LetterStream Blog

LetterStream’s 2025 Q1 Bonus Party at Snakes & Lattes!

Woohoo! It’s bonus party time again at LetterStream!

On Wednesday, May 21st, the LetterStream team headed to Snakes & Lattes in Tempe for our quarterly bonus celebration. The theme? Olympic Board Game Night. The vibe? Energized, connected, and a little competitive (in the fun way).

Let me tell you how it went.

A Night of Teamwork

We split into teams, grabbed some game boards, ate some food, sipped on yummy lattes, and dove in. No printers, no tracking numbers—just great people, games, and a lot of laughter.

Some teams came to win. Others just came to eat delicious food and roll dice. Either way we got to be together as a work family.

The board game “Olympics” wasn’t just a clever name—it turned into an actual team showdown, with rounds of strategy, bluffing, guessing, and cheering each other on.

We didn’t crown a champion, but let’s just say some teams walked away feeling very accomplished.

Food, Lattes, and That Off-the-Clock Magic

Snakes & Lattes was the perfect setting. Chill atmosphere, excellent menu, and enough coffee to keep us wide awake even after the longest round of Monopoly.

More importantly, it gave us the chance to catch our breath and catch up. These quarterly parties aren’t just about having a good time—they’re also about being together. Getting to talk about something other than mail job or turnaround times. It’s about saying thank you for the hard work that each team member puts in day after day, quarter after quarter, year after year. And a little bit about finding out who’s really good at trivia. Or who’s been quietly training for this moment their entire board-game-loving life. We’re here for it all.

Celebrating Accountability, LetterStream-Style

Each quarter, we highlight a core value, and this time, it was Accountability.

Just like every other bonus party we had a great slideshow to represent the last quarter and showcase our progress and even ways we can continue to improve. We also take the time to recognize new team members, highlights, promotions and new changes. We love to recognize that our team shows up for each other, owns their part of the process, and keeps things moving when it matters most. Q1 demanded that and our team delivered.

Like we mentioned above, this party was our way of saying thanks— in real time, with real connection and of course, with lots of really fun times!

Until Next Time…

To everyone who helped make the night happen—thank you. For showing up, playing along, and being the kind of team people are proud to be part of.

Q1’s in the books. Q2, we’re coming for you—with a little caffeine and a lot of momentum!

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.

Stop Holding Onto Your Mail. Send It Out ASAP.

You know that stack of letters sitting on your desk? The ones you’re “waiting to send” until there are a few more to make it “worth it”? Yeah. That stack is not doing you—or anyone else—any favors.

Let’s talk about the myth that mailing more at once is better. Because honestly… It’s not, at least at LetterStream.

More Pieces Don’t Equal More Value

Somewhere along the way, a lot of folks got the idea that you should wait until you’ve got a big pile of letters before sending them out. Like it’s bulk trash day and you want to make it count.

We get the logic: maybe you’re hoping for a discount, or maybe batching just feels more efficient. But when it comes to important business mail—statements, notices, compliance letters, time-sensitive anything—that delay? It costs more than you think.

There’s no secret reward for holding onto mail like it’s fine wine. It doesn’t get better with age. There’s no “bulk magic” happening behind the scenes. The truth is: with the right system in place, sending one letter or 100 should feel exactly the same—easy, fast, handled.

And if you’re using a platform like ours, that’s exactly how it works.

Late Mail = Bigger Headaches

Here’s the part no one likes to admit: waiting to send mail can quietly wreck your timeline. Especially if you’re managing compliance deadlines, homeowner notices, invoices, or legal documents.

We’ve seen it too many times. A team waits to bundle everything up. They finally hit send. And by the time the mail lands, it’s already too close to the deadline—or worse, too late.

Then comes the damage control. The “we swear we sent it” emails. The callbacks. The fines. The escalations. And all because someone thought they’d get a gold star for waiting until they had a full stack.

You’re Not Saving Money by Waiting

Let’s be really clear: there’s no magical price break coming for your batch of 27 envelopes versus the 5 you had yesterday.

First-Class Mail rates are what they are. Certified Mail? Same deal. Whether you’re sending one or sending now, the cost per piece doesn’t drop just because you waited. And if you’re using a system that charges fairly for exactly what you send—no hidden minimums or batch penalties—you’re not getting some hidden bonus for holding back.

You’re just making your life harder.

Not Waiting Helps LetterStream, Too.

Here’s something else to consider—not just for you, but for the whole ecosystem.

When you wait and then drop a giant job all at once, it takes up one of our production machines for longer than necessary. That can slow down other jobs in the queue—yours included. When mail flows in more evenly, we’re able to keep things moving fast, clean, and on time for everyone.

It’s kind of like a highway: if everyone merges calmly, we’re all cruising. But when 500 cars try to get on the freeway at once, well… you’ve seen what happens.

So if your job is ready, go ahead and send it. It helps your own timeline—and makes the whole process smoother across the board.

Send It When You Have It

That’s our advice. Simple, but solid.

If you’ve got mail ready to go—send it. Don’t let it hang around your office. Don’t wait for a mystical “right time.” Don’t risk missing your deadline because you wanted to be more “efficient.”

We built our mailing platform to be ridiculously fast, no matter how many pieces you’re sending. Upload a PDF, click send, and it’s out the door. Whether it’s one notice or a thousand.

So go ahead—knock that letter off your list. The future you (and your clients, your board, your auditor, your accountant, and your sleep schedule) will thank you.

How to Protect Customer Data in Business Mail

Let’s talk about something that doesn’t get brought up enough in boardrooms, team meetings, or lunch-and-learns:

Mail can be a security risk.

Yep. Physical mail.

Everyone’s busy worrying about phishing emails and cybersecurity, which—don’t get us wrong—is important. But then they turn around and send out thousands of sensitive documents through mail processes that are… let’s just say, less than airtight.

If your current mail workflow involves unsecured spreadsheets, shared folders, or hoping Cheryl remembers to black out the SSN on page two—you’re not just trusting your process. You’re gambling with your customers’ data.

So let’s get into it. Because protecting customer data in business mail operations isn’t just a compliance box—it’s a reputation-saver.

First, Know What Counts as Sensitive

Before we even get to how to protect it, let’s be clear on what “customer data” actually means in this context.

We’re talking:

Account numbers
Billing statements
Social Security numbers
Medical info
Legal documents
Anything with a name + an identifier

Basically, if it’s the kind of thing someone would not want dropped in the wrong mailbox—or left face-up on an office printer—it needs protection.

The Danger Zone: Manual Mail Handling

Here’s where things fall apart:

Someone prints a stack of statements. They sit on a desk. Someone else walks by, picks them up, and realizes they’re out of order. Now they’re trying to re-sort hundreds of pages manually. It’s a mess—and if one page slips into the wrong envelope, boom, breach.

And even if nothing goes wrong, the margin for error is way too high.

The fix? Take the humans out of it. (Lovingly, of course.)

Automated mail systems are built to handle sensitive data with way more precision than even your most detail-oriented employee (and yes, we love them too). When done right, files are encrypted, processed securely, and sent without ever being touched by sticky fingers or office air currents.

What to Look for in a Secure Mail Platform

If you’re trusting a vendor (or considering switching from your in-house chaos), here’s what you should demand:

Data encryption in transit and at rest
Secure upload portals (no, emailing attachments doesn’t count)
Strict user permissions and access controls
Automated printing with no manual handling of documents
Audit trails and delivery tracking
Certifications (SOC 2 Type II, HIPAA, etc.—depending on your industry)

Basically: if they can’t tell you exactly how they’re protecting your customer data, that’s your answer. Keep moving.

It’s Not Just About Security. It’s About Trust.

Your customers assume their personal info is being handled responsibly. That’s the silent contract. And the second they get someone else’s document—or see their name misspelled on something confidential—that trust erodes.

And trust is a lot harder to rebuild than it is to protect.

How LetterStream Keeps Your Customer Mail Secure

This is exactly why so many businesses trust LetterStream to handle their most sensitive communications. From billing statements and medical letters to legal notices and compliance documents—we take privacy seriously.

Here’s how we do it:

Files are encrypted from the moment you upload them
No manual handling of printed materials—jobs are fully automated
Jobs are processed in a secure facility with restricted access
Every piece of mail is tracked, and all records are available in your account. Certified Mail gets more in-depth tracking, but every piece is tracked while going through the production process.
We’re constantly reviewing and improving our systems to stay one step ahead

In short: the mail goes out securely, on time, and without anyone needing to manually fold, sort, or double-check a stack of paper on their desk. That’s the kind of peace of mind your customers expect—and frankly, what you should expect too.

Wrap-Up

Protecting customer data through your mail operations isn’t optional—it’s table stakes now. Whether you’re sending 10 letters or 10,000, the risk is real, and the solution is straightforward: use a system that handles sensitive mail the way it should be handled.

Locked down. Tracked. Delivered without drama.

If your current setup is more “fingers crossed” than foolproof, it might be time to rethink it.

Start here:
Online Printing & Mail Services – Send Your Letters The Easy Way

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.

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.

Why Easily Sending Mail Online is the Future

Let’s be honest—“print and mail” doesn’t exactly scream cutting edge.

Most people still picture someone hunched over a clunky office printer, feeding in paper one page at a time while envelopes pile up like snowdrifts. It’s slow. It’s manual. It’s been “next on the list” for about two weeks now.

But here’s the truth: online printing and mailing isn’t just the future of business communications—it’s the present. And if you’re still doing it the old way, you’re missing out on speed, control, and a whole lot of sanity.

Let’s talk about why more businesses (the smart ones) are switching—and why the future looks a lot less like a jammed printer and a lot more like clicking “send.”

The Old Way Isn’t Working Anymore

There was a time when hand-stuffing envelopes made sense. Maybe you had one mailing a month. Maybe you liked the meditative hum of the folding machine. But now?

You’re juggling statement runs, compliance letters, customer notices, invoices cycles—and that’s just this week.

Manual mailing isn’t scalable, and it’s sure not built for teams trying to move fast. Not to mention: mistakes are easy, and nobody wants to resend 500 letters because of one column in a spreadsheet.

Online Printing Means You Don’t Need a Mailroom

When you move to an online platform, something magical happens: the mail still goes out, but you don’t have to touch it. Or buy stamps. Or stand in line at the post office wondering how your life got here.

Instead, you upload your file, choose your options, and hit send. Done.
Print. Insert. Mail. Track. It all happens behind the scenes while you do literally anything else.

And yes, it still counts as “real mail.” USPS delivers it. Your customers, vendors, or homeowners get a letter in the mailbox—on time and professional-looking.

You Get Speed and Accuracy

Let’s say you’re sending time-sensitive statements or legal notices. You need them to:

Go out fast
Be delivered to the right address
Have proof they were sent

With online mailing platforms, you get all three. Your job’s processed fast (sometimes same day), tracking is baked in, and you can access your full mailing history whenever someone says, “Hey, did we ever send that?”

Spoiler: Yes. Yes, you did.

Your Team Doesn’t Need to Be in the Same Place Anymore

Here’s a big one: remote teams.
It’s 2025. Not everyone works in the same office anymore. So why is your print-and-mail process stuck in 2012?

With an online platform, anyone on your team—remote, hybrid, in-office—can send mail from wherever they are. No printer? No problem. No one to sign off on postage? Still fine. Everything happens online, with visibility and control from wherever you’re working.

The Future Is Already Here

This isn’t some “someday” tech. It’s already how thousands of businesses are handling their most important mail. And once you switch, you’ll never go back.

Seriously—ask anyone who’s made the leap. They’re not hunched over a printer anymore. They’re sipping coffee while the compliance letters are sent for them. That’s the future we’re talking about.

If your mail process still involves toner cartridges, folding paper by hand, or someone saying, “I’ll run these to the post office after lunch,”—well, you already know the answer.

You’re ready.

Start here:
Online Printing & Mail Services – Send Your Letters The Easy Way

Compliance Notices: How to Not Mess Them Up When Mailing

You know those moments when you’re walking out the door and someone says, “Hey—did that compliance notice ever go out?”

And your stomach drops because… maybe?

Sending compliance notices is one of those things that sound simple—until you realize how many ways they can go sideways. And if they do, they don’t just vanish quietly. They boomerang back with consequences: fines, missed deadlines, legal drama, angry homeowners… you name it.

So let’s talk about how to actually get them right. Not perfectly. Not ideally. Just reliably, repeatably, and without the panic attack.

Stop Printing Compliance Notices by Hand

First off: stop printing them in-house if you don’t have to.
Unless your team really loves late nights with paper cuts and jammed printers, it’s just not worth it. We’ve seen too many “oops, we forgot the second page” situations. Not a great look when you’re trying to hold someone accountable for a violation or notify them of a deadline.

Automating compliance mailings is your best friend here. When the system is doing the heavy lifting—printing, stuffing, mailing, tracking—it means fewer fires to put out. That’s not lazy. That’s smart.

Use Certified Mail for Compliance Tracking

Next: use Certified Mail when it counts.
If your notice could ever be questioned—“We never got it!”—Certified Mail gives you that neat little paper (or digital) trail that says, “Yeah, you did.” And you can pull that proof up anytime without rifling through a file drawer from 2019.

It’s the kind of backup that keeps arguments short and lawyers bored.

Write Compliance Notices Clearly

And please, don’t write compliance notices like you’re auditioning for legal drama.
You don’t need five paragraphs of preamble or vague “pursuant to Section 47-B” language unless it’s required. Say what the issue is. Say what they need to do. Say when it’s due.

Simple compliance language is always better:

Use headings or bullet points
Be clear about timelines
Avoid unnecessary jargon

Save the fluff for your next holiday card.

Don’t Wait Until the Last Minute

Timing is everything. If the notice needs to land by a certain date, send your compliance letters early.

If the deadline is Friday, don’t mail it Wednesday and cross your fingers. USPS does a good job, but they can’t time travel (yet). Give it a few days’ buffer, or pick a faster delivery option if the timeline’s tight.

Have a bunch to send? Even better. Batch early, schedule often, and stop cutting it close.

Keep a Record of Every Notice You Send

Whether it’s for legal reasons, your records, or just peace of mind, proof of mailing matters.

The best way to do that? Use a system that keeps a timestamped record of every compliance notice you send. You can pull it up later without digging through piles of paper or wondering who handled it last.

Compliance Mail Doesn’t Have to Be Complicated

Look, we know these notices aren’t exciting. They’re not supposed to be. But they are important, and they deserve better than being last on your to-do list.

When done right, they protect your business. They back up your policies. They show you’re buttoned up and paying attention.

When done wrong… well, let’s just not go there.

If you’re still folding notices in your office kitchen with last year’s envelopes? It might be time for a new game plan. Start here: Free Signup – LetterStream

How to Add a Return Envelope When Creating a Job

Look, not every mail-related question is a high-stakes compliance issue. Sometimes it’s just: “Hey… how do I add a return envelope to this thing?”

And, we get it. If you haven’t done it before, this stuff can feel weirdly tricky. But here’s the good news: it’s incredibly easy—and we made a video to walk you through it, just in case clicking buttons under pressure isn’t your thing.

Watch below to see a walk-through of how to add a return envelope or keep reading to get the quick breakdown:

So, if you’re sending out statements, invoices, ballots, or anything else where you actually want a response (like, in the mail, with a stamp and everything), you’ll want to include a return envelope.

Let’s break it down.

What’s a Return Envelope and Why Does It Matter?

A return envelope is exactly what it sounds like: a second envelope, tucked inside your mailing, that your recipient can use to mail something back to you.

They open your letter
They see the return envelope
They use it
Everyone wins

This is especially common for:

Payments (yep, checks are still a thing)
Forms and ballots
Surveys and reply cards

If you don’t include one, your return rate drops. People are busy, and no one wants to hunt down an envelope like it’s 1997, you know? In fact, you can’t find just one and no one wants to buy a whole pack of envelopes either. So, best case scenario is to include one yourself for your customers.

How to Add a Return Envelope to Your Mailing

Ready? It’s literally one step. (Told you it was easy.)

When setting up your job online, when you get to the inserts page, simply click on the blue “Add An Envelope” button and select with #9 you want to choose.

Boom. Done.

The return envelope will be inserted automatically along with your letter or statement. No extra work. No extra clicks. It’s already built into the workflow.

Still unsure? Don’t forget we made a YouTube video that shows you how to add a #9 return envelope.
Because sometimes it’s just easier to see it than read about it.

🎥 Watch: How to Add a Return Envelope: https://www.letterstream.com/redir?utm_source=video&utm_medium=emailvideo&utm_campaign=emailvideo&utm_id=email&link=https://www.youtube.com/@LetterStream

A Few Bonus Tips

Want it pre-addressed? No problem.
Need a windowed return envelope? That’s an option.
Need a #8 ballot or even a 6 3/4 return envelope? Both are options too.

We’ve thought through the logistics so you don’t have to.

Make It Easy for Them to Respond

If you want a reply, make replying easy. It’s that simple.

Adding a return envelope removes friction, increases response rates, and gives your mail that “oh wow, they actually thought this through” energy.

We’re not saying it’ll make your recipients love you more—but… actually, yeah, it might.

If you’re not already a customer, you can create a free account here and if you’ve used us before simply log in here to get your mailing our quickly and easily with or without a return envelope included.

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.

HOA Made Easy – Visit Us At The CAI National Show

We know your CAI schedule is already filling up with sessions, meetups, and maybe even a Disney detour (we won’t judge). But before the madness begins, here’s your reminder that HOA mailing doesn’t have to be the slow, painful, paper-cut-filled task it’s always been.

The countdown is on! CAI’s 2025 Annual Conference is just around the corner (May 7th–May 10th), and LetterStream is officially in preparation and packing mode. If you’re heading to Orlando, make sure Booth 333 is on your must-visit list.

LetterStream at CAI National Show
May 7th – May 10th
Orlando, Florida
Booth #333

You’ve Got Mail To Send

If you’re still printing notices, stuffing envelopes, and sprinting to the Post Office before 5pm, let’s talk. Because honestly? You don’t have time for that. We built LetterStream so you can send your HOA mail online—without needing a dedicated mailroom (or a spare afternoon).

Certified Mail with tracking? Easy.
First-Class letters and postcards? You bet.
FedEx 2Day from your laptop?
Yes, really. Poscards? We even offer two sizes!

We’ve got solutions for property managers, board members, and anyone who’s ever asked, “Did someone remember to mail that?”

What Kind of HOA Mail Are We Talking About?

All the important stuff. You know—the things that have to get out, on time (not waiting for someone to go to the Post Office or a vendor to keep them in the queue for days or weeks before sending), and with proof they were sent. We help with:

Annual meeting notices (complete with proxy ballots and agendas)
Statements
Violation letters (with tracking, of course, and an option for an electronic signature)
Financial disclosures
Postcards and community updates
Welcome packets for new homeowners
Ballots for elections
Coupon sheets and booklets

If it needs to be mailed and it affects your community, we’ve probably seen it—and send it.

Booth 333: Where Your Mail Problems Go to Disappear

We’re bringing live demos, real mail samples, and real people who can answer your questions (the weirdly specific ones too—we’ve heard it all). Got compliance questions? Curious about our integrations, yes we have an API that connect to CINC and other HOA software? Want to know how long it actually takes to send 3,000 violation notices? We’ve got you.

And yes, there will be ribbons again for our awesome customers who love to showcase that they love LetterStream!

I love LetterStream ribbon at the CAI show.

Who Should Swing By?

HOA managers with too much on their plate
Board members looking for better ways to get mail out fast
People who hate printers (our kind of people)
Anyone who’s ever said “Ugh time for another mailing to be done and sent”

Even if you’ve chatted with us before, stop by! We’re always updating our tools and adding new features—and if you’ve never used us? It’s time!

See You in Orlando!

Come say hey! at Booth 333 during CAI’s 2025 Annual Conference in Orlando. Whether you want to talk bulk HOA mail, Certified Mail tracking, or just need a break between breakout sessions, we’ll be there.

Let’s finally make mailing the easiest thing on your to-do list.

How to Avoid Common Online Mailing Mistakes

Avoiding common mistakes when mailing online isn’t just about saving face—it’s about saving time, money, and possibly your sanity. Whether you’re sending one letter or a thousand, the truth is: mailing online sounds foolproof… until you hit send and realize you just mailed 200 letters to a zip code that doesn’t exist. Oops!

We’ve seen it all. So we figured we’d save you from the usual slip-ups and help you mail smarter, not harder.

The Classic: “Wait, That’s Not the Right Address”

This one tops the list every single time. The address looked right… until it was sent back faster than your coffee hit this morning’s inbox.

Here’s the thing: mailing platforms aren’t mind readers. If the address is off, the mail won’t get there. (And no, USPS can’t deliver based on “well it’s close enough.”)

LetterStream tip: Always double-check your spreadsheet before uploading. Clean columns. No extra commas. Full zip codes. You’d be surprised how many people forget apartment numbers—like the mail is supposed to guess the unit.

Thinking “Online Mail” Means Instant Delivery

Let’s just clear this one up: you’re not sending email. You’re sending real, physical mail—paper, envelope, postage stamp, the whole deal. It still has to go through printers, folders, inserters, and a quick ride with USPS or FedEx.

This means that clicking “send” is just step one. Give it a little breathing room.

LetterStream tip: Build in a day or two for processing—especially for time-sensitive stuff like legal notices or HOA violations. Need tracking or signatures? Certified Mail or FedEx 2Day might be the better route.

Uploading a Glitchy File and Hoping for the Best

Let’s talk about your letter file. Is it clean? Do the addresses line up in the window? Did you accidentally attach last month’s version? These are things to keep in mind and that can be a make or break for your business-critical mail.

LetterStream tip: Before uploading, preview the proof. That little preview button? It’s your best friend. Use it. We promise, future-you will thank you when you don’t accidentally send a test letter to your boss.

Picking the Wrong Postage

This one’s sneaky. You’re in a rush, and without thinking, you pick First-Class Mail when you really needed Certified Mail with an Electronic Return Receipt signature. Or you go all-in with Marketing Mail for your billing statements (spoiler: not a good idea).

Quick breakdown:

First-Class: Fast and reliable for statements, notices, invoices.
Certified Mail: Great when you need a paper trail.
FedEx 2Day: Ideal when timing is critical.
Marketing Mail: For big batches that aren’t urgent.

Formatting Your Data Like a Puzzle

Merged cells, hidden columns, emoji in the address field—oh my. The more “creative” your spreadsheet is, the more likely something will go sideways.

LetterStream tip: Stick to the basics. Name, street, city, state, zip. No formulas. No filters. No random unicorn emojis (no matter how cute they may be). 🦄

And definitely no mixing home and work addresses in the same field. Yes, we’ve seen it.

Skipping the Proof (Again)

We get it—you’re busy. But you know what’s really time-consuming? Fixing a batch of mail after it’s been sent.

LetterStream tip: Pause. Breathe. Preview. Even if you’ve sent the same letter a dozen times before, it takes just a second to catch that typo in the footer or the page that broke in the middle of your sentence.

Waiting Until the Last Possible Minute

We hate to be the bearer of bad news, but if your “urgent” letter gets submitted at 4:59 PM expecting same-day miracles… you’re cutting it close. Plan ahead, always.

LetterStream tip: Get it in early. And if it’s truly an emergency, check out expedited options. We’re fast—but we’re not magic (well, not every time).

Wrap-Up: Mail Online Like a Legend

Mailing online should feel easy—because it is, once you dodge the common traps. Check your addresses, preview your work, choose the right postage, and keep your data clean. (Honestly, most of these are just good life advice, too.)

And if you’re looking for a mailing partner that actually helps you avoid these issues—not one that leaves you staring at a support portal at midnight—LetterStream is here for it.

We make mailing online simple, reliable, and just a little more fun than you’d expect.