What to do, and when, so the right people at every location don’t miss the window.
Every HR team running open enrollment across more than a handful of locations knows the feeling. The notice went out weeks ago. You’re fairly sure most people saw it. And you won’t find out who didn’t until the window has closed and someone’s asking why they’re not on the plan.
It’s not that anyone dropped the ball. You built the list from the roster you had in August, sent it to every location, and moved on to the eleven other things in your week. Open enrollment gets one honest shot a year, and usually you can’t even know who has read the email, the notice, or whatever else you sent. When it goes wrong, whoever didn’t see it in time is simply out of luck until next year’s window opens.
That’s worth building a system for. Five steps, run the same way at every location, every year, so the outcome doesn’t depend on someone managing to follow up with everyone in a busy week. It is the same principle SHRM lands on for enrollment communication: build the core message once, then send each group only the part that applies to them.
The Open Enrollment Checklist
Define the eligible group as a rule, not a list (6–8 weeks out). Work out who’s actually eligible at each site, usually a set of positions or a tenure threshold, with exceptions by location, and write it down as a rule, not a list of names. A rule survives turnover; a list starts going stale the day you build it.
Send the primary notice to exactly that group (4–5 weeks out). Send one message to the eligible group at each location, covering the plan details, the deadline, and what people need to do. Put it somewhere they’ll actually see it, even without a company email address.
Send a reminder to everyone (2–3 weeks out). A reminder goes out next to the whole eligible group, a gentle nudge that the deadline’s coming, not a targeted one yet. That’s what step 4 is for.
Check who’s still unread, then send a second reminder (1–2 weeks out). A few days later, check who’s still unread and send a second reminder only to them. That depends on knowing who’s actually opened it, not just that the message went out. A delivery report alone won’t tell you that, and most channels won’t either. This step and step 5 still work without it, they just can’t be targeted.
Send managers the names, and note who never looked (final week). Hand each location manager the not-yet-enrolled list from your benefits system, and note separately who never opened the notice at all. That’s who managers can coach on where to look for company messages, so they don’t miss it next cycle.
Why these five, together
Each step only works because the one before it did its job: the eligible list stays accurate, the right people get reminded, and the list of who to chase keeps getting shorter, down to a handful of names by the final week instead of a full roster. None of it is hard on its own. What’s hard is running all five the same way, at every location, every year, when the thing holding it together is a spreadsheet that gets a little less trustworthy each cycle it’s reused, in the same crowded stretch as everything else you’re locking down before the holiday rush.
That’s the part worth automating.
How Woven makes this easier to run
None of this requires Woven. You can run all five steps with the tools you already have, and plenty of operators do. What Woven changes is scale: set the process up once, and it runs the same way at every location, every year, without anyone rebuilding a spreadsheet or manually checking who’s read what.
The eligible group is a rule you write once: all Assistant Managers, at these six locations, minus the two sites on a different plan. Woven keeps it current as people are hired, promoted, and moved between sites. Next fall, the rule is still right.
Send the notice as a Communication and Woven tracks who’s opened it, person by person, on their phone through the app, no company email address required. Where it matters, you can require an acknowledgement.
Reminders run the same way every cycle: the first goes to everyone, then a second goes out a few days later to whoever’s still unread. Woven checks who’s actually opened the notice at the moment that second reminder fires, not back when you scheduled it, so the list narrows itself. There’s nothing to rebuild by hand.
The one step that stays human is handing names to managers. The not-yet-enrolled list still comes from your benefits system; what Woven adds is knowing exactly who never opened the notice at all, so managers spend the final week coaching a handful of people instead of chasing a full roster.
Common questions
When should open enrollment communication start?
Early enough that both reminders still have room to work before the deadline. For most teams that’s 6–8 weeks out for the first notice, following the checklist above.
What actually causes open enrollment communication to break down across locations?
Usually one of two things. Either the message goes to people who aren’t eligible at that location, or it goes to the right group and nobody can confirm who saw it, so the same handful of people get missed every year and nobody notices until the window has shut.
How do you reach employees who don’t have a company email address?
Through something they already carry. For most frontline teams that means their phone: a push notification to an app they’re already signed into, rather than an inbox they’ve never logged into. The test is whether you can tell afterwards who opened it.
What if someone still hasn’t acted after the final reminder?
By then the list should be short. Handle it the way you’d handle any short list of exceptions: directly, through whoever runs that location. A fourth mass message won’t reach anyone who ignored the first three.
Should every location use the same checklist?
Yes, and that consistency is most of the value. What changes from location to location is the eligible group itself and how big it is, not the process for reaching it.
Does Woven administer employee benefits or manage open enrollment itself?
No. Woven doesn’t select plans, manage eligibility data, or run the enrollment platform. What it handles is making sure the right people at each location receive, see, and act on enrollment communications from whatever system administers the benefits.
What to do, and when, so the right people at every location don’t miss the window.
Every HR team running open enrollment across more than a handful of locations knows the feeling. The notice went out weeks ago. You’re fairly sure most people saw it. And you won’t find out who didn’t until the window has closed and someone’s asking why they’re not on the plan.
It’s not that anyone dropped the ball. You built the list from the roster you had in August, sent it to every location, and moved on to the eleven other things in your week. Open enrollment gets one honest shot a year, and usually you can’t even know who has read the email, the notice, or whatever else you sent. When it goes wrong, whoever didn’t see it in time is simply out of luck until next year’s window opens.
That’s worth building a system for. Five steps, run the same way at every location, every year, so the outcome doesn’t depend on someone managing to follow up with everyone in a busy week. It is the same principle SHRM lands on for enrollment communication: build the core message once, then send each group only the part that applies to them.
The Open Enrollment Checklist
Define the eligible group as a rule, not a list (6–8 weeks out). Work out who’s actually eligible at each site, usually a set of positions or a tenure threshold, with exceptions by location, and write it down as a rule, not a list of names. A rule survives turnover; a list starts going stale the day you build it.
Send the primary notice to exactly that group (4–5 weeks out). Send one message to the eligible group at each location, covering the plan details, the deadline, and what people need to do. Put it somewhere they’ll actually see it, even without a company email address.
Send a reminder to everyone (2–3 weeks out). A reminder goes out next to the whole eligible group, a gentle nudge that the deadline’s coming, not a targeted one yet. That’s what step 4 is for.
Check who’s still unread, then send a second reminder (1–2 weeks out). A few days later, check who’s still unread and send a second reminder only to them. That depends on knowing who’s actually opened it, not just that the message went out. A delivery report alone won’t tell you that, and most channels won’t either. This step and step 5 still work without it, they just can’t be targeted.
Send managers the names, and note who never looked (final week). Hand each location manager the not-yet-enrolled list from your benefits system, and note separately who never opened the notice at all. That’s who managers can coach on where to look for company messages, so they don’t miss it next cycle.
Why these five, together
Each step only works because the one before it did its job: the eligible list stays accurate, the right people get reminded, and the list of who to chase keeps getting shorter, down to a handful of names by the final week instead of a full roster. None of it is hard on its own. What’s hard is running all five the same way, at every location, every year, when the thing holding it together is a spreadsheet that gets a little less trustworthy each cycle it’s reused, in the same crowded stretch as everything else you’re locking down before the holiday rush.
That’s the part worth automating.
How Woven makes this easier to run
None of this requires Woven. You can run all five steps with the tools you already have, and plenty of operators do. What Woven changes is scale: set the process up once, and it runs the same way at every location, every year, without anyone rebuilding a spreadsheet or manually checking who’s read what.
The eligible group is a rule you write once: all Assistant Managers, at these six locations, minus the two sites on a different plan. Woven keeps it current as people are hired, promoted, and moved between sites. Next fall, the rule is still right.
Send the notice as a Communication and Woven tracks who’s opened it, person by person, on their phone through the app, no company email address required. Where it matters, you can require an acknowledgement.
Reminders run the same way every cycle: the first goes to everyone, then a second goes out a few days later to whoever’s still unread. Woven checks who’s actually opened the notice at the moment that second reminder fires, not back when you scheduled it, so the list narrows itself. There’s nothing to rebuild by hand.
The one step that stays human is handing names to managers. The not-yet-enrolled list still comes from your benefits system; what Woven adds is knowing exactly who never opened the notice at all, so managers spend the final week coaching a handful of people instead of chasing a full roster.
Common questions
When should open enrollment communication start?
Early enough that both reminders still have room to work before the deadline. For most teams that’s 6–8 weeks out for the first notice, following the checklist above.
What actually causes open enrollment communication to break down across locations?
Usually one of two things. Either the message goes to people who aren’t eligible at that location, or it goes to the right group and nobody can confirm who saw it, so the same handful of people get missed every year and nobody notices until the window has shut.
How do you reach employees who don’t have a company email address?
Through something they already carry. For most frontline teams that means their phone: a push notification to an app they’re already signed into, rather than an inbox they’ve never logged into. The test is whether you can tell afterwards who opened it.
What if someone still hasn’t acted after the final reminder?
By then the list should be short. Handle it the way you’d handle any short list of exceptions: directly, through whoever runs that location. A fourth mass message won’t reach anyone who ignored the first three.
Should every location use the same checklist?
Yes, and that consistency is most of the value. What changes from location to location is the eligible group itself and how big it is, not the process for reaching it.
Does Woven administer employee benefits or manage open enrollment itself?
No. Woven doesn’t select plans, manage eligibility data, or run the enrollment platform. What it handles is making sure the right people at each location receive, see, and act on enrollment communications from whatever system administers the benefits.
