Open Enrollment Checklist for Small Business Owners

Key takeaways

• Start 60 to 90 days before your window opens. Most small businesses start too late and lose room to negotiate before the conversation even begins.
• Benchmark your plan every year. Renewing a fully insured group plan out of habit is one of the most common ways small businesses overpay.
• Treat employee communication as part of the job, not an extra. The materials and support you give people decide whether they choose well.
• Put compliance on the same checklist as everything else. The deadlines do not move to fit your schedule.

Open enrollment shows up once a year and asks for everything at once. Plan decisions, employee communication, compliance deadlines, and payroll updates all land in the same few weeks, and most small businesses are working through it without a benefits team to lean on.

The cost of getting it wrong is real. In a survey of more than 1,000 benefits-eligible workers, Equitable found that 53% regretted the choices they made during the prior year’s open enrollment. Employees who end up on the wrong plan tend to be less satisfied, quicker to blame their employer, and more likely to leave. Most of that is avoidable with a process.

Here is every step, in the order it needs to happen.

Before enrollment opens

1. Review last year’s plan performance

Pull your claims reports, gather employee feedback, and talk with your broker about what drove cost. If you have been taking renewal increases without comparing alternatives, this is the year to run that comparison. Level-funded plans and ICHRA are both worth understanding before you default to renewing what you already have. ICHRA gives you a fixed monthly contribution per employee and lets each person pick their own plan from the individual market.

2. Revisit your contribution levels

Confirm the percentage of premium you cover for employees and dependents. If you offer an ICHRA, check that your monthly allowance amounts still line up with what individual plans actually cost in your employees’ zip codes, because those numbers move every year. If you have not looked at your contribution structure in more than a year, now is the time.

3. Audit your voluntary benefits

Check that dental, vision, accident, and hospital indemnity are still priced competitively and that people are actually using what you offer. If you are not sure what employees want, a short survey before the window opens will tell you fast.

4. Prepare your communication materials

Before the window opens, build a side-by-side plan comparison covering premiums, deductibles, out-of-pocket maximums, and network type. Set your enrollment dates and put them out on at least two channels. Schedule a live Q&A so people have somewhere to bring questions.

More than half of employees rely mostly on what their employer hands them to make these decisions. If your materials are thin, people will rush the process or skip it.

During enrollment

5. Distribute the federally required notices

If you sponsor a group health plan, a specific set of notices has to go out, each with its own timing and delivery rules. That includes the Summary of Benefits and Coverage, the Medicare Part D creditable coverage notice, and COBRA notices. Document that they went out. If you want a reference, Decisely’s benefits compliance guide walks through each one.

One thing to watch this year on the Part D notice, which is due before October 15: the bar for what counts as “creditable” coverage got higher for 2026. Under the revised standard, a plan generally has to pay at least 72% of expected drug costs to be creditable, up from the old 60% test. A plan that paid as well as Medicare Part D in 2024 or 2025 may not clear that bar in 2026, and high-deductible plans are the most exposed. Confirm your plan’s status with your carrier or TPA before the notice goes out, because the answer may have changed.

6. Confirm your ACA obligations

If your business averaged 50 or more full-time equivalent employees last year, you are an applicable large employer. That means offering coverage that meets minimum value and affordability standards and filing Forms 1094-C and 1095-C with the IRS. For 2026, coverage counts as affordable if an employee’s share of the lowest-cost self-only plan stays at or under 9.96% of their household income, up from 9.02% in 2025. The penalties for missing the mark went up too, so it is worth running the math.

A change worth knowing: you no longer have to automatically mail a 1095-C to every full-time employee. You can post a clear, accessible notice telling employees they may request the form, then provide it within 30 days of a request. You still have to file with the IRS, and a few states keep their own furnishing rules.

If you grew close to the 50-employee line this year, confirm your headcount before the new plan year starts. Under 50 does not mean zero obligations. Your plan type decides what applies.

7. Update your plan documents

If your plan design, premiums, network, or covered benefits changed from last year, update your Summary Plan Description and send a Summary of Material Modifications before the new plan year begins. Skipping this is an ERISA violation.

8. Keep the window open long enough

Two weeks is a reasonable standard. Send a reminder at the start, again at the midpoint, and a few days before it closes. The employee who misses the deadline because nobody told them it was coming turns into a retention problem.

After enrollment closes

9. Reconcile elections against carrier records

Check that what employees elected matches what was sent to your carriers. Mismatches create billing errors and coverage gaps, and they tend to surface at the worst possible moment, when someone needs care. Catching them before the plan year starts is far easier than fixing them after.

10. Update payroll deductions

If contribution amounts changed, get those updates into payroll before the first paycheck of the new coverage period. If your benefits and payroll systems do not talk to each other, this has to happen by hand before the plan year begins.

11. Follow up with anyone who did not enroll

Pull a list of everyone who did not submit elections and find out whether they are waiving on purpose or simply missed the window. For anyone waiving, collect a signed waiver. That preserves their right to enroll through a special enrollment period if they lose other coverage mid-year, and it protects you from a dispute later.

Check it all off with Decisely

Every item on this list is something we handle. Healthcare solutions, ICHRA administration, voluntary benefits, compliance support, and HR tools all live in one place, which means fewer systems to coordinate and fewer things slipping through the cracks on a deadline. Open enrollment turns into a process you run instead of a scramble you survive. Get started with Decisely and see what that looks like for your business.