Join LetterStream at the 2025 CAI National Show in Orlando

LetterStream is off to CAI’s Annual Conference in Orlando to talk all things HOA mail, and we can’t wait to see you there!

LetterStream is packing up our favorite mail samples and heading to CAI’s Annual Conference & Exposition: CommunityNOW, happening May 7–10, 2025. If you’re planning to be there, come find us at Booth 333. We’d love to say hi—and show you how easy sending HOA mail can actually be with the right online mail platform.

Yes, we said easy and HOA mail in the same sentence. Stick with us.

Why We’re Showing Up

If you’re in community management, you already know that mailing things—violation notices, annual meeting packets, financial disclosures—isn’t always your favorite part of the job. It’s time-consuming. It’s manual. It’s repetitive. And let’s be honest, it’s easy to mess up.

That’s where we come in.

We built LetterStream to take that entire task off your plate. No more printing. No more envelope stuffing. No more rushing to the post office before it closes. Just upload your files and we’ll handle the rest—like, really handle it.

CAI’s Annual Conference is one of our favorite events of the year because it gives us a chance to connect in person with the people who are doing the hard work of keeping communities running. Whether you’re a board member, a community manager, or the go-to person for “who’s mailing what,” we’d love to show you how our HOA mailing services and automated mailing solutions can make your job way less stressful.

What You’ll Find at Booth #333 (Besides a Bunch of Friendly Humans)

We’re not just showing up with brochures and a handshake. We’re bringing real solutions—and a chance to see how they actually work in the wild.

Swing by and we’ll walk you through how easy it is to:

  • Send Certified Mail without ever leaving your desk
  • Upload your files and let us handle the printing, stuffing, and mailing
  • Improve your mailing process without adding more work to your plate

You’ll get to see real mail samples (yes, the actual stuff we print), ask us anything about timelines, compliance, integrations—you name it—and pick our brains about how to make your next big HOA mailing way less painful.

Whether you’re a seasoned community manager or just figuring out what “annual disclosures” even are, we’ve got tools (and stories) to share.

Also, we might actually have snacks. But no promises.

What Makes Mailing with LetterStream Different?

We’re not just another platform. We’re a team of real people who actually get what HOA teams deal with day-to-day. So we built tools that actually solve the problems—not just talk about them.

Here’s what that looks like in practice:

You log in, upload your files, and we handle the rest
No supplies, no equipment, no guessing. Whether you’re sending first-class mail for HOAs, certified letters, or even FedEx, it’s all done from your computer.

You get tracking on certified mail and FedEx
Need to prove it was delivered? You’ll have the receipts (digitally speaking).

You avoid the common mailing mishaps
We’ve built in checks so you’re not losing sleep over missed pages or mismatched envelopes.

You get hours back in your week
Because let’s face it—your to-do list is long enough without “go to the post office” on it. With our print and mail service, you can send hundreds of letters in just minutes.

Come Say Hello

Whether you’ve used LetterStream before or are just hearing about us for the first time, we’d love to meet you. Booth #333. Orlando. May 7–10. Mark your calendar, circle it in red, set an alarm—whatever works.

Let’s talk about the mail you send, the problems you’re trying to solve, or even just which session had the best coffee. We’re all ears (and envelopes).

LetterStream offers bulk printing and mailing services allowing companies to send physical mail online. Whether it’s online Certified MailFirst-Class MailFedEx 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.

LetterStream small logo

Going Out On A Limb

I Love LetterStream Ribbon

We decided to try a different kind of giveaway at our booth at the National CAI Trade Show this year, and to be honest, it could have backfired on us.

This year we took the risk of offering “I Love LetterStream” ribbons to our customers and API partners as they stopped by our booth. We were hoping that a few would attach the ribbon to their trade show attendee badge. But whatever happened, we knew it would be a learning experience.

You see, when you ask someone to wear a ribbon that says they love you, you open yourself up to a whole lot of scrutiny. Would our customers and partners love it or hate it?

We waited patiently as the Expo doors opened and attendees started filing into the aisles. Then the first visitors approached our booth, they looked up to survey our exhibit, they noticed the LetterStream banner, and then we heard these words… “LetterStream!!, We love LetterStream!!” We breathed a sigh of relief and passed out the “I Love LetterStream” ribbons, which were quickly applied to their trade show badges.

Indeed it was a risky move, and one that might have caused us to be accused of excessive boldness. But in the grand scheme of things, it certainly created an honest feedback mechanism. And we discovered what we hoped would be true; that our customers LOVE the LetterStream experience. We passed out slightly over 100 ribbons at the Community Association Institute (CAI) national trade show and the CAI Arizona show.

We work very hard to provide incredible speed, impeccable accuracy and crazy good service; and we are tickled to know that it is appreciated by our customers.

To our customers and API partners that were happy to wear our ribbons, we say “Thank You!”. Thank you for your feedback, your partnership and your appreciation.

For those who aren’t that familiar with LetterStream, check out some of the positive things our customers are saying about us on our testimonials page. And if you have something you want to add, please keep the comments coming!