and understands your business needs and goals. 

Why using a PEO broker saves you time and money

One of the smartest moves for Tampa small businesses looking for affordable health insurance is working with an experienced insurance broker like ProHealth PEO rather than trying to navigate the complex world of PEOs and insurance on your own.

What is a PEO?

A Professional Employer Organization (PEO) bands their customer's employees together under one umbrella.

That way, a smaller company can access enterprise-level benefits at an affordable rate. Additionally, a PEO acts as a one-stop shop for a business's onboarding, payroll, multi-state SUI compliance, and HR functions.

What exactly is a PEO broker?

There are over 800 PEO providers in the marketplace. A PEO broker is your advocate in finding the right Professional Employer Organization for your business. 

Think of them as matchmakers who connect your small business with the PEO that best fits your specific needs. The best part? PEO brokers like ProHealth PEO offer their services to small businesses for free.

Benefits of using a PEO broker for your small business health insurance in Tampa:

  1. They do the vetting for you. Not all PEOs are created equal. A broker like ProHealth PEO has already done the hard work of vetting the PEO marketplace, checking their financial stability, negotiating pricing, and evaluating their product market fit.
  2. Objective recommendations. Since a good broker works with multiple PEOs, they can provide unbiased advice about which one truly fits your business needs rather than trying to force-fit you into a one-size-fits-all solution. They don't work for the PEO’s, they work for you.
  3. Industry expertise. PEO brokers understand the nuances of different industries and can match you with PEOs that have experience with industries like yours in the Tampa area.
  4. Ongoing support. A broker continues to resolve billing or operational issues that arise. They’re licensed to provide advice and education to employees who have questions.
  5. Cost savings. A good broker will have relationships with multiple PEOs that allow them to secure better rates than you might get approaching a PEO directly. Plus, their services are free since they’re compensated by the insurance carrier or PEO directly, and it doesn’t inflate the cost a small business pays for insurance or PEO fees.
  6. Time efficiency. Instead of researching dozens of PEOs, fielding sales discovery calls, sitting through numerous demos, and receiving quotes and pricing in different formats, a broker streamlines the process so you can focus on running your business. They’ll weed down the field and bring only those options that fit what you’re looking to accomplish (eg price savings, enhanced support, more robust benefit offerings)
  7. Simplified comparison. A good PEO broker provides a clear comprehensive side-by-side of several options, making it easy to view differences in coverage, costs, and network.

For Tampa small businesses, working with a broker like ProHealth PEO can make offering health insurance feasible much earlier than would otherwise be possible, and with much less hassle.

Conclusion: Finding the right timing for your Tampa small business

There's no one-size-fits-all answer to when your small business should offer health insurance. While you must provide coverage once you reach 50 employees, many Tampa businesses find value in offering health benefits much sooner.

The right time depends on your:

  1. Financial stability
  2. Growth goals
  3. Hiring needs
  4. Industry competition

Small business health insurance in Tampa is an investment in your company's most valuable asset - your people. When implemented successfully, health benefits can drive growth through improved recruitment, retention, and overall business performance.

The process becomes significantly easier when you work with experts who understand the local Tampa market and can guide you to the right solution for your specific business. Let the Pro Health PEO team help you find the right partner today!