“SendSquared is totally customizable to the way we do business.”
Case Study · St. George Island, Florida (Florida's Forgotten Coast)
Collins Vacation Rentals Fifty Years on St. George Island. The Last Five on SendSquared.
Shawn Montgomery, Director of IT, Collins Vacation Rentals
50 years
Renting homes on St. George Island
Collins has been letting homes on the island since the mid-1970s, long enough to have built a very particular way of working. Any platform they adopt has to fit that, not the other way round.
5 years
The most recent five, on SendSquared
"You've been with SendSquared a couple years now, right, maybe five?" "Yes, right, yeah, five years." Shawn Montgomery, Director of IT, speaking at VRMA 2026.
300+
Properties on one platform
"We manage over 300 properties and SendSquared has been instrumental in streamlining operations. Consolidating all communications into one platform while maintaining personalized guest experiences has been transformative for our team."
4 tools
Consolidated into one platform
Rezforce for the call center, Guest Notify, Reach for marketing, and NavisHMS for housekeeping all collapsed into SendSquared.
Pain free
How the migration actually went
"I told them that when we switched over it was easy and pain free. Between the Navis engineer and Roy everything went smoothly. And that both Roy and you were onsite to insure everything worked."
Quick Facts
- Industry:
- Vacation Rental Management
- Market:
- St. George Island, Florida (Florida's Forgotten Coast)
- Portfolio:
- 300+ properties: beachfront homes, villas, cottages, condos and townhomes
- Vendors replaced:
- Rezforce (call center) · Guest Notify · Reach (marketing) · NavisHMS (housekeeping)
- Interviewed:
- Shawn Montgomery, Director of IT, at VRMA 2026
- In business:
- Roughly 50 years, since the mid-1970s
Shawn Montgomery is Director of IT at Collins Vacation Rentals on St. George Island, Florida. Filmed at the SendSquared booth at VRMA 2026, he talks through five years on the platform: founders who write the code themselves, an on-site visit that shaped the product around how Collins actually works, customizations that start with a phone call, and support that runs through direct cell numbers rather than a ticket queue.
What I like about SendSquared is that Nic and Roy are not only just the owners, but developers. They come to our office. They took time with us, find out how we work, and they built the platform around what our needs were.
SendSquared is totally customizable to the way we do business.
The Transition
Before vs After SendSquared
Before
Guest communication spread across separate channels and tools, each with its own inbox and its own history for a 300+ property portfolio.
After
One platform carrying the communication for every property, which Shawn describes as "transformative" precisely because consolidating it did not cost them the personalized guest experience.
Before
Software bought off the shelf, where a workflow that does not match the vendor's assumptions is simply something the team works around.
After
A platform the founders adapted to Collins after sitting in their office: "anytime that we have any customizations that need to be done, they're just a phone call away."
Before
Vendor support that runs through a ticket queue, where an outage during peak booking season waits its turn.
After
Direct access to the people who wrote the system. As Shawn put it: "To be able to talk with the developers directly is a rare thing ... It is of great comfort to me to know that when we have issues you guys are handling it directly versus a tech support team that does not have your knowledge of the system."
Before
Four separate vendors covering the call center, guest notifications, marketing and housekeeping, each billed and supported on its own.
After
One platform covering all four, with a migration Shawn described to a prospective customer as "easy and pain free" because the teams were onsite to see it through.
Why It Works
The partnership behind the platform
Collins Vacation Rentals has been renting homes on St. George Island for roughly fifty years. That is the single most important fact about this account: five decades is long enough to have developed a very specific way of doing business on a 28-mile barrier island where the season, the weather, and the repeat-guest relationships all behave differently than they do inland. That is exactly the kind of operator that generic hospitality software fits badly, and before SendSquared the work was split across four vendors: Rezforce on the call center, Guest Notify, Reach for marketing, and NavisHMS for housekeeping. What Shawn Montgomery keeps coming back to is not a feature list but an access model: the two people who own SendSquared are the two people who write it, they came to the office to learn how Collins works before building, and five years in they are still reachable by cell phone when something goes wrong. He has made that case himself on reference calls for other operators, telling one prospect worried about migration risk that the switch was easy and pain free because both teams were onsite to see it through. For an IT lead responsible for guest communication across 300+ properties, that shortens the distance between noticing a problem and having it fixed to about one phone call.
Full Transcript
Word-for-word from the conversation
Thanks, Shawn. Just tell me, you've been with SendSquared a couple years now, right, maybe five?
Yes, right, yeah, five years.
Well, maybe just tell us what you like, how things have been going.
All right, well, what I like about SendSquared so far is that Nic and Roy are not only just the owners, but developers. They also develop the platform. They come to our office. They actually came in. They took time with us, find out how we work, and they built the platform around what our needs were. And anytime that we have any customizations that need to be done, they're just a phone call away. They're receptive to all our ideas. They listen to our input, and we see actual results that come out of that. SendSquared is totally customizable to the way we do business.
Whenever we do have an issue or something goes down, I have direct contact with not only the owner, but the developers, to get things done and fixed immediately.
And how has it been with our support, and being able to help you when things go wrong?
Yeah, the best thing that comes out is when we do have an issue. And I don't know if you want me to say this or not, but I have their cell phone numbers. I have Nic's cell phone number, and I have Roy's cell phone number. And Nicole is always right there to help us too. So whenever we do have an issue or something goes down, I have direct contact with not only the owner, but the developers, to get things done and fixed immediately.
Great. And what else could we maybe do to help you?
Right now, it's to keep Natalie happy, our head reservationist who takes care of all of our clients.
More Client Stories
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