19. Why Every STR Operator Needs a Guest Sales Team

The best guest sales team may already work inside your STR business.

In this episode, Steve and Petar explain why every short-term rental operator needs a deliberate sales function, even if it is just one focused hour a week. They cover founder-led sales, phone outreach to past guests, CRM tracking, personalization, and why human connection stands out in an AI-heavy market.

Key takeaways:
• Why guest services alone is not a sales strategy
• How founder-led sales builds skill and creates growth
• Why calling past guests can outperform another email
• What guest data and CRM activity to track
• How personal outreach creates repeat bookings and loyalty

Learn more at https://yada.ai/demo

Transcript

SPEAKER_01 0:00

Good morning and welcome to the Fully Booked Short-Term Rental Podcast. I'm here with my co-host Steve on a wonderful Friday morning. And we're going to talk about a really cool topic today, which is why every short-term rental company and every short-term rental operator should have a sales team. So not just a customer support team or a guest services team or a cleaning team or a turnover team, but why having a sales team within that organization is critical. And that doesn't just need to be a team of 10 people, that can be yourself. If you've got three, three listings, that sales team is an hour a week of your time or two hours a week of your time. So that's a really fun topic because it's overlooked and often kind of left to linger by the wayside. So let's kick it off, Steve. You're uh you're kind of our resident. Uh, you know, I used to hate calling people, and now I love being on sales expert here. So yeah, let's let's get started with that.

SPEAKER_00 0:59

For sure. And I think that honestly, if if there's one mindset change that you can actuate in your business, it would be that. It's easy to send an email. A lot of people still don't do it, but like it's easy to just you know spin up a program, send out a message, and say, okay, I've done I've done my job at trying to get my past guests back. But it takes a certain amount of courage to pick up the phone and call a number and risk uh you know being rejected, risk someone saying, Oh, sorry, I'm busy, um, risk, you know, wrong number, all of that kind of stuff. And so a lot of people don't do it. But the benefit on the other side of picking up the phone, making that real-time connection with a person who has already stayed with you, mind you, is enormous. And so the the starting point for kicking off a sales team within your business is saying, I want to talk to my past guests. Yeah, we don't have to talk to all of them. Some of them you probably don't want to reach out to for whatever reason. Maybe it's you know the average daily rate wasn't high enough for you know uh people reach out. Maybe you know, they didn't have a great experience or you didn't have a great experience with them. But for the the handful that you do want to reach out to, this is your chance to be of service, right? If you see sales as a kind of service, then suddenly it changes the picture entirely. So that's kind of the starting point mindset-wise for building that sales team internally.

SPEAKER_01 2:40

Well, and the numbers are there as well. I mean, if you look at software, you get a lot of platforms that'll charge $100 a month or $200 a month, et cetera, where they will have somebody call you and talk to you and develop a personal relationship with you. Meanwhile, like a lot of these reservations and stays are $1,500, $2,000, in some cases, like four or five or six thousand dollars that we've seen. And it's completely impersonal. It's completely done through the platform like Airbnb, booking.com, whatever. Uh, and there's this hesitation to actually call up that person that stayed and see if you could do the same thing for them next year. And I would just, you know, I'd before we continue any deeper down this, you know, or through this conversation, I would just say it's super important to recognize that these are really high value, like in many cases, like high value transactions that are happening, high value bookings. And you need to be on top of building those relationships with these folks that are staying there in the same way that pretty much every other company in the world is focused on building their relationships with their customers. So, you know, there's there's little difference. I mean, aside from this being hospitality and the other maybe being software or industrial tools or whatever, uh, there's always that relationship and sales aspect to it.

SPEAKER_00 3:56

Yeah. And the best hospitality brands are already doing this.

SPEAKER_01 4:00

Yeah.

SPEAKER_00 4:01

They have that inside sales team. They probably call it something more like uh, you know, guest services or concierge or some kind of thing that recognizes what you're actually doing is building a relationship over time. Yeah. Sales gets this bad rap of being impersonal, pushy, you know, aggressive, just being about the number. But when we're talking hospitality, it is about being of service. It's about how can you extend that hospitality beyond this day and actually help them make that next decision, right? Because if you think about the psychology of sales, inertia is the thing that usually wins the day.

SPEAKER_01 4:43

Yeah.

SPEAKER_00 4:43

People will just sit there until something sparks them to take action. So maybe it's, oh my God, the summer's coming up and we haven't booked our vacation yet. What am I going to do? So there's that moment of panic, that moment of, oh gosh, I have to spring into action. There's the mental load of where do I find this information? Where should we stay? All the decision making involved. If you reach out before that, you save them from that whole process and you get the business. But there's service involved, and that's what makes it hospitality.

SPEAKER_01 5:17

It is. And there's a lot of precedence for it. If you look at hotel uh brands, especially once you start getting into the higher range niche or boutique or luxury, uh, a lot of those, a lot of those companies have very developed and very, very capable internal. I mean, they're not called sales teams. To your point, they're they're usually concierge teams or or guest services teams and things like that, but they're really there to uh you know establish the relationship between four seasons and whoever's staying there, so that the next time they go to Maui or the next time they they they you know take a family trip, they're staying there. And and it's not just about like building the relationship, but a lot of it is also using the information that's available to you to make it magical in a way. So at Four Seasons and Ritz, uh, I have a really good friend there who spent quite a few years advising. Um, hospitality is all about creating these magical moments and aggregating a bunch of magical moments, like one after the other, so that every time you stay, you feel like you're living a different life. And you know, in a lot of ways, like that's why people travel, like that's why they go on vacations. They want to change up their routines. So if you stayed, for instance, at um, and I'm using this as an example because they really uh they have a really good um ecosystem around this, but if you stayed at four seasons, uh they have something like 10 different types of sheets and pillows, and everyone, like if you're paying you know $1,000 a night, you really want to be treated well, right? And the same thing goes for short-term rentals. Like if that house costs like two, you know, $2,250 a night to rent, or even if it's like five or seven hundred dollars a night to rent, your preferences, and if you can like relatively easily and relatively inexpensively respect someone's preferences and go out of your way to make their visit in line with what their preferences and wants and needs are, that builds like such a degree of loyalty between you and these folks that are staying with you. So at four seasons, it's not like a ton of things. It's not like you know, everything from your room temperature to like what color walls you want. Like, usually it's like how firm do you like your pillows? And and that's like the 70% that gets you, or like 60 or 70% that gets you um the most satisfaction for like maybe 1% of effort, but like your coffee preferences and your pillow preferences take you from like you know, a 10 out of 100 to like a 70 or an 80 out of 100 of like holy crap, these people care about me. So if you're an STR operator and you're picking up that phone for that first phone call between you and someone that stayed with you, it's not just an opportunity to build a relationship, it's also an opportunity to figure out what their preferences are for the next time around. So, what kind of pillows do they like? What kind of coffee do they like stocked? And if I mean a lot of operators live in this misconception that it's all just revenue that comes in from the marketplace and that it's one and done, they're in and out. But if you go through these through this process after they leave and actually understand what their preferences are and talk to them, uh, they're gonna come back again and again and again because you take care of them way better than anybody else will take care of them.

SPEAKER_00 9:00

Yeah, it makes an impression. That's that magical moment. Yeah, like the uh the definition of hospitality as being you're living in kind of an alternate life, kind of your your elevated life experience. And that's yeah, that is one of the things that I love about travel. It's like don't have to do the cleaning, don't have to do the cooking, it's just kind of all happening around me. So that's uh that's really cool.

SPEAKER_01 9:23

And I think this is one thing where where we as an STR industry can learn from broader hospitality, which has been around for probably, I mean, there were inns in the time of Odysseus of Odysseus, so at least like 5,000 years. So it's so at the very least, it's a five to ten thousand-year-old industry that has you know learned a couple of things throughout that 10 millennia span. And personalization and magical moments are like the underpinning of elevating yourself from like average to exceptional, and anything that's exceptional is worthy of repetition, and you see this across the board, like even during COVID, like even in that whole period after when travel was seeing these massive, enormous shifts in how people moved around the globe and how they traveled. The brands that really have done personalization and magical moments better than anybody else are the brands that developed amazing relationships with their guests, are the brands that not only survived but thrived and moved faster and made more money and continued building better than any of the other ones.

SPEAKER_00 10:48

Yeah. So let's say you've made the decision, okay, we're gonna start selling. You realize, yes, there's a way that this can be a service, this can be a point of connection and improvement of the product and the experience. What are the systems that you need? Let's start with some of the basics. A CRM has been around, you know, since the days of uh notebooks. I guess you kind of have your cards and you write down the information on the back of each card. Uh, obviously, there are much better tools now, but you need some kind of a place to have that guest record that has all the information on it, including who has made the last phone call, what were their last communication touch points in terms of email, SMS, OTA messages. Um, the more centralized you can have all of that information, the more personalized and helpful that outreach is going to be. And the less you're nervous, the less nervous you will be when that phone starts ringing. You're like, I don't know who this person is. If you have that full record, you're gonna know who that person is and you're gonna be ready to make that connection.

SPEAKER_01 12:00

Yeah. So in terms of systems, you need a way to keep track of your information, what their preferences are, when they last stayed, why they stayed, who stayed with them, where are they coming from. So these are your basic personalization preferences, as well as a couple of key things like what their coffee preferences are, what their favorite pillow preference are, you know, just everyone's is going to be a little bit different, but some things are pretty consistent. So you need to have a way to centralize all that information and then act on that information. So if it can be proactive and remind you, hey, this person's six-month anniversary is coming up after that stay, this is a great opportunity to have a touch point with them and have a phone call with them. Or this is a person that spent $10,000 with you, but you don't have their basic basic preferences lined up and you don't have their basic preferences filled in. So here's a great, like, this is a great reason to have a phone call to really understand like what their what their optimal preferences are, so that the next time they come around, you can service that and really provide that for them. So it's pretty straightforward. I mean, shamelessly we're gonna self-plug Yada. We do all of that stuff and we do it pretty, pretty darn well. Uh, I think that's that's pretty safe to say. But whatever system you use, whether it's you know, Google Sheets with drop downs for where they're coming from and why they're staying and how much they paid and and all this type of stuff, with some sort of task management to just remind you to get in touch with somebody like three months after they stayed, a month after they stayed, six months, and then a year after they stayed. Uh you know, that's it sounds like simple, but it's not. But at the same time, it is because you just need a uh a system of record for your contacts and any sort of extra information you have about them, and then a system of record to uh remind you to get in touch with them.

SPEAKER_00 13:54

Yeah. And that that is one of the cool things with Yada is the uh kind of touch points, kind of the automated guest journey touch points that can be used not only for proactive outreach via email and SMS to those guests, but also to create those tasks and reminders internally for your team so that you can uh so that you can know who to call next, especially if you have a large guest list and um it can be a little intimidating, you know, who who needs my outreach, uh, so you can create those journeys based on um what tier of guests you want to reach out to, and then those tasks will surface for you. So you don't even have to do the thinking, you just have to show up and call, which as someone who shows up and calls, uh having the thinking done for you in advance is really helpful.

SPEAKER_01 14:42

Yeah. Yeah. So, Steve, if you were if you were running a luxury, like a luxury set of properties right now, let's say you had 10 cottages in Treasure Island, Florida. It's kind of cool because I just thought of that the other day. I was looking at a an apartment there, and you'd been in in business for let's say 18 months. Like, what is the first thing that you start doing today after like having this insight hit you that you need to start like building really good relationships with your past guests? Like, what's the first thing that you do?

SPEAKER_00 15:22

I mean, if it's 18 months, I probably already know my top 10% of people that I'm gonna start building that relationship with and inviting them back. Um, but I would turn that knowledge that's in my head into a dashboard that I can start working with. And then I would develop the outreach conversation. Like, what are the points that I want to bring up, mostly around the question of do you have another trip planned for next year? You know, what could we do to make your next stay with us even better? Uh, so that way it's both I'd be learning and I'd also be kind of opening up the door to be of service for booking that next trip. Uh, and then I'd be ready to uh to take some reservations, um, you know, just have the have the uh direct booking panel up and ready to um line them up with their next day.

SPEAKER_01 16:17

In those conversations, what what what would your script look like? I mean, are you are you more focused at that point on on just reconnecting with them or just collecting the extra information so that the next time they stay with you, their experience goes from like a nine out of 10 to a 10,000 out of 10?

SPEAKER_00 16:39

I think when you're making a sales call, which in the end this is, it helps to respect the other person's time. You're not just calling to chat them up, you're calling to see if you can take some of that load, like we talked about earlier, some of that planning and deciding and all of that. Take some of that load off their plate. Yeah. And so um I would get right to it. I remind them of who I am and you know what the context was for their last stay, uh, and say some some kind of a reason for calling, such as uh we've opened up our calendar for next summer, uh, we have some of the best dates available. I wanted to see if you had another trip planned and if we could offer you one of those.

SPEAKER_01 17:24

Well, to that point, one of our early team members, Alex, has driven so many successful repeat bookings by telling his past guests about improvements that they've made to his houses. So if he got a new hot tub built in or a new bocce ball court, I think in in one of his places, and then in the third one, they fenced off part of the um like the driveway and made a pickleball court in there. Like these are all really cool things that you want to share with your past guests because you know, even those, even if there are small improvements for for his properties, they're also really good reasons for somebody to come in and and maybe augment or or or even do something new this time around that they didn't do last time around. So, you know, if there's like a cool update that you can share, um, that could also be a really, really powerful way to start that conversation and and have that be part of the conversation.

SPEAKER_00 18:17

Yeah. It it brings to mind one of my the most surprising insights from the book uh Influence by Robert Chialdini. It's kind of the the the manual for how to sell and why it works on us human beings. And that's uh the causality, like using the word because people just want to know that you have a reason. And research shows that the reason doesn't even have to be sensical. Like if you're if you want to cut in line to make copies, if you just say, Hey, can I cut in line to make copies at the copier machine back when there were copier machines, uh, you know, you have a certain success rate. But if you say, I want to cut in line to make copies because I need to make copies, your success rate actually increases. Yeah, and so I'm calling you because the calendar just opened up, I'm calling you because we just installed a hot tub. It doesn't even have to be a huge thing. I'm calling you because I was thinking about you and wanted to reach out. Like, as long as there's a reason behind your outreach, it's going to put people on your side. It's going to bridge that gap between, well, why is he calling me? to okay, this is cool.

SPEAKER_01 19:32

So let's shift gears a little bit and talk about how does somebody spin up a sales mechanism within their short-term rental operation. What does that look like? And what does the training for that look like? My reason for wanting to bring this up because I think a lot of folks think it's more complicated and more scary than it actually is, when in reality, it's one of the simplest things that you could possibly do. So I'm gonna go on like a little bit of a one-minute spiel here, but like if you get VAs to do guest communications, like that's actually kind of tough, right? Like they need Notion or Google Docs or PMS data, they need a bunch of different data sources to be able to answer relatively basic questions, and then they're kind of handcuffed because they if they need to solve a problem, they're 10,000 miles away or 8,000 miles away. They can't really do anything in person. So, what a lot of folks do is like the hardest parts are already done. Like you've already figured out turnover and guest comms and guest support with offshore or inshore or VA teams or whatever, the sales mechanism and the sales motion is really one of the easiest to get started with and the most rewarding. So if it's your property management company and you've got 10 listings, this is something that you should be doing like two hours a week or even an hour a day, is just looking at your Pascast database and calling in and texting into the folks that are gonna be um that are gonna be the most um you know likely or or eager to book again. And then as you scale, this is continues to be within your wheelhouse because if you're uh responsible for running a portfolio or a short-term rental management company, like ultimately revenue, calendar filling, etc., is your primary duty. Everything else stems from that. If you have more repeat bookings, you have more money coming in, you can spend on better VAs or customer support and things like that. So it all starts from this ability to really influence the calendar as much as possible. So I would say that this is one of those like critical business operations and parts of the business that if you're not doing it yourself, whoever's doing it is as tied to the hip as you are as they can possibly. Possibly be. So I want to get your thoughts on that, Steve, as well.

SPEAKER_00 22:03

Yeah, I mean, founder-led sales is the key to success. You don't want to outsource that, especially if you feel a little nervous about it. You're like, oh, I'll let someone else do that because that just seems a little scary. Like, that's kind of the signal that you should be doing it. And it is a great growth opportunity. I believe that business is a chance to grow not just your wealth, but also your personal capacities and experience. And being able to call and make that connection, close business is an awesome thing to be able to do.

unknown 22:37

Yeah.

SPEAKER_00 22:38

I want to talk for just a second about the tools. We talked about Yada. Obviously, you can kind of track what you're doing within Yada. I want to talk about the actual phone calling tools because this is something that I've been really impressed with. You can just use your cell phone. Feel free to just, you know, start ripping calls from your own, you know, your own personal phone. That does have a certain limit. And also, you know, you may not want to have your personal phone in, you know, in everybody's inbox. I do recommend, and this is what we use at Yada, uh, the product called Quo. We're actually a close partner of theirs. And uh what that allows you to do is have a single number for anyone who's doing that outbound selling. So you can, you know, you can do the selling one day, your co-founder can do the selling another day, and it's all coming from the same number. And then you can use that same number to integrate with Yada to send your outbound texting so that um as you're doing your sales messaging, it's all coming from that same, you know, your brand, your number line, and you can share it and keep notes and just have that layer of visibility. Um, and and the pricing is super reasonable, not to turn this whole thing into a quo pitch, but they are an awesome company, an awesome partner of ours.

SPEAKER_01 23:53

And their their their mobile app is good, so calling from there is really sleek. Uh at Yada, we are developing like voice-to-voice capabilities internally as well. So if you have a Yada number, pretty soon you'll be able to do that from within our platform and click to call and have all the context there as well. But whether you use Quo or Yada uh or or even another like internet telephony service, uh, it is better than having it tied to your own phone, mostly because as your team scales, you can have multiple people using that same line. And that's really important. Um because you don't want to be bound by by whatever's in your pocket. So if you can get everybody on your team onboarded who needs to be doing that type of sales, if you can have it in a place where you can uh within one view, like look at your records and act on those records with a phone call, uh, that that's gonna make life a lot easier.

SPEAKER_00 24:49

Yeah. And just to wrap up, how you know it's working is through tracking.

SPEAKER_01 24:55

Yeah.

SPEAKER_00 24:56

Have a system within your CRM that is tracking calls made, that is tracking opportunities created. So people who have connected and said, Oh, I'm interested, and then tag those bookings with this was done with a phone call, and then you'll be able to see. Yeah. Two months from now, six months from now, did that make a difference? Um, and I would give it several months rather than several weeks because as we all know, the booking window is what it is in terms of uh how you know when people plan trips. Um but if you if you've run it seriously for three to six months, you'll be able to see that it's that's driving results for you for sure.

SPEAKER_01 25:40

That's all there really is to it. You you need to be on the phones, you need to be building relationships with your guests. It is a core part of building a short-term rental, like a stable, reliable, repeatable short-term rental business model, uh, and and really is the foundation of really great hospitality. So if there's one takeaway that you take from from from this week's episode, is that uh calling and talking to your contacts is super important, probably more important than almost anything else. Having good tools where you can do that and track results and track performance over time, and even just track what's been done over time and activity over time is super, super important as well. So, with those two things, and with a nice system where you can look at your personalization and any sort of past data that you have about somebody, you'll be in a really good place to activate that guest list even better than you were before.

SPEAKER_00 26:31

Yeah. And just one little piece of nuance as we wrap up here. Uh there is so much AI slop in our world now that an actual person taking the time to make a phone call is remarkable. And so this does give you the opportunity to stand out as a human who cares. And so when you see it that way, it um it really does highlight that this is a hospitality touch rather than an impersonal machine, right? It's it's your chance to stand out in a world that is uh starting to become very homogenized and and a little bit annoying at times. This is a really magical moment.

SPEAKER_01 27:17

Very, very, very good insight. You gotta, it's the human touch.

SPEAKER_00 27:22

Right on. So if you'd like to learn more about what Yada could look like to help you build your sales team, we'd love to show you that. It's at yada.ai/slash demo. And hope to see you there. We'll talk to you next time.

SPEAKER_01 27:37

Hope to see you there until uh until the next episode.