Jacob Messina is the CEO of Stayntouch, a leading hospitality technology firm that provides cloud-based property management systems (PMS) for hotels. Under his leadership since 2022, Stayntouch has achieved record growth and become one of the fastest-adopted PMS platforms in the industry, enabling hotel clients to implement new systems in as little as 48 to 72 hours. Jacob's diverse hospitality background began at age 15 in frontline restaurant and hotel roles, later building Loews Hotels' digital marketing practice from scratch and overseeing technology for 150+ properties at MCR Hotels.
Jacob Messina, CEO of Stayntouch, breaks down how a cloud PMS built by former hoteliers cuts implementation from months to days and staff training from weeks to about an hour. He explains why distribution is the most overlooked revenue function for independent hotels and what to do about it.
Before leading Stayntouch, Jacob spent six months at Loews Hotels manually merging guest profiles in Opera V5. Forty hours a week of clicking through multiple screens for a task that should have been automated. That experience shaped his view of what hotel technology should do: give time back to the people using it, not create more work.
At MCR Hotels, he oversaw technology across 150-plus properties. When a soft brand inspection failed a week before opening, his team had to stand up an entire independent tech stack in eight days. Stayntouch made it work. That scramble became the catalyst for productizing fast implementations. Today, Stayntouch can get a hotel live in 48 to 72 hours.
Three principles drive the company under Jacob's leadership. First, customer support where you talk to a real person within seconds. No phone tree, no callback queue. Second, 1,200-plus integrations offered at no cost, with a fully open API for anything not yet connected. Third, intuitive design that gets a new front desk agent checking guests in within an hour, even if they've never worked in a hotel.
One counterintuitive decision stands out: Stayntouch deliberately slowed its release cycle from every two weeks to every four to six weeks. Not because development couldn't keep pace, but because hoteliers are already tracking updates from six to eight other systems. Shipping faster than operators can absorb creates waste, not value.
On distribution, Jacob's advice is straightforward. Stack your channels from lowest to highest cost of acquisition. If you know what you're paying Booking.com, put a portion of that spend toward driving direct bookings instead. In OTA-heavy markets like Hawaii, that channel shift is where the margin lives.
The conversation also covers ancillary revenue. Stayntouch's upsell module is included free in the PMS subscription and runs inside the mobile check-in flow. Guests can upgrade based on room attributes and local experiences. Jacob points to Castle and MacNaughton in Hawaii as groups that have made this work by investing in clear room-type definitions and content that tells the story of what makes each property worth the upgrade.
On his early career at Loews Hotels, where he spent six months merging guest profiles in Opera V5 for 40 hours a week:
"Our systems within hospitality are still far behind where we need to be as an industry. However, we're catching up rapidly, which is exciting." — Jacob Messina
On why understanding frontline hotel operations is non-negotiable for building technology that gets adopted:
"Without a good solid understanding of how hotel operations work, you're just building software for the sake of building software." — Jacob Messina
On Stayntouch's design philosophy of giving hotel staff time back to focus on the guest:
"Here's something that used to take nine clicks. How can we do it in two? Even just that is giving someone time back to interact with a guest." — Jacob Messina
On how independent hoteliers should think about channel shift from OTAs to direct bookings:
"You know what you're paying your OTAs. Why wouldn't you pay a similar amount or a portion of that to get business direct? That's an easy way to think about how to make channel shift happen." — Jacob Messina
This episode is sponsored by Lights On.
Lights On helps hotels grow revenue more consistently by managing pricing, distribution, and digital marketing together.
We help hotels identify new revenue opportunities, so they don't leave money on the table. We also manage the full revenue and marketing operation, enabling the on-the-ground team to focus on the guest experience.
If your hotel needs stronger revenue growth, visit lightson.co to learn more.
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Kin Sio: Welcome back to the Lights On Podcast. I'm Kin Sio, CEO of Lights On and your host today. On this podcast, we share stories from across hospitality about building and growing hotel businesses.
This episode is sponsored by Lights On. Lights On helps hotels grow revenue more consistently by managing pricing, distribution, and digital marketing together. We help hotels identify new revenue opportunities so they don't leave money on the table. We also run the full revenue and marketing operation so the team on the ground can stay focused on the guest experience. If your hotel needs more revenue growth, visit lightson.co to learn more.
So before introducing today's guest, I want to give a big thank you to Rose Serrano from Stayntouch for actually bringing a really good guest today. Please go check out their website at www.stayntouch.com — they are one of the fastest growing PMS platforms in the industry right now.
My guest today, no surprise, is Jacob Messina, CEO of Stayntouch. Jacob started his hospitality career in restaurants and front desk at 15, graduated from Cornell Hotel School, and built Loews Hotels' entire digital marketing practice from scratch. After that, he moved on to MCR Hotels, overseeing technology across 150-plus properties. And from there, he took the helm at Stayntouch in 2022. Stayntouch since then has been taking the hotel world by storm, posting record growth and becoming one of the fastest-adopted cloud PMS platforms in the industry. Welcome, Jacob.
[1:54]
Jacob Messina: Yeah, thanks for having me here today, Kin. Appreciate it.
Kin Sio: So let's start with your beginning. You started working in the hospitality industry — in the kitchen space, front desk — as a teenager before you went to Cornell. What did you learn about running a hotel from that experience that Cornell did not teach you?
Jacob Messina: A lot. I think it's really important for everyone to experience the hotel and restaurant industry at a line level before you ever think about being in strategy or management. Being able to see how hard individual team members are working around the clock, whether it's in kitchens, front of house and restaurants, front desk down to housekeeping and hotels — it's really important work that in some cases is back-breaking labor and in some cases is really grueling. So it's a really important learning lesson for me. Hospitality is a very difficult industry. It's difficult to find people that want to be in this industry and have a career in it.
Kin Sio: I see. How does that translate into your role right now? Because it's hospitality, but it's more on building technology. Do you find those initial experiences help to build and shape the products that Stayntouch builds today?
Jacob Messina: Incredibly. I think hands down one of the things we work on the most is making sure that we are understanding what our customers are asking us for and also understanding what they may be asking for in the future. So without a good solid understanding of how hotel operations work, you're just building software for the sake of building software.
And that is what a lot of people in the space think — "Oh, we're solving the world's problems one at a time." The reality is you need to understand how people interact with the software at a line level. And that comes down to knowing — and it's different by hotel, by market, union versus non-union. These are important things to understand because it's going to change the implementation and the usage of your product at a hotel.
Kin Sio: Exactly. Because you're not doing scientific research — the things that you build have to be adopted by real people out there. And it's definitely a good perspective thinking about how software should be built.
[4:30]
So moving on. You did that, starting from essentially the front line at a hotel, then you moved on to school. After school, you landed your job at Loews Hotels, a luxury management group. There you were part of the distribution team. You spent lots of time manually merging guest profiles in Opera for like 40 hours a week. So what did that work show you about what's broken in hotel technology?
Jacob Messina: Well, it was a really challenging situation. Just to take on that, it was my first job out of college. It was during 2009 when the industry was facing some really difficult times with the recession. I was thrilled to have a role within Loews Hotels as a brand that I really wanted to work with.
And my first job, as you mentioned — I think it was around six months, all I did was manually merge these profiles. One, it told me there's got to be a better way. Two, the systems are holding people back. They're not enabling people. And now we're in a space many years later where these repetitive tasks are ripe for automation. And these are great use cases for AI as well.
Just to think that I was spending 40 hours a week for all this time doing something that now you could use AI agents to do agentically or even just provide recommendations on. Our systems within hospitality are still far behind where we need to be as an industry. However, we're catching up rapidly, which is exciting.
Kin Sio: I see. When did you realize the problem was the system itself and not just the process? Because you could have a great technology product, but the process, when it's not aligned, could create similar friction. So how did you differentiate both?
Jacob Messina: I would say it was pretty easy to spot the problem here. One of the problems was that looking at these profiles, it was actually up to the user — in this case me — to make a distinction of, is there enough information between these two profiles that it's the same person. For that to be a completely subjective process is not great. It leads to errors and you can't automate those kind of things.
So at that time I was doing things like creating a rubric for when we do these. Now you need those in order to automate. However, part of the problem there too is merging a profile in Opera V5 is not an easy process and it requires multiple screens, multiple clicks, and to do that thousands of times a day is just busy work.
So at Stayntouch, what we do a lot of is — all right, here's something that used to take nine clicks. How can we do it in two clicks? How can we really shorten this experience? And even just that is giving someone time back to interact with a guest, to think about how we're going to delight and surprise the guest with their next stay. It's the stuff that we want to be doing more of in hospitality, not the back-of-house operations component.
Kin Sio: Yeah, and I'm willing to bet the contracts tell the same story. So, time passed — MCR Hotels.
[7:55]
There was an occasion where you find out you're opening — I think it's like a Hilton soft brand hotel — and literally a week before opening the whole inspection failed and you had to go independent. And I think that's the first experience you encounter with Stayntouch as a customer, not as part of the Stayntouch team. What was the experience like?
Jacob Messina: Sure. So the story you bring up there, Kin, is an interesting one. In the role that I had at MCR, we were managing and owned branded hotels and independent properties. Our independent properties ran on Stayntouch and we had a great partnership there. That specific property you mentioned was supposed to become a soft brand, and for multiple reasons ended up surprisingly not becoming one.
So at the time I got a call saying, all right, we're going to go independent and the hotel needs to open in eight days. Trying to stand up an entire independent tech stack is something that generally in best-case scenarios you spend 90 days on. However, you're happy when you have six months to do it. So it really forced me and my team to think — all right, we have eight days. We can't not go live or not open the hotel. We have to have a continuous operation.
And it's really where the technology versus the partnership comes in. I had an extraordinarily strong relationship and partnership with the Stayntouch team, and as a result, they were able to move mountains to make that happen. Now, that's great and all if you can do this every now and then, but the question is — how do you productize that?
So years later, I moved into the seat of running Stayntouch and this is one of the questions I posed to the team. It used to be you had 120 days, then it became 90, then it's 30, now it's eight. What if that becomes the normal? How do we shorten our processes and provide our customers with the tools to be able to set things up on their own, to be able to learn how to use the system?
So we launched our Stayntouch Academy, which has online learning — this is years ago. And we built out configuration tools which let hotels go live in as quickly as 48 to 72 hours should they need to.
[10:22]
Kin Sio: Gotcha. So through that experience — because now you were in the customer seat at Stayntouch, now becoming part of the team — obviously the whole transition and implementation piece, what you mentioned from usually taking months, your target is trying to shorten that to days. Aside from that, were there other big surprises when you joined Stayntouch, just seeing how the team was thinking at the time versus a customer mindset? What other surprises did you find and how did you solve those?
Jacob Messina: Yeah, I think there are going to be surprises as you go in any company you join. One of the big areas that we focused on at the beginning is using some of my background and my history in this space to make sure that we were speaking the same language as our customers.
And that comes from first listening to customers to make sure that you're solving real problems. I find often software companies create a problem just to solve it. And we don't want to be that kind of company. So a lot of what we did is make sure that we were listening to customers, understanding where their challenges were, but also where the opportunities they saw.
That didn't mean that we needed to be the company to solve all those things too. And I think that's also an important mindset that more software companies need to adopt. There's this thought that I need to be all things to all customers or all people. I don't personally believe in that mindset. I believe it's important to be really good at what you do and then bring in partners for the areas that you need to expand and show that unified front with a customer.
So that's why we've always leaned into — we don't need to go build it. We can just partner with the other people that have done a really great job and are excelling in the space and then bring that joint solution to market.
Kin Sio: Yeah, that makes a lot of sense. Going deep and focused on one thing and bringing other champions — people good at other things. And as a result, you try to adopt this very consultative approach.
[12:37]
Jacob Messina: I mean, oftentimes a conversation will start that I'm part of about the property management system. However, I often enjoy spending time with customers and helping them redesign their entire tech stack. And that's where we can be consultative, make recommendations based off of a unique property or a set of hotels. What are the right systems? It's different every single time. And that's important.
Kin Sio: Yeah. And I'm curious how that philosophy might have changed over time because Stayntouch — I think it's been around for over a decade now. It started, I think, founded back in 2012. Essentially, it's a group of people coming from Opera, right? So I'm curious, how does what you mentioned tie back to the creation of Stayntouch more than a decade ago? How much of the current product roadmap is still shaped by what those founders saw wrong — and probably one of the reasons why they left the legacy systems to build one? Does that change over time? What have you learned along the way that changed the roadmap or the philosophy over time?
Jacob Messina: Yeah, it's a great question, Kin. I think any company that's not changing over time is going to be left behind. So we do make sure that we are adapting as the market changes and as hotels change. However, if you're just changing for the sake of change, it doesn't work.
So we have a number of core principles within the organization which stay as differentiators. For example, customer support is incredibly important to us. That is something that will never change. We want people talking to people and really getting people in touch with those that can help them as quickly as possible. So you call our support line — it's not a phone tree, it's not "wait for this person" or "get a call back." Within seconds, you're going to be connected with someone who can help you. That's a really big piece of what we do. And it's very different than how other PMS companies operate in that space.
[14:49]
I would say our integrations focus is another big component of that. Again, like I mentioned earlier, we're not trying to be all things to all people. So it's important we have really strong integrations to other companies. And a big part of what we've done there is we don't charge for them. That's something that will remain a constant within Stayntouch.
And then third, I would say the other core principle is around intuitiveness and ease of use. Many systems out there, especially the legacy property management systems — it takes weeks, months in order to learn them. I can speak to that from experience when I was working at the front desk and even in later parts of my career. I've used 12 different property management systems in my career to date. That can't happen anymore. We need systems that someone can walk in from another industry and be able to use even if it's your first day working in a hotel. The cost of training someone over weeks and months is extraordinary. So anything you can do to shorten that is really important. And we do make those our three core principles across everything we do.
Kin Sio: Yeah. And honestly, in our industry in hospitality, the turnover rate for labor is around 75 percent. So no one can afford somebody coming in, training for months on the PMS system, and then this person is gone. Now we have to do the same thing for the new person coming in again, which is sometimes a hidden cost when it comes to technology selection.
[16:22]
Which I think recently, there's a good case in the local market in Hawaii. I think you guys pulled off some crazy magic again. The Waikiki Circle Hotel — they were at the time transitioning to a new management group. And part of that, they adopted Stayntouch as the new PMS system. And you guys did the whole deployment and transition in three days, which is kind of unheard of in our local industry here. Can you share more about what that experience looked like and why you guys could do it in two to three days versus other systems where a transition takes months? What's the key thing that drives that efficiency gain?
Jacob Messina: It's a great question, but with a very complex answer — we can take it in a number of different ways and maybe I'll take it three ways.
So one is we have a really top-notch implementations team. We're not just selling you a piece of software and saying, go have fun, hope it works out for you. It's a curated, white-glove experience, which is really important because every person in hospitality is doing two to three jobs in addition to their day job. So to think that you're going to be able to do a full technology transition is unrealistic unless you have the support of a partner. So we really tried to build it out that we are guiding people through this process.
For the Waikiki Circle, the way that we were able to do that is a lot of coordination and planning up front, doing a transition with a trusted member of our team on site to be able to coordinate, make sure everyone is trained, and feels good about things.
But it's also the configuration and standardization that we do in the system itself that goes a long way, especially when you're part of a group like Castle — to be able to build out standards once that can be easily copied and pasted across your different properties. That goes a long way to get a hotel live very quickly, but also a year down the road ensuring that you have consistency of all of your rate codes, market codes, transaction codes. That's where the devil in the details can really come out long term if you're not taking a strong focus on that up front.
[18:44]
Kin Sio: I see. So how did the staff training work? Because I came up through the hotel years, right? When I think about transitioning, just thinking about bringing the team along and learning new systems — I think that's always one of the biggest hurdles. So how did you guys approach staff training during a short transition period?
Jacob Messina: Sure. So a couple different ways. We have an online learning academy which is highly configurable based off of the type of hotel, the type of business that they do, and where they're located. So that can all be done ahead of time. The nice part about that too is managers get readouts to make sure that their employees are doing the work ahead of time so they can be successful for day of go-live.
We also have on-site support which will do additional training. The reality is making the system more intuitive makes all these steps a lot faster and easier. To be honest, we have hoteliers that start using our system who have never worked in a hotel before. Maybe it's their first opening and they're able to understand how Stayntouch works because it is intuitive. To do a check-in takes about an hour to be proficient at our front desk module and just to be able to go through the screens. So that amount of training being condensed really does make it for a smooth transition and an easier opening on that front.
[20:14]
Kin Sio: Yeah. And in my opinion, sometimes the onboarding speed and cost translate directly into cost savings that people don't think about. And this is the part where it really shows — especially that the team on-site at the property can start using the new PMS effectively within days versus months. The occasions or experience that we've heard is people still don't know how to use the system months after the transition. It just feels like lots of money left on the table because I think one premise about an effective PMS is not just being the source of truth of all the data, but also the opportunities to start creating upsell or additional revenue opportunities. If the team is not really understanding all the features presented, it's just money left on the table for sure.
Jacob Messina: Well, and on that front, Kin — it used to be that property management systems did a release every one to two years of new functionality. And that is very different in the cloud space. We do releases every four to six weeks. So it's really important that hoteliers are staying on top of new feature releases, but that's very difficult to do.
So not only do we have release notes and everything there, but we also have a customer success team that works with all of our customers to make sure that they are aware of the new features coming out.
In a situation like Waikiki Circle, on day one they're not going to be able to get everything up and running and using the full breadth of the PMS. That's when they move to our transitions team and then our customer success team. They really roll out — here's your 60 days post go-live, here are things you want to be testing and trying. And then you move on to our customer success, which is the long-term management and making sure that when there's a new feature that's going to be great for your hotel, you don't miss it amongst everything else.
[22:20]
Kin Sio: Interesting that you mentioned your feature release cycles being like four to six weeks. At some point, you guys could go as fast as two weeks turnaround. It's kind of counterintuitive that you did not go as fast as you could, but instead you actually made it slower to four weeks — which is still so much faster than a traditional PMS. What was the decision behind that change?
Jacob Messina: Yeah, so there's a couple things that are weighed there. There's always quality versus speed — that's one. So we always want to make sure that we're releasing top-quality product and it's not going to break other things down the line — integrations, et cetera.
And then the most important, I would say, is that our customers have information overload and we're aware of that. We are one very crucial part of their technology stack, but there's also many other players who also have different release cycles. So to think that a hotelier is able to stay on top of the release notes of six or eight different systems — that is a very difficult task, and that's a full-time job right there. So we do try to make that much simpler. It's why we do scheduled releases. It's why we've worked through it with our customer success team, so that way you're not missing out on upside or new functionality or a feature that's been released just because you missed a single set of release notes.
Kin Sio: That's great. This is one of the things going back to your earlier comments on building software for people. Knowing people, knowing how the industry works, knowing the information overload — not necessarily going as fast as you technologically could, but choosing to go at a pace that matches how people in this industry take in information and adopt things over time. Just one example of thinking human-first when it comes to technology.
Jacob Messina: Definitely.
[24:22]
Kin Sio: The other part — and I think you've mentioned this in some past interviews — distribution is one of the most overlooked functions in hotel technology. Why does that matter? And I ask that particularly for our independent hotel audience because a lot of hotel owners in the independent world did not grow up professionally in the hotel industry. So sometimes when it comes to revenue management, distribution — these concepts are very foreign to them. Can you explain why distribution is often overlooked and what revenue is left on the table if an owner doesn't think about this the right way?
Jacob Messina: Yeah. So that was a really critical part of my career. After I thankfully graduated from manually merging profiles, I was part of a distribution team at Loews Hotels and it's where I got to really learn — it's kind of like you learn how the sausage gets made in hotel technology. It's how systems are integrated with one another, where those integrations fail. And then you get into the onward distribution — how you're getting your ARI, your availability, rates, and inventory, to the likes of wholesalers, OTAs, et cetera.
I think distribution is often overlooked or it doesn't get the attention it deserves because people are focused very much on the likes of Expedia, Booking.com, and their OTA partners. And it's important to have a focus on making sure you're getting the most top line out of them. However, distribution is an area of controlling your channel management where you can work on improving the bottom line, improving your cost of goods sold, making sure that your channel mix is in a better place.
Obviously, historically driving more direct business is always for the best, and I highly recommend to all independent hoteliers — think about what it is that you can offer that's different than your third-party distribution partners. Have that value proposition built out and make sure that it's lucrative enough. You know what you're paying your OTAs. Why wouldn't you pay a similar amount or a portion of that to get business direct? That's an easy way to think about how to make channel shift happen.
And then the way that I always look at it is I'd like to stack my lowest cost of business — which is obviously the direct channel — down to my highest cost of business. And then you start optimizing and moving people from highest to lowest or highest to medium and then to lowest. That channel shift and channel mix is really critical to drive profitability, especially in the Hawaii markets which are an OTA-dominated territory with a big footprint.
It doesn't mean you can't partner really heavily with the OTAs to drive business, but you need to do it in a profitable manner to make sure that you're not driving unprofitable business to your hotel.
[27:23]
Kin Sio: Yeah, and the way to start thinking about it — to your point — internally sometimes we call it the cost of acquisition by channel. Before knowing that, it's hard to know if your hotel could be getting a lot of business but it's not coming the right way with the preferred channel mix — the whole OTA reliance conversation, right? Then it could cost a hotel more than they would be expecting.
Jacob Messina: Yeah, I mean, I can't tell you how many times I saw hotels that were thrilled that they've driven X amount of occupancy or RevPAR. And these are important metrics, but they're not end-all-be-all metrics. RevPAR, for example, is one that can be very easily distorted. It doesn't take cost into consideration. So you can be driving great RevPAR but you could still be underwater in terms of the cost that you're putting out there in order to drive that.
[28:24]
Kin Sio: Yeah, beyond the channels. So when it comes to revenue, I think the other part that people are not thinking enough about is ancillary revenue. All of the channel considerations we mentioned are focused on room revenue. But I know there are ways that — especially as the market is hitting a downturn right now — people are thinking about additional ways to drive more revenue streams. What should a hotelier think about when it comes to finding ways to get more revenue streams, especially using technology like Stayntouch?
Jacob Messina: So that's an area that we spend a lot of time on, especially in markets that are facing headwinds and challenges. Sometimes you're not going to be able to hit your top-line revenue just by heads in beds. So it's — how do you extend that and have other things that you're offering to customers?
What we've done at Stayntouch is we have a tool set that's offered within our PMS for free, including the number one revenue generator — our upsell module. This is included in our subscription cost. It's part of a mobile check-in flow that allows someone to upgrade their rooms based off of specific attributes. And you can set and configure that. It's all inventory controlled. And then there's also the ability to add activities and add-ons too.
Those are great ways to drive additional revenue for a hotel. And it's important to do it in a way that you're not paying exorbitant commissions or transaction costs. So these are things that if you work with your partners and find the ones that are not going to be charging you for these, it's a great way to drive additional revenue and have little or no cost to the hotel.
Kin Sio: Gotcha. So sometimes it sounds like a lot from a hotel perspective — now trying to find ways to connect all these additional revenue streams. And Stayntouch has some features that help with the integration. Talking about your philosophy on the consultative approach of helping integrate with different vendors or partners to make some of those happen — are there particular ways that Stayntouch helps with implementing some of those additional revenue streams? If, let's say, a hotel now thinks about building a package, adding experiences, doing some sort of cross-selling — what are the ways that Stayntouch can help be almost like a nervous system to connect all of these together?
[31:06]
Jacob Messina: Yeah, I think there's no one-size-fits-all to that type of question. One of the ways that we work in terms of the consultative approach is we'll work with a specific hotel, they'll explain some of the challenges they're facing. And it's an area where we're able to pull from the thousands of hotels we work with to be able to provide recommendations there and see what's worked. But I think also what's not worked — if we can advise customers saying, "We've had hotels try these three things, they ended up spending a lot of time on it and it didn't get them the results," that can help others not go down that same route and waste time and energy.
I always recommend working in the local community, creating partnerships that are exclusive or bring added value to your properties — that's something really important. A big learning for me during my time at Loews Hotels was how do you bring the outside in? How do you make your hotel uniquely local? Especially when it comes to group business, it's a huge opportunity — how do you get corporate travelers to experience your location and your destination when they may never step outside of the property and outside of the footprint of your hotel or resort?
So being able to bring that outside in, I think, is a really important piece. And then once you have that messaging created and that product, working with your partners — whether it's the likes of Lights On to tell the story of it through marketing, whether it's your channel partners — how do I get into the right messaging locations for the experiences that you're offering? That's where you want to leverage those partnerships and relationships to tell that story. And I think the digital marketing angle and what you guys do from a content perspective greatly helps with that.
[33:06]
Kin Sio: That makes total sense. So for a hotel owner — especially in the boutique and independent space — many times, technology and PMS will be the last thing a person thinks about. For someone who's just never thought about the missed opportunities or the pain that could be brought by the current PMS, for somebody starting to evaluate — what could change, or what could be the additional opportunities by having a refreshed technology stack or PMS — what should this owner evaluate first when it comes to thinking about technology?
Jacob Messina: Yeah, I think whenever I get asked that type of question — and I get it fairly often when I'm talking to hoteliers — it's important to think about where you are today and where you want to be and need to be in the future. And it's important to think through that kind of short, medium, and long term when you're building out any tech stack. Because if you find a solution for today and they're not growing or adapting to the market conditions, you could be in a situation six months, two years, three years where they're no longer the right partner for you.
So I think it's always important when you're evaluating new technology to understand where they're going and what their mission statement is. For us, it's about solving problems for hoteliers, and we do so on a very rapid basis. We want to be that partner today and also grow with hoteliers as they grow too. So that I think is one of the major areas.
And then in terms of the position we play, it's not always just about what Stayntouch can do for a hotel. It can be the other solutions that we enable access to. So for example, we have 1,200 integrations that we offer at no cost to hoteliers, and that allows them — and we also have a fully open API. So if you find an integration partner that's already integrated with us, it's very easy to set up. However, if you find a partner that we haven't worked with before, they can easily write to our APIs and be up and running in weeks at that point too.
So it allows boutique hoteliers to define a tech stack that works for them. It's one of the greatest parts of not being a branded hotel — you have that flexibility of your technology, and you can build something really unique that speaks to your guests and your employees and the way they need to use technology.
[35:23]
Kin Sio: Yeah. I'm curious — for hotels that finally make the switch from another PMS to Stayntouch, what's the most common thing these hotel owners say they wish they would have done sooner after they make the switch?
Jacob Messina: The comment we get the most is how easy it is to learn to use the system. I think people are used to on-premise and legacy systems where it takes months, and it takes that long for people to feel comfortable. Changing a PMS can often be a stressful situation. It doesn't need to be, but it's a mission-critical system for a business that's running 24/7.
So we get a lot of comments about how smooth the transition is — everyone thinks it's going to go poorly. But we do hotel transitions to Stayntouch when they're running 100% occupancy with no issue. I think people assume that it'll be six months before they hit maturity of using the product. But in reality, because of that intuitive nature and easy training, it can be a week or two weeks before people hit that maturity level. That I think is a really big surprise for hotels.
[37:00]
Kin Sio: Great feedback. Thanks, Jacob. I have one last question for you. Before I ask it, I just want to again point our listeners to the website at www.stayntouch.com to learn more about what this PMS is capable of. Honestly, super intuitive — we do have lots of clients adopting Stayntouch and I have good experience with it.
So last question for you. I know that we've been partnering and collaborating with lots of our mutual clients in the islands in Hawaii. And people always say Hawaii is such a unique, different market from everything you'll see in other regions. So what have you learned navigating the differences and challenges here? And who are the best champions for you as you are helping hoteliers adopt Stayntouch?
[37:35]
Jacob Messina: Yeah, so I would say in the Hawaii markets — it's obviously one that has been challenged with some of the overall macro market trends that they've faced. We have some great customers. Castle and MacNaughton have been really solid users of our platform. And one of the things I find with them is they're not shy about asking us questions and asking what's working for other hoteliers. What do they see as trends or opportunities that we may be able to take advantage of?
And I always find that having that open dialogue and conversation — versus a vendor relationship that's just fully technical and tactical — is really important. And it makes our team feel bought in to help them win. So we're often bringing things to them in terms of, "How can you do better packaging? Does this work for you?" Sometimes it's not going to be the right fit, but we want to be that consultative partner and proactively bring ideas on how you can best use the technology.
I think for the Hawaii market especially, because it's obviously a beautiful destination, having a really strong upsell strategy — being able to have very clear definitions of room types and be able to showcase those benefits — that's something that I know the MacNaughton group has done a really great job of in using our system and being able to upsell there. It's a great way to drive additional revenue.
Kin Sio: Great feedback. And our listeners from Hawaii — definitely take that to heart when it comes to thinking about technology, especially what's still unique about our market and how you should take the best advantage out of it. Thank you, Jacob.
Jacob Messina: I was just going to add one last piece — content. Really important. It's one thing to say I have these amazing rooms. To be able to tell that story is incredibly important. So I think that's where technology and the content really come together.
Kin Sio: Great feedback. Thank you, Jacob. We've been talking to Jacob Messina, the CEO of Stayntouch. Jacob, where can people learn more about you and Stayntouch?
Jacob Messina: Please feel free to reach out via our website, stayntouch.com, or for the Hawaii markets, the infamous Rose Serrano is a great resource there and she knows the market incredibly well.
Kin Sio: Everyone knows Rose here. All right, thanks, Jacob.
Jacob Messina: Thanks, Kin. Appreciate it.
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