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Open Enrollment Checklist: 90-Day Prep for OK Employers

Jul 27
2 min read

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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Service 1st Benefits
Norman, Oklahoma
(785) 694-8035
Serving Norman, Oklahoma City, Edmond, Moore, Midwest City, and the greater OKC metro area.

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