Most open enrollment communication guides focus on strategy. This one focuses on what comes next: execution.
The planning work is done. The segments are built. The channel mix is decided. What this post covers is the week-by-week campaign that runs from the moment the enrollment window opens to the moment it closes: what goes out, to whom, through which channel, and why the timing of each touchpoint matters.
The gap between a well-planned open enrollment campaign and a well-executed one is often where enrollment outcomes are determined. According to MetLife's 2025 Employee Benefit Trends Study, 38% of employees find it difficult to understand their employer's open enrollment communications, a figure that speaks less to the quality of benefits packages available and more to the quality of the communication programs designed to explain them. The week-by-week cadence below is built to close that gap.
For the strategic foundation behind this playbook, such as the planning framework, segmentation approach, and channel strategy, see the OneBenefits Open Enrollment Communication Guide. This post picks up where that one leaves off: at launch.
Before the window opens: the pre-launch checklist
Before the first campaign email goes out, four things need to be confirmed:
- Segments are finalized. Every employee should be assigned to a communication segment: at minimum, new hires, employees with families, and all other eligible employees. Ideally, additional segments exist for remote or frontline workers who need different channels, and for employees approaching retirement who need different content.
- The chatbot is loaded with this year's documents. If a benefits chatbot is part of the communication infrastructure, it needs to be trained on the current year's plan documents before the window opens, not after the first wave of employee questions arrives.
- Managers have been briefed. A short manager communication brief, covering what's changing, what employees are likely to ask, and what the correct answers are, should go out at least three to five days before the all-staff campaign launches. Managers who are informed before employees are contacted become a first line of support. Managers who aren't become a source of confusion.
- The campaign calendar is scheduled and confirmed. Every touchpoint for the full enrollment window should be scheduled before day one. Reactive campaign management during an active open enrollment window is where errors happen and deadlines get missed.
Week one: launch and awareness
Day one: the launch email
The launch email is the most important single communication in the OE campaign. It sets the tone for the entire enrollment period and is the first thing employees will use to decide whether the process feels manageable or overwhelming.
What it should cover:
- The enrollment window dates (open and close)
- A plain-language summary of what's changing this year
- What employees need to do and by when
- Where to go for more information (portal link, chatbot, FAQ resource)
What it should not do: try to cover everything at once. OneDigital's State of Open Enrollment 2026 report notes that a communication approach designed for desk-based employees often fails to reach frontline workers, remote staff, or the family members who play a role in benefits decisions. The launch email should be the starting point of a conversation, not the entirety of it. Keep it short, clear, and action-oriented.
Segmentation: Send a version tailored to new hires that acknowledges this is their first enrollment with the company and provides additional context on the basics. Send a version to employees with dependents that leads with family coverage changes. The all-other-employees version covers general plan changes and enrollment instructions.
Channel: Email, primary. For frontline or non-desk employees without reliable email access, follow immediately with an SMS alert linking to the enrollment portal.
Days two through four: chatbot and portal activation
The 24 to 48 hours after the launch email goes out is when the first wave of employee questions arrives. This is the moment the chatbot earns its value.
A chatbot trained on this year's plan documents intercepts the most common questions before they reach the HR inbox. HR's role in this window is monitoring what's coming in, not answering it individually.
If a pattern of questions emerges that wasn't anticipated, such as a specific plan detail that's generating confusion or a process step that employees are getting stuck on, that's a signal to push an FAQ update or a targeted supplemental email before the pattern becomes a flood.
End of week one: engagement check
By the end of week one, pull the open rate data on the launch email. The question isn't whether the number is high or low in absolute terms; it's which segments underperformed relative to expectation.
A segment with a significantly lower open rate than others is a candidate for an early follow-up, either through a different channel (SMS if email underperformed) or a resend with a different subject line. Catching this at the end of week one, rather than in the final 48 hours, is what makes mid-campaign adjustment possible.
Week two: education and deepening engagement
Week two is the content phase. The launch email covered the what and the when. Week two covers the why: the information employees need to make an informed decision rather than defaulting to last year's plan.
The plan comparison email
Send a focused email covering the plan options side by side. Instead of going through every detail of every plan, focus on the three or four variables that actually drive most employee decisions: premium cost, deductible, out-of-pocket maximum, and network type.
SHRM notes that communication format and channel preferences tend to vary across employee populations. A plan comparison that works well as a detailed email for a desk-based employee may work better as a short video walkthrough for a frontline workforce that processes information differently. Where possible, offer both.
Segmentation: Employees with families get a version that includes dependent coverage costs and family out-of-pocket calculations. Employees approaching retirement get a version that includes Medicare coordination information. New hires get a version that explains the comparison framework before presenting the options.
The HSA/FSA education email
Health savings accounts and flexible spending accounts are among the most underutilized benefits in most packages, and among the most misunderstood. A dedicated email covering how each account works, contribution limits, and the use-it-or-lose-it rules for FSAs does more for utilization than any other single piece of education content in the OE window.
Send this mid-week two, to all eligible employees. Keep it short. The goal is comprehension, not comprehensiveness.
The benefits-beyond-health email
Most OE campaigns focus almost entirely on health plan selection. The Hartford's 2025 Future of Benefits study found that 75% of employers report that workers under-utilize the benefits and services made available to them, and much of that underutilization is driven by simple unawareness. The open enrollment window is an opportunity to surface the programs employees may not know they have, such as EAP access, fertility support, financial wellness tools, tuition reimbursement, or mental health resources.
A single email highlighting three or four of these programs, written in plain language, builds the awareness that drives utilization throughout the year. Send this toward the end of week two.
Week three: reminders and re-engagement
By week three, enrollment data will show a clear split: employees who have acted and employees who haven't. The focus of this week is to reach the second group without exhausting the patience of the first.
The mid-point reminder
Send a reminder email at the midpoint of the enrollment window. This email should be shorter than the launch email. Use a subject line that conveys urgency, two or three sentences confirming the deadline, and a direct link to the enrollment portal.
The targeted SMS nudge
By week three, the engagement data will show which employee segments haven't interacted with any campaign touchpoint. These are the employees most likely to miss the deadline. Send a targeted SMS reminder specifically to this group, not to everyone.
A mass SMS reminder sent to employees who have already enrolled creates noise and trains employees to ignore future SMS communications. A targeted SMS sent only to non-engaged employees creates urgency where urgency is warranted. The message should be short: enrollment closes in X days; here's the link. Nothing more.
Manager re-engagement
Send a brief follow-up to managers with enrollment data for their teams: how many have enrolled, how many haven't, and a suggested talking point for a team meeting or one-on-one check-in. Managers who know who hasn't enrolled are more effective at driving the final push than any all-staff communication.
Week four (final week): the deadline push
The final week of open enrollment is when communication intensity peaks. The goal is urgency without panic. Employees should feel the deadline is real, but they should also feel they have enough time to act.
Daily deadline countdown
Send a short email on Monday of the final week noting how many days remain. Send another on Wednesday. On the day before the deadline, send a final reminder via both email and SMS.
Each of these emails should be three to five sentences at most. Subject lines should be direct. "Your enrollment window closes Friday" tells employees what they need to know before they even open the email, whereas "Important benefits reminder" tells them almost nothing.
Chatbot office hours
If HR capacity allows, offer a designated window of live support during the final week, whether it be a Slack channel, a phone line, or a brief Zoom office hours session, so employees can get answers to last-minute questions. The chatbot handles the volume, while HR handles the edge cases the chatbot can't.
The final hour
Send a final SMS reminder on the morning of the deadline. Keep it to two sentences. Include the exact closing time, not just the date.
After the window closes: the post-campaign checklist
Within 48 hours of enrollment closing:
- Send confirmation emails. Every employee who completed enrollment should receive a confirmation of their elections. Employees who didn't receive a confirmation are more likely to reach out to HR wondering if their elections went through, generating avoidable support volume.
- Pull the campaign analytics. Open rates, click-through rates, SMS engagement, chatbot question volume, enrollment completion by segment. Make a note of these numbers immediately alongside analysis on what drove the gaps, because they're the foundation of next year's campaign plan.
- Note what the chatbot was asked. The questions the chatbot fielded most frequently are a direct read of where the upfront communication left gaps. They're also the questions most likely to repeat next year, unless next year's campaign addresses them proactively.
- Follow up on missing documentation. Employees who enrolled but haven't submitted required dependent verification or other documentation need a targeted follow-up within the first week after close.
A note on automation
The week-by-week playbook above is executable manually, but it's also the kind of program that consumes significant HR bandwidth during the weeks that HR has the least bandwidth to spare.
The value of automating this workflow isn't just efficiency. It's consistency. A campaign that runs automatically doesn't miss the Wednesday reminder because someone was focused on something else. It doesn't send the deadline SMS to employees who already enrolled because the segmentation is built into the trigger, not the send.
OneBenefits is built to run this kind of campaign: segmented, multi-channel, automated from launch to close, with real-time analytics that make mid-campaign adjustment possible without manual data pulls. For HR and benefits teams, that means the final week is spent on the edge cases that need judgment, not on manual sends and data entry.
Final thoughts
The week-by-week structure above isn't a rigid script. Enrollment windows vary in length, workforce compositions vary in complexity, and the right cadence for a 200-person technology company looks different from the right cadence for a 2,000-person manufacturing organization with a significant frontline workforce.
What doesn't vary is the underlying logic: start with a clear launch, deepen engagement through the middle weeks with targeted education content, use data to identify and re-engage non-participants before it's too late, and close with urgency that's earned by the communication that preceded it.
The campaigns that execute this playbook well tend to share one outcome: the final week is manageable, because the first three weeks did the work.