Open Enrollment Made Simple: A 10-Minute Employer Checklist

The busy season (November–March) shouldn't be stressful, but for many employers, Open Enrollment (OE) turns into an HR nightmare.

As a veteran-owned agency, we believe in clear, efficient execution. Here is our 10-minute checklist to ensure your OE runs smoothly, keeps your team informed, and minimizes the headache for your office.

The 10-Minute Employer OE Checklist

Time	Task	Notes
Minute 1	Confirm Your Broker's Strategy	Do they have multiple quotes ready? Are they presenting new, cost-saving ideas like level-funding? Treeline handles this for you.
Minute 2	Lock-in the Renewal Date	Finalize the renewal or carrier switch date. Give your employees at least two weeks' notice before the deadline.
Minute 3	Prepare the Enrollment Packet	Gather digital copies of the Summary of Benefits and Coverage (SBCs) for all plans (Medical, Dental, Vision). Keep it simple—don't share 100 pages of legalese.
Minute 4	Schedule a Quick Meeting (Optional)	If you have 20+ employees, schedule a brief, recorded Q&A session. Keep it to 20 minutes maximum.
Minute 5	Check Your Eligibility List	Verify which employees are eligible for the plans, including new hires and any changes in full-time status.
Minute 6	Review HSA/FSA Limits	Confirm the current year's contribution limits and communicate them clearly to your staff.
Minute 7	Confirm Compliance Updates	Did any state or federal regulations change? Your broker should flag these. We handle compliance updates for you.
Minute 8	Set the "Enrollment Closed" Deadline	No exceptions. Encourage employees to enroll before the last day to avoid late-night chaos.
Minute 9	Send the Kick-Off Email	Send a clear email with the SBCs, the deadline, and contact info for your benefits advisor (that's us!).
Minute 10	Enjoy the Calm!	Your employees are now taken care of. Focus on running your business, not chasing forms.

Stop managing enrollment and start simplifying it. Schedule a free benefits consult today.