Open Enrollment Strategy for Employers: How to Run a Smarter Process in 2026

Open enrollment is one of the most important periods in your company's benefits calendar. It is also one of the most mismanaged.

For many employers, open enrollment is a scramble — a few weeks of frantic emails, confused employees, and last-minute decisions that lock the company into another year of suboptimal coverage. But the employers who get the best outcomes treat open enrollment as a strategic event, not an administrative chore.

With healthcare costs projected to climb by as much as 9 percent in 2026 — the largest increase in over a decade — getting open enrollment right has never been more important.

Here is how to run a smarter process.

Start Planning Immediately After the Last One Ends

The most common mistake employers make is waiting until 60 days before renewal to start thinking about open enrollment. By that point, your options are limited, your timeline is compressed, and your decisions are reactive rather than strategic.

The best employers begin planning for the next open enrollment as soon as the current one wraps up. This means conducting a debrief while the experience is fresh: what went well, what caused confusion, what questions employees kept asking, and where the process broke down.

It also means starting your benefits review early. Request claims data from your carrier, analyze utilization patterns, and begin conversations with your broker about what changes to evaluate for the next plan year.

Know What Changed This Year

Every year brings regulatory updates that affect how you structure and communicate your benefits. In 2026, several changes are worth paying attention to.

HSA contribution limits have increased. For 2026, individuals can contribute up to $4,400 and families up to $8,750. If you offer a high-deductible health plan with an HSA, make sure your employees know about these higher limits — and consider whether an employer HSA contribution would make the plan more attractive.

The dependent care FSA limit has also increased for the first time in decades, rising from $5,000 to $7,500 per household. This is a meaningful change for employees with childcare expenses and worth highlighting during enrollment.

ACA affordability thresholds have been adjusted, and penalty amounts for applicable large employers continue to increase. Make sure your plan meets the affordability and minimum value requirements before enrollment opens.

Mental health parity rules under the Mental Health Parity and Addiction Equity Act have also been strengthened, with expanded documentation requirements taking full effect. If you have not reviewed your mental health and substance use benefits for parity compliance, now is the time.

Design Your Plan Options Before Enrollment Opens

Open enrollment is not the time to be finalizing plan designs. By the time employees start making elections, you should have already completed your renewal negotiation, finalized which plans you are offering, modeled the cost impact of any changes, and prepared comparison materials.

If you are considering adding a new plan option — such as a high-deductible plan alongside your existing PPO — the analysis and decision-making should happen well in advance. Launching a new plan option during enrollment without adequate preparation and communication is a recipe for low adoption and employee confusion.

The most effective approach is to present employees with two or three clear plan options, each with a straightforward comparison of premiums, deductibles, out-of-pocket costs, and key features. Decision fatigue is real. More options does not mean better outcomes.

Communicate Early, Simply, and Often

Employee education is the single biggest lever most employers are underutilizing during open enrollment. Research consistently shows that a significant portion of employees do not read or fully understand the benefits communications they receive. Many end up selecting plans that are not the best fit for their situation.

The problem is usually not that employees do not care. It is that the information is too complex, too dense, or delivered too late.

Start communicating at least three to four weeks before enrollment opens. Use plain language — not insurance jargon. Explain what is changing and why. Provide clear side-by-side plan comparisons. And offer multiple formats: email summaries, short videos, printed one-pagers, and live or virtual Q&A sessions.

If you are making changes that affect employee costs — new deductibles, different copays, higher premiums — address them directly and honestly. Employees respond much better to transparent communication about cost increases than to discovering changes after they have enrolled.

Help Employees Make Better Decisions

Most employees are not benefits experts, and they should not have to be. But they do need help understanding which plan makes the most sense for their situation.

Consider providing a simple decision-support framework. For example, a chart that shows which plan is likely to cost less for someone who rarely visits the doctor versus someone who has regular prescriptions versus someone expecting a major medical event in the coming year.

HSA education is particularly important. Many employees are unfamiliar with health savings accounts or underestimate their value. Explain the triple tax advantage, the fact that HSA funds roll over year to year, and how an employer contribution can offset the higher deductible.

Some employers are also beginning to use digital decision-support tools that ask employees a few questions about their expected healthcare usage and recommend a plan based on their answers. These tools can significantly improve plan selection and reduce the number of employees who end up in plans that do not match their needs.

Do Not Forget About Non-Medical Benefits

Health insurance gets the most attention during open enrollment, but it is not the only benefit employees need to evaluate.

Make sure you are giving employees adequate time and information to review their dental and vision coverage, life and disability insurance elections, FSA and HSA contributions, voluntary benefits like accident insurance, critical illness, or legal plans, and retirement plan contributions and employer matching.

Many employees miss opportunities to optimize these elections because the focus is so heavily on medical insurance. A well-organized enrollment process gives equal attention to the full benefits package.

Set Clear Deadlines and Follow Up

Missed enrollments are a persistent problem. Some employees fail to complete their elections due to procrastination, confusion about the deadline, or simply forgetting.

When an employee misses the enrollment window, they may lose access to coverage or be defaulted into a plan that does not fit their needs. This creates frustration, increases HR workload, and can affect morale.

Set a clear deadline and communicate it repeatedly. Send reminder emails at the one-week and two-day marks. Have managers check in with their teams. If your benefits platform supports it, use automated reminders and progress tracking.

Some employers also find it helpful to extend enrollment hours or offer dedicated time during the workday for employees to review and complete their elections, particularly for hourly or shift-based workers who may not have easy access to a computer.

Audit After Enrollment Closes

Once enrollment is complete, the work is not over. Conduct a post-enrollment audit to verify that all elections were processed correctly, payroll deductions are accurate, carrier enrollment files match your records, COBRA notices are sent to any employees who lost or declined coverage, and compliance documentation is in order.

Catching errors in the first few weeks is much easier — and cheaper — than discovering them months later when an employee needs to use their coverage and finds out something is wrong.

Build a Year-Round Benefits Communication Strategy

The employers who get the best results from open enrollment are the ones who do not treat it as the only time they talk about benefits.

Year-round communication — a quarterly benefits newsletter, periodic reminders about HSA contribution opportunities, wellness program updates, and mid-year check-ins — keeps employees engaged with their benefits and reduces the learning curve when enrollment comes around again.

When employees understand their benefits throughout the year, they make better decisions during open enrollment. And better decisions lead to lower costs for both the employer and the employee.

The Bottom Line

Open enrollment is one of the highest-impact opportunities you have to manage your benefits costs and improve employee satisfaction. The difference between a well-run enrollment process and a disorganized one can be tens of thousands of dollars in misallocated spending and a workforce that is confused and frustrated with their coverage.

Start early, communicate clearly, simplify the decision-making process, and follow up after enrollment closes. These are not complicated steps, but they require planning and intentionality.

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Want help building a smarter open enrollment strategy? Schedule a free benefits strategy review and we will help you plan an enrollment process that reduces costs and improves the employee experience.