Most enrollment campaigns fail on timing, not on writing. Here is the eight-week sequence that gives employees room to understand their options — and gives you a completion curve that does not spike on the final day.
Ask an HR team what went wrong last enrollment season and you will rarely hear "our messaging was unclear." You will hear that everything landed at once, that the questions arrived in the last 48 hours, and that a large share of employees simply re-elected whatever they had before.
That is a scheduling problem. Employees need time to read something, think about it, talk to whoever shares the decision, and come back. Compress that into a two-week window and you get exactly what compression produces: default behavior. Spread it across eight weeks with a clear job for each phase and the same content performs completely differently.
Here is the sequence, week by week.
Weeks 8–7: internal readiness (nothing sent yet)
The two weeks before your first message are the ones most often skipped, and they determine whether the rest holds up.
- Lock the facts. Final rates, plan changes, contribution amounts, and dates — confirmed with your carrier and broker. Sending a correction later costs more trust than starting a week late.
- Map your reach by segment. Office, remote, frontline, shift, and dependents. For each, answer honestly: if we sent something important today, what share would see it within 48 hours? This number drives every channel decision that follows.
- Pick the two or three behaviors you actually want. Active elections instead of defaults, HSA enrollment, a specific underused program. A campaign that wants everything communicates nothing.
- Write the whole sequence now. Drafting all eight weeks up front is what keeps each message to one action. Written week-to-week, messages accumulate leftovers from the last one.
- Brief managers before employees hear anything. A manager who learns about a plan change from their team has lost credibility you will need for the next six weeks.
Week 6: the save-the-date
Goal: get enrollment onto people's calendars. Channel: email plus a posted notice wherever frontline staff work.
This message is short and deliberately light on plan detail. It answers four things: when the window is, that action is required, what happens if they do nothing, and what is changing at a headline level. That is it.
The "what happens if you do nothing" line is the highest-value sentence in your entire campaign, and most employers omit it. Whether the consequence is rolling into the current plan or losing coverage entirely, stating it plainly is what converts enrollment from an administrative notice into a decision.
Week 5: what is changing, and why
Goal: remove surprise. Channel: email, intranet or portal post, manager talking points.
Now go into the changes with specifics: new rates in per-paycheck dollars, plan design differences, any carrier or network change, and anything being discontinued. Lead with the practical impact on the employee rather than the mechanics of the plan.
If something is being removed or reduced, address it directly and give the alternative in the same message. Silence around a takeaway does not make it land more softly; it just moves the conversation to the break room, where the version people hear is worse than the truth.
Week 4: plain-language education
Goal: build actual understanding. Channel: email, mobile site, on-site or virtual sessions.
This is the week that determines the quality of the elections you get. Publish a comparison organized by employee situation — rarely see a doctor, managing a chronic condition, covering a family, planning a baby — rather than by plan name. Include the real per-paycheck cost for each coverage tier, because that is the number people make decisions on.
Two things belong here that are almost always missing. First, the value of the employer contribution stated in dollars: employees consistently underestimate it, and it is the single most effective way to make coverage feel valuable. Second, the programs beyond medical — telehealth, mental health support, HSA matching, condition management, EAP scope — which is where most of your unrealized value sits. Our guide to benefits education covers how to frame these so people act on them.
Week 3: bring in the household
Goal: reach the person who actually decides. Channel: a forwardable email plus a no-login mobile link.
Dependents drive a substantial share of claims, and in many households the person weighing the family's healthcare decisions does not work for you. If everything you have sent so far lives behind a corporate login, they have seen none of it.
Send something explicitly designed to be forwarded: family coverage costs, what is covered for dependents, and the family-relevant programs. Make sure the link opens on any phone with no credentials. This single message frequently produces more changed elections than the three that preceded it.
Week 2: open the window
Goal: convert the informed into the enrolled. Channel: email, Teams or Slack, text for frontline segments, posters on site.
Announce that enrollment is live with one action and one link. Keep it to a few lines — everything explanatory has already been sent, and repeating it here dilutes the ask.
This is also the moment to make help visible: a named person, a phone number, on-site hours, or a text line. From this point forward, the employees who have not enrolled are increasingly people who are stuck rather than unaware, and a human contact recovers more elections than another link does.
Week 1: targeted reminders only
Goal: close the gap. Channel: email and text, to non-completers only.
Suppress everyone who has already enrolled. This matters more than it sounds: blanket reminders punish the people who acted early and train your whole population to ignore the next campaign. Targeted reminders let you increase frequency without increasing fatigue.
Two touchpoints is usually right for this week — one mid-week email, one text about three days out. Each states the deadline, the consequence, the time required, and a working link. Nothing else. Our SMS guide covers consent and opt-out requirements before your first send.
Final 48 hours: one last push
Goal: catch the stragglers. Channel: text, with a help path.
A single final-day message to non-completers, including a phone or text number for help. Expect a meaningful share of your total elections to land here regardless of how well the earlier weeks went — some people simply operate on deadlines. The point of the previous seven weeks is not to eliminate this spike but to shrink it enough that your team can actually handle the questions it produces.
Make sure someone is genuinely available. A last-chance message pointing to an unstaffed inbox is worse than not sending it.
The week after close: the most wasted opportunity in HR
Goal: turn elections into usage. Channel: email, mobile site.
Nearly every employer goes silent here, and it is the highest-attention window you will get all year. Employees have just made a decision and are briefly interested in the consequences of it.
Send a confirmation that lists what they elected, what it costs per paycheck, when coverage begins, and what to expect in the mail. Then add two concrete setup actions — register the carrier account, download the telehealth app, activate the HSA. Those two actions are what separate an election from actual utilization.
Then keep going. The natural handoff is straight into a year-round cadence, because everything you just explained will be forgotten by February unless something reintroduces it.
If you only have three weeks
Sometimes the calendar is already against you. A compressed plan, in priority order:
- Week 3: combine the save-the-date and the changes message. Lead with dates, the consequence of inaction, and cost changes. Accept that this one message has to do two jobs.
- Week 2: the situation-based comparison with real per-paycheck numbers, sent in a format employees can forward home.
- Week 1: targeted reminders to non-completers only, escalating to text at 72 hours and again on the final day.
- After close: do not skip the confirmation. It is cheap, it is high-attention, and it is what makes next year easier.
What you should not do when compressed is drop the household message or the multi-channel reach and rely on email alone. Those are the two cuts that quietly cost the most.
How to tell whether the timeline worked
The metric that tells you most about your timing is the shape of your completion curve. A campaign with a working early phase produces a flatter curve — steady completions from the day the window opens. A campaign that started too late produces a hockey stick in the final two days.
Alongside that, watch the share of employees making active elections rather than defaulting, your reach percentage in each workforce segment, and the volume and timing of questions to HR. Questions arriving in week 4 are a sign the campaign is working; questions arriving on the final morning are a sign it started too late. For turning any of this into a number leadership responds to, see measuring communication ROI.
Key takeaways
- Start six to eight weeks out; most enrollment failures are timing failures, not writing failures.
- Spend the first two weeks on internal readiness — locked facts, a reach audit, and the full sequence drafted at once.
- State what happens if an employee does nothing. It is the highest-value sentence in the campaign.
- Name cost increases early rather than burying them; hidden increases cost trust you need later.
- Send one message built to be forwarded to the family, with a link that needs no corporate login.
- Suppress completers from reminders so you can raise frequency without causing fatigue.
- Use the week after close to confirm elections and prompt two setup actions.
- Judge the timeline by your completion curve, not by open rates.
Frequently asked questions
How far in advance should open enrollment communication start?
Six to eight weeks before the window opens, with the first two of those spent on internal readiness rather than sending. The early phase is not about plan detail — it gets enrollment onto people's calendars, flags what is changing, and tells them what they will need. Campaigns that begin when the window opens reliably produce deadline-day spikes and passive re-enrollment.
How many messages should an open enrollment campaign include?
Typically eight to twelve touchpoints across the run-up and the window, phased from awareness to education to action. The count matters less than giving each message a single purpose and a single action. Fatigue comes from repeating the same all-in-one announcement, not from frequency itself — and suppressing employees who have already enrolled lets you send more without annoying anyone.
What should you send in the last week of open enrollment?
Two or three short reminders to employees who have not yet enrolled — one mid-week email, one text about three days out, and one on the final day. Each should state the deadline, the consequence of not acting, roughly how long enrollment takes, and a working link, plus a real phone number for help. By this point non-completers are usually stuck rather than unaware.
What if we only have a few weeks before enrollment opens?
Combine the announcement and changes message into one, follow with a situation-based plan comparison using real per-paycheck costs, then run targeted reminders to non-completers escalating to text. Do not cut the household message or drop to email only — those two reductions cost the most reach for the least saved effort. And still send the post-close confirmation.
Want this timeline built and run for you? See what a managed enrollment campaign looks like.
Kate transforms complex ideas into clear, actionable employee communications that drive behavior change, leading projects from strategy through production. A Texas A&M communications graduate and IABC member.
