VendorVibes: Lasoh Tech Uses AI to put Guests At Center of Communication for Vacation Rentals

Orlie Benjamin uncovers a brand new solution for putting guests at the center of a vacation rental stay through AI powered guides. Still new to the industry, this software solution has bigger plans for expanding to solve even more pain points around guest communication.

Transcript

00:00 – Welcome to Vendor Vibes

Rebecca Lombardo: Hello everyone, I’m Rebecca Lombardo, fractional CMO. Today I’m here with Orlie from Lasoh. Hello, how are you?

: Hi Rebecca, I’m doing well. How are you?

Rebecca Lombardo: Good, thanks for joining Vendor Vibes. I’m looking forward to asking you about your company. So — what does your company do?

Orlie Benjamin: Lasoh is a software company that enables operators of vacation rentals to own their book of business and drive more revenue through guest relationships. I’d describe it as the industry’s first guest management system. Right now, we’re all using PMS software — it holds our pricing, our inventory, our photos — but the real view of the guest is missing. In other industries I’ve worked in, that’s a critical piece of both driving revenue and having good business insights. So that’s what Lasoh is doing: introducing the ability to drive more revenue through guest relationships.

01:01 – What Makes Lasoh Different

Rebecca Lombardo: Would you say that’s what really makes your company unique?

Orlie Benjamin: I think so. From what I’ve learned about the industry so far, there are a lot of solutions playing in some part of this space, but most are either purely guest-experience-focused or purely marketing-tech-focused — none of them are blending the two together. From my perspective, a great experience is what enables really good marketing. Blending those two things matters, because the guest sees a company as one single thing, regardless of which department or person they’re actually interacting with. So enabling a business to engage with the guest consistently across their whole journey is really important, and from what I can tell so far, nobody else is really doing that.

Rebecca Lombardo: I think you’re right — I’ve interviewed a lot of companies in this space, and nobody’s answer has been quite like that. So how would you describe your ideal customer?

01:58 – Defining the Ideal Customer

Orlie Benjamin: My ideal customer has less to do with portfolio size and more to do with values and distribution strategy. Someone could operate just three units, but if they own and operate them and genuinely care about being a brand — owning guest relationships, driving rebookings, maximizing revenue from booking to arrival, and giving guests a great experience without pouring in a ton of extra time — that’s the right fit, regardless of size.

That said, I think the more likely profile is a larger operator, because of business life stage. The first thing most operators focus on is profitability. The second is operational excellence. And only the third is revenue maximization. A lot of smaller operators are still working through profitability and operations — getting to revenue maximization is almost a “first world problem” at that stage. A later-stage business is more likely to have the luxury of focusing on maximizing revenue, which is why I’d guess our customers skew a bit larger.

Rebecca Lombardo: That’s almost like Maslow’s hierarchy of needs — food, water, shelter first, and eventually you get to self-awareness and enlightenment.

Orlie Benjamin: We’re working on enlightenment over here.

Rebecca Lombardo: [laughs] That sounds about right. So it’s not really about number of properties or location — it’s more about values, and where a business is in its own evolution of just being able to put one foot in front of the other.

03:49 – Brand Strategy: Lego vs. Crest

Orlie Benjamin: And I think it ties directly to business strategy too. Take a couple of examples: Lego is a business with strong brand recognition, does a great job selling emotionally, licenses its IP, and owns its distribution from a direct-to-consumer and retail perspective — it’s a real brand. Now compare that to Crest, a toothpaste brand. Crest is really a product distributed through retailers, and they’re largely at the mercy of that distribution channel. No one goes to crest.com to buy toothpaste — it’s something you pick up as an add-on when you’re already at the store for something else.

I think about vacation rentals the same way. Are people looking for an experience? Are they looking to engage with a brand? And what’s the operator’s actual strategy — are they content being part of the trip while staying essentially white-labeled and invisible to the guest? Airbnb is great for that, because it takes marketing entirely off the operator’s plate. But if an operator wants more control over their business, wants repeat customers, wants to maximize revenue through ongoing touchpoints and engagement — to me, that’s a brand.

So fundamentally, the first question is: does this operator have a strategy to actually be a brand? Do they have a brand name, a direct booking website, and a plan for touchpoints beyond whatever a distribution channel owns? That’s the foundational business-strategy question. Once they decide to be a brand, the next question is what people, systems, and processes let them actually operate like one — and that’s where Lasoh comes in.

05:52 – Is a PMS or Website Required?

Rebecca Lombardo: So is there a prerequisite to working with Lasoh? Do I need a PMS? Do I need a website?

Orlie Benjamin: In our current product, we only work with customers who have both a direct booking website and a PMS integration. That said, we’re launching a new product very shortly that’s just a digital house manual — no direct booking site or PMS required. I see the house manual as the very first touchpoint in the guest experience, so we’re going to offer that on its own, without all the other bells and whistles.

So we’re really thinking about this in two tracks: if someone’s ready to fully commit to the whole infrastructure, we offer that. But if they’re earlier in their journey — focused a bit on improving the experience, but not yet ready to go all-in on being a brand or diversifying their distribution — the house manual is a nice starting point.

06:55 – A Customer Success Story: The AI Guide

Rebecca Lombardo: Can you think of an example of a brand that was really happy with what you built for them?

Orlie Benjamin: We have a guide feature that’s AI-generated, and it’s been incredibly helpful — because everyone wants to improve their guest experience, but that usually comes at the cost of time. Here’s how our AI guide works: we send a short survey to every guest we have information for — and part of what we do is gather information for everyone in the traveling group, not just the person who booked. We ask a few questions about what they care about, and then, using the recommendation set the host has already curated, our AI engine builds a personalized recommendation for each guest, based on what the host has approved.

Imagine every single guest getting a personalized recommendation experience without the host having to do any extra work — they just review and approve it, because we want a human supervising the AI. That’s exactly what customers are excited about right now: they can level up the guest experience without committing more time, when those two things are usually in direct tension with each other.

Rebecca Lombardo: That’s amazing. So you basically just need the guest to answer one question?

Orlie Benjamin: Their email address, whether it’s a special occasion, and then the third question is: “Why are you coming, and how can we help make your stay great?” People’s answers are genuinely interesting. Some are very personal — we’ve seen things like, “I have celiac disease, and I want to make sure there are places everyone in the group can eat without me imposing on the group — can you help me find restaurants with great gluten-free options I can recommend for the trip?” That’s a deeply personalized ask from one individual. Other times, it’s one person asking on behalf of the whole family, coordinating for the group.

We’ve seen a lot of different use cases, and that variety is what makes it interesting. What’s also really valuable is that the information you learn about each guest gets pulled in and stored in our system, so the operator builds a running picture of who their guests are — which opens up a natural dialogue without having to front-load a big effort to get to know everyone.

Rebecca Lombardo: That’s amazing — so that information stays attached to that contact?

Orlie Benjamin: Exactly.

Rebecca Lombardo: Incredible.

Orlie Benjamin: The philosophy is simple: know your guests, and drive more revenue from knowing them.

09:24 – How to Connect

Rebecca Lombardo: That sounds great. If someone listening wants to talk to you, what’s the best way in — what’s the next step for someone who wants more information?

Orlie Benjamin: They can absolutely reach out to me on LinkedIn — my name is spelled exactly as it sounds, and it’s unique enough that I’m the only Orlie Benjamin on LinkedIn. People can also book a demo directly through the Lasoh website. Honestly, I’d also encourage people to reach out even if they’re not specifically looking to learn about the product — I love listening and learning about pain points too, because I try to stay incredibly customer-centric in how I think about solving problems for this industry.

My background is in marketing in other industries, and there are real nuances to this one that I’m still learning through conversations with customers. So even if someone doesn’t want to talk about the software at all, if they just want to share frustrations about their own marketing experience, that’s genuinely valuable insight for me — it helps shape how the technology evolves to actually solve real pain points.

Rebecca Lombardo: You heard it — free therapy session with Orlie, or just a chance to voice your concerns and problems. I’ll also say, you’re so good at asking questions — every time we talk, I think, wow, she’s really sharp. Your ability to listen and ask the right questions is something I genuinely respect as a peer. Thank you so much for coming on the show.

Orlie Benjamin: Thank you so much for chatting with me — always a pleasure. Hopefully I’ll see you at the next conference. But thanks again so much for having me today, Rebecca.

Rebecca Lombardo: Thanks for having me — and I’ve really appreciated hearing your opinions and pain points as a respected marketer in this industry. I know you’re going to be a big part of this journey going forward.

Orlie Benjamin: We’re excited. Cheers, everyone!