Your guide to open enrollment: How small businesses can win the season

For most U.S. companies, open enrollment season runs from September through December—a critical window when employers select and adjust employee benefits for the year ahead. For small businesses, this time can be especially stressful. From deciding what benefits to offer, educating employees, and chasing down late-enrollers, open enrollment has the potential to distract from other critical work.

The good news? Rippling can help you get ahead of open enrollment and streamline the entire process.

What is open enrollment, and why does it matter?

Open enrollment is the annual period when employees can enroll in, update, or waive employer-sponsored benefits like medical, dental, vision, and more. Most companies run open enrollment between September and December, with coverage beginning in January. It’s a high-stakes time for employers with with benefits being an important factor in employee satisfaction. In fact, in a survey by Glassdoor, 51% of 2,700 professionals were not satisfied with their 2024 benefits package. But with the right preparation, open enrollment is an opportunity to reduce costs, offer competitive benefits, and build a better employee experience.

How to prepare for open enrollment season

The best open enrollment experiences don’t happen by accident—they start with proactive planning. Below are five key steps to help small and medium-sized businesses navigate open enrollment with confidence, clarity, and control.

Step 1: Start early—and set clear goals

Waiting until the fall to prep for open enrollment is one of the most common (and costly) pitfalls. Instead, start early and approach the season like you would any strategic initiative.

Ask yourself:

• What’s changed about my workforce? (headcount, geography, etc.)

• What do we know we want to keep or change?

• What kind of talent do we want to attract and retain? (remote, entry-level, local, etc.)

• Are we offering plans our employees actually use?

• What’s our budget, and can we stretch it further?

• What is the goal of our benefits program, and are we meeting it?

Remember to consider everyone in your employee population. Don’t assume everyone needs the same thing from their benefits. Some employees may need more robust healthcare, while others may prioritize a cheaper option. 

Step 2: Choose plans that fit your team—not just your budget

Many small businesses default to offering the same plans as last year, but this approach can cost more than it saves. By giving your employees options, shopping around, and exploring flexible spending accounts, you can save money while offering great benefits to your employees. 

Here are our top tips for choosing employee benefits plans:

• Shop around: Insurance isn’t one size fits all. Do research on different types of insurance and explore different carriers and plans.

• Consider spending accounts: If your employee population is young and healthy, a high-deductible health plan paired with a health savings account (HSA) may be a great option. 

• Remember multi-state compliance: If you’re hiring across multiple states, you may need broader coverage and support to meet local regulations.

• Don’t stop at health insurance: Benefits packages that include things like mental health coverage, fertility treatments, and commuter benefits can attract and retain top talent. 

With Rippling, you can offer medical, dental, vision, flex, commuter, fertility, and even pet insurance—all in one system. You can also analyze enrollment trends and plan usage to make informed, data-driven decisions year over year.

Step 3: Consider a PEO to save time, money, and complexity

Running a small business means wearing a lot of hats—but benefits, HR, and compliance shouldn’t slow you down. That’s where Rippling PEO comes in. It’s the easiest way to provide affordable, big-company benefits and receive HR and compliance support, all in one unified platform.

With Rippling PEO, you get:

• Top-tier benefits: Access big-company benefits at affordable rates from leading carriers.

• Comprehensive compliance: From ACA and COBRA reporting to state and local payroll tax account setup, leave the busy work to us.

• Expert guidance: SHRM- and PHR-certified advisors are on the ready to advise on everything from leave policies to terminations.

Rippling PEO isn’t just about simplifying open enrollment—it’s about taking benefits, compliance, and HR work off your plate so you can focus on growing your business.

Step 4: Make enrollment easy and error-free

One of the biggest pain points during open enrollment? Chasing down employees to enroll and manually syncing elections with payroll.

Rippling eliminates that friction by:

• Automatically inviting employees to enroll

• Sending reminders via workflows and email nudges

• Letting employees compare plans, see costs, and make updates on desktop or mobile

• Automatically updating payroll deductions in real time

You can track enrollment progress in a single dashboard, flag missing submissions, and rest easy knowing everything is compliant and synced.

Step 5: Stay compliant without lifting a finger

Small businesses are often at risk of missing key compliance requirements. Rippling automates the most time-consuming tasks—like COBRA and ACA filings, benefit eligibility tracking, and notices—so you can focus on your business, not paperwork.

If you’re offering benefits across multiple states, Rippling even handles complex local filings and registrations: everything from payroll tax accounts to commuter benefit ordinances.

Finish open enrollment in days, not weeks

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Mistakes that can derail open enrollment, and how to avoid them

Even with the best intentions, open enrollment can quickly go off track without the right planning. Here are some of the most frequent missteps small businesses make, and how you can steer clear of them this year:

• Waiting too long to start: A last-minute scramble often results in rushed decisions, missed deadlines, and limited plan options.

• Repeating last year’s playbook: Your team and business have likely changed. Sticking with the same benefits year after year may no longer meet your employees’ needs.

• Focusing only on medical coverage: Overlooking supplemental benefits like mental health services, commuter perks, or fertility support means missing out on what employees actually value.

• Relying on disconnected systems: Managing benefits across multiple platforms creates unnecessary admin work and increases your risk of compliance issues.

Streamline open enrollment with Rippling

Open enrollment doesn’t have to be a logistical headache. Whether you’re using Rippling PEO, bringing your own broker, or using Rippling brokerage, Rippling gives you one unified platform to manage your benefits administration—from plan selection and enrollment to compliance and payroll.

With Rippling, you get:

• A true all-in-one benefits platform: Every benefit—from medical to 401(k)—is connected to the same system as your payroll and HRIS.

• Flexibility: Join our PEO, use Rippling Brokerage, or bring your own broker—without disrupting workflows. As your business needs change, your benefits strategy can evolve too without ripping and replacing systems.

• Empowered employees: A modern interface lets employees compare plans, see costs, and enroll in plans, all from desktop or mobile.

Whether you’re preparing for your first open enrollment or looking to simplify a complex program, Rippling gives you the clarity, control, and confidence to deliver a benefits experience your employees will actually use and love.