1st of the Month Wrangle: Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Send us a message! In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to continue the conversation around vacation rental marketing and what it takes to make it more effective, more personal, and more guest-centered.

Transcript

00:00 – Welcome to the First of the Month Wrangle

Alex: It’s the first of the month, which means it’s time for our First of the Month Wrangle, brought to you by Lasoh. Every month, we take one big idea shaping the vacation rental industry, and instead of just talking about it, we actually pull it apart — what’s working, what’s not, and what people aren’t saying out loud. And we’ve got Orlie Benjamin, CEO of Lasoh, here to help us do just that. Okay, Orlie, let’s wrangle it.

Alex: Welcome to Alex and Annie, the Real Women of Vacation Rentals. I’m Alex.

Annie: And I’m Annie. And we are back for the June First of the Month Wrangle, presented by Lasoh, and we’ve got Orlie Benjamin here with us. Orlie, so good to see you again.

Orlie Benjamin: Hi Alex, Annie, thanks for having me. It’s always a pleasure to be on the show.

This episode is the second part of a series exploring different aspects of vacation rental marketing. In the previous conversation, the trio discussed what’s missing from marketing and what operators can actually do about it. This time, the focus shifts to a simple but powerful idea: stop marketing properties, and start marketing to people.

00:57 – Marketing to People, Not Just Properties

Orlie Benjamin: That’s actually a huge goal of what Lasoh is trying to help operators accomplish, because so much of the marketing that current systems enable is really focused on the property. Unless a company has a really good tech stack — some form of CRM, a database for guests and leads, that’s connected to their PMS — it’s really hard to be guest-first in your marketing strategy.

Ideally, you have a guest management system with some level of integration into your property management system, so you can think about who your guests are and where they’ve stayed. Then you can start asking what story you want to engage a guest with, instead of only focusing on what story you tell about a property. This is a classic approach in retail, which is part of my background, and it’s something I’ve seen really work: knowing your customer and engaging them based on who they are, not just the property. Both matter, but mixing the two is really important.

Annie: Yeah, and I think at the heart of all this is the importance of data to be able to do that. In the absence of the information vacation rental managers need to market to people rather than properties, the default becomes, “This home needs bookings, it’s not performing as well as the others — let’s send an email blast, let’s do a Facebook post.”

On my side of the business, if I go to a company’s Facebook page, I just see property after property after property. Some of them are beautiful, but what’s actually going to get someone to engage? It’s worth thinking about why people go on vacation in the first place. You want to stay somewhere nice, but you’re usually going for a reason — a family trip, an event, something like that. Getting that guest-level data can be complicated. How do you approach that with Lasoh, and how do you think you can improve that process for managers?

03:19 – Building a Guest Data Foundation

Orlie Benjamin: It starts with having a place to put data, and a way to pipe data into that place. That’s fundamentally what our tech stack does at the foundational level. We also build what I’d call “action layers” on top of that, which I’ll get into shortly.

If you compare this to other industries, what matters is having a way to use your system of record — your property management system — and take whatever data you have around the booker or guest and move it somewhere else where it can be managed in a way that’s designed around the guest, not the property. Property management software is really about asset management. A PMS has three core functions: inventory management for the property, payment processing for the booking, and channel management for distribution. The guest often doesn’t fit cleanly into that equation, because managing inventory is a different discipline than managing guests as a CRM.

Some PMSs have some guest management functionality; some have none. But even where it exists, the level of sophistication is still very early. It’s hard for a PMS to be everything to everybody, and that’s why Lasoh exists — to create a place where the guest is managed as an asset with the same sophistication as a property, and where information, context, and intent can flow in not just from the PMS, but from other sources, like a website or our guest portal.

When you think about this guest marketing system — “CRM” is really more of a generic industry term — you want a place to capture context both in a structured way and, since we’re building AI-native, in unstructured ways too. For example, a handful of sentences about why someone is coming can be captured and associated with that guest, and our AI agent can read that without anyone having to manually groom the data — which is one of the most time-consuming parts of managing a CRM.

I was talking to a property manager at a recent VRMA Xchange conference, and she pointed out that no matter which PMS you look at, they all claim to have a CRM, but it’s so basic it doesn’t really function as one.

Annie: So what you’ve built is something to layer in — but I want to address what people are probably thinking: “Oh no, another piece of tech to manage.” Tell us how Lasoh actually interacts day to day, because I think it’s not another layer you have to manage like your PMS or channel management.

07:03 – Action Layers: Turning Data Into Revenue

Orlie Benjamin: That’s a great segue into the action layer concept I mentioned. You’ve got a place to store data — great, everyone needs that — but just having data doesn’t mean you can unlock value from it.

Our goal at Lasoh is to help operators revenue-maximize their business. You make money based on how many guests you can unlock, how much they spend per transaction, and how often they come back. Recurring revenue is fantastic — the cost of acquisition is low, since there’s no distribution channel cut or added marketing spend. I think recurring revenue is the biggest opportunity right now, with spend per transaction close behind if upsells are done right.

So Lasoh has built an ecosystem that improves the guest experience. We have a guest portal — think of it like a Disney app — but unlike other guest portals where engagement isn’t captured, our portal is actually a “mousetrap” for data. Whatever guests engage with — preferences, recommendation requests (which our AI agent manages), what they click on, who’s in their group — all of that context and intent gets captured.

On top of the data living in the CRM, we’ve built action layers — essentially my brain distributed across a whole bunch of AI agents that do most of the work of driving marketing and value. For example, we have pre-designed campaigns where all the setup is done for you. Take the “laggard” campaign: it looks at how a property is performing relative to last year and relative to comparable properties in the portfolio, using a scraping process to track the competitive landscape. Bringing in data from KeyData or PriceLabs would make it even smarter, but our goal isn’t to be a pricing tool — it’s to drive demand.

So one lever is pricing, but the next step is actually reaching people. The campaign identifies which guests or leads should receive a last-minute deal message, and it can build that campaign — email or text — automatically, since there’s a built-in email generator. In three or four clicks, you have a full marketing campaign that identifies the opportunity, segments the right guests, and builds the messaging. That’s work that might otherwise take a business three days and several people, or one person putting in a lot of hours — and it can be done in about five minutes.

That’s a game-changer, because it democratizes marketing. It shifts the model from building everything from the ground up to supervising something smart and making sure it aligns with your business so you can unlock revenue from it. I think that’s the direction technology is heading — it can now take action on our behalf, rather than requiring us to do all the groundwork ourselves.

10:20 – Reading the Data: Luxury vs. Urgency Messaging

Annie: Exactly — it’s like I’ve been going down the Claude rabbit hole lately, building my morning brief, my afternoon brief, and so on. It’s nice to have something you can launch and then tweak as needed, which is kind of what I’m envisioning here. I have a question, though.

I was recently analyzing email campaign data for an education company I work with. I put it into Claude and asked what was working and what wasn’t. It was fascinating — not surprising, but fascinating — to see that this company’s guests, who are in a luxury market with luxury homes, don’t respond to last-minute deals. Urgency means nothing to them. They’re not enticed by specials; they respond much more to things like pictures of families on the beach and having a longer time window to book.

I think what happens is that when someone steps into a marketing role, most of the marketing they’ve ever seen — for anything they’ve bought — leans on urgency and last-minute offers. But it’s really important to understand what your specific audience responds to. So I’m curious: does your system surface that kind of insight? If an operator on Lasoh ran a mix of urgency emails versus lifestyle, book-ahead, luxury-style messaging, would it point out where the opportunities are and where they should focus?

Orlie Benjamin: Yes — that’s the beauty of having agentic segmentation, agentic engagement management, and agentic-driven analytics. Say there are 30 campaigns available; as an operator, you choose which ones to launch. The segmentation component we’ve built has a “match score,” which is a fairly complex algorithm based on recency, frequency, and monetary spend — how recently someone stayed, how frequently they’ve been contacted, and how much they typically spend. That lets us segment guests into cohorts, like high-value luxury guests versus deal-seekers.

The point of this AI segmentation is the level of nuance you can apply to guest profiles — you could have 20 tags on a single guest — and the segment generator can digest that at a speed our brains simply can’t match, then recommend action based on the match score. It flips the traditional model: the approach becomes fewer, better emails to highly qualified people, rather than sending one or two generic messages to a large list and learning through unsubscribes or spam complaints. You’re sending highly targeted messages to a smaller number of people with higher intent, based on that match score. So yes, it’s built in — in that way and many others — and that smart segmentation piece is a huge part of it.

Annie: It’s a bit like comparing email marketing today to direct mail back in the day. We used to get mailboxes full of postcards and magazines, and then it shifted to email because it was more economical. Now my inbox is insanity — I’d love just one email a month from the companies I subscribe to instead of ten a week. Most brands are still taking the “hit the masses” approach. But when I do get a postcard or a magazine now, I actually pay attention to it, because I think, “they took the time to really send this to me.” I feel like what you’re describing — democratizing marketing — is adopting a bit of that philosophy: making messaging more meaningful and impactful for the people who receive it.

Orlie Benjamin: Yeah, I generally have a philosophy in life: fewer, better things. Quality over quantity, whether it’s my wardrobe or my approach to marketing.

13:34 – Pre-Trained Agents and the Human in the Loop

Alex: I love that. I have a question — I’ve recently been learning all this AI terminology, and honestly, I feel like we’re all drinking from a firehose on this topic. With Agent Sync AI — you’re training your agents to answer these kinds of questions. For a property manager, I’d imagine — and I’m just guessing here — that it might be easier to get an agent up and running in a smaller market than in a huge destination market like Orlando, versus somewhere smaller. Is that fair? What does it actually look like to train the agent to position things correctly to a guest?

Orlie Benjamin: The agents come pre-trained on marketing, but the business itself is why I think a human still needs to be involved. I like to use the analogy of baking bread: think of it as though we gathered the ingredients, mixed them at the right ratio, put them in the oven, and now they’re half-baked and frozen — you decide when to throw it in the oven and get the fresh bread. Making fresh bread from scratch every time is really onerous.

So the efficiency we’ve built comes from pre-training a variety of agents on marketing best practices. There’s a whole infrastructure of action-oriented agents sitting on top of the data layer — a copywriting agent, a design agent, a segmentation agent, an orchestrator agent, and more. The value we bring is in pre-training that whole team of agents on marketing, so democratizing marketing means bringing a full marketing team of agents into a software environment. The operator knows what they’re trying to accomplish, and they can start from scratch, or lean on a toolbox of use cases — “books are now open,” “we have a new property,” “it’s been a year since you stayed, come back,” stay-iversaries, book-iversaries, and other lifecycle moments.

That’s the difference between product marketing — marketing the property — and lifecycle marketing, where the CRM becomes much more useful, because it’s about who the guest is and what you can uniquely say to them. With that data, plus pre-designed use cases — a book-iversary message, a “happy half-birthday, have you planned your birthday yet?” nudge — a lot of the marketing people want turns out to be persistent and consistent. Pre-kitting those use cases clears the way for operators to spend more time on the bespoke, edge-case things that are unique to their market.

Annie: Music to everybody’s ears, saving them time. I think that’s the one thing I hear consistently — managers want to do all of these things, but there just aren’t enough hours in the day, and property managers already wear enough hats as it is. Removing a layer of marketing through automation is genuinely helpful.

Orlie Benjamin: I think people just aren’t doing it because they don’t have the time. There are larger operators who do — I had a call earlier today, and it was actually shocking. I won’t say who the business was, but they built their own PMS and their own marketing tech stack on top of Salesforce. They have an entirely custom stack because they care that much. That’s not a typical operator — they also come from the hotel world, where building your own system is expected.

On the other end of the spectrum are operators with a PMS who have more operational work than they have time for, where marketing becomes a privilege — something you only get to focus on if you have the bandwidth. Yes, a good system saves you time, but more importantly, it lets you make more money with a lower operating cost. That’s true of any genuinely good AI-native system: it lets you expand your team by bringing in AI agents to do work you’d otherwise need to hire for, so you can manage a larger portfolio with a smaller team — growing the business without proportionally increasing costs, because your team can do more with less.

19:14 – Building Brand Equity Beyond the OTAs

Annie: Yeah, and I think this conversation is happening across a lot of companies right now — do we keep investing in direct bookings, do we get into direct bookings? We know we’re getting a lot of business from Vrbo and Airbnb, and in some cases making more money on those channels than on our own direct bookings, because of the markup. That’s fine, but the bigger picture is that if you’re building a business you might eventually want to sell, a company with its own brand, audience, and guest history is far more valuable than one that’s relied entirely on OTAs.

We’ve had Jacoby from C2G and Jason Sprinkle on the show before talking about exactly that — buyers look at your booking mix in a sale process, and a heavy OTA mix isn’t as attractive as a company with its own audience and platform. So that’s one part of the bigger picture here.

A Word From Our Sponsor

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21:54 – The Multi-Occasion Guest Conundrum

Annie: Here’s a marketing conundrum I’d love your thoughts on, because I don’t know that I have the answer, and I don’t know if this has been solved yet. A guest comes in for a girlfriends’ getaway in October. You’ve gathered data on what they did, where they went, and the time of year. That same guest could come back later as a couple, or with their kids, or with their parents.

The hard part is when you put people into buckets — this is why they come, this is when they come — and then only market to them for that one reason. Do you miss the opportunity that they might want to come back for a completely different occasion, if you never send them a message reflecting that? I know this has been a long-standing conversation in the industry. How do you think about that, and is it something Lasoh is building toward — collecting more touchpoints after the stay, like post-stay surveys, so guests don’t get locked into one bucket?

Orlie Benjamin: I agree wholeheartedly that all of this has to happen. I’ll use some marketing terminology here: there are three types of emails you can send. One-to-one, where only one person receives it. One-to-some, which is segmentation. And one-to-all.

One-to-all is what most people are doing right now, and it’s the easiest thing to do — you just say, “I want to send this message to my whole file.” No problem, and of course you can do that with what we’ve built too. It’s table stakes, which is honestly why I barely talk about it — it’s already solved. What excites me is one-to-some and one-to-one.

One-to-some matters because you can burn out your list if you over-rely on one-to-all messaging that isn’t relevant. Being smart about the mix of one-to-all and one-to-some — and how frequently you contact people, which ties back to that recency, frequency, and monetary metric — is the right way to go. It’s really about how thoughtfully you engage your audience. That’s also why I’d never tell anyone to put marketing fully on autopilot — you still need critical thinking. The goal is to spend more of your time on that critical thinking, using one-to-all campaigns where appropriate, while unlocking the one-to-some approach that used to be too much work to execute.

24:55 – How Lasoh Was Built: Research Before Product

Annie: One of the things I’ve delighted in watching is how thoughtful you’ve been in building this out. I remember the conversation we had — it must be a year and a half ago now — when you first reached out to me cold, before we knew each other, to show me what you were building. I think it’s worth noting that you did a lot of research, a lot of talking to people, before you ever came out with a product. Sometimes tech companies come out with an assumed answer to a problem without really identifying all the layers of it, and I think you did that groundwork. I think that’s one of the things Lasoh has done really well — understanding how multi-layered this challenge is for operators.

One of the things we wanted to touch on today is where you’re taking Lasoh next — this ongoing “learning tour,” if you will. You mentioned off camera that you want to talk directly to the people using it, and you shared a bit about the next strategic layer of Lasoh. Can we dive into that?

Orlie Benjamin: Thank you for that — I’m definitely a lifelong learner. I always tell my son: you win, or you learn, and either way there’s a positive outcome. The only real failure is not learning. For the first twelve months of this business, I went to conferences and reached out to strangers to figure out whether the problem I believed existed was actually real. I did surveys, gathered feedback from a variety of operator types, and confirmed there’s a real gap around owning your customer data and unlocking revenue from it — and that the problem isn’t just the lack of a system, but the lack of action around using it.

Those became the pain points we identified, and you have to fall in love with the problem, because we’ve pivoted a lot along the way and continue to evolve the product as we talk to people. That’s why I’m excited to announce that we’ve established a founding member program. We’ve been building this product for almost a year with a very small number of highly engaged customers — who we actually call partners, not customers, because our promise to them is that we’ll listen to their problems and solve them as part of our product strategy, as long as they stay engaged with us. If this is something you care about, you probably want to help solve it too.

I call them partners rather than customers because to me, “customer” implies something hands-off and fully turnkey, and I’m a big believer in under-promising and over-delivering. The founding membership program invites 10 businesses — capped at 10 — to work hand-in-hand with me and the team on identifying problems. I tell everyone it’s fun: you get to complain, and all I do is try to solve your problems.

Annie: And all the complaints get listened to?

Orlie Benjamin: Not all of them — just the legitimate ones. But I can handle it. And that’s actually the hard part of product strategy: you have all these problems, so how do you prioritize the ones with the most value? That’s why research and listening matter.

29:19 – Inside the Founding Member Program

Orlie Benjamin: So the first benefit is that direct collaboration on product problems. Second, highly discounted pricing. Third, a real sense of community among the founding members — a cohort that helps each other solve problems, which is valuable in itself: having other people who understand your perspective and can help you think through what you’re working on. And finally, if you’re a business that believes technology will be part of how you compete — working smart, not just hard — this is for you. There’s a lot of smart capability emerging right now, but it’s also honestly a little terrifying how quickly AI is changing everything.

Those are the four things I think are valuable about the founding member program. We have several spots left. We’ve done zero outreach on this so far — we debuted it at VRMA Nation three weeks ago, and since then I’ve been in four cities in two weeks for various conferences. This is really the first time I’m talking about it publicly like this. Our website reflects it, and we’re about to start reaching out to people we’ve talked to in the past to invite them in.

Annie: Walk us through what that looks like — if someone joins as a founding member today, what happens on day one?

Orlie Benjamin: Entry will likely be staggered, but I’d describe it as a cohort or group experience — not quite like starting college on the same day, but everyone ends up in the same overall experience. There’s an orientation phase where we get to understand each other’s businesses. Then a listening and discovery process: how are you operating, and how can we imagine solving problems around that? From there, it’s continuous engagement — new tech previews, design feedback, new upsell features to try — intentionally designed across different PMS types, operator sizes, and geographic regions.

We’ll engage with the group collectively as well as one-to-one, since certain priorities will matter more to some businesses than others depending on their strategy — but there’s a consistent baseline of engagement for everyone. There’s also a dedicated point of contact — our head of account management and onboarding — who acts almost like a camp counselor. And I’ll be high-touch too, present for almost everything. It really is camp, where you get to complain and someone solves your problems.

Annie: I love that. What’s it called in college — not your advisor, but the person on your floor?

Orlie Benjamin: Your RA, yeah.

Annie: Hopefully none of the faculty members get in trouble.

Orlie Benjamin: I’m sure they won’t.

Annie: Did you say how many people, or how many cohorts?

Orlie Benjamin: Ten businesses total, one cohort.

Annie: Perfect.

Orlie Benjamin: I expect it to fill up pretty quickly. We want it to be a mutual fit — on our website, you can apply, we’ll demo the software to make sure it makes sense for your business, and we’ll also learn about your business. It’s a partnership, not a customer relationship. The website even says this isn’t a hands-off SaaS experience — it’s for early adopters who want to be engaged.

The reason we’re doing it this way is that we’ve built something I feel really good about, but I know there’s more to build, and I’d rather work closely with a small number of highly engaged partners to make it better for the whole industry — then commercialize it for everyone once that founding group is satisfied, and we have real facts: how much more revenue they’ve made, how much time they’ve saved, how much operational friction they’ve reduced through proactive communication. We want to build real case studies. Most people want to wait for someone else to figure it out first — there’s a concept that roughly 15% of people are early adopters. It’s better to work closely with that group first, and then everyone else benefits from what’s learned along the way.

33:28 – A Familiar Story: The Value of Being Heard

Annie: If you’re listening to this and you’re constantly reaching out to your PMS, or whatever software you use for CRM, email, or marketing, and you’re not getting answers or having your requests seriously considered for upgrades — this is for you. From my own history at Condo World, we built something similar to what you’re describing. We built our own PMS, and used Revinate as our email marketing platform, which is really built more for hotels, but we did some pretty sophisticated things with it. It was expensive, but it worked well — though I don’t think that’s realistic for everyone listening to this show.

Orlie Benjamin: I’m very familiar with Revinate — a former employee of mine came from there.

Annie: It’s a good platform. But what I loved about building our own system was having input on everything we were building — as the marketer, being able to say, “What if it did this differently?” and having that heard. Not that you’re asking founding members to build your entire system — the system is already built — but you want to be able to shape it so it truly accomplishes the mission of democratizing marketing for operators everywhere. If you’re someone who likes having your hands in things and having your input genuinely considered, this is a great opportunity that doesn’t come around often: a platform inviting you to help build what the future looks like.

Definitely recommend checking it out if you’re interested. Where should people go to find it, Orlie?

Orlie Benjamin: We’ll be updating our landing page, which will be linked here with the application process. You can also go to our homepage and look at the partner section — that’s where you’ll find either the “book a demo” option or the waitlist application. It’s in a couple of places on the site.

Annie: Awesome.

35:30 – Wrap-Up and How to Connect

Annie: Well, we’re trying to democratize marketing every other month here, and we’ll be back with you for the third edition of the First of the Month Wrangle series — the August edition. Until then, what’s a good way for anyone who wants to reach out to you directly?

Orlie Benjamin: They can email me at orlie@lasoh.io, send me a LinkedIn message — I check those myself — or come through the website. If they use the waitlist feature on the site, we’ll follow up, and it’s actually more meaningful because it asks some smart questions that help me follow up with business contacts appropriately. There are a lot of ways to reach me — I’m on the internet.

Annie: On the interwebs — that’s L-A-S-O-H dot I-O.

Orlie Benjamin: Correct. Thank you for knowing how to spell that.

Annie: Lots of practice.

Annie: Awesome. Well, thank you, Orlie, for joining us. And for anybody who wants to get in touch with Annie and me, you can go to alexandanniepodcast.com. Until next time, thanks everybody.