For HR and benefits administrators, open enrollment isn’t just another task on the calendar. It’s the Super Bowl of communication season. Every employee needs to receive accurate, timely information about their benefits—and if even one packet goes missing, the fallout can be serious.
Deadlines are strict. Compliance matters. And the margin for error? Pretty much zero. That’s why preparing for open enrollment season isn’t just about having documents ready—it’s about having a system that ensures those documents get into the right hands, at the right time.
When Mailing Becomes the Bottleneck
Let’s be honest: most HR teams don’t struggle with putting benefits information together. They struggle with the logistics.
Printing hundreds (or thousands) of packets. Stuffing envelopes. Labeling. Tracking. Double-checking that every single employee is accounted for. It’s tedious, time-consuming, and frankly, not the best use of a benefits manager’s skills.
That’s where things fall apart—because the people responsible for building great employee experiences get stuck acting like a mailroom.
The Playbook for Getting Ahead
Here’s how smart HR teams prepare:
- Start Early. Draft and finalize your documents before the rush. Uploading early to LetterStream means you can schedule jobs to go out exactly when needed.
- Segment Your Audience. Remote employees? Different states? Contractors vs. full-time? Tailor packets without duplicating effort.
- Track Everything. With reporting and tracking with Certified Mail flats, you don’t have to wonder if packets went out—you’ll know.
- Automate the Hard Parts. Upload once, and let the system handle the printing, stuffing, and mailing.
What Happens When You Don’t Prepare
Picture this: an HR director at a mid-size company of 800 employees. She waits too long to organize her mailing and ends up printing packets in-house. Printers jam, staff burn overtime hours, and packets still arrive late to several remote employees. Cue confusion, missed deadlines, and a stream of angry emails.
Now, picture the same director uploading packets through LetterStream. Everything’s queued, printed, and mailed within two days or even better, by the next business day. Every employee has what they need to make informed choices. The director? She’s not pulling an all-nighter—she’s home at dinner.
Why Open Enrollment Mail Deserves Extra Care
Unlike casual reminders or newsletters, open enrollment packets contain sensitive, business-critical information. Employees rely on them to make decisions that impact their health, finances, and families. A late or missing packet isn’t just inconvenient—it’s disruptive.
That’s why using a reliable print and mail service is less about convenience and more about trust. You’re not just sending mail—you’re safeguarding your employees’ futures.
Get Ready For Open Enrollment Season
Open enrollment comes fast. The HR teams that win the season are the ones who prepare their playbook ahead of time. When using a company like LetterStream, you don’t just survive the crunch—you own it.
Upload your documents, set the game plan, and watch your packets get delivered on time, every time.
Because the real win? Giving employees the clarity they need without burning out your team. Learn more about LetterStream here.
LetterStream makes printing and mailing a breeze!
LetterStream offers bulk printing and mailing services allowing companies to send physical mail online. Whether it’s online Certified Mail, First-Class Mail, FedEx 2Day, or postcards, we give both small businesses and large corporations that time and freedom back to work on tasks that better serve the company. If you’re interested in creating a free account, you can do so, here.
