Sept. 10, 2025

How Property Managers Can Offer Flexible Cancellations Without Losing Revenue – with Sasha Lawler of Roam

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Flexible cancellation policies are no longer optional in today’s vacation rental market. Guests expect them, OTAs prioritize them, and competitors are already adapting. But for property managers, relaxed policies often feel like a direct threat to revenue and owner trust.

In this episode, we talk with Sasha Lawler, CEO and Founder of Roam, about how her company is eliminating that trade-off. Roam’s embedded insurance model allows managers to offer flexible bookings that attract more guests while ensuring income is protected even if cancellations occur.

Sasha shares her 15+ year journey in hospitality and vacation rental tech, the conversations with property managers that inspired Roam, and why now is the moment for the industry to catch up with hotels and airlines in offering flexibility.

We discuss:

1️⃣ Why strict cancellation policies create tension between managers, owners, and guests

2️⃣ How Roam’s model differs from traditional travel insurance

3️⃣ The tech behind embedding refundable and non-refundable rate options into booking sites

4️⃣ Why smaller operators are leveraging Roam to stabilize revenue and win new owners

5️⃣ How turning cancellations into a strength can improve guest trust and long-term brand growth

If cancellations have ever kept you up at night, this episode will show you how flexibility can protect (not jeopardize) your revenue.

Connect with Sasha:
LinkedIn: https://www.linkedin.com/in/sasha-lawler-a4b33677/
Website: https://goroam.io/ 

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#vacationrentals #shorttermrentals #cancellationpolicy

Alex Husner  
Welcome to Alex & Annie: the real women of vacation rentals. I'm Alex, and I'm Annie, and we are joined today with Sasha Lawler, who is the CEO and founder of Roam. Sasha, it's so good to see you.

Sasha Lawler  
Good to see you, Sasha, I

Annie Holcombe  
think feel like we've known you for a really long time, but actually, it's funny enough, we didn't actually have to think meet in person until this spring, which is completely crazy, because we've been in this industry, like running around each other for a long time. But before we get started, why don't you introduce yourself and tell us a little bit about your background?

Sasha Lawler  
Yeah, it's an abomination. It took so long for us to actually, actually meet, right? But yeah, I feel like I grew up in this industry a little bit. I've been in hospitality vacation rentals for about 15 years now. I started my career working on site in hospitality for a small luxury guest ranch out in Colorado, in sales and reservations. Great experience. And moved over to the tech vacation rental side of things. I worked for blue tech marketing out in Carbondale, Colorado, and ran their sales and marketing team and got a we got acquired by inhabit. I was promoted to lead go to market sales and marketing for all 13 brands within inhabit. And that was just a wonderful opportunity to learn way more about all these businesses. But more importantly, property managers. It was a great experience to have 1000s and 1000s of conversations about what it's really like, right? And what property managers are really struggling with, and in so many ways, that's, you know, kind of where Rome was was born.

Alex Husner  
That's great. So what was the problem that you were seeking to solve, or what maybe kind of give us a look behind the curtain of what were like the conversations you were having with managers that made you think this is what I need to do right now.

Sasha Lawler  
Well, I think a lot of it really came from like having these conversations with property managers, and they're like my Airbnb or my VRBO rep has been telling me to relax my cancelation policy. Sasha, I can't relax my cancelation policy. Like, what am I going to do? Tell an owner that a 10 grand reservation that booked 11 months out, 15 days out, canceled. Sorry, you can't make your mortgage this month, the guest canceled. So we just really quickly recognized that managers were stuck between this rock and a hard place of I want, obviously, I want to not get filtered out on these OTAs. I want to give travelers this seamless booking experience. We want to give travelers this flexibility. But hey, we're running a business. We've got owners to answer to. If I do this, I'm not protecting the asset. You know that I'm in really in charge of protecting, so really, that's what we set out to do, is remove this trade off between owners travelers in the market. And I think it couldn't be more timely, right? Like vacation rentals is the last standout. It's the last travel sector that hasn't adopted flexible booking, and where flexible booking really isn't standard. Hotels have done it post covid flights, airlines, and now it really is, vacation rentals that are that are left standing. So that's what we're really kind of setting out to solve. Can you tell

Annie Holcombe  
us a little bit about how the actual program works? So you it's actually, if I understand it correctly, it's you're working directly with the property managers, as opposed to working with the consumer Correct?

Sasha Lawler  
Yes, that's correct. So very, very different than travel insurance, which all of our managers continue to merchandise, and they still should right, like I need to get medevac out, Graham, I get sick my flight 24 hours before it gets canceled. That's what folks are still buying insurance for Rome is very different. We're a commercial insurance product that really sits on the back end. So we work with property managers and we say, Hey, you go to market. Go relax your cancelation policy. Justify those higher rates. Charge a premium for it, and we're essentially sitting on the back end. And our technology integrates directly with the property management software, so we have real time access to all of these reservations. We see when a booking comes in, we cover it. We also assume a booking gets canceled, so that we're able to really automate this claims process. And what we're doing is we're saying if a guest cancels and you're not able to rebook the property, we're paying you back directly on the back end. So it's really this embedded commercial insurance that's giving managers the freedom to go to market with the policies that drive results while protecting their income and owner's income, and it's a playbook that has been used by really, the largest consumer brands, right? Like you think about Uber. You get into an Uber. You're not buying insurance, but that ride is protected. That driver is protected. You sign up to be a host on Airbnb. You've got damage and liability insurance, including. Good with your host profile. So some of the biggest brands have already leveraged commercial insurance to deliver these kind of like wow experiences. We're essentially just taking that playbook and bringing it to VR.

Alex Husner  
Gotcha. Okay. And so is it if a property management company signs up with roam, is it automatically included on all their reservations,

Sasha Lawler  
yeah, so that's a great question. There are we want to be flexible, right? Like we understand not every market's the same, not every property manager is the same, and not every strategy should be the same. So we want to offer managers a lot of flexibility in how they leverage this, how they merchandise this. So what we have one option where it is essentially fully embedded into every single booking. They say, hey, we want to update our cancelation policies globally. And this works really well on the OTAs, where today you can't really merchandise a refundable, non refundable rate. And we also give property managers flexibility in terms of how they work with us. Some folks say, gosh, I just want to relax my cancelation policy on the OTAs. I'm going to keep my strict cancelation policy on my direct booking website. So in those instances, yes, you're updating your cancelation policy. Globe, globally, every single reservation is protected. We are, I told you, I didn't have any big launches, but we do. So I'm incredibly excited about this one. I think this is going to be game changing for us. We are launching a model. I mean, we've gotten a lot of feedback in the market. It's early. We launched in January, and we are essentially delivering an option where managers can essentially merchandise on their direct booking websites, the ability for travelers, again, not buying travel insurance, but the ability to choose a refundable or a non refundable rate at checkout. And on the back end, we're ensuring we're protecting those reservations in which the traveler selected that refundable rate. And I think the beautiful thing about that is it's a no brainer, right? Like, don't displace your existing rate strategy. Leverage a non refundable booking to get more guaranteed revenue on the books, to build up that bottom line. Don't displace that, empower it, add the flexibility. It's just like the beautiful have your cake and eat it too. So we're pretty excited about that.

Alex Husner  
Yeah, and that makes perfect sense, because when you definitely you see that more with the hotels, I would say that it's like, you know, when you go to check out, normally, if you're on a direct booking website for a hotel, you've got a few different rate codes there. You can do like the bed and breakfast special, or you can do the advanced purchase, which is what you're talking about, where you get maybe 5% discount, but it is non refundable. Or you can go with whatever the current special is, that maybe it's 10% off, 15% off, but it's refundable. But I mean, that's where it becomes a problem, and to have that revenue on the books for managers or any type of accommodations is huge to get ahead there. But my question would be, how does this work with the property management system? Because I know with some of my clients, when we've looked into doing something even without this program, but just kind of been floating that idea around. Most of the property management systems don't have that ability. There are the ones that I've worked with. But how does that work between Rome and the PMS?

Sasha Lawler  
So we're actually working directly with the website companies to merchandise multiple rates. Yeah, so really kind of taking what's in the PMs and then pushing that to the direct booking websites to be able to merchandise that. In terms of how roam works with the PMs, we're essentially ingesting that reservation data, the booking data, the unit data, to be able to manage the program, manage the policies. And the biggest piece for us, as the biggest piece for me, was working with property managers for so long, and like being the 13 different tabs on their computer, was like, this, can't this can't be another manual burden. So we're automatically processing those claims every month, so there's no like manual burden for a manager to figure out the rebooking or calculate anything our technology is doing all of that. How does how

Annie Holcombe  
does that work with the OTAs and I'm thinking just off the top of my head, like the new policy that was announced this week with Airbnb, where they're going to do the buy now, pay later scenario, it's tied to the cancelation policy. So do you have to have different structures for OTAs versus direct bookings? Or is it seamless for those reservations? Because it's you're just looking at the reservation information, yeah.

Sasha Lawler  
So because of that integration, we have the ability to see where this booking has come coming from. Are you the merchant of record? Are you not the merchant of record? So you do have the ability to kind of bifurcate your strategy and say, Yes, I want to go all in. Airbnb does not. Let me merchandise to rate options like I can on my IC and D website, so they have a different coverage model for those Airbnb or verbal bookings. And they're saying, hey, I want to give the flexibility of the option on my direct booking website, which also I think will be a game changer as well, right? Because you're offering you know you're, you're saying to the guests, like, do you want the best rate? Come to my website, right? Like, I think the merchandising, even of that non refundable rate, is going to be a powerful signal to travelers that are on that booking page. They're really going to feel like they're they're getting something. They're making a choice. I'm choosing this non refundable rate, and I'm getting something for it.

Alex Husner  
So, yeah, yeah. And I think that's, that's one of the biggest problems that, you know, a lot of companies run into, is okay, in order to compete on VRBO, Airbnb, you've got to have a more relaxed cancelation policy there. But you you never want the policy on the OTAs, or the price in the OTAs to be better, more lenient than what you have on your own site. But like, in a lot of cases, that has to happen, you know, for companies that are more reliant on the OTAs and it's like, you know, you're never going to be able to get ahead on building more direct business if what somebody can get on the channels is better. But at the same time, it's like, well, what comes first? You know? I mean, like, you need to get the bookings in to turn them into repeat guests at some point. But it really becomes a struggle there. So I think this makes a lot of sense, but actual execution of it, as far as the website is concerned, that makes sense. That's probably been fairly straightforward. I feel like I've been working with IC and D or some other website providers, but the back end side of what you've built is really the secret sauce, right? I mean, or the relationship of how, however you do the insurance side. So like, tell us about that process, because when you weren't in the insurance industry. So like, how did you even get started on figuring out, okay, who's gonna insure all this

Sasha Lawler  
money? Yeah, I mean the two, the two pieces. And I think the experience that I've had in this industry, working for so many tech companies in the space and really recognizing that, you know, I think there is a huge need for a data normalization layer. We didn't want to be scrappy about it. We didn't want to be the startup that ran our business and spreadsheets. It was very important to us that right out of the gate we were building a platform for scale, right? So thankfully, we have a great team of investors and advisors behind us that have been in VR tech for quite some time to offer that strategic guidance and support. And my co founder and chief product officer, his name is Austin. He worked at blue tent with me. That's where we met, way back in the day when we had maybe fewer gray hairs than we do now, but so he's worked for with these PMS APIs for years, right building these custom websites. So the translation between building that, ingesting the data, and creating this normalization layer that allowed us to create an API endpoint that our carrier is now right to it really just kind of was a beautiful, like, culmination of, like, grateful for mentors, advisors, investors, and then Austin's impact really has been a game changer.

Annie Holcombe  
So in my mind, I'm thinking, How did you take this into and Shark Tank is the only thing I can think about. But you had to take it to people and pitch this. And insurance is always one of those. We were talking about camera like, insurance is just one of those, you know, conversations that nobody likes to have and and it's, it's, it can be, I'm sure you feel like a therapist at times, because people want to tell you all their woes about insurance. But when you took it, put it conceptually, down on paper, and you had to go pitch it to somebody to say, like, invest in this. How did you put that together? And, like, what kind of research went into doing that?

Sasha Lawler  
I mean, a lot. I think looking back, I maybe was slightly insane, right? Yeah, building a brand new product, pushing a pretty legacy, slow to move industry. It took a lot of beating on doors. I feel incredibly grateful that we found some of the best capacity partners in the world. These A rated capacity partners that have billions of dollars on their balance sheet behind us, who are actually ensuring the risk. But in terms of, like, building our team, we raised a very small, you know, seed round. I didn't have the resources myself to bootstrap this, but it really was, I think just selling the vision, like selling the opportunity, like there is a massive need for this. And I think some of it happened organically, right like I wasn't chasing money right out of the gate. I really was very naturally searching for advice and going to folks that I trusted or respected, those who had built businesses in this industry before, and I. Think that's been, I can't understate the importance of not going it alone and building a team around you that has the strengths and the experiences, maybe that you don't. I think that really has been a game changer. I'm incredibly grateful for for that.

Alex Husner  
Yeah, and we talk about this all the time on the show, but it's like all the things that you've done up to this point have prepared you for this opportunity. Because, I mean, you were overseeing, you know, blue tent and then the other companies, and it's like you learned so much in that process of, like, the how websites are done, and the other insurance companies that are part of inhabit so I'm sure just all that you lost most in those years like that also probably gave you a bit of the confidence I would think right of like, okay, I've learned enough about all these different areas, and I can see this one need that no one else is tackling.

Sasha Lawler  
Yeah, yeah. Definitely the years of yeah, great experience seeing how it's done, and I definitely don't think I would have had the confidence without the mentors that I've had. Though I think sometimes externally, you need folks to say and see and believe something in you. But I also feel like so much of it has been happenstance, right? Like one of our key advisors, who we work closely with on a daily basis, his name's am at and he, 1015, years ago, helped build the first commercial insurance product at Airbnb. He built the program at Uber that insured the first Uber Black cars way back in the day. And you sit here, you think, like, how did I you? How did how do we build this team? And so much of it is just like happenstance is like having the conversations, asking for the intros, and it came from an intro to an intro to an intro and just asking a ton of questions. So yeah, a lot of luck, a lot of luck,

Alex Husner  
and all new hard work too. Yeah, a lot of hard work and experience. So how big is the team? Now, at this point,

Sasha Lawler  
our team is relatively small. Now we've got really, it's Austin and myself, and we have several developers behind us who have been working with us, really, since the beginning, but we're really in Grow mode right now. I think we're looking to hire several positions customer success and sales, and I think that's one reason I'm very excited to be in Charleston next week. We're excited to grow the team. We're at really a pivotal point.

Annie Holcombe  
So, yeah, it's been exciting. So in terms of growth, where are you at? Or, I guess, adoption, where are you at with the number of property management groups you work with, and say, the number of properties that you're insuring.

Sasha Lawler  
So we work with about 20 different property managers at this point, really, spanning all across the US, in different markets, tons of different types of inventory, like the luxury Lake properties, all the way down to like condos and destin in terms of units. I should know this off the top of my head, but I don't, that's okay.

Annie Holcombe  
It's like, it's like, it's always a metric. I ask about it. I'm so always, always curious. I remember I worked with somebody years ago, and I go, how many, how many units are in that building? They're like, I don't know. There's a bunch, you know. Like, it's just a weird metric that I always, always ask about. So going into the the Women's Summit, one of the things that Alex and I really we talk about is women leaders, women, women in the business and insurance, is, I feel like it's notoriously led by men, like there's not a lot of women kind of at a leadership level. So when you think about you, your contemporaries say, in other types of insurance, do you have any other women to look to, to go to for mentorship within this weird world.

Sasha Lawler  
You're right. Insurance is a legacy slate, Legacy space. So it certainly is very male dominated, should I say, like seeking insurance mentor, um, but I think there are some great women. You know, in the space. There's a company in the UK called pickle insurance. They have a founding CEO who is a female so, I mean, there there are, and there are so many great advisors and investors and actuaries and underwriters who are strong leaders, female leaders in the industry. But you're right. I think, I think, I think the course of that is changing a little bit. But I mean, on the VR side of things, there are certainly so many women in the industry that I know and respect, and I have on speed dial at all times. And I think maybe that's one of the biggest learnings I've had in this whole experience as so organically, this group of supporters has come around, not only Rome, but but me, and seeing the folks that you know have been able to offer support for offer mentorship, are willing to do it without getting really anything back, really the genuineness of that really just underscores, like I'm in the room. Industry like this is a very special thing, and I know that because I've worked in other industries before. After I left inhabit I worked in Prop tech and multifamily for a little while. It's just, it's just different ecosystem, right? When you're managing assets for a gray star, it's very different than managing assets in the vacation rental industry, it's a bit more personal. And I think maybe that's what makes our industry, even on the vendor side, feel a little more personal.

Alex Husner  
Yeah, for sure. And I think, I think that's the the nice thing too, about our industry, of like, you know, you're developing this go to market strategy and how you're going to get this out to everybody, but it's like, you know, it's not like you just came up with this insurance tool or a technology platform that could be for any type of industry where, now you've got a you're starting, literally from scratch, you have connections, and, you know, a lot of these people, right? So it's like, you've got a little bit of a head start there on how you get this out there. But I am curious. I mean, like, from the go to market strategy on this, like, what does that look like? I mean, what, how are you going to how are you going to grow this? What is the plan to to get this out to the masses?

Sasha Lawler  
It's a part the plan as of now, is to be very strategic and smart about how we grow, right? I've seen a lot of other players come into the space, and I think to your point, there are, like you walk on the showroom floor at a conference, it looks so much different these days than it did back in 2017 so there are a lot of there are a lot of, you know, traditional players outside of the industry who are have looked into this industry, and they see a tam right, like they see a total addressable market. They're doing a calculation on evaluation, and that's how they build the business. That's how they build a product. We want to do things differently, right? Like I think true innovation, for it to be meaningful, has to be built from within, because there are so many nuances that property managers deal with on a daily basis that make a product built outside of the industry less applicable or less impactful. So that's a really long winded way of saying like, we want to be smart about our growth. We want to partner with the right property managers and know that our revenue, just like our customers, revenue, is an outcome of delivering a really great experience and delivering really great results. So I think for us, it's like, I don't want to have a like, massive HubSpot automation campaign. I want to sit next to a property manager. I want to understand their business. I want to understand what their owners care about. You know, what their carrying cost is, how they're thinking about their revenue strategy. I think all of those things lead to an outcome. I don't necessarily want to be focused on that outcome.

Annie Holcombe  
I love that. And your customer, like your ideal customer. I think of Alex, and I talk about all the time that kind of the pie. Kind of the pie of the industry. You know, being the smallest portion of the pie is the the large operators, and there's so many of these people out there that are 1235, units, and they really don't know how to get to them, but they're, like, the biggest segment of the industry. And that's kind of what all the channels are fighting for, and all the different providers are fighting for. But I feel like what you're providing is something that gives them, would give them more stability to be able to grow their business. So how do you do you see yourself reaching into that and tapping into that side of the business? And if so, like, how are you looking to do that? Because I just always talk to people all the time, and it's just everybody's like, Well, how do we get to them? How do you speak to them? There's just no. We have vrma for the traditional operator, but for these smaller groups, it's kind of hit or miss.

Sasha Lawler  
Yeah. I mean, I think platform partnerships certainly are critical to that, right? The way that we've built our technology is really set up for a white label play. There's no reason a marketplace couldn't embed this into their platform to offer that flexibility to guests, then that would help service kind of that smaller end of the market. And certainly, I think I've been surprised, you know? I think my original thesis was, you know, I think the only larger managers would be attracted to this. And I think very quickly, when we came to market, I quickly realized exactly your point. What you saw, really intuitively, is the smaller property managers love this just as much, because it gives them that stability. It gives them the ability to not only, not only secure the income, not only be more competitive on these OTAs, but in terms of like leveraging Rome, leveraging this protection for an early adopter in their market, it's a growth acquisition strategy, their ability to attract new owners by saying, hey, no one else in the in this market. It can offer not only the most competitive listings, but guarantee your income in a way that I can. So I think that's how a lot of folks are seeing this as like, yes, it's great. I'm taking this and I'm running with it, and it's now my top bullet point for owner acquisition. And I think that plays to the larger property managers as well. Because I think the flip side of that as as a if I'm managing my own property, and a property manager comes to me and says, if you, if I do that, if you, I do this for you, I can guarantee your income. Why wouldn't I go with a large property manager? Right? Right, right? So I think there's several ways that folks can, you know, distill this down to not only be a revenue engine for their bookings, but also for acquisition.

Alex Husner  
Yeah, do you see this as something that you could also roll out though to smaller hosts or individual hosts?

Sasha Lawler  
We do, yeah, absolutely. I think, yeah, yeah. I think to the conversation is like access to the smaller hosts, right? And I think that would be unlocking more PMS integrations. We have a very well documented we're an API first platform, so any PMS could easily come in and write to our API and give their users access to our insurance, to our embedded booking protection, and then again, back to the like the platform play. You know, if they're for platforms who are looking to grow their distribution models, embedding this right into you know that booking experience for the traveler would be, I think, a no brainer?

Alex Husner  
Yeah, no, absolutely. I mean, I think there's so many different approaches here that for the larger managers to be able to say to owners, you know, try to get them onto their program like I'm going to be able to, I'm going to be able to promote your property to the fullest extent, both on the OTAs and on our own site, but you don't have to worry in those cases, because it's like it is. I mean, if you've got a large home, even if it's not a large home, if it's a three bedroom condo, and it's canceled just a few days prior to arrival, it's going to be really hard to find somebody that's going to book that without you cutting the rate significantly. So I think this makes sense on so many levels. And you know, there's so many different ways that companies have done or have tried to handle this over the years. And I think, you know, some of the more legacy companies have been around for a long time. They have different things in place that, you know, you can get your money back if somebody rebooks the property. And that was the case that the company I was with for many years, and it can be crazy though, because the guest is that had to cancel, is calling and emailing me. Did it get rebooked? Did it get rebooked? And it's like, oh no, like, it's just, it really has it's always been a problem, but I think now, with the OTAs prioritizing the cancelation flexibility, it's made it even more of a problem that it's now it's the problem is, how do you keep your direct site as the best option for somebody to book on? So I think it's awesome. I really, really think this is going to be something that

Sasha Lawler  
takes off. Yeah, well, I'm excited to hear that. And I think you're right. I most managers I talked to have been in that similar situation, of like, I think intrinsically, all property managers want to do the right thing, and that's why they have these gray area policies of, if it rebooks Because cost of acquisition right? It's like, you want that traveler to be happy. You want them to come back. And it's a huge operational burden. I've seen people managing it in spreadsheets, and someone last week, tell me they spend four hours on that spreadsheet in the summer every week. It's just massive versus, like, let them, let them walk, refund them their money. And you know, you're getting covered on the back end. It really, right?

Annie Holcombe  
Well, and I'm stressed that it removes from the manager to not have to worry about, like, I remember going into reservation offices, it was like, the reservation was like, we had five cancelations today, and then you're like, freaking out, like, how are we going to fill in those holes? Well, now it's like you can really focus and breathe and not get down the rabbit hole of like, despair, because you had cancelations well.

Alex Husner  
And the hard thing is too. I mean, you know, travel insurance is great, but travel insurance traditionally only covers certain things. I mean, it covers job loss and hurricanes and like, unforeseeable events, but it doesn't. It's not canceled for any reason. So if you just can't make it, something came up, you know, and if you're a reservationist or you're a company, and you've been pushing to buy the travel insurance, and you you bought it, but now you have to cancel, but it doesn't fit into that criteria, and now the company is saying, Well, you only get your money back if the property is re rented. It's like, you're pretty pissed off as a guest, and that's such a good point on the on the customer acquisition, Sasha is like, you know that guest is not going to come back and stay with you. And you know if that was a booking that came in from a. Paid at you probably, you know, paid pretty heavy for that in the grand scheme of things. So it's, it's definitely, it's a portion of the business that really touches the entire brand and the future success of the company as well.

Sasha Lawler  
Yeah, that is really what makes me very excited, and I think what sets us apart so much from travel insurance, which I agree, certainly has its place, but it's not a reason people book with you, right? Like it is an add on in many ways, it does create friction in that back end of the booking process, but this isn't travel insurance. This is revenue certainty built into every booking. And I think what's exciting to me is we're taking this pain point and we're turning it into a competitive advantage. I mean, I do so much research on property managers websites before a call to figure out what their cancelation policy is, and I'm telling you, it's like doing brain surgery. It's like buried in the terms and conditions, and it's just like, let us eliminate that. Like, instead of apologizing or hiding this cancelation policy, advertise that like, have it be a brand promise that you wave in the marketplace, that flag, that reason, that, like, I'm going to book with ABC property management company every time, because they let me cancel, right? Like, I think the brand experience impact on the owner side and the traveler side is the most, the most fun piece.

Alex Husner  
And I think it's not like implementing this is just going to have just a wave of cancelations. I mean, people don't book reservations thinking like, this is going to be fun. I'm going to go book this one, then I'm going to cancel it. I'm going to book this one, then I cancel that. Like, nobody does that, right? Does that, right? That's not fun, because it opens you up to, I mean, it's far more flexibility. And I know, I mean, just years ago and using booking.com Like, I remember, we would get a lot of bookings that would come in, and a lot of them would cancel. Because in some cases, people would use it for a similar thing, that they'd book a couple different options, and then whichever one that they thought was going to be the best one, they would keep because they made it so easy. But like, the culture of vacation rentals, I don't think it really mimics that of like, if you found the perfect home, and like, you're going to want to stay there, but you should be able to, if you can't, things come up. I mean, it's life. You know, you don't want to be indebted to something that you can't even get to enjoy. But my my question would be, so does does this replace travel insurance? Like, what do you even need travel insurance for? Because if it is, it's canceled for whatever reason it is, whether it is a hurricane or a job loss. Like, does this eliminate the need for that?

Sasha Lawler  
I don't think so. I think there certainly still is a place for I think it creates a conversation of like, what risk should the manager bear and what risk should the traveler bear? Right? And there are still so many things that travel insurance covers that offering that a flexible cancelation policy doesn't right. It's like, I tear my ACL on the ski hill, and I got to get medevac out of Vail. I'm buying travel insurance when I go ski at Vail. Or, you know, I'm bringing grandma to the beach vacation. What happens if she gets sick, you know, during or or trip interruption insurance. Or my flights are getting, you know, my flights get canceled. Or, you know, all of those, you know, cancelations that happen really during the trip. There's still a need for those things, I think, to be protected. And there are things obviously above and beyond the accommodation that are part of that investment that you're making when you travel that need to be protected. But I think kind of bifurcating those two things and knowing like as a consumer, I am making a decision to book a property, not because they have travel insurance, but because they're making it really easy for me to book and they're letting me cancel, right? So the question in a travel or consumers mind is like, do I book the property that is no refund or a 60 day cancelation and buy travel insurance, or do I just book the property that has flexible cancelation and add travel insurance if I want to, if I need coverage for all these other things? Right? So that's the choice that folks are making, and it's it seems to be a pretty, pretty clear one. The debt, as the data shows,

Alex Husner  
yeah, it makes sense too. Because, I mean, travel insurance, in a lot of cases, is a great revenue source for property management companies too. So I think if there's a way to do the blend of the two there, it makes sense. But what, what does the financial piece of this look like? I mean, how is it? I'm sure it varies by company. But like, what? What is the model of how they're charged for this?

Sasha Lawler  
Yeah, so the exact price is determined kind of during this underwriting process where we're taking a look at their historical cancelation data, but as a percentage or percentage of the reservation, i. Um, because folks are adding a premium amenity, they're offering flexible cancelation, they're able to now actually show up in searches on OTAs you have the ability to justify a higher rate. So all of our customers are, you know, taking that premium price, embedding it in the nightly rate, in their PMS, um, so that when it gets syndicated out to their direct booking website or these channels. They're essentially passing off the cost, or covering the cost during that, you know, embedding it in nightly rate to cover the cost so that their commissionable net night net nightly rate stays kind of like net neutral. So I think that's another beautiful part of it. Is like managers are passing off the cost and seeing a pretty massive return in terms of increased conversion, driving more reservations. The impact on organic ADR growth has been like another surprise for me to see in the data, right, like the number of reservations that are booked more than 60 days out. It's like in that instance, you don't even have to raise your rate. You're just organically getting a higher rate because they're you're giving them the confidence to, like, not wait till the last minute to book What?

Annie Holcombe  
What in terms of availability? Is it available just in the US, or do you have Are you able to do this outside the US?

Sasha Lawler  
So right now we're protecting property managers who are based in the US. So we, yeah, we can protect property managers that have, may have a few properties outside of the US, but as it stands today, currently, for property managers in the US,

Alex Husner  
yeah, I could definitely see this being used overseas, though. So hopefully when you get to that point, you'll have to let us know we can come back on on the show, because we have a lot of people over in Europe that listen to the show. And I think it's, it's, it's a concern globally and an issue so, but I know insurance isn't always that simple to just say, okay, we can open it up. So Well, this has been really awesome to hear about this Sasha, and before we hit play, had mentioned that I was excited for this recording, because this conversation has just organically come up with a few of my clients recently, of them kind of brainstorming an idea like this and saying, like, Could we do it? And, you know, it may be, but it's like, that's the conversation. Of conversations have more gone towards, like, a self funding kind of model, which isn't practical in all cases, and I think this could be, end up being, you know, a financial nightmare for companies if they didn't have someone that was backing on the other side of it. So this seems like a great solution, but thank you for coming on, and we're just, we're excited to by time this airs, we'll be back from the Women's Conference, but we're excited to see you next week at the Women's Conference.

Sasha Lawler  
Yeah, thank you guys so much for the opportunity to kind of geek out about flexible cancelation of live and breathe and yeah, just it's been, I got, it's been a great chat. Excited to see you guys next week in Charleston.

Annie Holcombe  
Well, I did a session a couple of years ago at dorm, and I joked about it. We were just talking about this the other day. It was like I was like I was doing a session on the thing that salise talked about. And probably the least sexy is insurance. And I think what you know, you can turn it on its head and make it sexy again, because people are going to want to talk about this is a really great product and and, like you said, very timely, considering what the channels are doing to try to make more flexible booking policies for the consumer, and so this is going to give managers the peace of mind that they need to be able to play in all the areas that they should be able to play in. But if anybody wants to get in touch with you, what's the

Sasha Lawler  
best way to reach out? Best way is Sasha at Go realm.io S A, S H, A at Go realm.io Yeah, reach out with questions, comments, feedback. I love, love to hear all of it. Right. That's how we learn. That's how we grow. Awesome.

Alex Husner  
Well, we will make sure to include that in our in our show notes, along with your website and LinkedIn profile too. But if anybody wants to get in touch with Annie and I, you can go to Alex and Annie podcast.com and until next time, thanks for tuning in, everybody.

Transcribed by https://otter.ai

Sasha Lawler Profile Photo

Sasha Lawler

Founder/CEO

Sasha Lawler is the Founder & CEO of Roam, the first cancellation insurance platform purpose-built for the vacation rental industry.

Sasha brings over 15 years of experience in hospitality and vacation rental tech. Sasha started on the front lines—booking stays and managing reservations for a major hospitality brand in Colorado. She then transitioned to tech as the VP of Sales for Bluetent, a start-up digital marketing and website company and was promoted to the VP of Sales for InhabitIQ post acquisition, leading go-to-market strategy for the top 13 leading property management software, payments and insurance companies in VR.

After leading sales teams for Multifamily SAAS platforms, Sasha saw a massive gap: the industry’s outdated approach to travel protection didn’t match how modern travelers book, cancel, and expect flexibility. Combining startup grit with enterprise expertise, she launched Roam to flip the script on traditional travel insurance.

Instead of insuring the traveler, Roam protects property managers’ booking revenue from guest cancellations—empowering managers to offer simple and flexible policies that drive more bookings without risking revenue or owner trust. The result? Happier guests, loyal owners, stronger margins, and a competitive edge in a volatile market.

She lives in Bend, Oregon, with her husband, five-year-old son, a vintage 1984 camper, and an unshakable loyalty to Duke’s mayonnaise.