How HospitalityTech entrepreneur Henry Bennett created, after YourWelcome (product marketing series)

Thibault Masson

Updated on:

henry bennett property care

In our vacation rental tech product marketing series, we interviewed Henry Bennett, the CEO and co-founder of the YourWelcome tablets and the software platform. Henry shared how he built out of observing how and why his clients and their cleaning staff were using his tablets. He explained why the cleaning and housekeeping modules offered by PMSs were lagging behind specialized solutions. In terms of go-to-market strategy, he showed that was able to get 5,000 properties on board fast because he could rely on the tech integrations and the customer base of YourWelcome. After talking to customers and prospects, he realized that YourWelcome’s solutions appealed to several stakeholders but that they needed to be addressed differently. While the YourWelcome tablet attracts people who care about guest experience and messaging, he launched the website to talk to operational teams within property management companies who needed to hear a different value proposition.

While property care is an established software category in the US, Henry saw signs that Europeans were very interested in the topic, as COVID-19 protocols are still important to European travelers. Finally, Henry shared how inflation and cleaning staff shortages were forcing property managers to automate as much as possible in order to preserve profitability. vs yourwelcome tablets

How do you validate a new vacation rental tech idea?

Thibault Masson: As a vacation rental tech entrepreneur, how do you validate business ideas? Maybe you can walk us to the example of You only not only have one but two services in the industry.

Henry Bennett:

Although YourWelcome and are two services, it is one product. YourWelcome is the smart tablet for vacation rentals. Pre-pandemic, we were in about 18,500 properties represented by over 1,500 vacation rental managers. When working with so many companies, you realize no vacation rental company has the same processes as another company. 

Some problems are the same whether you are based in Orlando or London: Getting more occupancy, making sure the properties are clean, acquiring more properties, and growing. Yet, the ways property managers run their business can be very, very different.

We’ve always had a housekeeping element within the YourWelcome tablet. So cleaners were always able to log onto the tablets and use them, as there’s a very simple checklist. Just before the pandemic, we noticed that it was increasingly becoming one of the core features of YourWelcome.

So, looking at the behavior of our users, we did not doubt that we were going to expand and build out a task management platform specifically for vacation rentals. That bit of software itself is actually quite complex. There are loads of task management softwares on the market, but they are industry-agnostic. But when you’re building task management related to vacation rentals, you know that things have to be different. All the automation around task generation, scheduling, and assignment of the tasks to the cleaner must be built around bookings, check-ins, and checkouts. So that’s different from all normal task management.

Now, we decided quite early that we couldn’t really sell that as a standalone product alongside the tablets. Because we did a bit of market research, and pretty much whenever you say to people, “YourWelcome,” the first thing that people come back with is, “Oh the tablet guys.” Or, “The hardware guys.”

So, we thought this was going to be very challenging to both say: “We’ve got this product over here where it’s all centered around hardware. Meanwhile, over there, we have an amazing bit of software that automates assigning all of your property care and task management cleaning needs, but you don’t need the tablet for that.”

So we took the view that we would have two different sales channels that link into one backend portal. We then acquired what we believe is the best-in-class domain name, In the US, especially, property care is a hot topic.

So I think the short answer to your question is, we already had a lot of customers using our tablets for basic task management. Building out a complete task management platform for vacation rentals was the next logical step. We knew what their needs were. We saw the increasing need on our own tablets. We knew there’d be a market there before we started. Which wasn’t the case with YourWelcome, which was very much more instinct vs reality. We just knew it would work.

How do you pitch a new product category?

Thibault: With YourWelcome, you were creating a new category of products. In a way, property care exists as a term, but your type of solution may be new to the industry again. When you’re entering two new categories, you have to evangelize the market and make people understand what it’s about.

This is how you do it on You are talking to property managers;  that’s who the product is for. And what property managers know, as a kind of software, are PMSs (property management systems). So, on your website, you present side-by-side what a PMS and what can do (see illustration below). vs breezeway

How do you usually try to explain these complicated concepts to potential customers?


Do you know it’s easier this time around? We talk to a lot of customers. Everyone says they are not happy with their PMS. Actually, I have a lot of sympathy for PMSs, because they’re trying to do a lot of things that are very complex. In the industry, keeping up with all the different channels, the different protocols these channels are doing, is a very challenging task. If you’re Guesty and you’ve raised $70 million, you probably can go after all sectors, but it’s still quite slow.

One of the things we identified quite early is that the basics of property management haven’t changed. You’ve got to make sure the property’s clean. You’ve got to try and ensure you have a consistency of products across potentially multiple cities, multiple countries. That is really, really hard.

Property management systems, until fairly recently, were not really focused on the management of cleaners and maintenance staff. It is also quite complex, because some people have in-house cleaners, freelance cleaners and use third-party companies is to fill in the gaps.

So we spotted what we thought was a niche in the market. But actually when you think about it, if the property is not clean, then the guests can’t get in. It’s absolutely crucial. 

PMSs are going to massively improve their housekeeping and cleaner management down the line. But right now, they can retain their customers because is a great bit of technology that integrates fully with them. Similarly, lots of people use Xero for their accounting outside of their PMS, because that is seen as the best-in-class accounting software.

It’s very hard for a PMS to create software that works, on one hand, for a venture-backed Airbnb management company that is looking to scale and has less focus on the actual nuts and bolts of property management, and, on the other, for a property manager who’s been around for 50 years, that has 50 properties, run them amazingly well, previously using legacy software. Marrying those two together is a really hard business. So I think there’s always going to be companies like us that can exist in that ecosystem around it.

Go-to-market: AdWords would not scale. Better take the existing product and launch an additional website with a value proposition that focuses on the operational side of property management.

Thibault: is “powered by YourWelcome”. What does it mean?


So is just a sales channel. It is a website to buy that section of our product. So it is powered by YourWelcome. We’ve built up a pretty good brand globally in vacation rental software. YourWelcome Limited is the company that owns YourWelcome and

YourWelcome Limited has all the connections with the PMSs that feed into our main platform. If people want to buy property care software, they come in via If they want to buy YourWelcome tablets, they come in via YourWelcome.

Paying for Google AdWords is not the way that you are going to scale up your vacation rental tech business. The two ways you’re going to do are word-of-mouth and high-quality SEO. Our view was that, with that domain and the SEO, we can target people looking for housekeeping solutions.

We could become a domain authority on Google very quickly. Whereas if we try to mix and match it with YourWelcome, that wholesale channel becomes quite a mixed messaging.

And we think we’d lose an opportunity, which is, due to COVID-19, developing a significant housekeeping task management platform. The opportunity is now, not in six months’ time, because other people will enter the market. So that’s why we decided to do it that way around. vs breezeway

Thibault: So everything the software does, everything that’s offered on, is also available through YourWelcome?


Correct. It is the same portal. It’s just that some of it is commented out. In an ideal world, we would prefer to have one sales channel. It’s just the reality of how, like if you think about it, if someone’s looking in a company for guest experience, that is a different person from the one who’s looking for operational backend software. We’ve got to target both sides of that business.

In America, we’re up against companies that have a lot more money than us. We’ve got to be more nimble, outcompete them, use different strategies. 

Thibault: Very interesting way to allow stakeholders to discover your solution, from different sides. People in charge of operations and of guest communications are not the same people, in larger companies. But even if these are different stakeholders, there’s still one crucial issue at some point. They will ask, “Okay. It’s a great solution. I like But how does it integrate with my PMS?”

I’m guessing that benefits from all the integrations that you’ve already done for YourWelcome. How many integrations do you have and how crucial is it in terms of distribution?


This is one of the reasons why we launched this, and we knew that it would be successful. YourWelcome has 42 PMS connections. It’s very difficult for a startup company to come out of nowhere and start integrating with PMSs. Because the first question they ask is, “How many companies are you working with? Do we have a mutual client?”

When you look at who could develop a platform like ours, there actually aren’t that many companies out there who could say: “First, we got all the integrations. Second, we are going to give this software away for free for the first year for most of our tablet customers.” Thus, we’ve signed up about 5,000 properties to

That is not something you can do just coming into the industry cold. So we had a huge competitive advantage walking into this on that basis. This is why we think it was a good strategy to do this.

Scaling fast with an aggressive pricing in the US and additional features for the European market

Thibault:  Some features, such as guest ID aggregation and verification, probably talk more to people who have properties in Spain or other countries in Europe. You’re also targeting US property managers. Am I right to think that some features talk more to one side of the Atlantic than the other?


In the US, property care as a genre is well established. 80% of YourWelcome tablets are distributed in the US. There’s a couple of other people that have done this. The PMSs in America have already started looking into it. So what we’re doing is coming in with a super attractive price point: $2 per property per month. We’re going for scale very quickly. It’s a self-service platform. The idea is to have it very well documented, with a very good onboarding, so that you’re able to set it up and run it fast. pricing

But in Europe, when talking to customers, we noticed another need around guest communication. Property managers run it off a combination of PMS, Excel, WhatsApp, email, and it’s a bit of a mess. They are also looking for housekeeping and scheduling We’ve actually seen a pretty much slightly quicker growth in Europe. I think that is purely because also COVID-19 has hit Europe so much worse in terms of being able to travel. Consumers in Europe want to know the COVID protocols and about the cleaning prior to arrival.

Whereas in the US, when I talk to my US sales team, and it’s not quite like this. They’re almost like, “Are you guys still talking about COVID-19?” You’re like, “Yes. We’re still talking about it, a number of countries are still on lockdown.” 

So a short answer to this question is, the product is conceived as an American genre that already exists, that we believe we can take to Europe successfully, and also very quickly. So if you look at our PMS integrations, we integrate with most, I’m not going to say all, but most of the leading European PMSs as well as the US ones. Which gives us a very solid start to go.

Automation to fend off inflation and cleaning staff shortages

Thibault: Is there any question I should have asked you, I forgot to ask, but I didn’t ask?


There’s been a huge crunch in the ability to be able to get cleaners. To recruit them and also to retain them. And inflation and rising wages are rocketing. And we all know that the cleaners are the bedrock of property managers. If you don’t have cleaners, the property managers themselves have to go in and actually physically clean those properties. I think that, you are going to have to manage more properties with the same or less staff. Otherwise, your costs are going to rocket. There’s not many ways that you can do that other than optimizing how you do your processes.

Now, I think this is going to become a bigger and bigger topic. In the past, everything was a bit sexier. We were talking about ADR, nightly rates, etc. We were talking about guest experience, all the sort of fun bits of property management.

Whereas I think now the real focus is going to be on the nuts and bolts of “How do you get guests in? How is it clean?” Maintaining reviews and ensuring consumer confidence means it’s clean and it’s safe.

I think that really property care as a genre is going to play a huge part in that. Not just our product, but whoever else comes into this space. We’ll also see PMSs starting to put more onus on it, rather than it being like “Yeah. I know you’ve got to do it, but it’s not the sexy bit of this industry”. 

Thibault: Costs are rising. Inflation, for example, inflation in Spain last year was 6%. So it means that cleaners’ wages also have to rise by at least 6%. Because as you said, you want to retain the best ones.


I’m based in London, and we have the impact of Brexit as well. Now, no one wants to talk about it, but a lot of the cleaning staff for vacation rentals came from Europe. I was in Devon recently; we were going to see some clients. We were driving past hotels with signs up saying, “We’re no longer open Sunday, Monday, Tuesday.” They said: “We can’t get the staff to do it.” This industry is not going to die based on inflation, but I think there’s going to have to be some changes around.

There’s only a certain amount you can up your nightly rate before it doesn’t become affordable for a family traveling there or you’re suddenly competing with luxury hotels.

How to find out more about and YourWelcome

Thibault Masson: So Henry, if people want to know more, let’s say, about either YourWelcome or, what should they be doing?


So if you go onto our website, that’s, you’ll be able to book a demo, or indeed just get in contact. And if you’re interested in YourWelcome tablets, which is a physical point of sale that you install in your properties, that’s

Thibault Masson:

Fantastic. Thank you so much for your time, Henry. We are meeting again on January 24. We’ll be talking about trends in the industry, and we just heard that you’ve already taken the pulse of a few of those trends already that you know about.

And we’ll be talking with Your.Rentals and Rented about the trends in Europe. So if you love this topic, make sure not to miss the conference.

european holiday rental conference

Video: Henry Bennett on launching

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