An easy-to-follow guide for small business owners ready to take the leap.

Offering health benefits for the first time is a major milestone for any small business. Not only does it signal growth, but it also shows your team that you’re invested in their well-being. The process, however, can feel overwhelming if you’re new to it. From understanding your options to making sure your employees are informed and enrolled, there’s a lot to consider.

Most leadership teams jump into the process without stopping to ask, "When should a small business offer health benefits? How do we know if we're ready? What should we look for before making major investment decisions?"

That’s why we created this straightforward, jargon-free guide tailored specifically to small business owners and their executive teams. Whether you have a team of 3 or 50, this checklist will walk you through every step, helping you feel confident in your decision and supported along the way.

‍

When Should Your Small Business Start Offering Health Benefits?

1. Do Your Research

Before making any decisions, get a solid understanding of the different health benefits solutions available. Options include:

• Professional Employer Organizations (PEOs)
• Self-funded health plans
• Traditional insurance via brokers
• Shopping the Healthcare Marketplace

Take time to evaluate which type of plan might work best for your team size and budget. Knowing where you stand ahead of time will make this process run efficently once you start shopping for health plan options.

👉 Learn more about the different options for available for small businesses

‍

2. Talk with Your Team

It’s important to understand what your employees actually want in a health plan.

• Are they looking for affordable premiums?
• Do they need dental or vision?
• How important is mental health coverage?

You might be surprised at how much insight you gain just by asking. Create a quick anonymous survey or host a team meeting to collect feedback. Don't assume you know what your workforce deems a high. priority, allow them a chance to speak freely and raise their concerns.

‍

3. Schedule Discovery Calls

Once you’ve narrowed down your list of potential benefits providers, set up discovery calls with each of them. This is your chance to:

• Ask questions about their offerings
• Understand their pricing structure
• Gauge how well they align with your business needs and employee feedback

You should walk away with a clear picture of whether they’re a good fit. Once again asking yourself, when should a small business offer health benefits? Is there a time of year that works best for first-time offers vs roll-overs? You should have all these questions answered after you've taken time to review each providers employee plan stack.

‍

4. Align with Internal Stakeholders

If you have a leadership team, accountant, or HR consultant, loop them into the conversation. Be sure to align on important topics such as:

• How the cost of benefits will impact the company budget?
• Are there any legal or tax implications?
• Does everyone support the proposed solution?

Getting internal alignment ensures a smoother implementation. You'll be able to lay out a game plan and prepare for a smooth and successful open enrollment.

‍

5. Make Your Decision

Once you've gathered all your information, it's time to move forward. Now it’s time to:

• Review final proposals or agreements
• Ask any lingering questions
• Officially select your provider and sign on the dotted line

This is an exciting step — you’re almost there! Your internal stakeholders have agreed on details such as employer contribution, plan stack for W2 workers vs contractors, and you're ready to implement your hard work and get your team covered.

‍

6. Schedule Onboarding

Work with your new benefits provider to schedule an onboarding for both you and your team. Here you’ll have the opportunity to:

• Learn how to administer the plan
• Review important documents
• Set up employee info sessions or Q&As

A great provider will make this step easy, clear, and supportive. You will have a clear understanding of who your account manager or point of contact is, and you will have follow up meetings set to aid in the process so you aren't left alone if challenges arise.

‍

7. Begin Employee Enrollment

After your onboarding conversations, it's time for your team to officially enroll. Be sure to:

• Ensure everyone understands the options available
• Send clear instructions and deadlines
• Offer help for anyone with questions

Make this step feel approachable, not stressful. Meridio makes this easy by providing you with pre-drafted materials and guides to share with your team.

‍

8. Keep the Conversation Going

The relationship with your benefits provider shouldn’t end after enrollment. Continue to touch base regularly by:

• Scheduling a 6-month or annual check-in to evaluate how things are going
• Encouraging employee feedback on the benefits
• Notifying your provider of any changes like new hires or terminations

Health benefits should evolve with your business, so keep communication open and ongoing.

‍

What This All Means

Choosing to offer health benefits as a small business owner is a big move, but one that can lead to better employee retention, improved morale, and a stronger team. By following this checklist, you can confidently take each step knowing you’re doing what’s best for your people and your business.

‍

At Meridio, we specialize in making affordable, easy-to-manage health benefits accessible to small businesses like yours. If you’re ready to get started, we’d love to be part of your journey. Download our free guide, “First-Time Benefits Checklist for Small Business Owners,” to make your benefits selection and implementation process easier.