11. Growth in a Box: STR Marketing Automation for the AI Age

Most STR operators have the guest data. What they don’t have is a system that turns it into bookings.

In this episode, we unpack the idea of Growth in a Box: how Yada helps short-term rental operators automate the marketing that usually gets ignored like repeat guest campaigns, winbacks, loyalty, upsells, booking anniversaries, gap-night outreach, and direct booking follow-up.

Instead of relying only on OTAs or one-off email blasts, Yada helps operators build an ongoing growth engine from the guests they already have.

We cover:
* How past guest data becomes a direct booking asset
* Why marketing automation matters for STR operators
* How Yada combines campaigns, journeys, loyalty, and AI Signals
* What it means to create more repeat bookings without adding more manual work

Key takeaway: you don’t need more random marketing tasks. You need a growth system that runs consistently.

Get a free revenue assessment and see what messages Yada would create for which guests at yada.ai/demo

Transcript

SPEAKER_01 0:01

Hello, everybody, and welcome to the STR Sovereignty Podcast. My name is Steve Hasi from Yada. I'm here with the CEO and co-founder Peter Oydrovich. And today we're going to talk about growth in a box. And you know, that's like uh just you know, you kind of turn the crank and the jack in a box pops up with growth in a box, you turn the crank and the money pops up. So uh that's the goal for all software in the end. Um, how we're gonna make that happen? Let's uh let's dive into all things growth and software. You ready, Peter?

SPEAKER_00 0:33

Yeah, no, this is a really exciting topic because so much has changed in the way that software is being built over the last couple of years. And uh so much more is possible now than it was even a year or two ago when it comes to having software and tools that just work out of the box for a specific industry, in this case, short-term rentals, uh, that really make that marketing uh process, marketing lifecycle, repeat bookings, filling empty calendar nights, et cetera, uh very easily doable in a way that, you know, even a very short time ago was incredibly labor-intensive and split across a lot of fragmented tools. So, you know, I think uh what we're gonna be talking about today is some really fascinating stuff.

SPEAKER_01 1:16

I want to start on that point that you mentioned in terms of fragmentation.

SPEAKER_00 1:20

Yeah.

SPEAKER_01 1:22

The average STR operator has about seven different tools, and that's on the low side. You've got your property management system, you've got your revenue management system, you kind of go on and on through the whole stack. It's a lot of software.

SPEAKER_00 1:38

Yeah.

SPEAKER_01 1:38

Property management tools are trying to build it all into their own stacks. It's like, hey, cut all the other stuff, you can use it all here, but it's never going to be top quality. And so you kind of want to go to how does the business work and get the best tool for that part of the business? And so when we talk about growth in a box, one of those areas is going to be marketing. How do you reach out to your past guests? How do you increase revenue per stay? If you can get all of that into a single tool rather than five or six tools, you are getting much closer to that promise of how you can have great software for your business.

SPEAKER_00 2:15

Yeah, and I think especially on the growth side, you know, this is something that hasn't really been done before in short-term rentals and in any uh, you know, hospitality setting, because um, you know, to your point around software fragmentation, uh, it is one of the most complicated and kind of resource-intensive problems to solve in any uh vertical and in any business, like building a really, really good and really effective marketing, uh, marketing pipeline and marketing lifecycle. Um and uh it's it's been one of those things that you can't really solve with like a quick aggregation of points solutions, just because of how interconnected every aspect of marketing is and how interconnected every aspect of growth is. So this ability to do it with with just a couple of clicks and one integration, I think is is very uh you know, very, very novel for the short-term rental space and more broadly the hospitality space. If you look at hotels, um, you know, boutiques, things like that in general. Um, and yeah, like in in short-term rentals, you know, you've got probably like at least seven or eight pieces of software that the typical operator requires to run, you know, that's fine for things that don't like hugely need to talk to one another. Like if you build a um, you know, if you if you add like a revenue, like a rev ops tool that does dynamic pricing, that only really needs to talk to one thing, which is the uh the the booking sites through the OTA and it you know it has its own data sets and it kind of um you know it it works in a silo to optimize listing price. Um so you you you can end up in a situation where you have like seven or eight tools tacked onto a PMS that do these old point solutions for marketing that just breaks down when you try to do it in in tools that are not like a complete solution for marketing. Um just because it it's it's the data flow kind of breaks down, the data uh lives in silos where it's it's hard to extract. So what we're doing here uh at Yada is is really unifying that whole data layer, um, unifying the marketing experience so that when you connect with Yada, you do get like the ability to market immediately without having to cobble together a bunch of different tools.

SPEAKER_01 4:32

Well, and I think you hit on something that matters a lot. It's one thing to have a unified tool set where it's just more convenient. You know, you have your revenue optimization inside your property management system. It's like, hey, one bill instead of two. Okay. But it doesn't change things dramatically by being a unified item, it just makes things a little simpler for your business. When it comes to marketing, though, having data spread across four or five different systems means it's a worse tool, right? Your setup is less optimal than if you have it in a single tool that's able to reference all those other data points and actually speak to it intelligently. So when we talk about the AI age, the thing that makes AI go and like really shine is if it has good data. So that it knows as much context as possible. Past C's, past conversations, guest information, previous messages, messages that are most effective. Once you layer all of that on top, you have a completely different thing than just, yeah, I can send texts. So what? So what if you can send a text to everybody if you don't know what you're supposed to be saying? That makes the difference for a growth, you know, a real growth engine.

SPEAKER_00 5:50

Yeah. And and growth is one of those things, like like I think one of the things that really separates like stepping out of the the um kind of the the hobbyist uh the hobbyist way of building a business with a really you know intentional way of building a business, like like being intelligent about growth and being very intentional about growth is is one of those things that that that separates like it's what separates good businesses from bad businesses. And whatever business you're running, whether it's a software company like us or whether it's a short-term rental property management or a boutique hotel or whatever, marketing and growth are the things that require the most data. Uh primarily because you're operating a very high at a very high degree of scale, and you only have like so many opportunities to reach out to somebody to send somebody a message, et cetera. Like you're you're you're kind of compressed, like you're very compressed between uh two realities, which is you you need to message somebody effectively. So they open an email or click on a link and open a text message, and the other reality, which is you have unfilled nights on your calendar. So you need to be really intelligent about filling those nights as securely and as as kind of um you know, as as as like with as much probability as possible. So your marketing stack needs to be something that takes all of that into account when you're sending messages. And you know, there's a lot of tools out there that have proven to be like kind of effective, but but in general, like not very effective at marketing in hospitality. Not because they're bad at getting messages out, like you can spin up MailChimp and get a million messages out a month. That's just the the issue is that you know, A, it's gonna be really hard to figure out if if your messaging is working, if your offers are uh actually yielding results, like if there's something that you could do to maybe improve your offer or improve your timing or improve the audience or the segment, um, that you just don't get if if you're kind of if you're doing the same thing on marketing that you're doing with the rest of the the STR management stack, which is to cobble you know half a dozen point solutions together to try to solve that problem and work around that.

SPEAKER_01 8:04

And let's think about what the ultimate thing could be. When you're talking about sending messages, talking about marketing, the ideal would be having one person look at the full history of each guest that stayed with you and writing the perfect message for that guest. Yeah. You can start to approximate it with you know personalization tokens and some smart uses of that data. But what takes it to the next level and what makes it just a whole different ballgame is when you apply, you know, in this case a large language model to all of that information that a human would otherwise be looking at and craft the message from there. That is where that kind of ingestion of data and having it all in one place makes all the difference. Because if you're able to send a personal message rather than just a blanket message, you are going to double, sometimes even triple, your response rate. Obviously, it's better to send something than not send something, but if you can send something personal, not just personalized, but actually personal, that is that's marketing, that's marketing for the AI age, right?

SPEAKER_00 9:20

That is the promise that AI Well, actually, a really cool anecdote here in a story that I wanted to share with the viewers. So I was I was talking to an operator recently who um they were they were putting into effect uh uh uh quite a bit of marketing resources a couple of years ago, uh before this intelligence layer was uh even available. And uh they had built out a really, really sophisticated system of essentially like a table of everyone that had stayed in the past, and you know, probably like you know, 15 or 20 attributes attached to each guest. Like, where do they stay? How much money did they spend? Do they have any preferences, etc.? And then building these like quasi-personalized uh emails and messages and things like that that was essentially like mad libs, like it was like a you know, 15 variable madlibs thing that that um never ended up really working because there was no good way to unify that intelligence layer. So they had all these different sources that they would manually go in and update a spreadsheet and things like that. And they they they got about as close as anyone's ever gotten to at that point, uh, to a genuine like marketing intelligence layer and a go-to-market intelligence layer for their portfolio, uh, but never were were never able to actually make it work because it was um it was like a manual labor, uh, a manual uh a manual effort tacked onto something like MailChimp that they were using uh to get the messaging out of, you know, get the messaging out the door and into guests and guests inboxes. And what we're seeing that we can do now with Yada is um, you know, even even our most basic implementation of the of a data layer is like you know, 10 to 15 times more granular than whatever it is that they had, because we can you know build build an incredibly accurate map. I think the average guest journey is something like you know, 80 or 90 individual like rows that represent who that guest is, what they did, what preferences they have, uh behavioral uh parameters around them. Like do they book two weeks in advance or six weeks in advance or two months in advance, demographics like age, location, uh spending power, like all of these things we can now uh aggregate and ingest and use within Yada and combine it with our with our intelligence layer so that all of those messages that you know even previously, you know, where uh that that kind of like Frankenstein Madlib's um uh output was was you know the top of the line and like the most uh optimal output that you can get, like even that is like you know, a one out of ten compared to like the eight out of ten or nine out of ten or ten out of ten that we can do now with intelligence in a unified marketing platform to get the messages out to the right guest at the right time.

SPEAKER_01 12:11

Yeah, because if you think about it, there are so many points on that guest journey. Yeah, if you're just trying to get the best email out the door, you're never gonna do it. Some things need to be automated based on timeline. And you know, most property management systems have kind of an automations flow, but they stop basically around the stay, right? If you can increase it, you know, before this day to have some things that increase that uh booking value, and then if you can automate based on you know booking anniversary, once they've returned home, how do you check in with them there? Um, and then of course, the uh if they're local, how are you reaching out to them to reference the fact that they could just pop by for a weekend? Have they stayed for weekends in the past? All of these things that if you were just sitting back, having a drink and thinking about the best ways to reach out to people, you'd be doing. Except you're not sitting back taking, you know, you're turning turning things over, you're trying to grow your business. So you need the software to be solving those problems for you.

SPEAKER_00 13:16

Yeah. Well, that's where we where we really invest. Um, you know, the vast majority of RD research is goes into building that intelligence layer so that those things like highlighting the right guest who lives half an hour away who could come by for the weekend, uh, you know, that that person is highlighted when you have an empty weekend like two weeks in advance, and not highlighted when it's already 95% occupants and you've you've got folks flying in from all over the country to visit. Um, you know, those those are going to be much more high-value leads and much more high value guests at that moment. But then you've got that that segment of people who live half an hour away who'd be more than glad to come in on a shoulder weekend or an off-season weekend and fill a room or fill a property that would otherwise be empty. Um that's really what the uh what the the massive step function increase here is compared to what marketing in hospitality might have looked like a year or two ago. The big step function increase is that unified data layer, that unified um data platform that powers marketing, plus the intelligence layer on top of that, that takes all of that data, turns it into very proactive messaging, turns it into very personalized outbound and very personalized messages and personalized responses that then uh can can lead to direct bookings and direct engagements and repeat bookings and all these things that really um in many ways could be quantified as free revenue and free cash flow because it's it's essentially activating an asset that would otherwise be sitting empty.

SPEAKER_01 14:47

I mean, it is such an exciting time to be in business. Yeah. Because the idea that you just have to put up with crappy software that makes you do a lot of work is going away. And so you're looking at a tool and it seems like you're gonna have to do a lot of work and you're gonna have to be very skilled. I'm sure you got skills, I'm sure you got plenty of skills, but you shouldn't have to have skills in every aspect of running a business. The software should start giving you those powers.

SPEAKER_00 15:18

Yeah.

SPEAKER_01 15:18

Unless you're seeing that, you're not working with the right team. You're you're you're, you know, keep keep looking because we are now in an age of building a business where you do not need to have skills, you just need to put the right team together.

SPEAKER_00 15:33

Yeah. Put the right team together and then make the right choices when it comes to the tools that you're using. Um, and if you're if you're smart about those choices, and if you're if you're uh I would say ambitious enough to understand that that you know the future does not equal the status quo that exists right now, especially when it comes to these step function things that I just talked about, that that your you know your your results and the outcomes that you see are going to be really, really impressive and really enviable.

SPEAKER_01 16:05

And it's funny, like you look at these companies that are heavily funded, you know, uh Salesforce.com, you know, all kinds of Oracle, these huge industries, they um they're kind of they're all aiming for this same thing. Like let us automate your growth. Yeah, that's what you should be expecting, right? It's it's the direction everyone is aiming in. And if you're not getting those vibes from your software, from the people that you're that you're working with, they're probably operating from the old model, which makes sense. Like the old model worked for a very long time, and that's kind of what people expect from their software. But um growth in a box, growth in a box, just it's what you know, it's what's possible.

SPEAKER_00 16:56

Yeah, and I would I would also also say to the listeners and to the viewers that you know the next wave of adoption and tools that that um that are going to be most interesting in this industry and in many others are tools that combine the service layer and the software layer into one uh one cohesive unit. Um, so when you talk about growth in a box, I think the best way to talk about that would be the best way to describe it in a way would be that this very deeply intertwined uh relationship between services and software that up until this point has not really existed. And or at least has not existed in any sort of capacity beyond the most basic of automations. Um so especially when it comes to growth and especially when it comes to uh certain aspects that are incredibly difficult and like resource intensive, but don't necessarily touch the real world as much as like operations and turnover and cleaning and things like that might do, where you still have a massive human in the loop, um a massive human-in-the-loop pres uh kind of angle to it. Exactly, like requirement to it when it comes to growth and marketing, et cetera. It's like data-wise, the most intensive and process and workflow-wise, the most intensive aspect of any business. And I think that anybody who runs a business or has built a business will will tell you that like shipping product is easy. I'm I'm an engineer, I have a great team of engineers around. Like building great product is is you know, it's very difficult from an intellectual standpoint, but you have a pretty good idea of how to do it. When it comes to growth, there's no uh there's no way around it beyond just activating the data, being relentless about pursuing opportunities, being relentless about um chasing down every possibility to increase revenue, increase margins, uh book repeat customers, et cetera. And in short-term rentals and in hospitality, it's much the same thing, except for that because it is uh a specific industry like short-term rentals and like hospitality, you you now get the stability with company, you know, with platforms like what we're building uh to automate essentially the entire pipeline and data layer and process layer that that goes into that and uh and do it with just a couple of clicks as opposed to spinning up an entire team to run um to run growth and to run marketing and to run the reporting and analytics and loyalty and all this stuff that goes into it.

SPEAKER_01 19:35

Honestly, that's my favorite part about the conversations about you know AI job displacement. It's not that AI is going to be displacing a bunch of jobs. Sure, there are things that are gonna be automated or gonna go away or gonna change. What it means is the people that didn't have the money for those jobs or you know, the bandwidth or the expertise, get those workers from the AI. So that's the big promise, and what you should be looking for and how the software you work with treats AI, not just for answering questions, but actually doing that service layer for you and doing it at a very high level.

SPEAKER_00 20:09

And and doing that service layer for you in a step function way. So, you know, we view things as upsells, for instance, as a really nice beneficial part of running a short-term mental business. And they're not, you know, they are an incredibly potent way to drive growth, but compared to something like a full marketing stack that can reach out to your entire guest book and integrate that with a loyalty layer and things like that, it goes from, you know, let's let's you know, data-wise, like you know, one or two data points to the per per stay to you know, probably 1500 to 2000 data points and decisions and and and calculations per per stay and per repeat, say, that goes into it. So it's compressing this this massive, like multiple order of magnitude step increase in complexity, offering that same step increase in results to the customer and to the user, but without the step increase in effort and time and resources need to be spent that need to be spent. So it's like a 1% increase in in work for uh a 1,000 to 2,000% increase in marketing results and growth and retention results and all of these things that that you know come into play to uh to really build a sustainable business model that doesn't rely on OTAs, that doesn't rely on first-time bookings, and that really um you know activates that that that uh that guessbook of of multiple thousands of of emails and phone numbers that that uh a typical operator might have in there.

SPEAKER_01 21:40

That's fabulous. Um my favorite thing is when something really complex like what you were just talking about kind of works its way up into something really simple, which is just here's this software, use it, grow your STR business. And that's yeah, that's really what we're working on is you know. Have all this complexity, all these considerations, all of this data and stuff that's happening underneath the hood. But for you, yes, turn this on. Okay, this looks good, make it happen. And then away you go. And it's covering all these different aspects of the guest journey. Like the fact that something like this doesn't exist for the STR space is ridiculous. Like that is why they're here to build this. Right? Like we're here building it because, like, right now you kind of have to be really smart with a big team of people with a lot of time and money to make this happen. That should exist in software, and that's that's why we're doing it.

SPEAKER_00 22:34

Yeah. And the only folks that were doing this before, you know, before now were brands like Four Seasons and Waldorf, like you know, brands that had a team of people that were able to sit through all of this personalized data, fill out customer profiles, and then get reminded to reach out to folks on booking anniversaries and things like that. Uh and and now you don't need a team to do that. You can just do that with one piece of software.

SPEAKER_01 23:00

Yeah, brilliant. So if this sounds like something that you want to include in your business and you are not yet a Yada customer, come on by, check it out. We'd love to have a chat. Head over to yada.ai slash demo. We'll connect and uh walk you through not just what Yada looks like, but actually what messages Yada will be creating and for whom uh you can actually have it uh use your data in that initial walkthrough. It's a lot of fun.

SPEAKER_00 23:28

Exactly. It's really exciting stuff, and you know, it's uh it's also really exciting to see the real-time results that we get with Yada. So seeing all of the conversions that happen, the repeat bookings that get generated, the uplift revenue, like it's it's really exciting stuff to be on all sides of it, whether you're you're the you know the user using Yada, whether you're the guest that's getting good outreach and loyalty points and good engagement from you know the wonderful brands that you stayed with, or whether it's us on the Yada side, being able to see these amazing results happen across the board for both guests and operators is is just really exciting.

SPEAKER_01 24:08

You know, in a world where we can all use a little uplift, here you go, folks. Here's the uh here's the uplift.

SPEAKER_00 24:16

Yes, indeed.

SPEAKER_01 24:17

Thanks for listening. We'll talk to you next time.

SPEAKER_00 24:21

Take it easy, everybody. Until next week.