2027 Open Enrollment Preparation
Open enrollment may only happen once a year, but the decisions made during that period can impact employees and employers for the next 12 months and beyond.
Too often, organizations treat open enrollment as a last-minute administrative task. Benefits decisions are rushed, communications are delayed, and employees are left scrambling to understand their options before deadlines arrive.
The reality is that a successful open enrollment season starts months before enrollment begins. Employers that prepare early have more time to evaluate their employee benefits strategy, educate employees, and create an enrollment experience that drives engagement and appreciation. Those that wait until the last minute often face increased confusion, lower participation, and avoidable frustrations. Many employees spend less than two hours reviewing their benefit options during open enrollment, making early and effective communication even more important.
Why Open Enrollment Is More Important Than Many Employers Realize
Open enrollment is more than selecting a health plan. It’s one of the few times each year when employees actively evaluate the value of their employer-sponsored benefits package. During this period, employees decide which plans best meet their needs, compare options available, and determine whether their current benefits support their personal and financial goals. It’s also an opportunity for employers to showcase the investment they’re making in their workforce.
When employees understand and appreciate their benefits, they’re more likely to see value in staying with their organization. Conversely, when benefits are poorly communicated or difficult to understand, employees may underestimate the total value of their compensation package. Many workers don’t fully understand the benefits they already have access to, which can lead them to seek opportunities elsewhere for benefits they may already receive.
The Cost of Waiting Until the Last Minute
Every year, employers underestimate how much planning, coordination, and communication goes into a successful open enrollment season.
When preparation starts too late, organizations often encounter challenges such as:
- Employees making uninformed benefit elections
- Increased questions and administrative burdens on HR teams
- Poor participation in voluntary benefits
- Missed communication opportunities
- Confusion around plan changes and enrollment deadlines
- Lower employee engagement with benefits offerings
The longer an organization waits to plan, the less time employees have to understand their options and make informed decisions.
Review Your Benefits Strategy Before Enrollment Begins
Open enrollment season is the perfect time to evaluate whether your benefits package still aligns with employee needs.
Employee expectations continue to evolve, and benefits that were considered competitive a few years ago may no longer be enough to attract and retain top talent.
Research continues to show that employees value benefits such as:
- Affordable health insurance coverage
- Flexible work arrangements
- Paid leave programs
- Retirement savings plans
- Mental health resources
- Family-building and reproductive health benefits
- Caregiving support
- Financial wellness resources
- Professional development opportunities
- Voluntary benefits such as disability, critical illness, and hospital indemnity insurance
Before open enrollment, employers should gather employee feedback and evaluate whether their current offerings reflect what employees value most.
Develop Your Communication Strategy Early
One of the biggest mistakes employers make is focusing solely on plan selection while overlooking communication. Even the best benefits package won’t provide value if employees don’t understand it.
An effective open enrollment communication strategy should begin well before enrollment opens and include multiple touchpoints throughout the process. Employees consistently report wanting additional guidance and education regarding their benefit options.
Successful communication plans often include:
Educational Meetings
Group presentations can help employees understand available plans, key changes, and enrollment deadlines.
Individual Support
One-on-one meetings provide opportunities for employees to ask questions based on their specific situations.
Multi-Channel Communication
Not every employee consumes information the same way. Consider using:
- Emails
- Enrollment guides
- Videos
- Presentations
- Printed materials
- Online enrollment resources
Providing information through multiple channels can improve awareness and encourage participation.
Ongoing Reminders
Frequent reminders about deadlines, enrollment instructions, and available resources help ensure employees stay informed throughout the process.
Use Open Enrollment as a Retention Tool
Benefits remain one of the most influential factors in attracting and retaining employees. In a competitive labor market, open enrollment presents a valuable opportunity to reinforce the full value of your employment offering.
A well-executed open enrollment strategy helps employees:
- Understand their benefit options
- Appreciate their employer’s investment
- Make more informed decisions
- Feel supported throughout the process
When employees understand the value of their benefits, they’re more likely to remain engaged and connected to their organization.
Start Preparing Now
The most successful open enrollment seasons don’t happen by accident. They result from months of planning, thoughtful communication, and a clear understanding of employee needs. Starting early gives employers time to refine their benefits strategy, educate employees, and avoid the headaches that come with last-minute enrollment efforts.
The sooner planning begins, the more effective and less stressful the enrollment experience becomes for everyone involved.
Partner With Tower Street for Open Enrollment Success
At Tower Street, we help employers lead a more organized, strategic, and effective open enrollment process from start to finish. Our Employee Benefits team works proactively throughout the year to evaluate benefits offerings, develop communication strategies, coordinate enrollment timelines, and create employee education materials that drive engagement and understanding.
From enrollment guides and presentations to employee meetings and benefits communication campaigns, we help take the heavy lifting off your team so you can focus on running your business. By starting early and partnering with Tower Street, employers can reduce administrative burdens, improve employee participation, and create a more successful open enrollment experience for everyone involved.
Whether you’re preparing for 2027 open enrollment or looking to strengthen your overall employee benefits strategy, we’re here to help every step of the way.
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