Originally published 6/30/21, Updated on 4/7/23

You’ve survived the Great Resignation, the Great Onboarding, Quiet Quitting, and now you face other challenges—recession worries, potential layoffs—it’s been a wild ride in the world of HR. But yet again, another annual hurdle is on the horizon—open enrollment. In these rapidly evolving times, it can feel like an uphill battle to make your team members (remote and in-person, new and old) focus on benefits. 

But let’s focus on some good news! The workforce is more diverse than it’s ever been. Your team members want more benefits and financial education—91% of employees agree it’s important to understand their benefits. On top of that, 89% of employees use open enrollment as an opportunity to consider health decisions, expenses, and anticipated needs for the year ahead. Moreover, six in 10 folks agree that living through the pandemic led to more financial awareness among younger generations (especially in comparison to their older counterparts).

Bottom line: open enrollment is a huge opportunity for you as an employer to promote your inclusive benefits offerings, encourage smarter benefits choices, and drive year-round engagement.

It all comes down to devising the perfect open enrollment strategy for your team. As such, we’ve created a step-by-step open enrollment communication timeline to manage and succeed with the planning process. Let’s get started! 

Planning and Strategy 

As Benjamin Franklin once said, “If you fail to plan, you’re planning to fail.” 

Okay, that’s the last cliche quote we’ll use in this guide—but it’s true! So, before we dive into the open enrollment timeline itself, you’ll need to lay the groundwork with a pre-enrollment strategy. 

We know it’s easy to get into the weeds when planning for open enrollment, especially for remote and hybrid teams, so we’ve broken this process down into five easy steps. 

Step 1: Identify changes for this year 

According to our HR Priorities Report, employers are doubling down on mental health offerings and holistic wellbeing support after another tumultuous year. Additionally, the rollercoaster workforce (i.e., people leaving their jobs in droves, mass hiring, remote onboarding, rounds of tech layoffs, etc.) further highlighted shortcomings in the areas of HR, healthcare, and financial wellness. 

As a result of this and other shifts, you’ll need to take a second look at your current benefits offerings to see what’s working and what isn’t. Work with your HR team and managers to understand utilization of current programs. Often, the problem isn’t that you need more benefits, it’s that you need better benefits utilization of the programs you do have.

ALEX uses predictive analytics to help you simplify the benefits puzzle.


Step 2: Review last year’s open enrollment strategy and materials 

There’s no better way to plan ahead than by looking back on past efforts. Take stock of the previous year’s open enrollment, including your plans, execution, resources, and results.

As you evaluate, ask yourself: 

  • What materials (digital and physical) did you send to employees last year? 
  • Which communication channels did you use?
  • Where did you see the most engagement or participation?
  • What went right/wrong? 
  • Did you have goals in place that you didn’t reach? If so, how could you avoid those challenges this year?

Step 3: Establish clear goals 

How can you measure success without having set goals in place? (Hint: you can’t). Develop your open enrollment goals based on current benefits offerings with last year’s lessons in mind. 

The key is to make each goal quantifiable, so you can definitively analyze your performance post-open enrollment. 

Formula for writing open enrollment goals

“Accomplish [quantifiable goal] by [action].”


  • Increase HDHP enrollment by 30% by providing more personalized benefits education materials.
  • Reduce the amount of time spent answering benefits questions by investing in benefits engagement technology.
  • Achieve at least 20% enrollment in our new mental health benefit by sharing employee testimonials about why it’s helpful.

Step 4: Gather employee feedback on the process 

During the open enrollment timeline, it’s important to keep in mind the main objective—getting employees to understand their benefits. That’s what makes this planning step so important—to confirm they did indeed understand and engage with their benefits this past year. Perhaps you sent out a post-open enrollment survey last year that you can reference? 

If not, you can also send out a quick employee engagement survey to gauge the effectiveness of your past communications and ask for honest feedback on the overall process. 

Use this information to guide your strategy.

Need help with your overall employee messaging? Get customized benefits communications with Jellyvision Custom Solutions.

Learn more

Step 5: Choose your channels

Now that you’ve gathered needed improvements, lessons learned, employee feedback, and set clear goals, you can decide how to deliver your open enrollment messaging. 

We recommend a more virtual approach than you might be used to (more on that later). But we understand every organization is different, so choose from the following channels to focus on:

  • All-company meeting
  • Benefits guide
  • Email campaigns
  • Posters
  • Intranet ads
  • Postcards or other mailers
  • Brochures
  • Benefits fairs/vendor presentations
  • Benefits engagement platforms, like ALEX
  • Mobile apps, like ALEX Connect

Make this year’s benefits presentation your best ever.

Learn how

Open enrollment communications timeline

Now, let’s get down to the nitty-gritty—executing your strategy. Follow this open enrollment communications timeline to ensure proper delivery of applicable resources and messaging to your people. You’ll note we’ve included links to additional resources for help along the way. 

8-12 weeks before

First stop: the benefits guide and resources. 

Embrace virtual 

Even if your team is back in the office or using a hybrid work model, there’s no reason to ditch the digital methods you’ve used the past few years. Virtual open enrollment means less footwork for your HR team, lower expenses for print material, and increased access for your employees. 

In other words, your people don’t have to go searching through a pile of documents but instead can log on to your benefits dashboard (via their desktop or phone!) and easily access open enrollment information at any place or time.

You need to meet your employees where they live, and for most, that’s on their digital devices.

For a successful virtual open enrollment, ensure you have these six must-have tools.

Read more

Update your benefits guide 

The benefits guide is the bible of your open enrollment process. But unlike testaments set in stone, you should update this resource yearly to reflect your latest offerings. 

Here are a few pointers to optimize your guide: 

  • Call out your most important info at the beginning. Greet the skimmers by dedicating one of your first pages/sections to a brief (bulleted list with any new details, what’s the same, and how to enroll). 
  • Use call-to-actions as much as possible, i.e., tell people the next steps to take and point them in the right direction. 
  • Link to or highlight your benefits engagement platform. Mention all ways to access it like via desktop, an app, or by creating an account. (For example, with ALEX ID, users can create an account and it will save their information and make educated suggestions throughout the year!)

For a deeper dive, check out our guide, Nine Tips for an Engaging, Readable, Not-Boring Benefits Guide.

Read now

Dust off the rest of your enrollment materials 

Time to pull out the enrollment materials you’ve used in the past. Here’s where you’ll make strategic cuts based on employee feedback. Don’t reuse any materials or content that saw little to no engagement. Make sure to audit and update anything you send it out.

No need to reinvent the wheel here! Use our easy, customizable templates to create common open enrollment materials.

Download now

4 weeks before

Publish intranet ads 

For those with an in-house intranet, create ads and announcements to remind your team that open enrollment is on the horizon. If you have a large headcount, consider targeting your ads to appeal to different audiences. 

Pro tip: Tools like ALEX Connect can send push notifications straight to your employee’s pockets. Repurpose your intranet ads for those mobile messages.

Promote everywhere 

Your main objective a month out should be to raise awareness that open enrollment is happening. You want to explain to employees that it’s a critical time to get the most out of their benefits while reassuring them that your HR team and benefits support tools are there to help. 

Don’t forgo any opportunity to toss in a reminder, like your HR team’s email signature. 

Leverage managers and leaders

HR can’t reach all of your people alone. Enlist the assistance of leadership throughout your company to communicate important open enrollment messages and deadlines to their direct reports. 

But remember, managers and team leads are busy people too, so you want to leave enough time in your open enrollment communications timeline to warn them you’ll need their help. To make the process easier, offer them a toolkit that includes basic open enrollment talking points and FAQs.

To better connect with employees, share our seven open enrollment tips with your HR team and managers!

Read now!

1-2 weeks before 

Mail out and distribute any physical resources 

While we can all try to go digital as much as possible, we know there are certain times when you might have to share physical resources. Since snail mail takes a little longer than virtual counterparts, plan for materials (like your physical benefits guide or postcards) to arrive one week before open enrollment. 

For those companies with in-office workers or hybrid teams, you can also hang up posters or on-site visual announcements to raise awareness the week before open enrollment. 

Jellyvision Custom Solutions can help you create and distribute all of your open enrollment materials.

Learn how

Send the open enrollment intro email 

The time has come to officially announce the kick-off of open enrollment. To get on your team’s radar, send a company-wide email with bulleted info. This communication should highlight need-to-know dates and essential details. 

Outline expectations for the following few weeks, including: 

  • Open enrollment start and end dates 
  • Invitation to company-wide meeting
  • Link to your benefits engagement platform if you have one (Like ALEX!)
  • Links to any other open enrollment resources, like your benefits guide or FAQs 
  • Short but persuasive reminder that open enrollment is the one time per year when employees can make changes to their benefits

Pssst! We’ve got six ways to level up your open enrollment emails to employees.

Improve those emails!

Hold a company-wide meeting

Sometimes, all the communications and resources in the world can’t compete with good old-fashioned meetings. 

Assemble your employees for a company-wide gathering one week before open enrollment starts. This event can be in-person, virtual, or hybrid—dealer’s choice! For larger teams, consider hosting a few different time slots to fit within everyone’s schedule.

And let’s be honest, there will be people who won’t make it or just won’t pay attention. C’est la vie! To address this inevitable issue, record at least one of your sessions so employees can reference it later. 

Want to optimize your presentation for your company-wide? Check out our seven easy ways to improve your slide deck/PowerPoint!

Learn more

Share FAQs

FAQ documentation is your best friend. It makes life easier for HR folks. And you can bet, if one person is wondering about something, others likely are too. So keep a running list of FAQs with clear and concise answers. Make the responses conversational and easy to follow, avoiding any jargon.  

You can share these in an FAQ page on your intranet or email them out to your team.

Guess what? ALEX can eliminate the need for FAQs. Book a demo and find out why!

Book a demo

During open enrollment 

Send email and text reminders 

Employees need reminders during the open enrollment process to, you know, actually enroll in their benefits plan. Most people equate figuring out and choosing health insurance to a trip to the dentist, so, unfortunately, they’ll likely put it off. Your job is to convince them it’s not nearly as bad. For instance, they can save money, invest more in their future, and access more robust benefits! How exciting! 🎉

Pro-tip: A benefits engagement tool like ALEX can help you make this process a little less tedious and highlight how to wisely navigate open enrollment. 

Send email reminders throughout open enrollment and especially in the days leading up to your deadlines. Encourage your team to access resources, ask for help, and use their benefits engagement platform. If you can, consider sending text reminders or pinging them on your messaging platforms like Slack. This can help reach those remote team members and avoid over-stuffed inboxes.

Our virtual open enrollment playbook has lots more tips on using texting and other tools in your approach.

Get the Playbook

Host office hours (virtual or in-person) 

Office hours offer a low-pressure way for your employees to ask questions, seek advice, and troubleshoot any issues. Scatter some time slots throughout the week where your HR team members are open for business. Remember, people will procrastinate, so you may want to increase office hours closer to your open enrollment deadlines. 

Check out how one of our customers creatively used ALEX to reach a multi-generational, distributed workforce and boost mobile engagement by 33%.

Learn more

Remind leadership to plug open enrollment 

You may have already asked them and sent them a tool kit—but you know that HR is all about that follow-up. So circle back with your managers, team leads, etc., and remind them to help you promote open enrollment. A simple mention in a meeting, a team slack, or even an email can go a long way with employees, especially when it comes from the people they work with and trust. 

After open enrollment


You made it! You deserve a pat on the back and a little R&R. 


We know, the last thing you want to do after the marathon of open enrollment is start planning for the next year. We get it! But it’s beneficial to quickly review your process and results while it’s still fresh in your mind so you can document for next year. It’s a lot easier to discuss what went wrong and right now than in eight months. 

To simplify this exercise, leverage our guide, The Post-Open Enrollment Survey Every HR Team Should Send

Get the guide

Empower employees to engage with their benefits all year long 

Your people can (and should) engage with their benefits all year long, not just at open enrollment. While it’s not easy, it’s on your HR team to encourage benefits utilization, remind them of the advantages of your offerings, and maximize your organization’s investment in your programs. It’s a tall order, we know!

So don’t go it alone. A platform like ALEX can be your partner in all things benefits. Tools like ALEX ID allow folks to create an account, opting in for year-round reminders and tips about how to best use their benefits. ALEX Connect moves benefits communication to your employee’s favorite device—their mobile phone! Jellyvision Custom Solutions can be an extra team member during those busy open-enrollment months. We’ll help you create unique assets—flyers, emails, you name it! On top of all of that, ALEX is getting a make-over this fall, just in time for Open Enrollment, to offer an even better experience for our users.

Chat with one of our team members to learn more!

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