Open Enrollment Checklist: 90-Day Prep for OK Employers
Ninety days before your plan year ends is when open enrollment prep should start — not 30. Here's exactly what to do at each stage so nothing gets rushed.
We've written before about the mistakes that come from starting late. This is the checklist that prevents them.
90 days out: Review and shop
Pull your current plan's claims experience and utilization from your broker or carrier
Re-shop the market — even if you like your current carrier, you need a real comparison to negotiate from
Decide if plan design changes (deductibles, contribution structure, adding a level-funded option) are worth exploring this year
60 days out: Decide and communicate
Finalize plan selections and contribution strategy
Draft employee communications — what's changing, what's staying the same, and why
If you're changing carriers or platforms, confirm ID card timelines so there's no coverage gap on day one
45 days out: Build the enrollment process
Load plan options into your enrollment platform (Employee Navigator or similar) if you're not still doing this on paper
Schedule employee meetings or one-on-ones — don't rely on a single all-staff email to cover plan changes
Prepare answers for the questions you already know are coming (cost changes, network changes, dependent eligibility)
30 days out: Open enrollment window
Open the enrollment window and actively monitor completion — don't wait until the deadline to see who hasn't finished
Send reminders at the halfway point and 3 days before close
Flag employees who haven't started, not just those who haven't finished
14 days out: Close and confirm
Close enrollment and audit for errors — missing dependents, wrong tier selections, incomplete forms
Submit final enrollment to the carrier with buffer time before the plan year starts
Confirm ID cards and platform access will be ready for day one
After go-live
Send a short "how to use your new benefits" reminder in week one — this is when claims questions spike
Log any issues that came up this cycle so next year's 90-day window starts from a shorter list
Skip the spreadsheet next year
If this timeline sounds like more coordination than your team has bandwidth for, that's exactly what a broker should be managing for you. Talk to Service 1st Benefits about running your next open enrollment start to finish.




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