HOA mailing | LetterStream Blog

What A Fantastic Event! Thanks For Another Great CAI National Show

We Just Got Back from the CAI National Show—and We’re Still Buzzing!

Let me just say this: if you work in community management and didn’t make it to the CAI National Conference in Orlando this year… you missed a good one.

I’ve been to more than a few trade shows in my time, but there was something about this one—maybe it was the energy in the room, the conversations around real challenges HOAs are facing, or maybe it was just the Florida sunshine—but CAI National 2025 hit different.

To everyone who stopped by booth 333 to say hi, ask questions, or just grab a sticker (Yes, we saw you), thank you. Your curiosity and openness are what make these events worth showing up for.

HOA Mail Conversations That Matter

What stood out this year wasn’t just how busy it was (though it was busy). It was the quality of the conversations.

We talked to HOA managers juggling ten communities and vendors looking for ways to streamline board notices. We met folks brand new to their roles and seasoned pros who just needed to stop printing late at night and folding paper with a ruler. (There are way too many of you out there.)

And the common theme? Everyone’s looking for smarter, faster ways to get the job done—without sacrificing accuracy, security, or their sanity. That’s kind of our whole thing.

A Better Way to Handle HOA Mail

So here’s what we showed (and heard) at the booth:

Most of our mail goes out the next business day—50% goes out same day.
You can send mail to one community or a hundred. No minimums.
Our Certified Mail is trackable, timestamped, and accounted for. No guessing.
We already integrate with many HOA software platforms (CINC fans, we see you).
You don’t need a giant mailing team—you just need a good platform.

If you’re new to LetterStream, our platform lets you send real mail online in just a couple of minutes. Upload your file, choose your options, click send. We handle the printing, folding, stuffing, addressing, postage, and tracking. That’s it.

What We Offer HOA Managers

We make life easier for HOA pros. Period.

Whether you’re sending:

Violation letters
Certified mail
Annual meeting notices
Statements
FedEx 2Day mail
Ballot and proxy mail

You get the tools, tracking, and peace of mind without the late nights and jammed printers.

Why We Keep Showing Up

We don’t go to these shows to sell you stuff. We go to listen, to learn, and to be part of a community that’s trying to make things run better. That’s why we’re proud to be part of CAI and why we keep showing up for you.

To the CAI organizers, attendees, and fellow vendors: thank you for the conversations, the connections, and the laughter. We’re grateful for the work you do and are thrilled to be a small part of helping you do it more efficiently.

Until next time—log in, upload, and get back to what matters. We’ll handle the mail.

To learn more about sending HOA mail online, click here.

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.

How Your HOA Mail Process Could Actually Hurt Your Community

I’ve seen it too many times, HOAs doing their mailings in-house, and it’s hurting communities.

When we first started working with HOAs at LetterStream, I kept seeing the same thing over and over: Good boards. Hardworking community managers. Total chaos when it came to mailing important documents.

Maybe you’ve lived it, too—ballots that didn’t reach homeowners. Certified letters sent too late to meet compliance rules. Financial disclosures stuck on someone’s desk while the clock kept ticking.

It doesn’t seem like a huge deal at first. But every missed notice chips away at homeowner trust. Every late mailing risks compliance headaches. Every misstep invites unnecessary drama—and I don’t think any of us need more of that in community management.

Mailing isn’t just paperwork. It’s one of the few official ways your board communicates with your homeowners. When the mail goes wrong, it makes everything else harder.

And honestly? I think a lot of communities deserve better.

The Problem Isn’t the People—It’s the Process

In my experience, it’s never about people not caring.
It’s about asking small teams to manage too many manual steps: printing, folding, stuffing, labeling, mailing, tracking. Every one of those steps is a chance for something to get missed.

And let’s be real—HOA offices weren’t built to be full-service mailrooms.

That’s why we built LetterStream to help HOAs send mail online—real, trackable mail—without the piles of paper, the runs to the post office, and the constant worry about what fell through the cracks.

Instead of burning out your team, you can just upload your files, pick your mailing options, and get on with the work you actually want to be doing.

Because running a community is hard enough without the mailing disasters.

A Better Mailing Process = A Stronger Community

When your HOA mailing runs smoothly, a few things happen:

Homeowners trust that important information will reach them.
Elections feel clean and legitimate.
Legal compliance becomes a whole lot less stressful.
Your board looks organized and professional—and that matters.

It’s not flashy. It’s not exciting. But consistent, reliable mail builds a stronger, healthier community. Period.

What LetterStream Brings to the Table for HOAs

We didn’t build LetterStream for perfect-world HOAs with unlimited budgets and full back-office staff.
We built it for the real world—the one where you need to get 500 meeting notices out this week, track 75 certified violation letters, and maybe handle an election or two… all without dropping the ball.

Here’s what you can expect when you use our platform:

First-Class Mail, Certified Mail, FedEx 2Day, postcards and other business mailing options—all handled online.
No minimums—whether you’re sending one notice or a thousand.
Next-business-day processing to help you stay ahead of deadlines.
Return envelopes and custom options for elections and billing packets.
Detailed tracking and full reporting, right in your account—no digging through piles of green cards.
A simple, clean platform that doesn’t require hours of training to figure out.

It’s professional mailing, built for the realities of HOA management—not for some fantasy land where mailing days never get hectic.

Heading to CAI? Let’s Talk About It

If you’re coming to the CAI National Conference in Orlando, May 7–10, we’ll be there too at Booth 333.

No big sales pitch, just real conversations about how to make HOA mailings easier, cleaner, and way less stressful.

If you’ve ever wished for an easier way to handle notices, ballots, and Certified Mail, come find us. We’ll show you how it’s done. Or if you want to get a head start? You can send HOA mail online today with LetterStream.

How to Easily Send Open Enrollment Mailings

Ah, open enrollment season—the annual ritual where HR professionals juggle deadlines, employee questions, and mountains of paperwork, all while trying to ensure that every employee gets the right benefits package for the year ahead. It’s a high-stakes operation, and let’s be honest—getting those open enrollment packets delivered on time is non-negotiable.

That’s where we come in.

LetterStream’s got a knack for making your open enrollment season not just manageable, but downright easy. How you might ask? Well, our professional mailing services can take the weight off your shoulders and ensure timely delivery, all while keeping things efficient, secure, and—dare we say it—enjoyable.

Why Sending Out Open Enrollment Materials On Time Matters

When it comes to open enrollment letters, timing is everything. Employees need these materials to make important decisions about their health, retirement, and other benefits. If packets are delayed, it can lead to missed deadlines, confusion, and frustration for everyone involved. That’s something no HR team wants to deal with.

By using a professional mailing service, like ours, it ensures that your open enrollment materials are sent out when they’re supposed to be. We’ve fine-tuned our process to make sure that everything from health plan details to enrollment forms are sent out on time, giving you one less thing to worry about.

Precision and Efficiency: Our Secret Sauce

Not to brag but we must say that we’ve mastered the art of efficient mail processing when it comes to open enrollment mailing services and all printing and mailing for that matter . We know that HR teams have enough on their plates, so we’ve designed our services to be as hands-off for you as possible, especially when it comes to high-volume mailing processing regarding employee benefit communications. Just upload your documents to our secure platform, and we’ll take it from there.

And yes, it really is that simple.

Security First: Protecting Sensitive Information

Don’t worry, we haven’t forgotten that open enrollment packets contain some of the most sensitive information your employees will ever receive. Personal details like Social Security numbers, health information, and financial data are all part of the package, and we know that keeping this information secure is paramount.

That’s why we’ve built our platform with security at its core. We use top-tier encryption and secure data-handling practices to ensure that your employees’ personal information is protected every step of the way. You can trust us to handle your mailings with the utmost care, so you can focus on what you do best—supporting your team.

The Perks of Outsourcing Your Open Enrollment Mailings

Outsourcing your open enrollment mailings to a professional service like us isn’t just about saving time—it’s about working smarter. It allows your HR team to focus on the bigger picture, like helping employees make informed decisions about their benefits.

And let’s face it, outsourcing can be more cost-effective in the long run. No need to invest in printers, paper, postage and the hours it takes to prepare mailings in-house. Plus, you’ll have peace of mind knowing your materials are in good hands and will be sent out on time.

How LetterStream Simplifies the Process

We get it—open enrollment is a beast. But we can help you can tame it. Our platform is designed to be user-friendly, so you can upload your documents, choose your mailing options, and hit send—all in just a few clicks.

Our efficient workflow and advanced technology mean that you can trust us to handle your open enrollment mailings quickly and accurately. We take care of everything from printing and inserting to postage and delivery, so you can focus on what matters most—supporting your employees during this crucial time.

We take pride in our attention to detail and precision. With our efficient workflow, you can be confident that every piece of mail will be sent out quickly but with quality in mind. Accuracy is key during open enrollment, and we’ve designed our processes to eliminate errors and ensure that your communications are flawless.

Ready to Simplify Your Open Enrollment?

Open enrollment season comes with its fair share of challenges, but managing the mailing process doesn’t have to be one of them. With LetterStream’s services, you can rest assured that your letters will go out on time, sensitive information will stay secure, and your HR team will have more bandwidth to focus on other important tasks.

If you’re interested in simplifying your open enrollment process, take a moment to explore our offerings or get in touch to learn more. And, if you’ve been managing mailings in-house, this might be a good time to consider a more streamlined approach. Your HR team will appreciate the extra time and fewer headaches.

To learn more about how to send mail online, send Certified Mail online or about our other online mailing solutions for business mailings, click here.

Our state-of-the-art printing and mailing facility is optimized for high-volume jobs like open enrollment. We handle everything from printing and inserting to sealing and sending. And because we know time is critical, we offer expedited processing options to ensure your materials are out the door in record time.

The Best Option for HOA Printing and Mailing

Effective communication is the backbone of any successful homeowner association (HOA).

It’s the key to keeping residents informed, engaged and satisfied.

Yet, for many HOA managers and community managers, handling the printing and mailing tasks can be daunting. We know this first-hand because we’ve talked to so many homeowner managers and HOA self-managed communities that are doing all of these tasks themselves.

It’s a lot!

However, it doesn’t have to be a lot and this is where specialized HOA printing and mailing services come into play.

These services are designed to streamline the HOA mailing process allowing for timely and professional communication with residents.

Ok, let’s dive a little deeper in the world of HOA printing and mailing services, shall we? We’ll explore some of the benefits, challenges, and key considerations for implementation.

by Tierra Mallorca

Understanding HOA Printing and Mailing Services

HOA printing and mailing services are specialized offerings tailored to the unique needs of homeowner associations. As experts in the industry for over 20 years, specifically working with homeowners associations, property management companies and HOA software companies we know the specifics of what is needed.

Home owners associations encompass a wide range of tasks, from keeping track of the fees due for HOA invoices and organizing events to handling the mailing process of sending out HOA coupons, HOA statements, HOA violation notices, HOA annual meeting notices, HOA ballots and more…you get the point.

The goal of a printing and mailing company specializing in HOA mailings and one of our goals specifically at LetterStream is to alleviate the burden on HOA managers and team members who often juggle multiple responsibilities, at least when it comes to mail.

By outsourcing these tasks to a dedicated company, HOA managers can focus more on strategic planning and community building while ensuring effective communication is maintained.

The Importance of Effective Communication in HOAs

Let’s be honest here. The backbone of a thriving homeowner association is effective communication. It fosters a sense of community, encourages resident participation, and ensures transparency in HOA operations.

There’s also the fact that there are legal requirements for HOAs to provide certain notices and documents to residents. Again, this is done through the communication HOAs have with their communities. These can include meeting announcements, financial reports, invoices and voting materials.

By using a company that understands the industry and HOA printing and mailing services, the HOA communities and HOA community managers can ensure they meet these legal obligations while enhancing their communication strategies.

Challenges in HOA Printing and Mailing

Like we mentioned above, printing and mailing tasks in-house can be a daunting task for HOAs.

One common issue is the time and effort required to handle these tasks. From dealing with invoices and fees due to stuffing envelopes, applying postage and driving the letters to the post office, these tasks can consume significant resources.

Other challenges HOAs face when printing and mailing on their own include:

Ensuring accuracy and compliance
Time-consuming tasks
High costs of equipment and supplies
Errors in mailing addresses or content
Difficulty in tracking and reporting
Compliance with postal regulations and HOA bylaws
Resident dissatisfaction

These challenges are not to be taken lightly and can impact the overall efficiency and effectiveness of HOA operations.

Selecting the Right HOA Printing and Mailing Service Provider

Choosing the right service provider is crucial for the success of your HOA’s printing and mailing operations.

Several factors should be considered. These include:

Experience in handling HOA printing and mailing tasks
A comprehensive range of services, from products to delivery
Competitive pricing and bulk mailing options
Positive customer reviews and testimonials
Understanding the legal and compliance side

Benefits of Outsourcing to Specialized Services Through LetterStream

Outsourcing to specialized HOA printing and mailing services can offer several benefits.

Firstly, it can result in significant cost and time savings. These companies have the expertise and equipment to handle large volumes of printing and mailing tasks efficiently.

That is where LetterStream comes into play.

Being experts in the industry for over 20 years we know the ins and outs of what HOAs really need when it comes to their mailing, including the knowledge and understanding of compliance with postal regulations and HOA bylaws.

Not only have we spoken to many community managers, but we’ve also participated in improving our products and services throughout the years to better serve the HOA industry and HOA software companies specifically.

We can’t tell you how many times we’ve heard, “Ugh I dread when it’s time to do mailings. We have to make a whole night of it.” or “We use another company but they take forever to just send out our stuff and the process isn’t simple.”

That’s so frustrating for any HOA and it’s frustrating for us to hear that HOAs have such a hard time getting the services they need and that they end up having to sacrifice their personal and family time to make sure community needs are met.

To sum it up, LetterStream helps you save on your overhead costs of supplies, postage and equipment, along with saving not only your time but the company’s times as well.

by Blake Wheeler

Enhancing HOA Operations Through Effective Printing and Mailing Services

HOA printing and mailing services offer numerous benefits. They streamline communication, ensure legal compliance, and save time and resources. These services also enhance community engagement through professional and timely delivery of HOA communications.

Choosing the right service provider is crucial. It’s important to consider their expertise, technology, understanding of HOA mailings and ease of use. A good provider will offer a seamless transition, ongoing support, and services tailored to the HOA’s needs.

To learn more about HOA mailings, click here.

LetterStream helps HOA communities print and mail violation letters, statements, annual meeting notices and anything else an HOA may need through First-Class Mail, Certified Mail, postcards and FedEx 2Day.