The Frontline Open Enrollment Playbook: How to Drive Benefits Participation

When Mollie Cook joined Nye Health Services as VP of Team Experience, one of the first things she needed to understand was how the organization actually talked to its employees.

She had come from a much larger company. So when she had an important message to get out to team members — she remembers it being benefits open enrollment — she asked a simple question: how do we do that here?

The answer surprised her.

For benefits enrollment, at an organization with hundreds of employees across multiple sites, who are constantly moving during their shift rather than sitting still at a desk, a flyer by the time clock wasn’t going to reliably reach everyone. Mollie knew that approach wouldn’t work.

Her story reveals a bigger problem. Enrollment participation for salaried employees is often treated as a decision barrier: they see their options, weigh the plans and choose whether or not to enroll. But for frontline teams, it’s far more often a communication barrier. People aren’t necessarily turning down coverage. They may never have known what their potential benefits are and when the enrollment window was open.

That distinction matters because it changes what you need to fix. If employees are actively declining coverage, the answer may be a better plan design or clearer plan education. But if they never what benefits were accessible to them and/or when to access them, then no amount of plan redesign will help. The answer is getting the right information to the right people at the right time, which comes down to the communication channel and the cadence.

There's a second reason to get this right. Plan redesign, richer employer contributions, and expanded benefits education all cost real money and take a full cycle to implement. Drastically improving how many of your employees know that you actually have richer contributions or expanded benefits costs a fraction of that. It's also the only fix that tells you what the underlying problem actually was. Imagine a marketing campaign that reached 5% of your potential customers, and that 5% looked nothing like the other 95%. Nobody would read that response as a verdict on the campaign, and enrollment data works the same way. Once a campaign reliably reaches everyone, the participation numbers that come back finally mean something: the people who didn't enroll saw the information and made a choice.

This playbook focuses on the delivery side, because that's the part communication can fix. It explains why frontline enrollment breaks down, lays out a five-touch campaign designed to fix it, and covers the timing rules that help each message land. It also shows how to make enrollment a two-way conversation, and how to fund the approach with dollars that may already be available within existing benefits contracts.

This guide includes three practical tools to help: a message template pack, a broker question kit, and a readiness assessment.

What is open enrollment communication for frontline employees?

Corporate benefits communication assumes three things: an inbox people check, a login they remember, and a few quiet minutes at a desk. Those assumptions hold for the office. They fall apart on a production floor, in a care facility, across a restaurant group, or anywhere people spend a shift on their feet.

Jennifer Schultz, National Director, Talent Strategy & Programs at The Goodman Group, puts the gap in six words: "4,000 employees. No one has emails."

Ashleigh Griffith, Director of Marketing at Quality Brand Group, describes what that produces in practice:

That is the enrollment problem most frontline organizations can relate to. The people who need the reminder most are the ones the message never reaches.

Three groups own this together, and enrollment campaigns tend to stall when only one of them is in the room. HR and benefits leaders own participation and the annual number that gets reported up. Operations leaders own the hours the window eats from site leaders fielding questions. IT owns the connection to the HR system and the benefits record keeper. A plan that works for all three moves quickly.

Why open enrollment breaks on the frontline

1. The email does not arrive

Email is the weakest link in frontline enrollment. Some employees never provide a personal email address (and most are not provided with a corporate email address). Others change personal addresses every few months. And employees who do have a company address often have no routine reason to check it during a shift. A mobile number, by contrast, tends to stay the same for years and is already sitting in the HR system.

Jeremy Edmonds, EVP of People and Culture at Snooze, saw it in their own data:

An enrollment list built on email decays between enrollment windows. One built on mobile numbers stays current.

2. The message reaches some people, in some version, at some point

When a distributed team depends on information passing through several hands in a “command and control” fashion, the message changes shape along the way. Site leaders relay what they remember, on whatever schedule the shift allows. Details drift. Some locations hear a version of it, some hear it late, and some never hear it at all.

Bianca LaFountain, VP of Talent Acquisition at GPM Investments, describes it as a game of telephone:

For benefits enrollment, a different version of the message is worse than no message. A changed deadline, missing eligibility detail, or incomplete instruction can prevent someone from enrolling—and make employees less confident that the information they’re receiving is accurate.

3. The portal is the wall

Every step between reading the message and finishing enrollment is a place to lose someone. An employee reads a reminder on a break, opens the link, and hits a login screen for a system they used once last year. They don't remember the password. The chance they come back to finish later is slim, and in the enrollment numbers that friction looks identical to a decision not to enroll.

That's why access, not features, is usually the first requirement. Jeanette de Sousa, Corporate Director of Human Resources at Mainsail, identifies the hurdle:

The shorter the path from message to action, the more employees complete it. Anything that adds a registration step or a password reset costs participation that has nothing to do with the plans on offer.

4. Nobody can confirm it landed

Most organizations have no reliable way to know whether frontline employees received an enrollment message. They know the notice went out, but they don't know who it reached.

That gap becomes a problem when participation comes in flat. If the campaign looks complete, the natural conclusion is that employees saw the message and chose not to enroll. The next year's fix gets aimed at plan design, cost, or education, all of which are expensive and none of which address the actual failure. Without visibility into reach, the data can't distinguish between employees who declined coverage and employees who never knew the window was open.

You can't diagnose an enrollment program without first confirming the message was received.

5. One announcement has to do too much work

Even when the right message reaches employees, a single announcement is rarely enough to drive action.

Frontline employees are receiving enrollment information in the middle of everything else competing for their attention: customers, coworkers, shift changes, operational updates, and the demands of life outside work. They may see an enrollment announcement and intend to come back to it later. Without a follow-up, “later” can easily become “after the deadline.”

That’s why enrollment communication has to work as a campaign, not an announcement. The first message creates awareness. Follow-ups reinforce what matters, answer questions, surface the deadline, and give employees another opportunity to act.

A message sent is not the same as a message acted on. A campaign helps close that gap.

What good looks like

Organizations that improve frontline benefits enrollment are rarely just writing better emails. They’re changing how, and how often, they communicate.

The channel piece is straightforward. Text puts the message on a device employees already carry and check; on average, text messages have a 98% open rate, and most are read within three minutes. Instead of asking employees to go find enrollment information, the information comes to them. No download, no account creation, no password required.

Cadence matters just as much. A single announcement assumes the employee sees it, has time to read it, and is able to act on it when it arrives. For someone moving through a frontline shift, that’s a lot to assume. Repeating the message throughout the enrollment window isn’t overcommunicating; it’s creating multiple opportunities for employees to see the message and act before a fixed deadline passes.

Here’s a real enrollment message from a senior living operator:

It's a strong example because every word does a job. Employees know the window is open, where to go, what action to take, what happens if they do nothing and exactly when the deadline hits. There’s one clear ask, no jargon and little room for ambiguity.

That’s the standard: make the message easy to receive, easy to understand and hard to miss.

A campaign like this runs on infrastructure: a way to reach every employee directly, a list that stays current as people join and leave, and visibility into who acted. Those three things are what separate a campaign from a send. Solutions built for frontline communication and engagement, goHappy among them, exist to provide them.

How to create a better benefits enrollment campaign

Touch 1: Awareness, 30 days out

What it needs to do. Give employees time to think, gather questions, and talk to a spouse or partner before they need to make a decision. No action required yet; the goal is to make sure no one is surprised when enrollment opens.

What it needs to say. The enrollment dates, one sentence on what, if anything, is changing, and where employees can go with questions.

Suggested copy:

Open enrollment starts [DATE]. You'll have until [DEADLINE] to pick your benefits for next year. Nothing to do yet. Questions? Text BENEFITS or talk to [CONTACT].

Worth automating. Schedule this touch in advance so every employee gets the same runway without someone having to remember to send it. For a busy leadership team, benefits reminders are better running in the background than living on someone's to-do list.

Touch 2: Kickoff, day one

What it needs to do. Open the enrollment window and make the next step unmistakable. Employees should immediately know where to go, when they need to act and where to get help.

What it needs to say. Link first. Deadline second. Help contact third. That’s it.

Suggested copy:

Open enrollment is open now: [PORTAL LINK]. Pick your benefits or decline them by [DEADLINE, with time]. Your current benefits will not carry over automatically. Need help? [CONTACT].

A note on auto-rollover. Include that line only when it is true for your plans. When it is, say it plainly. Employees who assume last year’s elections will carry over may otherwise have little-to-no reason to act.

Touch 3: Midpoint, targeted

What it needs to do. Reach employees who still need to act without continuing to remind those who have already completed enrollment. This is where the campaign becomes targeted rather than repetitive.

What it needs to say. Reinforce the same core information, but shift from announcement to reminder. Make the time remaining explicit.

Suggested copy:

Reminder: you haven't completed your benefits enrollment yet. [DAYS] days left. Takes about [X] minutes: [PORTAL LINK]. Deadline [DEADLINE]. Questions? [CONTACT].

How to target the reminder. Start with the distinctions that change what an employee needs to do: full-time versus part-time, hourly versus salaried, union versus non-union, since those often carry different eligibility, options, or deadlines. Then layer in site, shift, and language. In most communication solutions this is set up once as a saved audience, not rebuilt for every message.

Stop messaging the people who are done. This matters more than it sounds. An employee who already enrolled and then gets another reminder has two ways to read it, and both are bad. Either they assume something went wrong with their election and go back to check, or they decide the message was not meant for them and start skimming past whatever comes next. The second one is the expensive outcome, because it costs you the safety alert and the shift request later in the year, not only this reminder.

Doing this by hand is not realistic inside an enrollment window. When the communication solution connects to the HR system and the benefits system of record, enrollment status updates on its own and the midpoint reminder reaches only the people who still need it. goHappy handles this automatically.

Touch 4: Urgency, three days out

What it needs to do. Move employees who intended to enroll but haven’t acted yet. At this point, the message is no longer about awareness or education. It’s about the deadline.

What it needs to say. Lead with the time remaining. Give employees one action and one link. Nothing else to compete for attention.

Suggested copy:

3 DAYS LEFT to pick your benefits. Deadline is [DEADLINE] at [TIME]. After that you'll wait until next year. [PORTAL LINK]

Touch 5: Final call, deadline day

What it needs to do. Give remaining employees two final opportunities to act. One message on the last day still assumes someone sees it at exactly the right moment. Send once in the morning and again around midday.

What it needs to say. The morning message states the hours remaining. The midday message gets even shorter.

Suggested copy, morning:

TODAY is the last day to pick your benefits. Deadline [TIME] tonight. [PORTAL LINK]

Suggested copy, midday:

Last call. Benefits enrollment closes at [TIME] tonight. [PORTAL LINK]

The five touches work because each one does a different job. Awareness gives employees a runway to think and ask questions. Kickoff gives them a clear path to act. The midpoint catches the people who intended to and haven't. Urgency makes the deadline concrete. The final call catches everyone else.

The goal isn't to say the same thing five times. It's to make sure one missed message doesn't become a missed enrollment window, and to reach the point where every employee who didn't enroll made that choice with the information in hand. That's what turns participation numbers into something you can act on.

The rules that make the five touches land

Two best practices worth reiterating:

Space the touches out. Urgency fatigue is real. Five messages clustered in the final week create noise and train employees to ignore the sender. Five messages spaced out across the enrollment window creates multiple opportunities for employees to see information, ask questions and act before the deadline.

Write for an employee reading between tasks. Keep messages short, use plain language and give employees one clear action at a time. Benefits terminology may be familiar to HR teams, but employees shouldn’t need benefits expertise to understand what to do next.

The goal is not to send five messages. It’s to make each touch useful enough to move employees one step closer to completing enrollment.

Make enrollment answerable, not just readable

Every enrollment campaign generates questions: Where do I enroll? What’s my password? Where can I find the relevant plan information?

If employees don’t have an easy way to get answers, those questions can become stopping points. They may ask a site leader who doesn’t have the answer, wait until HR is available or do nothing and enrollment doesn’t happen.

Give employees an on-demand path to answers

Some communication solutions let an employee text a single word and get an automated response: a benefits guide, a direct link to the portal, or instructions for reaching a person. In goHappy, this is a text keyword. It turns a one-way campaign into a two-way resource without adding staff to answer phones.

Snooze, a goHappy customer, uses this approach to help employees navigate benefits information. As Jeremy Edmonds, EVP of People and Culture, explains:

Employees have a clear next step when a question comes up, without having to track down the right person first. An employee with a benefits question at 9pm gets a personalized answer by 9:01pm.

Remove the questions that stall completion

Some questions are predictable, and those are worth solving before the campaign starts. Password resets are the clearest example. An employee is ready to enroll, clicks the link, and finds they can't get into the HR system. If resolving that means emailing HR and waiting a day, the enrollment doesn't happen. The same is true for employees who can't find the plan documents, don't know which plan they're currently on, or aren't sure whether they're eligible. Each one is a question with a known answer, and each one stops enrollment cold when there's no fast way to get it.

Milwaukee Tool, a goHappy customer, does this with text-based keywords to help their frontline employees resolve issues like HR-system password resets. This ensures a common blocker has an easy and intuitive solution for frontline employees and has the added benefit of saving time and resources for the shared HR service center that manages employees’ benefits questions.

The principle is simple: if you know where employees tend to get stuck, make the answer available before the question becomes a reason not to enroll.

Communicate in the languages employees use

Language is especially important during open enrollment because employees are making decisions with financial and healthcare implications. Enrollment messages, reminders and support resources should be available in the languages employees are most comfortable reading.

That means translating more than the initial announcement. The full campaign, including reminders, keyword responses and instructions, should provide a consistent path from message to action.

Look for funding in your existing benefits contracts

Benefits communication problems often get framed as budget problems. But before asking for new dollars it’s worth looking at the benefits contracts already in place.

Five Star Breaktime Solutions faced that exact challenge. With 45+ warehouse locations, 70+ corporate dining sites, and a culinary production center across a multi-state footprint, getting enrollment information to frontline employees was difficult. Printed materials had to physically make their way to each location, while new hires had just 30 days and relied on scheduled calls with benefits counselors to complete the process.

Five Star was already using goHappy to reach frontline employees day to day. What they wanted was to put it to work on benefits — a full enrollment campaign, benefits education that ran year-round, and wellness promotion alongside it. That meant a bigger program at exactly the moment when rising cost of goods and tariffs made new spending hard to justify.

So rather than ask for more budget, Steven Vosika, Director of HR Operations, went looking at money the company had already committed. He found wellness communication credits sitting inside Five Star's major medical and ancillary provider agreements — funds specifically available for employee benefits communication, and going unused.

That changed the conversation entirely. The expanded program didn't have to come out of the HR budget, because the carriers were already prepared to fund the kind of work it involved. Five Star could do more for employees and spend less company money doing it.

From there, the approach was straightforward:

1. Identify eligible credits: map available wellness and communication funds to uses such as open enrollment benefits education and wellness promotion
2. Connect enrollment data: integrate the HRIS so the campaign could distinguish between employees who had completed enrollment and those who still needed to act
3. Run the enrollment campaign where employees could be reached: use the communication solution (in this case, goHappy) to deliver enrollment messages directly to frontline employees throughout the enrollment window
   

The lesson isn’t that every benefits contract contains this funding. It’s that there may be more avenues available to support the programs you already know will benefit employees. Before assuming a better benefits enrollment campaign requires new budget, it’s worth exploring the dollars, credits and partnerships already in place. Even if you aren't running enrollment through a communication solution today, the lesson still holds. There may be a way to fund one without requesting incremental HR budget.

Five questions to send your broker

This was made to copy/paste. Send it out in an email today.

1. Do we have any existing wellness or communication credits in our current benefits contracts?
2. If yes, how much is available annually, and what are the eligible categories and restrictions?
3. If credits aren't in the contract, can we add an allowance now or at renewal based on utilization improvement?
4. What documentation or approval process is required to use credits for benefits communications?
5. Which of our current vendors typically offer credits: medical, dental, vision, EAP, or ancillary?

Objections worth working through

"Employees will find benefits texts annoying and opt out."

Frequency matters, but so does relevance. An enrollment campaign doesn’t mean sending every employee every message. Keep communication tied to a specific action and deadline, and stop sending enrollment reminders to employees once they’ve completed the process. That thoughtful approach will go a long way to combatting text fatigue.

"We already send enrollment emails and post announcements in the break room."

Sending a notice is not the same as reaching employees.

Before assuming the current communication strategy is working, answer three questions:

• What percentage of frontline employees have a working company email address they regularly use?
• Can you confirm which employees received the enrollment message?
• Can you identify which eligible employees still need to act before the deadline?

If you can’t answer some or all of these questions, low participation is difficult to diagnose. You know the communication was sent, but not whether employees had a fair opportunity to act on it.

"There's no budget for this."

Before treating budget as the constraint, review existing benefits contracts. Wellness, engagement or communication credits may already be available, depending on your agreements.

Use the five broker questions above to find out what exists before requesting new dollars to fund a frontline communication platform that can support this type of campaign.

"IT doesn’t have time for another integration before enrollment opens"

A strong frontline communication and engagement solution shouldn’t require a heavy lift from IT to get a benefits enrollment campaign running. Ideally, it already integrates with your HRIS to keep employee data current and can connect with your benefits administration system to bring enrollment status into the campaign. That makes it possible to target reminders to the employees who still need to act, and stop messaging those who have already enrolled.

If a deeper integration can’t happen before this year’s window, don’t let perfect be the enemy of good. You can still run a strong five-touch campaign with the employee data you have today, then add more sophisticated targeting and automation as additional systems are connected.

The 30-day pre-enrollment checklist

✔️  Verify the employee list. Reconcile it against the HR system, and account for new hires and terminations. Solutions like goHappy sync  with the system to keep this list current automatically.
✔️  Test the enrollment link. Open the portal on a phone, outside the company network and on a slower connection.
✔️  Write all five touches. Write and schedule every message before the enrollment window opens.
✔️  Build the necessary segments. Account for differences in eligibility, plan options, deadlines, site, shift and preferred language.
✔️  Set up enrollment-status suppression. Connect the benefits system of record so employees drop out of the reminder sequence once they complete enrollment.
✔️  Confirm rollover rules. Know exactly what happens if an employee takes no action, and communicate it plainly.
✔️  Name a help contact. Make sure employees know where to go with questions, and that the person or team providing support is prepared.
✔️  Plan for the predictable questions. Every enrollment cycle produces the same handful: where do I enroll, what's my password, am I eligible, where are the plan documents. Decide in advance how each one gets answered.
✔️  Review translations. Have benefits communication reviewed for clarity and accuracy in every language you plan to use.
✔️  Schedule the campaign. Space touches across the enrollment window, and focus on send times that are optimal for frontline employees to see and take action.
✔️  Define the final follow up. Decide in advance how you’ll communicate with eligible employees who still haven’t completed enrollment three days before the deadline.

Frequently asked questions

How do you increase benefits enrollment participation among frontline employees?

Start by making sure eligible employees can actually receive and act on enrollment communication. Use a channel they reliably access, repeat essential information throughout the enrollment window, target follow ups to employees who still need to act and provide a simple way to get help. Then use delivery and enrollment data together to identify where employees are dropping out of the process.

How do you communicate open enrollment to employees without company email?

Use a communication channel employees can reliably access without a company inbox. For many frontline workforces, that means text messaging. Keep messages short, link directly to the enrollment portal, state the deadline clearly and give employees a way to get help. Most importantly, don’t rely on one announcement; repeat the essential information throughout the enrollment window.

When should open enrollment reminders be sent?

Schedule reminders throughout the enrollment window so employees have multiple opportunities to see and act on them. goHappy customers generally see stronger engagement on morning sends, particularly midweek, than on messages that go out at the end of the day. Use your own engagement data to refine timing from one campaign to the next.

How many open enrollment reminders should employees get?

Use five campaign stages as a starting point: awareness before enrollment, kickoff on day one, a targeted midpoint reminder, an urgency message three days before the deadline, and a final call on deadline day. The purpose is not to hit a specific message count; it’s to create enough opportunities for eligible employees to receive the information and act before the enrollment window closes.

What should an open enrollment text message say?

Give employees the information they need to take the next step: where to enroll, when the deadline is, what action is required, and where to get help. If taking no action has a specific consequence, state that clearly. Keep the message focused on one action and avoid unnecessary benefits jargon.

How should you communicate open enrollment in multiple languages?

Provide enrollment communication in the languages employees use, and carry that language support through the full campaign. Because benefits decisions have financial and healthcare implications, translations should be reviewed for accuracy and clarity.

How can I fund a new benefits communication tool?

Start by checking existing benefits contracts. Depending on your agreements, medical or ancillary providers may offer wellness, engagement or communication credits that can be used for benefits communication. Ask your broker what credits are available, what qualifies, and what approval is required.

Run the enrollment window you want

Open enrollment participation depends on more than the plans you offer. Employees need to receive the message, understand what they need to do and have enough opportunities to act before the deadline.

That's what a well-run communication campaign creates: the right information reaching the right people at the right time.

Start with the channel: communicate somewhere frontline employees can reliably be reached. Build the cadence: use five purposeful touches across the enrollment window instead of one announcement. Remove friction: link employees directly to the next step and give them a way to get help. Then measure both reach and enrollment activity, so you can tell the difference between employees who chose not to enroll and employees who never had a real opportunity to. That distinction is what tells you whether next year's investment belongs in the plans or in the communication.

These tools can help you put the playbook into action:

• The Five-Touch Message Template Pack for copy you can adapt today
• The Broker Credits Question Kit for funding it without new budget
• The Frontline Enrollment Readiness Assessment for finding the leaks before the window opens