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

Alex and Annie · 2026-06-01 · 37 min

0:00--:--

Key moments - from our scoring

Substance score

59 / 100

Five dimensions, 20 points each

Insight Density12 / 20
Originality11 / 20
Guest Caliber13 / 20
Specificity & Evidence10 / 20
Conversational Craft13 / 20

The conversation centers on a fundamental shift in vacation rental marketing strategy: moving from property-focused campaigns to guest-centric engagement. Orlie Benjamin explains that most property management systems prioritize asset management over guest relationships, leaving operators to send generic email blasts and property listings rather than personalized communications. Lasso addresses this gap by creating a guest marketing system that acts as a CRM layer on top of existing PMSs, capturing data from multiple touchpoints - bookings, guest portals, website interactions - to build rich guest profiles. The platform uses pre-trained AI agents to automate campaign creation, segmentation, and messaging across email and SMS. Benjamin walks through the "Laggard campaign" use case, where underperforming properties are identified and targeted guests receive relevant offers in minutes rather than days. He emphasizes that better segmentation based on guest spending patterns, recency, and intent - rather than blast campaigns - drives higher conversion and ROI. The discussion highlights recurring revenue from repeat guests as the biggest opportunity, alongside upsell potential when messaging is genuinely relevant. For operators weighing direct booking investment versus OTA reliance, building a proprietary guest audience and brand increases business valuation substantially.

Key takeaways

  • →Property management systems handle inventory, payments, and distribution but lack the sophistication to manage guest relationships - requiring a separate guest marketing CRM layer like Lasso to drive guest-centric campaigns.
  • →AI-powered segmentation using match scores (recency, frequency, monetary spend) enables fewer, better-targeted emails to high-intent guests instead of mass blast campaigns, reducing cost and increasing conversion.
  • →Recurring revenue from repeat guests offers the lowest customer acquisition cost; pre-built lifecycle marketing workflows (bookaversaries, anniversaries, seasonal reminders) automate consistent engagement without manual effort.
  • →Pre-trained AI agents for copywriting, design, segmentation, and campaign orchestration democratize marketing by enabling small teams to manage larger portfolios without hiring additional staff.
  • →Operators with proprietary guest data, direct booking channels, and brand recognition command higher valuation in acquisition scenarios compared to businesses heavily dependent on OTA channels.

Guests

Orlie Benjamin

Topics in this episode

AI-native marketingCRM systemscustomer segmentationRecurring revenueProperty management systemsLifecycle marketingLassoguest marketingguest portallaggard campaigns

Questions this episode answers

Why can't property management systems handle guest marketing instead of needing a separate CRM?

PMSs are designed for asset management (inventory, payments, distribution), not guest relationship management. A guest marketing system needs to manage guest data with the same sophistication as property data, capturing context from multiple sources and enabling lifecycle-based engagement that PMSs aren't built to support.

How does Lasso's segmentation algorithm decide which guests get which campaigns?

Lasso uses a match score algorithm that analyzes recency (how recently they stayed), frequency (how often contacted), and monetary spend (revenue value) to assign guests to cohorts like luxury buyers versus deal seekers, then recommends highly targeted campaigns to qualified segments rather than blasting everyone.

What is the Laggard campaign and how does it work?

The Laggard campaign identifies underperforming properties by comparing current performance to historical performance and geographic/competitive benchmarks, then automatically segments guest contacts and generates personalized email or SMS offers (like last-minute deals) to drive demand - typically completing in minutes rather than days.

How does Lasso capture guest data beyond just the person who booked?

Lasso's guest portal acts as a "mousetrap for data," tracking preferences, recommendations requests, clicks, sorting behavior, and group composition. Combined with PMS integration and website data, this creates rich profiles for every guest, not just the booker.

Do you need to train Lasso's AI agents for your specific market or destination?

Lasso's AI agents come pre-trained on marketing best practices, but humans remain involved to guide strategy and customize for local nuances; Benjamin uses the metaphor of pre-mixed, half-baked dough that operators activate rather than building marketing infrastructure from scratch.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

12 / 20

The episode contains some substantive ideas about guest-centric marketing, CRM architecture, and AI-driven segmentation, but much of the content is product explanation and generic marketing philosophy rather than novel operational insights. The host does push back with a concrete example (luxury guests not responding to urgency), but Orlie's responses are largely conceptual rather than providing new frameworks or surprising findings about the vacation rental business.

So much of the marketing in terms of what systems enable right now seems to be really focused on marketing to properties...it's really hard to be guest first in your marketing strategy.
the approach here is actually fewer better emails to highly qualified people...you're sending highly targeted messages to a smaller number of people with higher intent

Originality

11 / 20

The core thesis - that vacation rental operators should shift from property-centric to guest-centric marketing - is sensible but not particularly novel. The CRM + PMS integration argument is standard SaaS thinking. While the AI agent execution is newer, the underlying strategic insights (data-driven segmentation, lifecycle messaging, recurring revenue focus) are recycled from e-commerce and hotel marketing. The founding member program model is somewhat distinctive but presented as tactical rather than conceptually original.

It's a really classic way to do marketing in retail, which is uh part of my background.
because recurring revenue, guests that come back are fantastic...The cost of acquisition is super low

Guest Caliber

13 / 20

Orlie Benjamin is the CEO of Lasso, a tool company, rather than a seasoned vacation rental operator or revenue leader with deep experience managing properties at scale. While she has retail marketing background and has done customer research, she is primarily a founder pitching her own product rather than an operator with battle-tested operational expertise. She has not demonstrated managing large portfolios or solving complex VR-specific problems firsthand.

So much of the marketing in terms of what systems enable right now seems to be really focused on marketing to properties.
I ran around to conferences and reached out to strangers trying to identify if the problem I thought that existed was a real problem.

Specificity & Evidence

10 / 20

The episode lacks concrete data, metrics, and named examples of real results. Orlie describes the Laggard campaign and segmentation logic abstractly but provides no case studies, revenue numbers, retention improvements, or specific customer examples. The one concrete example comes from the host (luxury market rejecting urgency), not from Orlie's experience or Lasso's results. There are no comparative benchmarks or quantified outcomes.

I was talking to a property manager at the recent exec conference, uh, the VRM exec that we were all at.
How recently did they stay? How frequently have they been contacted, and then how much money do they spend

Conversational Craft

13 / 20

The hosts ask reasonable follow-up questions and push back on assumptions (e.g., the luxury email example, the multi-purpose guest problem). However, the conversation is largely accommodating - the hosts don't deeply challenge Orlie's claims about AI capability, effectiveness, or competitive differentiation. There's limited skepticism about whether Lasso's pre-trained agents actually solve the stated problems or just shift manual work. The tone remains promotional rather than investigative.

Tell us how lasso actually interacts, because I think that that's what's really cool is that this it's really not like another layer that you have to manage
So I'm curious like, does your system point that out? Of like, you know, if you were, if they were on lasso and I did a mix of urgency emails versus, you know, more lifestyle

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

marketing43guest34lasso22property21data18built17first15system14management13email12guests11back11part11revenue10whole10founding10

Episode notes

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. This time, the conversation focuses on a simple but important question: can we stop marketing properties and start marketing to people? For many vacation rental operators, marketing often defaults to the property itself. A home needs bookings, a calendar has gaps, or a listing needs more visibility, so the message becomes centered around the unit. While property marketing still has a place, Orlie explains why stronger results often come from understanding the guest first. That means looking beyond the booking and thinking about who the guest is, why they are traveling, what they care about, and how operators can use that information to create more relevant communication. The conversation also explores why guest data is only valuable when operators can actually use it.

Full transcript

37 min

Transcribed and scored by The B2B Podcast Index.

Welcome to Alex Danani, the real women of Vacation Reddit. With more than 35 years combined industry experience, Alex Euser and Annie Holcomb have tuned up to connect the dots between inspiration and opportunity. Teach them to find the one story, idea, strategy, or decision that led to their guests to be a hard moment. Join them as they highlight the real stories behind the people and brands that have built vacation rentals into the $100 billion industry it is today.

And now, it's time to get real and have some fun with your hosts, Alex and Annie. It's the first of the month, which means it's time for our first of the month wrangle brought to you by Lasso. 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 Orly Benjamin, CEO of Lasso, here to help us do just exactly that. Okay, Orley, let's wrangle it. Welcome to Alex and the Ruleman of Vacation Rentals.

I'm Alex and I'm Annie. And we are back for the June 1st of the month Wrangle presented by Lasso. And we've got Orly Benjamin here with us. Orly, so good to see you again.

Hi, Alex. Annie, thanks for having me. It's always a pleasure to be on the show. So we're in the second part of this kind of series in talking about various things in the vacation rental business.

And we've been talking about marketing. And the last conversation that we had, we talked about what's missing from marketing and what people can actually do about it. So I think like this time we want to talk about stop marketing properties and start marketing to people. And so why don't we go, why don't we, I guess, start there and we can dive into it?

Absolutely. So that is actually a huge goal of what Lasso is trying to help operators accomplish because so much of the marketing in terms of what systems enable right now seems to be really focused on marketing to properties. And unless a company has a really good tech stack, which is some element of a CRM, which is a database for guests and leads, that's then connected to their PMS, it's really, really hard to be guest first in your marketing strategy. Because ideally, you have this guest management system.

And then you also have some level of integration with your property management system so that you can think about who are the guests, where have they stayed or have they stayed? And then you start thinking about what story do you engage a guest with, as opposed to focusing on what story you tell about a property. It's a really classic way to do marketing in retail, which is uh part of my background. And so that's for me something that I've seen really work, which is knowing your customer and engaging your customer based off of who they are, versus focusing on a property first story.

They both matter, but I think mixing them is really important. Yeah, and I think at the heart of all this is the importance of the data to be able to do that, right? So it's like it's almost, I almost feel like in an absence of having the information that vacation rental managers need to be able to market to people and not just market properties, the default is, well, this home needs bookings, it's not doing as well as the others or how as well as it did last year. Let's send out an email blast, let's do a Facebook post.

And, you know, what I see in in my side of the business is if I go to a company's Facebook page, I just see property after property after property. And it's like, you know, and some of them are really beautiful properties, but what is going to get somebody to actually engage? And I think it's important to think about like, you know, why people even go on vacation in the first place. Like you want to go and stay in a really nice place, but you're probably going for a reason, either for a family trip or for an event going on, or you know, something along those lines.

But getting that data of the guests can be complicated. So, how do you look at that with lasso and like how do you feel like you can improve that process for managers? I think it starts with having a place to put data and having a way to pipe data into that place. And that is fundamentally what our tech stack does on the foundational level.

We also have other things we do, which I would refer to as action layers, which I can get into a little bit later. But I think right now, if you were to compare this to other industries, you know, what's important is having a way to use your system of record, which is your property management system, and take whatever data you have around the book or guest and kind of put it somewhere else where it can be finessed and managed in a way that is designed to be around the guest, not around the property.

Because property management software is about asset management. I mean, really, the property management system has three functions. First, it's inventory management for your property. Second, it's payment processing, so you can take the payment for the booking.

And then third, it's channel management so that you can manage distribution. The guest, in most cases, doesn't fit into that equation because inventory management around property is different than guest management as a sort of CRM. Now, some of the PMSs out there have something, some of them have nothing. But I would still say the level of sophistication at what those CRMs are operating at is still very early.

It's very hard for a PMS to be everything to everybody. And that's why Lasso has been created is how do you create a place where the guest is the asset you're managing, just like the property, at the level of sophistication of a PMS? And then how do you create a method where information, context, intent comes in not only from the PMS, but from other sources, places like a website or our guest portal, which is why we built the guest portal. And so when you think about the CRM or the guest marketing system, which is really what we're referring to it as in this industry, CRM is more of like a generic industry term or generic marketing term.

But if you've got this guest marketing system that has places to drop context, both in like a structured way, and actually we're building AI native. So it doesn't all have to be structured. For example, there can be context around why someone's coming that can just be a handful of sentences that are captured that are associated with that guest. And our AI agent can go read that without somebody having to go groom and manage all that data, which is one of the most time-consuming aspects of managing a CRM.

I was talking to a property manager at the recent exec conference, uh, the VRM exec that we were all at. And she was really just discussing the fact that no matter what PMS you look at, they all say that they have a CRM, but it's so basic, it doesn't really, it doesn't really function in that way. And so what you've built is something to kind of layer in. But what I what I want to address is I think people are listening and they're like, oh my gosh, another piece of tech.

Tell us how lasso actually interacts, because I think that that's what's really cool is that this it's really not like another layer that you have to manage day-to-day like your PMS or your channel management. So that is such a good segue into that thing I referenced earlier, which is an action layer. So you've got this component around a place to store data. Great.

Everybody needs a place to store data. But just because you have data doesn't mean you can unlock value from it. And our goal at Lasso is to help people revenue maximize their business. And the way you make money is how many guests do you have in terms of what you can unlock?

How much money are they spending per transaction? And then how often do they come back? Because recurring revenue, guests that come back are fantastic, right? The cost of acquisition is super low, whether it's not a distribution channel cut or it's not marketing spend.

And recurring revenue is, I think, the biggest opportunity right now. But spend per transaction is also a big opportunity if upsells are engaged correctly. So what Lasso has done is it's built an ecosystem that makes the guest experience better. We have a guest portal.

Think like a Disney app, right? But unlike other guest portals where the guest engages with that app and there's nothing captured around what the guest is doing, that guest portal is actually a mousetrap for data. Whatever they're engaging with in terms of preferences and uh asking for recommendations, which we have an AI agent that manages, to what are they clicking in? What are they sorting in?

Like what who what who's in their group? So there's this whole component of like gathering context and intent in the guest portal. If you imagine you went to Disney, Disney's doing that with us too, right? Like what restaurant are we eating at?

What rides are we writing? How do you put all of that into the CRM and have all this context? So the guest portal is all about mousetrap for data. And then what we're doing is on top of the data that lives in the CRM, we have these action layers.

And they're basically my brain put into a whole bunch of AI agents to help you have to do very little work to drive marketing and to drive value. And I'll give you some examples. We have a um a total campaign section. We have pre-designed campaigns that all of the work is done for you.

I'll use the example of the Laggard campaign. The Laggard campaign looks at how is this property performing relative to how it did last year, relative to geographically, what else is in our portfolio. And we have a scraping process which we're looking at what's the competitive landscape doing. Now, bringing in information from key data or price labs absolutely would make this laggard use case even smarter.

Because the idea is whatever you can do around pricing is great. But our goal is not to be a pricing strategy tool with that campaign. It's actually to go drive demand. So one lever is to say, well, let's change pricing.

Cool. But then how are you going to get people to engage with that underperforming property? You actually send campaigns to them. And so the next step in that campaign is it actually identifies which guests or which contacts, I should say, because leads can be included too, should receive that laggard campaign message, which is last-minute deal or last minute opportunity.

And it can create a variety of campaigns via email and text message because there's an email generator that's built into it. So I'm literally talking about three to four clicks later, you have a full marketing campaign that is recognizing where opportunity is, segmenting who the customers are that you should engage with, and building the campaign via email or text. That's the kind of thing that might take a business like three days and a lot of people's hands touching to do, or one person who's putting in a lot of hours and to do it in literally you can do it in like five minutes.

That's just a game changer because this idea of democratizing marketing, like by making marketing really easy, by creating systems that essentially take action and make a lot of things really easy, and you oversee that action, it just changes the script from a build from the ground up to a how do I supervise something pretty smart and make sure it aligns to my business and then unlock revenue from it. And there's a variety of other use cases that I haven't identified. That's just one.

But the idea of pre-building things because it's doing taking the action for you. Um, that's where the future I think tech is going is technology can now take action on our behalf and manage to us versus us have to do all the ground work ourselves. Yeah, exactly. It's like I've been going down the clawed rabbit hole lately of building my morning brief and my afternoon brief and everything.

And it's like, okay, you know, it's nice when you just have something that you can kind of launch, but then tweak as as you need. And that's kind of what I'm envisioning as you talk about this. But um, I've got a couple questions. So the first one is gonna be so was just analyzing some data from some email campaigns for a vacational company that that I work with.

And I put it into Claude and I said, you know, tell me what's going on here, like what's working, what's not. And it was fascinating to see, I mean, not fascinating in a surprising way, but that this company, their guests really they don't respond to last-minute deals. Like urgency means nothing to them. They're not, they don't care about the specials.

They want it's a it's a luxury market and they're luxury homes, and they're much more enticed by seeing you know pictures of families on the beach and having more of a time window to book, which is great. But I think what ends up happening is if you're somebody who gets you know put into a marketing role within a company, you know, you're all we see in most marketing for anything that we buy is is urgency and last-minute stuff. But it's like it's really important to understand what people are responding to.

And so I'm curious like, does your system point that out? Of like, you know, if you were, if they were on lasso and I did a mix of urgency emails versus, you know, more lifestyle, lifestyle and you know, book ahead and luxury, would it point out to me where the opportunities are and where I should be focusing? Yeah, I mean, that's the beauty of having agentic segmentation, agentic management of engagement, and then agentic driven analytics, right? And so let's say there's 30 campaigns as an op as an operator, you can choose which ones you want to launch.

That segmentation component that we've built in has a match score. And that match score is like a pretty complicated algorithm. And that algorithm has to do with recency, frequency, and monetary spend. How recently did they stay?

How frequently have they been contacted, and then how much money do they spend, and how do we segment them into different sort of cohorts of customers, like high value luxury versus sort of deal seekers? And so the whole point of this AI segmentation is like the level of nuance that you can assign to guest profiles, like you could have 20 tags on a guest, and then that segment generator is smart enough to like digest at 10,000 X the speed our brains can do and provide a recommendation based off of activity because of the match score.

And so it's completely flipping the script on how we build things because the approach here is actually fewer better emails to highly qualified people. The cost structure here is, I mean, in most CRMs, it's like you send one or two messages to a lot of people and it may or may not stick. And you'll maybe learn through unsubscribe or spam classifications. Here, you're sending highly targeted messages to a smaller number of people with higher intent based off the match score.

So I think, yes, it's built in in that way and many, many other ways. And that's where that smart segmentation component is like huge. Yeah. Well, you think about like comparing email marketing now to direct mail back in the day.

And it used to be that we got tons of direct mail. I mean, mailboxes full of postcards and magazines and everything. And then all of a sudden, you know, that changed to more economically doing email marketing. But now, I mean, my email inbox is just it's it's insanity.

I would love to just get one email a month from you know the companies that I subscribe to instead of 10 a week. But I mean, most are still doing the you know, hit the masses approach. But you know, you look at what happened with direct mail. And now when I do get a postcard or I do get a magazine, I actually pay attention to it.

I'm like, wow, they took their time to really send this to me. So I feel like this the how you look at democratizing marketing is kind of like adopting that philosophy a little bit of let's make this much more meaningful and make it more impactful for the people that receive it. Yeah, I generally have a philosophy in life fewer better things, right? Like quality matters over quantity, whether it's my wardrobe or my approach to marketing.

Yeah. I love it. I have a question. So I've just recently learned all this stuff about AI, which I feel like we're all like drinking from a fire hose with this topic.

Um, but the agentic AI. So like it's you're you're training your agent to be able to answer these questions. For a property manager, I would have, and I'm just throwing this out there like guessing, but you know, someone who's in a destination that has a ton of stuff, just use Orlando as an example, versus where you are. Like it's probably easier in a smaller market to get that agent up and running than it is in a larger market.

Would is that is that fair? Or like what does it look like to actually train it to be able to position to the guests? They're coming pre-trained. So they're trained on marketing.

So the business itself is why I think the human still needs to be involved. Gotcha. Yeah. Or basically, I almost use this term, this this term with baking bread, it's part of it.

Like, think of it as like we went and got the ingredients, we mixed them at the right ratio, we put them in the oven and they're half baked and they're now frozen, and you can decide when to like throw it in the oven and get the fresh bread. But the process of making fresh bread is super onerous from the beginning, right? And so what we've done, the efficiency of what we've created is we've pre-trained a variety of agents on marketing best practices. And there's a whole infrastructure of action-oriented agents that sit on top of this data layer.

Everything from the copywriting agent to the design agent to the segmentation agent to the orchestrator agent. There's a whole bunch of stuff. And the value we're bringing is we're pre-training them on marketing. So democratizing marketing in this case means bring a whole marketing team of agents into a software environment where the person knows what they're trying to accomplish.

They can start it from scratch if they want. Or they can say, you know what, I really like that I have a whole toolbox here of stuff. And 80% of the time I want to focus on sending a variety of messages, whether it's books are now open or we have a new property, or hey, it's been a year since you stayed, and we love to remind you to come back, or it's your stay aversary and it's your book of versary. I mean, there's all these sort of lifecycle components because like product marketing is like we're marketing to the product, which is the property, but lifecycle marketing, which is where the CRM becomes much more useful, is like who is the guest and what can you uniquely say to them?

And by having that data around them and then identifying use cases that are pre-designed, that they just, you know, like every month there could be a bookaversary message, which is hey, like you booked this time last year, or hey, it's six months till your birthday, happy half birthday. Have you planned your birthday yet? There's all sorts of use cases that can be pre pre-designed. And then if there's all sorts of edge case things that are really unique to that market, that's where the build your own comes in.

But um in my limited research, it does seem like a lot of the marketing that people want is persistent and consistent. And so that pre-kidding gets a lot of the work out of the way so that they can do a better job on the bespoke things because all the other stuff takes less time. Music to everybody's ears to save them time. That's I think at the end of the day, every manager's look.

I mean, that's that's the one thing I hear consistently is that I they want to do all of these things, but it's just there's not enough hours in the day. And let's face it, property managers are already wearing enough hats as it is. So removing some of some layer of marketing that automates is really helpful. I think people are just not doing it because they don't have the time.

I mean, I think there's larger operators that do have like I had a call earlier today, it was actually shocking. I won't say who the business was with. They built their own own PMS and their own marketing tech stack on top of Salesforce. They have their entire own custom stack because they care that much.

Uh, that is not a typical operator. They also come from a world of hotel where like they expect to have to build their own system. On the other end of the spectrum are folks that have a PMS, they have more to do that's operational than they have time for. And marketing is like, it's a privilege to have time to think about maximizing revenue.

Yes, you can save time, but more importantly, you can make more money with a lower operating cost. And I say this not just for a lasso, but any really good AI native system that lets you almost expand your team by bringing in AI agents to do the work that you don't have to hire people for. You can now have a larger portfolio with a smaller team. And that doesn't mean you have to hire people.

It just means that you can probably grow your business without having to increase your costs because your team can do more with less. Yeah. Yeah. And I think, you know, this conversation is being had across many companies right now that it's like, okay, do we continue investing in direct bookings?

Do we get into direct bookings? We know that we're getting a lot of business from Virgo and Airbnb. And, you know, we're we're making more money on those channels, on those bookings than we are on our own direct because we're marking up the price, and that's all well and good. But I think, you know, the bigger picture here is if you're building a business and a business that, you know, someday maybe you want to be able to sell, a company that has a brand and that has its own audience and has its own guest history is much more valuable than a company that's just relied on the OTAs.

And we've had uh Jacoby from C2G and Jason Sprinkle on the show in the past to talk about that of, you know, that's that's something that buyers uh look at in that process because it's like if your mix is very heavily OTA, that's not as great as what you could get if you have a company that you know really has their own audience and has their own platform. So I think, you know, looking at the bigger picture there is one part of it. We'll be back in just a minute, but first, a word from our premier brand sponsor.

You hear us talk about this all the time. Everyone wants more revenue, less OTA reliance, and better guest experiences. But most property managers and hosts are still piecing all of that together manually, either across multiple tools or no tools at all. That's exactly why we like what Lasso is doing.

They've built the industry's only AI-native guest marketing platform to help operators increase revenue per stay, stays per guest, and booking conversion rates. So instead of just getting the booker's info, you're capturing data from every guest in the stay. Instead of sending generic messaging, you're delivering personalized experiences. And instead of hoping guests come back, you're building a system that helps turn one-time bookings into repeat guests.

And when you know more about every guest, not just the person who booked, you can create smarter opportunities for upsells, add ons, and experiences that actually feel relevant. That's where operators can increase revenue per stay without making the guest experience feel overly salesy. That's the secret sauce. It's all powered through LASO's smart marketing and guest portal products.

If you want to check it out, Lasso is offering Alexanney listeners the chance to apply to be one of their 10 founding members and enjoy 20% off Lasso products when you use the code Alexandani. This offer is valid through July 31st, 2026. Learn more at explore.lasso.

io slash Alex dash Annie. That's explore.lasso L A S O H dot IO slash Alex dash Annie. Here's a marketing conundrum that I would love to get your thoughts on because I don't know that I have the answer to this, but and I don't know if this has been built yet.

But a guest comes in and they are here for a girlfriend getaway and it's in October, and you've gathered the information of what they did, where they, where they went, the time of year, all that stuff. That same guest could want to come back as a couple or could want to come back with their kids or parents. The hard part is when you put people into these buckets of this is why they come, this is when they come, and you don't you just market to them for that reason, do you you do miss the opportunity if you're very specific about it, that they could want to come another time.

And if you don't send them, send them those messages, they're gonna miss out on it. You know, and I think this has been something we've been talking about for a long time in the industry. But how do you look at that? And is it possible for what you're building?

Because I think the cool thing about lasso is that you are it's built, but you are iterating into the future to collect more touch points after the stay of like, or if it's a survey or something to get more information about them so that you don't put them into a bucket too far down that you can't get them into a different bucket. Yeah, I mean, I agree wholeheartedly that all the things have to happen. And so I'm gonna use some like marketing um language on the three types of emails you can send.

One is one to one, which means only one person receives it, one to is one to some, which has segmentation, and the other is one to all. One to all is what most people are doing right now, and it's the easiest thing to do. All you have to do in lasso is say, I want to build this message and I'm gonna do my whole file. No problem.

That's why I think like it still needs a human to use critical thinking on what am I trying to say and who should I say it to. One-to-all is the easiest use case. It's what everyone's using, whether it's MailChimp or anything else, because there's no nuance to it. So that's already unlocked.

And yes, of course you can do that with what we're doing. So it's almost like I'm so not excited about one-to-all because it's already there that I barely talk about it. But yes, it's table sticks. What is exciting to me is one to some and one to one.

And one to some to me is meaningful because I think you can burn out your list if you do a lot of one-to-all and it's not relevant. And so I think being really smart around the mix of one-to-all and the mix of one to some is the right way to go. And then also thinking about how frequently do you contact folks, which is by the way, one of the metrics we look at. Like when were they last contacted?

Back to my recency, frequency, and monetary. So I think that it's about the mix of how you think about how you engage with your audience and being smart around some of the logic of how you choose to engage, which is why I would never tell anybody to put marketing on autopilot. Like you still need to do some critical thinking. It's just that you can spend more time doing critical thinking and having some one-to-all campaigns, and then all of a sudden unlocking the one-to-some that you normally couldn't do because it's so much work.

So many things to consider here. So, one of the things that it I've delighted in watching is how thoughtful you've been as you built this out. And you, you know, you came to me. I can speak the conversation you and I had.

I think it was, gosh, going on like a year and a half ago when you first started this. And you reached out to me kind of cold, like didn't know you, wanted to show me what you had and just where it's come from that. But what I think, I think that people, it's worth noting is that you did a lot of research. You did a lot of talking to people.

You did, you, you didn't come out with a product. I feel like sometimes some of these tech companies and tech offerings come out with uh an assumed answer to a problem, and maybe not really identifying all the layers of that problem. And I feel like you've done that work. And so anybody listening, I mean, I think that's one thing that lasso has done a really great job is it to understand how multi-layered this this problem or this challenge is for people.

Um, but I think one of the things that we were going to talk about today was like kind of what the next gen of lasso, like where you're taking it. And it's this continual, I want to say road to of learning, if you will. I mean, I think you you're really wanting to talk directly to people that are using it. And so you you were telling us um off camera about what your kind of the next strategy layer of lasso is, and maybe we can touch on that and kind of dive into where you're going with it.

Yeah, I mean, thank you, first of all, for that. I am definitely a lifelong learner. I always say this to my son: you win or you learn. And either way, there's a positive outcome.

The only failure is not learning. And so for the first like 12 months of this business, I ran around to conferences and reached out to strangers trying to identify if the problem I thought that existed was a real problem. I did actual research, I did like surveys, and I got feedback from a variety of different operator types that there is a miss around the ability to own your customer data and unlock revenue from it. And that the problem is not only that you don't have the system, but also the action around unlocking it is a problem too.

And so those are the pain points that we sort of identified. And you got to fall in love with the problem because we've pivoted a lot. We continue to evolve our product as we talk to folks. And that's why I'm really excited to announce that we've established a founding member program.

We have been building a product for almost a year with a very small number of highly engaged customers who we actually don't call customers their partners because our promise to them is that we will listen to your problems and we will solve them as part of our product strategy, as long as you help us make sure that we're doing it in a way that's meaningful. And as long as you commit to being engaged with us, because if this is something you care about, you probably want to solve it too.

And so we've taken that approach of these sort of early customers that have been very participatory. And I and I call them partners, not customers, because I think a customer is like a really hands-off, like everything's turnkey, ready to go. And I'm just a huge fan of like underpromising and over-delivering. And so this idea of the founding membership program is we would like to invite 10, capped at 10 founding members.

They get the opportunity to work hand in hand with me and the team around identifying problems. I always tell everybody it's fun, you get to complain. And all I do is try to solve your problems, and then all complaints will be listened to. Legitimate.

Yeah. I can do all of it. And that and that's actually the hard part about product strategy is like you have all these problems. How do you prioritize the ones that are worth solving that have the most value?

And that's why research matters and listening matters. So, you know, you get to work with me and the team around you get to complain and we'll try to solve your problems. So, first benefit. Second, highly discounted pricing.

And then third, a level of um community that comes amongst the founding members together and creating that cohort of like how do we solve problems together for each other, which is almost like a value in itself, which is just having that cohort of other people that understand your perspective and can help you solve what you're working on. And then I would say um finally, you know, if you're a business that thinks that technology is going to be part of how you want to compete, because you believe that working smart, not working hard, is how you want to do things.

And there's so much smartness happening right now, but it's also terrifying how quickly AI is changing everything. Those are probably the four things that I think are valuable to the founding members. We have um several spots left. I also have done zero outreach on this.

We debuted this at VR Nation three weeks ago. Since then, I've been in four cities in two weeks for a variety of activities, including, you know, software conferences. So we haven't really started selling. This is actually this access to the founding membership program.

This is really me saying it for the first time out loud, and our website reflects it. And we're about to start sending out messages to folks that we've talked to in the past to say, hey, if you want to be a part of this, we'd love to have you. Yeah, and maybe take us through what that's gonna look like that you haven't planned out so far. So somebody joins as a founding member now.

What's what happens on day one? Well, I think it's gonna be staggered entry in, but I would describe it as a cohort or like a group. So I'd say it's not the same as going to college because you don't have orientation at the same time. But um, if everyone ends up in the same experience, they all get entered into the group.

So there's some level of orientation into understanding the business and us understanding their business so that we can understand each other best. There's a listening and discovery process around, hey, how are you operating? And then how can we imagine solving problems around how you're operating? And then there's a continuous engagement around we've got new tech, who wants who wants to try this one, who wants to give us feedback on these designs, who wants to launch this, you know, new upsell feature.

And it's going to be very intentionally designed as a group across different PMS types, different operator sizes, and also different geographical regions. And so we'll be engaging with that group in um cohorted ways as well as one-to-one ways. Because once we know who each business is and what they care about, there might be certain things we focus on with one business that the other business doesn't align to their strategy. But some level of engagement in a consistent fashion.

Also, there's a camp counselor. So our head of um sort of account management and onboarding is like their go-to person. I would describe this as white glove, high touch. I'm also white glove high touch, going to be at almost everything.

And it's camp where you get to complain and someone solves your problems, really, is how I would describe it. I love that. What was the name that they would call it in college for the not your advisor, but the person that your RA, yeah. Yep.

Yeah. Hopefully, none of the founding members get in trouble. I'm sure they won't. No awkward walking to the shower with your shower caddy.

Exactly. That's great. And and did you say, did I miss it? Did you say how many, how many people is there going to be multiple cohorts, or do you is it one cohort?

And just okay. And then how many how many managers are you looking to put into this? 10 businesses total. 10.

Okay. Perfect. I expect it to fill up pretty quickly. Yeah.

And the we want it to be a mutual fit, right? So what we've created on our website is the ability to apply. And of course, we'll demo the software, make sure that makes sense for them. We'll also learn about their business.

You know, it's about a partnership, not a customer relationship. I think the website even says like this is not a hands-off SaaS experience. This is for early adopters that want to be engaged. And the reason why we're doing this is because we've built something now that I feel really good about in terms of providing value to folks, but I know that there's more.

And I would rather work with a small number of highly engaged folks to make it better for the whole industry. And then we'll commercialize the product for everyone once that sort of founding member group says we're satisfied, this solves our problems. We have facts that show how much more revenue we've made. We have facts that show how much time we've saved.

We have facts that show how we've reduced operational friction because of proactive communication. So we want to build case studies, and most people want to wait for somebody else to figure it out. There's this whole concept of early adopters versus everybody else. And usually about 15% of people are early adopters.

So better to just work with early adopters that are up for being a part of the ride, and then everybody else can benefit from that. Yeah. I think if you're somebody listening to this and you are constantly reaching out to your PMS or whichever software it is that you use to be the CRM or your email or marketing platform of choice, and you're not getting answers and you're not getting things taken into serious consideration of upgrades. This is for you.

And I know from my history and um perspective of when I was at Condo World, we had built kind of like the company you just described, we built our own PMS. We used Revenate as our uh email marketing platform that really actually is more for hotels, but we did some super sophisticated things with it. It was very expensive, but it worked well. But I that's not for everybody listening to this show, I don't think.

I'm actually very familiar with Revenate. Let's just say about them with some of their employees. Yeah, yeah. And it's it's it's it's a good, it's a good platform.

Um, but we had built a lot of things, and the and the thing that I loved about doing that was, you know, I did have input on everything that we were building. And as the marketer of the group, it was really cool to be like, well, you know, what if it did this a little bit differently? Or what if we did this? And you know, not that you're asking these people to completely build your system, the system's built, but you want to be able to adapt it to make it like truly accomplish the mission of democratizing marketing for these people and and for you know, many more across the world and country.

But I think if you if you're somebody that likes having your hands in things and being able to have put input and have it be listened to, this is a great opportunity that you don't hear about often of a platform coming out and saying, you know, I want you to help help build this and be part of you know what the future looks like. So definitely recommend everybody, yeah, if you're interested, go check it out. And what where do they go to find it, Orly? The link.

Well, um, we're gonna update our landing page with you. That'll be linked here to have the application process. Also, if they go to our homepage and look at the partners section, that's where the um either book a demo or the waitlist application exists. It's in a couple parts of the website.

Okay, awesome. Well, we're trying to demarc democratize marketing every other month at a time here. And we'll be back with you for the the third edition of uh the first of the month Wrangles series, which will be the August first of the month. Yeah.

Um, so until then, is there what's a good way if anybody wants to just reach out to you directly to get in touch? They can email me at orly at lasso.io. They can send my link, send me a LinkedIn message.

I check my own LinkedIn messages. They can come in through the website. Uh, if they come in through the website and do the wait list feature, we will follow up with you. And it's actually a little more meaningful because then I can follow up with business context because it asks some smart questions.

But there's just a lot of ways. I'm on the internets. Uh any of those things on the interwebs. And it's lassoh.

io. Correct. Thank you for knowing how to spell that. Yeah, I love it.

Awesome. Well, thank you, Orly, for joining us. And uh, for anybody that wants to get in touch with Annie and I, you can go to alexandanypodcast.com.

And until next time, thanks, everybody.

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