When gaps open up, StayBooked texts the clients most likely to book automatically. No blasting. No interruptions. Just a full calendar running on autopilot.
You check your books Tuesday morning. Every chair is covered through the afternoon. Looks like a full day. Fast forward to 10am. Three clients have rescheduled. You've got gaps you didn't see coming and no way to fill them from behind the chair.So you stop mid-cut, grab the iPad, and blast your whole client list: "We have last-minute openings today!" A couple bookings trickle in, but they're for Thursday and next week. Those Tuesday slots you wanted to fill? Still empty.That's not marketing. That's a fire drill. What if the right slot got filled before you even noticed it was empty? That's where Staybooked comes in.
Plug in Squire, Square, or Boulevard. We pull your client list, appointment history, and calendar for every provider in your shop. Two minutes. No complicated setup.
That Tuesday 2pm gap? We don't blast everyone about it. We find the client who's actually overdue, whose usual service fits the window, and who's booked Tuesday afternoons before. One open slot, one perfect-fit client, not a mass message to hundreds of people who aren't interested.
"Hey Marcus, it's been about 5 weeks since your last fade at The Common Chair. Cameron has a 2pm open today. Want it?"Short. Personal. Sounds like it came from your shop. And you didn't have to write it, schedule it, or stop what you were doing.
Client replies yes. The appointment lands in your calendar. You see it next time you check your books. The gap that would've sat empty all afternoon? Filled while you were behind the chair.
You've got Squire Engage, or Square Marketing, or some version of a mass SMS button. You press it, a booking or two comes in. It works... sort of. The slot you were actually trying to fill? Still empty. And now you've blasted everyone on your list to get there.
| Capability | Staybooked | Square Marketing | Squire Engage | Online Waitlist |
|---|---|---|---|---|
| Fills every gap without you lifting a finger | ✅ | ❌ | ❌ | ⚠️ (only if someone signed up) |
| Targets clients who are actually due | ✅ | ❌ | ❌ | ❌ |
| Matches the right service to the right slot | ✅ | ❌ | ❌ | ❌ |
| Fills the specific slot you need filled | ✅ | ❌ | ❌ | ❌ |
| Reaches clients who never signed up for a list | ✅ | ✅ | ✅ | ❌ |
| Sends personal messages, not generic blasts | ✅ | ❌ | ❌ | ❌ |
We start with a 45-minute paid research session to understand how
Whether or not you move forward after the research session is entirely up to you.
We build software for businesses where missed appointments mean lost revenue. Collectively, we have 15+ years of experience building and operating production AI systems for both large brands and small businesses where timing, reliability, and customer trust mattered. We’ve seen how easy it is for repeat clients to quietly fall off, and how hard it is for busy owners to catch it in time.StayBooked applies that experience to a simple problem: helping the right clients rebook at the right time, without adding work or annoying your customers.

Ian Dangla- Product & Systems
8+ years building customer automation at Meta and Rocket Companies, and helped scale Goodcall AI into a platform used by thousands of small businesses. Focused on making automation feel natural and drive real bookings.

Andrew Gasiorowski- Software & Automation
8+ years building business-critical automation at Rocket Companies and Goodcall before becoming a founding engineer at Haven AI, which has automated millions of back-office procedures for property managers. Focused on reliability, correct targeting, and handling the messy edge cases that matter in day-to-day operations.
We analyze their booking history. Sarah gets highlights every 8 weeks like clockwork? We reach out in week 7. For clients with irregular patterns, we use a simple rule: if it's been 6+ weeks and they usually come more often, they're probably due. Over time, the system learns each client's rhythm and gets smarter about timing.
Something like:"Hi Sarah! It's been about 8 weeks since your highlights. We have Tuesday 2pm or Thursday 4pm open — want one?"Short. Personal. Names the service. Offers specific times. Easy to reply YES.
They reply STOP and they're immediately removed. Simple, respectful, required by law.
No. Pay per filled slot. Cancel anytime. No minimums. No commitments. If we never book a slot, then you never pay.
Because we're still learning. We want real stylists using this so we can improve it. In exchange for your feedback, you get a lower rate than what we'll charge later.
We’re running a limited set of paid research sessions with appointment-based businesses to understand real rebooking workflows. This is paid research where we compensate to learn from you. Not a sales pitch. Go ahead and book a slot. If your business qualifies, you’ll receive $75 for a 45-minute call.
45 mins • $75 paid session • Research, not a sales pitch
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