Jul 15, 2026 · 39 min · 11 segments
In this episode, Conrad and Paul discuss why most vacation rental managers overlook outbound marketing, how to reconnect with past guests and inquiries, and the best ways to use calls, texts, emails…
Conrad O'ConnellHost
Paul ManzeyHost
What I find is most vacation rental managers that are serious about direct bookings are putting a lot of money into SEO.
They're putting money into their social content, et cetera, et cetera, et cetera.
And sometimes, not always, but sometimes I find that they do very little actually around their past guest list, or they do maybe, let's say, the bare minimum.
They're doing something, but it's not really well thought out, and it's something that I think we need to probably sit down and review and revisit for everybody.
I was on the call with someone this morning who has a list of roughly 500 people that have stayed, the people that have booked, and then another 2,000 or so on a StayFi email marketing list, and when he sends emails, he gets 40% open rates, and I'm like, "Oh, how often do you send an email?" He's, "Every four months, not very often." So w- good ti- g- good timing for me to think about this a little bit more, 'cause you're gonna pay money to acquire a guest through all those marketing channels, and it's much less expensive for you to keep the guest if they're willing to rebook or if they're able to rebook by sending them some of these outbound messages.
So what's your experience in this realm? I know it's not maybe what you have spent a ton of time on in your career, but obviously something you're very familiar with.
Yeah, I think it's funny to think about how we really focus on getting that, getting that direct booking, getting that in- that initial booking hopefully, but getting it to come direct, and then we do kind of let off on the gas pedal when we...
We remarket to people who have visited the site before, but it is, it's creating that true customer life cycle that's beyond just that first visit or hoping it's beyond that first visit here.
This is something that I think I've got my first really peek behind the wheel at with Track, because we were trying to create all these automations and triggers and everything like that, and it was...
So I think it... a lot of it was really just having someone else take a look at, have- having someone from not the SAS side of things, but the marketing side come in and take a look at things and say, "Well, we have to make this feel like a conversation, a, more of a communication." And I think that's a lot of what the outbound marketing is.
You talked about that a little bit as you're in, in the pre-show here, but it's active marketing.
You still actively put the campaigns together, but you're not having to dial the phone.
You're not physically sending the email, but you're sending those emails out there.
So I do, I think that this is, it's one of the parts of marketing that gets shared, I think, maybe more than anything else.
What I find is most vacation rental managers that are serious about direct bookings are putting a lot of money into SEO.
They're putting money into their social content, et cetera, et cetera, et cetera.
And sometimes, not always, but sometimes I find that they do very little actually around their past guest list, or they do maybe, let's say, the bare minimum.
They're doing something, but it's not really well thought out, and it's something that I think we need to probably sit down and review and revisit for everybody.
I was on the call with someone this morning who has a list of roughly 500 people that have stayed, the people that have booked, and then another 2,000 or so on a StayFi email marketing list, and when he sends emails, he gets 40% open rates, and I'm like, "Oh, how often do you send an email?" He's, "Every four months, not very often." So w- good ti- g- good timing for me to think about this a little bit more, 'cause you're gonna pay money to acquire a guest through all those marketing channels, and it's much less expensive for you to keep the guest if they're willing to rebook or if they're able to rebook by sending them some of these outbound messages.
So what's your experience in this realm? I know it's not maybe what you have spent a ton of time on in your career, but obviously something you're very familiar with.
Yeah, I think it's funny to think about how we really focus on getting that, getting that direct booking, getting that in- that initial booking hopefully, but getting it to come direct, and then we do kind of let off on the gas pedal when we...
We remarket to people who have visited the site before, but it is, it's creating that true customer life cycle that's beyond just that first visit or hoping it's beyond that first visit here.
This is something that I think I've got my first really peek behind the wheel at with Track, because we were trying to create all these automations and triggers and everything like that, and it was...
So I think it... a lot of it was really just having someone else take a look at, have- having someone from not the SAS side of things, but the marketing side come in and take a look at things and say, "Well, we have to make this feel like a conversation, a, more of a communication." And I think that's a lot of what the outbound marketing is.
You talked about that a little bit as you're in, in the pre-show here, but it's active marketing.
You still actively put the campaigns together, but you're not having to dial the phone.
You're not physically sending the email, but you're sending those emails out there.
So I do, I think that this is, it's one of the parts of marketing that gets shared, I think, maybe more than anything else.
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