Running a small business or managing a team of contractors comes with its own unique set of challenges, and healthcare benefits often top the list of “I wish I could, but…” conversations. If you’re nodding along because you’ve been there, you’re not alone. The reality is that traditional group health insurance plans simply aren’t feasible for many small operations—whether it’s due to cost, headcount requirements, or the nature of your workforce.
But here’s the thing: just because you can’t offer a comprehensive group health plan doesn’t mean you’re completely out of options. There are creative, cost-effective ways to help your team with healthcare costs that won’t break your budget or require you to navigate the complex world of group insurance administration.
The Small Business Healthcare Dilemma
Let’s be honest about what we’re dealing with here. Traditional group health insurance plans typically require a minimum number of employees (usually at least two to five, depending on your state), come with significant administrative overhead, and can cost thousands of dollars per employee per year. For a business with three employees or a contractor managing a small team, these requirements can feel like trying to fit a square peg into a round hole.
The frustration is real. You want to take care of your people, but the traditional system seems designed for companies with HR departments and benefits administrators, not for the scrappy entrepreneur running a marketing agency from their home office or the contractor coordinating a small crew of skilled tradespeople.
Enter the Unsung Heroes: HRAs and FSAs
This is where Health Reimbursement Arrangements (HRAs) and Flexible Spending Accounts (FSAs) come into play. Think of them as the Swiss Army knives of healthcare benefits—versatile, practical, and perfectly sized for smaller operations.
Health Reimbursement Arrangements: Your Secret Weapon
An HRA is essentially a way for you to set aside money to reimburse employees for qualified medical expenses. What makes this particularly attractive for small businesses is the flexibility. You’re not locked into a specific insurance plan or carrier. Instead, you’re creating a fund that employees can tap into for legitimate healthcare costs.
There are several types of HRAs, but the most relevant for small businesses are Individual Coverage HRAs (ICHRAs) and Qualified Small Employer HRAs (QSEHRAs). With an ICHRA, you can reimburse employees for individual health insurance premiums and medical expenses. The QSEHRA is specifically designed for small employers with fewer than 50 full-time employees who don’t offer group health insurance.
Here’s what makes HRAs particularly appealing: you control the contribution amount, the money you contribute is tax-deductible for your business, and employees receive reimbursements tax-free. It’s a win-win situation that gives you the ability to contribute to your team’s healthcare costs without the complexity of managing a group plan.
Flexible Spending Accounts: The Employee-Funded Option
FSAs work differently but serve a similar purpose. These accounts allow employees to set aside pre-tax dollars from their paychecks to pay for qualified medical expenses. While employees fund these accounts themselves, you’re providing a valuable benefit that can save them hundreds or even thousands of dollars in taxes each year.
The beauty of FSAs is that they’re relatively simple to administer through an FSA provider and don’t require you to contribute any money. You’re essentially offering a tax-advantaged way for your team to pay for healthcare expenses they’d be paying for anyway.
Making It Work in Practice
Implementing these solutions doesn’t require a degree in benefits administration. Many third-party administrators specialize in HRAs and FSAs for small businesses, handling everything from account setup to claims processing. The administrative burden on you is minimal, but the impact on your team can be substantial.
Consider Sarah, who runs a small digital marketing agency with four employees. She couldn’t afford a $2,000 per month group health insurance plan, but she could manage a $300 per month QSEHRA contribution per employee. Her team members use this money to help pay for their individual health insurance premiums and medical expenses, effectively reducing their healthcare costs while allowing Sarah to provide a meaningful benefit. This type of flexible support can be particularly valuable for employees facing unexpected healthcare challenges, including those whose security disability denied claims have left them with additional financial burdens during appeals processes.
The Contractor Consideration
For those managing contractors rather than employees, the landscape is a bit different. While you can’t offer traditional employee benefits to contractors, you can adjust compensation to account for the fact that they’re responsible for their own healthcare costs. Some businesses create informal arrangements where they help contractors understand their health insurance options or provide resources for finding affordable coverage.
Beyond the Basics: Creative Solutions
Sometimes the best approach combines multiple strategies. You might offer an HRA alongside other perks like a wellness stipend, gym membership reimbursement, provide practical lifestyle items such as a dishwasher-safe slow juicer to encourage healthy habits at home, or even a simple increase in hourly rates or project fees with the understanding that this helps cover healthcare costs.
The key is communication. Be transparent with your team about what you can and can’t offer, and involve them in the decision-making process when possible. Sometimes a smaller, more flexible benefit that actually gets used is more valuable than a theoretical comprehensive plan that never materializes.
Read More: Transforming Billing Operations: Why Statement and Invoice Mailing Services Are a Game-Changer
The Bottom Line
Not being able to offer traditional group health insurance doesn’t mean you can’t help your team with healthcare costs. HRAs and FSAs provide legitimate, tax-advantaged ways to contribute to your employees’ healthcare expenses without the complexity and cost of group insurance plans.
The goal isn’t to replicate what large corporations offer—it’s to find solutions that work for your specific situation and budget. Sometimes the most effective benefits are the ones tailored to your team’s actual needs rather than what you think you’re supposed to provide.
Your business may be small, but your impact on your team’s financial well-being doesn’t have to be. These tools give you the power to make a real difference in manageable, affordable ways.




