Open Enrollment Checklist for Small Business Owners
- Charlie Hopgood
- Jul 3
- 3 min read
Open enrollment only comes once a year — but the preparation should start well before your renewal date. Miss a step and you're scrambling. Do it right and your employees walk away with coverage they actually understand.
Here's the checklist we use with our clients at Service 1st Benefits.
60–90 Days Before Renewal
☐ Request renewal rates from your broker Your carrier should send renewal rates 60–90 days before your plan anniversary. If you haven't received them, ask. Waiting until 30 days out leaves you no time to shop alternatives.
☐ Review last year's claims data (if available) If you're on a level-funded or self-funded plan, review your claims report. Are there trends driving cost? Certain high-cost conditions? This informs your strategy.
☐ Decide if you're staying or shopping If your renewal increase is more than 5–8%, it's worth getting competing quotes. Your broker should bring you options — not just rubber-stamp the renewal.
☐ Evaluate your contribution strategy Is what you're contributing still competitive? If employees are paying significantly more than last year, expect grumbling — or departures.
30–45 Days Before Enrollment Opens
☐ Confirm your plan lineup Finalize which plans you're offering — medical, dental, vision, life, voluntary. Don't add confusion by offering too many options. Two to three medical plan tiers is usually enough.
☐ Update your employee census New hires, terminations, address changes, dependent updates — make sure your carrier and your enrollment platform have accurate data.
☐ Schedule employee communication Don't drop a benefits packet on employees and expect them to figure it out. Schedule a meeting (in-person or virtual) to walk through the plans. 20 minutes of education saves hours of questions later.
☐ Prepare your enrollment platform If you're using Employee Navigator or a similar platform, make sure the new plan year is configured, rates are loaded, and employees can log in.
During Open Enrollment
☐ Send a clear deadline reminder Email employees with the exact deadline to make elections. Send a reminder 5 days before and again 1 day before. People procrastinate.
☐ Follow up with non-enrollees Anyone who doesn't make an election may default to last year's plan or be automatically waived — depending on your carrier rules. Know which applies to you and follow up individually.
☐ Document waivers If employees decline coverage, get it in writing. You'll need this for compliance purposes and to protect yourself if they try to enroll mid-year.
After Enrollment Closes
☐ Submit final enrollment to the carrier Confirm all enrollment data is submitted accurately. Errors here cause ID card delays and coverage gaps — which your employees will blame on you.
☐ Confirm employee deductions with payroll New premium amounts need to be updated in your payroll system. Incorrect deductions are a headache to unwind.
☐ Distribute ID cards and plan documents Make sure employees know where to find their ID cards and Summary of Benefits and Coverage (SBC). This reduces calls to HR on day one of the new plan year.
Let Us Run It For You
Open enrollment is manageable when you have a process — but it's a lot for a small HR team (or a business owner wearing five hats) to execute alone.
At Service 1st Benefits, we manage the entire open enrollment process for our clients. Employee meetings, enrollment platform setup, carrier submissions, payroll coordination — we handle it.
Want a smoother open enrollment this year? Let's talk →

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