The Modern Hotelier #139: Building Technology to Help Hotels Elevate the Guest Experience & Drive Profit | with Jacob Messina
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David Millili: Welcome to another episode of the Modern Hotelier. Today, we are excited to have on Jacob Messina, CEO of Stayntouch. David, what was one of your favorite takeaways?
Steve Carran: Yeah, I think just in general, you know, getting to know Jacob and his background, I always love it when people are coming from hospitality and their path leads them into the tech side. And as a guy who's been there, loving that Stayntouch is really taking away some of the pain that these legacy systems have caused hoteliers for years.
David Millili: I agree. I mean, having, having that be my kind of alma mater, getting into the hotel tech side, um, Stayntouch always has a soft, soft. Part of my heart, but, I really love to see how they're growing and how they continue to innovate. And I love how we talked about how they have such strong partnerships with integrations.
And, you know, that's one of their main things is they just work so well with other people and they have great support as well. So, it was, it was great to catch up with Jacob, but we hope you enjoy the episode.
Steve Carran: Enjoy it.

David Millili: Welcome to the Modern Hotel Year, the most engaged podcast in hospitality. I'm David Mellilli.
Steve Carran: I'm Steve Caron.
Jon Bumhoffer: And I'm John Boomhoffer.
David Millili: Steve, who do we have on the program today?
Steve Carran: Yeah, David. Today we have on Jacob Messina. Jacob is the CEO at Stayntouch. Jacob is an experienced hospitality technologist with a focus on innovation and using technology to replace antiquated processes. Jacob's deep understanding of the Stayntouch customer experience, having been one, makes his leadership perspective and industry knowledge especially valuable.
Welcome to the show, Jacob.
Jacob Messina: for having me on guys.
David Millili: So Jacob, we're going to go through a couple sections. We're going to go through a quick lightning round. We're going to get to know you better, kind of where you grew up, your career, and then we're going to get into some industry topics. Sound good?
Jacob Messina: Yes, that's great.
David Millili: All right, so here we go. What's something that you wish you were better at,
Jacob Messina: Ooh. Uh, let's see, writing emails. I send too many of them and, uh, I can either be succinct or too, uh, long worded. And I always find in that middle ground is something I always want to be better at.
David Millili: right? What's your most used app on your phone?
Jacob Messina: Slack.
David Millili: What's, what's a luxury you can't live without?
Jacob Messina: cold brew coffee.
David Millili: What's the best piece of advice you've ever received?
Jacob Messina: It's a recent one, actually, uh, it's, uh, you can't solve, uh, tomorrow's problems with yesterday's talent.
David Millili: What's your favorite city and why?
Jacob Messina: Uh, New York City, I, I am a native, I'm very proud, and I love my city, and I think it's an extraordinary place that is very multicultural, there's always something going on, and it, it's one of the best cities in the world, if not the best.
Steve Carran: That's awesome. So Jacob, now we're going to kind of get into your background a little bit. What makes you tick? And like you just said, you led into the first question perfectly, born and raised in New York City. How did that really shape you into who you are today?
Jacob Messina: you know, I think one of the best parts about New York City is you're never bored growing up here. There's always something going on, uh, whether it's experiences, things to do, people to meet. it's an extremely vibrant place. And, you know, one of the cool parts is, at an early age, I was exposed to hospitality.
I'm not from like a hospitality, family by any means. but I grew up in an area of the city that, really changed due to hotels. Uh, it was actually the Ace, uh, hotel, the first property that opened, uh, opened two blocks from where I grew up as a child. it transformed the neighborhood. It was then the Kimpton Eventi and others that came in and it went from being a non residential neighborhood to restaurants opening and just the vibrancy of the neighborhood changed because of it.
So that was really my. First foray into seeing how, uh, hospitality can change, uh, you know, how people live and how people work. So.
David Millili: That's great. And so you went to Cornell for hotel administration. I'm guessing that kind of came out of what you just explained and where you lived. you know, was there a particular moment from that time that really strikes you that you knew you wanted to get into the hotel business?
Jacob Messina: Yeah, it was, uh, so I started on the restaurant side, I think at my first restaurant, uh, working in a kitchen, I was like 15 or 16 years old. And I realized really quickly, throughout that, that, culinary was a, passion, not a career for me. Uh, so it's an incredibly difficult, uh, line of work, and one that I enjoy.
And I knew that I needed to find something in this space, but something adjacent. And that's how I started working in hotels and working front desk at a few, uh, properties here in New York City. and from there, it was, that's what kind of started my love of hotels. Oddly, what also got me really into hospitality was, some early computer games like RollerCoaster Tycoon, The Sims.
These games where you're managing, uh, like, large sets of workforces in Rollercoaster Tycoon, you have to have enough maintenance people and, service teams and, you know, you're staffing, setting pricing. In a way, it's what got me bitten by this concept of running and operating complex organizations. The Sims is a great example, too.
Uh, you know, you're managing people's happiness, uh, you know, making sure their needs are met and fulfilled. Thinking through what you need to do next. so a little bit of an odd way to get into hospitality, but, uh, you know, computer games were a pivotal part of that. So
Steve Carran: You're speaking to every one of us who grew up in the 90s right there with, uh, with those two analogies. That's great. So I got to ask somebody who's Born, raised, now still lives in New York. Where's someplace in the city that might be a hidden gem that maybe you can share with us, whether that's an experience, a restaurant, or if you have the best pizza place in town, that's always a good, good spot to know too.
Jacob Messina: pizza place can be a controversial,
Steve Carran: Oh yeah. session. Let's see. terms of favorite spots, you know, New York's vibrant, there's lots of different things for lots of different people. I recently, went to this amazing, uh, spot called Mokyo, which is a Korean fusion restaurant, which I really enjoyed. That was great.
Jacob Messina: Also, um, pizza spots. I'm a convert. I used to be a John's pizza, and now I'm a Joe's pizza person. In my later years of my life, that took a lot of years to get over, uh, and onto that camp, but, I'm definitely Joe's pizza in person, not delivery. Uh, you gotta go for a slice.
Steve Carran: there you go. John's. Are you talking about John's on bleaker?
Jacob Messina: I, and I'm Joe's, which is right off Bleecker, so.
Steve Carran: Okay. Awesome. Good to know. so now we're going to talk about kind of how you got to where you are today as the CEO of Stayntouch. But your first job out of college was with Loews Hotel, who you actually interned with them. and you were there for 10 years and worked your way up to the senior director of e commerce and performance marketing.
What did you learn in those early years right after college that you still take with you today as CEO?
Jacob Messina: Yeah, actually a lot from the early days. So when I started at Loews, I was with their distribution team. and it's where I really got to learn the ins and outs of system connectivity. you know, distribution is an often overlooked and an afterthought of a hotel technology stack or teams even, and that's where I got my start.
So it was really thrown into all these systems that on a good day barely work together and on a bad day didn't work together at all. and my first job was actually manually merging profiles in Opera V5 for 40 hours a week. So if you can imagine, uh, just, uh, the epitome of a boring desk job as your first office job.
And for 40 hours a week, I would just manually merge profiles. and I did that for like four or five months, um, which was painful. And it made me really think of there's got to be better ways. There's got to be better solutions and always, uh, technology. And it's really what got me interested in always being curious about challenging the norms of technology.
Why do we do it this way? Why are we not looking for other sources of, uh, how to do things better or how to change, uh, industry norms from there though? I, uh, I was at Loews for 10 years, uh, which was a really great and exciting place for me. And I, I had a lot of opportunity within the organization to take on new initiatives.
and I ended up building out their digital marketing practice from scratch. Uh, we. started there, we're very much a traditional print organization. and I really, got to work very closely with our marketing leaders and we built out a performance media, team and organization, uh, and really rethinking the way that we targeted customers and, you know, started building some pretty, advanced tools and technologies that we were using at that point. 
David Millili: And so from LoLoewsyou went to MCR and you were the senior vice president of technology and innovation. what did you take away from that that also helped you now being CEO of a hospitality tech company?
Jacob Messina: Yeah, definitely. so while I was there, you know, I joined just about three months before COVID hit. It's an interesting time to, uh, start at a new hospitality organization. So, you know, some really interesting learnings there were, you know, we grew the portfolio very quickly. Uh, when I started, we were around like 76 hotels and, uh, by the couple of years later we're at 154.
So, things I learned is, you know, you gotta be ready for anything. is the first one, and it's good to have a plan, but it's also just as important to know when to leave that plan behind and to forge a new path. So, um, not everything that we were going to do was going to go towards what our standardization was.
Hotel deals came in very different shapes and sizes. and I think most notably, you know, there's a hotel that I worked on, uh, when I was at MCR. Uh, it was supposed to be Hilton soft branded, and eight days before, we were supposed to open the hotel, uh, it failed, uh, a Hilton inspection and had to be independent.
We got a phone call and said, Jacob, uh, we need to stand up a tech stack at this hotel in eight days. and honestly, this is how I got to know the Stayntouch team so well. You know, I picked up the phone and said, I need a big favor. And the team moved mountains for me. And I can't say that about other Organizations and companies that I've worked with that they could, lean into a partnership and know that this was something very important to me.
And by making me look good, they looked great as a result. And I was just a customer at this point. but that's how I got to know them.
Steve Carran: I believe I was there during that timeframe and I, I remember that it was, but it was crazy to see how quickly the team moved, to get the PMS up and running. It was, it was very impressive.
Jacob Messina: at that moment that was an anomaly, but one of the things that we've done at Stayntouch now is realize we have to be prepared for those types of phone calls. So how do we build teams and automations and organizations that are able to respond quickly?
Because deals are coming in very different shapes and sizes these days.
Steve Carran: Absolutely. So for the past two and a half years, you've been the CEO of Stayntouch. For some of our listeners that may not be as familiar with Stayntouch, can you give us a little background about what Stayntouch is? So
Jacob Messina: so Stayntouch is a cloud based property management system. We were born in the cloud, uh, have always been in the cloud. Uh, the company was started about 11 years ago. really excited that we have an extraordinarily tenured team. many of the original founding members are still with the company today.
which has been great because I have an organization and a team and Steve, you know, many of them well that. they know our product and our customers so well, and it makes it really fun every day. So we're a cloud based PMS. we really focus on property management system, uh, and we partner with many others out there.
So we have a really robust integrations platform with over 1, 200 integrations today. we are, um, dedicated to that in many different ways, but it's part of our strategy is to partner really closely with, uh, best in class solutions. And we believe we're at best in class property management solution. and really that's how we, uh, we partner and build there.
David Millili: And Stayntouch. They've achieved two of their highest performing companies under your watch. So congratulations to that. And what really can you give people listening? And what makes. Stayntouch unique versus some other of the cloud based PMS is
Jacob Messina: Sure. so the company was originally founded, uh, by a group of people that left, uh, the Opera product and The decision was how do we do it differently and how do we be a better solution for hoteliers and they identified a couple of different areas so the first and foremost our differentiator is our customer support.
So we have an incredible team, a global team. So we use a follow the sun methodology. Almost everyone on the team is a former hotelier. So when you call the call and pick up the phone and talk to someone, they understand the language where you're speaking and they understand the situations you're at. there's an issue with credit cards being down, they know that you have a line of people at the front desk.
It's not just a ticket you're going to file. So customer support, it's really top notch. Our average response time is under an hour. Average completion of a ticket is under 24 hours, which is unheard of amongst our competitors. our integrations approach is also very different. we don't charge for integrations.
And that is something that, you know, in my experience using legacy PMS is, uh, in some of the cloud ones as well, um, they charge for integrations either to the customer or to the vendor and partner. And to me, that is, um, that makes it very difficult to build a complex technology stack. most of our customers are really, more complex, dynamic, uh, boutiques, independence, regional brands, and Stayntouch as a piece of their tech stack.
We're not trying to be all things to all people.
Steve Carran: it's been exciting to watch Stayntouch grow since since I was there. What are your goals for the next two to three years on where you want to see Stayntouch be?
Jacob Messina: Yeah, that's a great question. So one of the things, Steve, since, you know, since your time at St. Touch, we've invested a lot into our multi property functionality, and we've built it in some really kind of dynamic and flexible ways. And so we want, you know, when we think of how we're building our product, we want to give independent hotels, management groups, small and medium sized.
Brands, the same types of tools and solutions that many others get by having, you know, other products out there or suites of products. so multi property has been a big piece for us. It's how we're expanding very quickly and how we've been building a lot of automations to really help people get up and running on systems faster and more smoothly too.

Steve Carran: So now we're going to go into the industry thoughts section here. So one of the debates we always hear about is standalone PMSs against all in one PMSs. Some tech vendors are moving more towards a consolidated system. what does that mean for hotels and how does Stayntouch view that shift?
Jacob Messina: You know, I, I don't think it's a bad strategy overall for all in ones. Um, I think it just depends on who your customers are. our customers tend to be, um, More complex properties. They have different needs, whether it's group sales and catering. they're larger properties that need more automations.
and they're looking for a system and a tool that is really specialized and focused on what they do. I found this about myself. Every company I've worked for. When you try to do too many things, you start doing them, poorly. You know, uh, it's It's just a fact of life. You can't have the same level of focus and the same level of success across everything.
You get pulled thin. so we've really taken an intentional focus on being a best in class property management system instead of trying to be all things to all people. does that mean we are not the right solution for some, hoteliers? Absolutely. But we really believe that the customers that we work with, based off of other conversations we have with them, they're looking for that flexibility.
They're looking for a strategic partner that is taking their feedback and incorporating into the product. And they see that over time, as well as being able to work with the other 12 different, parts of their technology stack to make them successful.
David Millili: with hotels, you know, dealing with the significant staff issues. How a Stayntouch, leveraging automation to help hotels address some of these challenges.
Jacob Messina: Yeah, it's definitely one of the biggest, uh, you know, issues and challenges that are facing our industry. And one that I don't think anyone believes is going to curtail or stop anytime soon. So. There's a number of different ways that we approach it, one of which is, um, we have a native kiosk product that's been part of our solution since the very early days, and I think what's notable about that is because it's a product we built.
It's not an add on or something we purchased. works 100 percent connectivity between the PMS and our kiosk. There's no latency or issues between that. so that is one component. Now, a lot of what we've done is we've built both automations within the system to help people perform tasks faster.
and that's reducing clicks. It's being able to do bulk uploads of rooming lists and things that are sometimes very labor intensive. And then the last one I would say is around training. you know, our system is extraordinarily simple to learn. it was kind of interesting. We just did a, uh, that was a class that we taught at the NYU Hospitality School where these were students that had never used a property management system before.
we handed them Stayntouch on an iPad and, uh, asked them to perform a check in. They were able to do it without any training before. I got my start, as I mentioned, working front desk at a hotel that was using Opera. It took me weeks, if not months, before I felt comfortable really doing a check in on my own.
So, being able to reduce that amount of training time, it's helping people save time on training costs and being able to get people at the desk faster.
Steve Carran: That's great. I think I saw, uh, Daryl was, uh, doing that training. So they had a good teacher too. He's, he's incredible at what he does. Uh, Um, so how is Stayntouch leveraging strategic partnerships to drive innovation and benefits to your customers? You mentioned, you know, your partners are a big part of what you do.
So curious to hear more about that. That's
Jacob Messina: I think it's a, it's a good question and it also kind of ties into the best in class versus all in one, you know, when you start trying to be an all in one, it creates some weird dynamics between your partners, you know, are you going to copy their business model? Are you going to replace their product with your own?
And because we are not going in that direction, we find that partnerships become even stronger and and people want to work with us and they want To bring customers to us as well. So, we have a really strong partnership focused, strategy, uh, in in that we have entire teams that are set up to support our partners.
And where that helps is we're not trying to reinvent the wheel. We're not spending time building things that already exist. So we've worked with great partners. We build amazing integrations with them. You know, a great example of this is we've been partnered with Toast for quite some time. We were the first direct integration into Toast.
and they're, uh, our largest point of sale, integration within Stayntouch. but that's one that we built with them and there was a lot of learning from both sides, you know, as they were getting into hospitality, you know, we really worked very closely with their teams to make sure they understood what it, how people were using our system and vice versa.
we have hotels that operate a front desk, a coffee shop and, uh, cocktail bar all from the same space and the same person. So you could be going from doing a check in on Stayntouch to processing an order through post point of sale and making a cocktail all at the same time. you know, you have to have systems that are very simple to use, simple to learn and make it easy for the employees there.
David Millili: That's great. And so what advice do you have for someone who's looking to become a CEO and how, what advice do you have for someone looking to be successful at that role?
Jacob Messina: great question. I, I hope someone has some of that kind of advice for me too at some point. But, uh, no, I, I think that, um, the advice that I would give to someone who's looking to run a company or run teams even within companies, I've been a big believer that trust goes a long way. when you trust your employees and you trust your team and you build and show them that that trust is real, you get a tremendous amount more, work product out of people.
I found this in my career as well when I've had bosses that I really trust and work very closely with. You're not spending time on CYA. you're getting work done and you're believing in the company mission and you really are aligning yourselves with what you're trying to do and what you're trying to produce.
I honestly think that trust is the greatest, amplifier of productivity. and it makes people really aligned with company goals, as well as just team goals too. So I would say build teams around trust. if you find yourself as part of a team, that doesn't believe in trust or is into micromanagement might be time to rethink how you're, you know, how you're a part of that team or if that team needs to be adjusted to.
Steve Carran: That's great. So Jacob, we have been asking you the questions this whole time. So we're going to turn the tables here and let you ask David and I a question.
Jacob Messina: all right. Let's see. so you, you get to talk to so many amazing, folks from across our industry. are there challenges that you are hearing more and more that, um, either are not being solved with technology or you feel that could be solved with a technology? 
Steve Carran: I mean, I think. We're still at that point where technology is still a little bit siloed. and having those strong integrations. I know you guys have, you know, strong integrations. And like you said, don't charge for integrations. But like having those siloed tech stacks still, where there's still not that open communication like we need.
So think that's one thing that 2025 is, you know, having more open APIs, sharing more data. in between each of these systems and really creating not only a great guest experienced, but a more personalized experienced for the guest as well.
David Millili: Yeah. And for me, I think it's a, it's a question of adoption. I would say doing a better job, educating hoteliers on how these solutions improve the life of the guest and the, the staff. you know, when I started out many, many, many years ago, you know, the internet was just taking off. So there was just a couple of little things that you could use.
Whereas today now. You know, whenever I'm running a company, I say, we're not only competing against our competitors. We're competing against every other vendor that's trying to get in the door. And I think a lot of times when I talk to companies, they don't have a clear, communication path for the hotel to understand why they should be using this technology.
And, and then that just opens the door for people, you know, getting the fear factor. Oh, it's going to take someone's job or my guest isn't going to like this. And it's like, no, it's like you, you know, I was talking to somebody the other day and I just. I was actually in NYU class and I said, well, do you ask why you're asking for their phone number or tell them why you need their phone number?
And he's like, no, we don't. And I'm like, well, that would, that would really help. Cause then that guest knows, Hey, if I give you my phone number, then I can communicate with you. I'm going to get offers. I can ask for, you know, but a lot of times it's just like in the booking engine, put your phone number.
It's not, it's optional. It's not required. And then, so anyway, I think it's the adoption and the, the education side.
Jacob Messina: Yeah, one of my favorite examples on that front, David, is like, if you think of how many e commerce companies that you interact with in a year and they ask you for your birthday and then on your birthday, how many emails do you get from the company? And it's like five out of a hundred and you're like, why did I give you this information?
It's such a simple thing there. Can you guys another question?
Steve Carran: Yeah,
Jacob Messina: So something I found, in both my career and with the customers we work with, one of the biggest kind of, Mentality shifts that needs to happen and it is going on is for technology to be look, uh, historically has been looked at as a cost center, not a profit or revenue center.
as you think about the listeners of your podcast, what advice would you have for, empowering people to make that shift and to move from thinking of technology as a cost center to how it can be revenue and profit driving?
David Millili: Yeah. So for me, there's a couple of simple things. I mean, one, you know, we're an age where if you do get that phone number, you do have the email, you know, you can offer, you know, early check in, make a little bit of money there, room upgrades, make a little bit of money there, late checkouts. one of the things that is very bizarre to me is in, when I got into the tech side in 2000, all of the booking engines then would ask for when you were arriving.
And now we don't really do that as much. And so you don't really know you're kind of blinded. And that, that's your. It's not your most important, but right now everybody's focused on the direct guest and the direct booking. So I think leveraging the technology that can help you make money and then leveraging something as simple, like I said, as, you know, text messaging, WhatsApp messaging to basically alleviate all the BS that goes on.
In the property. So, you know, you've got that front desk agent who doesn't want to put somebody on hold and you've got the guest who doesn't want to be put on hold, but probably nine out of the 10 questions can just be very simply answered if they could just text and say what times check out, what times the bar open till, you know, things of that nature.
So to me, that's where it needs to go. So I think you're right. I think you can look at it as you know, profit and revenue and you can look at it as cost savings with the way technologies can help
Steve Carran: think like using technology to know who your guests are, why they're traveling with you, kind of that personalization side as well, but, I'm going to travel totally different if I'm traveling for work than if I'm traveling for pleasure, right? So like, if I'm, you know, traveling for, for work, I might really like that late checkout because that conference gets over at two o'clock, right?
So just knowing who your guests are and if I'm there for leisure, let's talk about how you're, you know, partnering with hype with local companies, right? And I want to experience how the locals are living. So, you know, knowing kind of where your guests are coming from and why they're staying with you, I think can really drive some revenue opportunities into what upsells they might be more interested in. So, I know we've been asking you the questions this whole time, but those were some great questions, but our producer, John has been sitting and listening this whole time. So he's going to ask you the last question before we get you out of here, Jacob.
Jon Bumhoffer: I'm going to build off of kind of David, where you talked about with the education piece and then, um, what you were talking about with like utilizing that technology to, to make it more of a profit center. So it seems like businesses, when they invest in technology, they might, they're not using the full capability of it.
Some may be even using like 50 percent of what something can do. So on the education piece, how, what are the things that you see hotel years? Just like not utilizing the PMS for that. Maybe they should be. What are maybe some of the low hanging fruit things that they're not even thinking about when they have all of this technology at their fingertips.
Jacob Messina: It's a great question. Um, I'll be honest with you. Our biggest challenge and, um, work that we're doing this year is how do we get people to use more of our product? one of the most frustrating things that we find is, you know, we'll get a hotel that leaves us and we'll ask why and they'll say, oh, um, it's because you can't, you don't do this.
You're like, oh, well, actually we released that a year and a half ago It's an interesting and difficult situation when you moved from the legacy PMS is which we're doing updates every one and a half to two years, it was very easy to stay on top of what was coming because you had a two year heads up where modern property management systems like us that are in the cloud.
We're doing releases of new functionality every six to eight weeks, which is exciting because it gets to you faster, but it also means there's more work to stay on top of things. So, you know, how do we rethink our education, uh, and how we're communicating these changes is definitely a top, priority for us.
You know, we have a number of different ways. Sometimes it can feel like overkill, but getting people to use more and more of our product, for example, we have a great native upselling tool within our PMS that's been there since the very beginning, as well as mobile check ins. we have hotels that use that and offset their entire, uh, you know, monthly bill from Stayntouch just by being able to sell early check ins, room up sales, all of these things.
And we don't charge transaction fees or commissions or anything like that. It's just built in as part of the product. Mobile check in as well. You know, it's reducing, uh, labor time at the front desk, allows people to have conversations at the front desk instead of just doing administrative work there too.
You know, those are great tools that everyone should be leveraging. And whether it's a product of ours or through many of our integration partners, it's important to have those things in place.
David Millili: That's great. Well, that does it for another episode of the Modern Hotelier. This is where Jacob, you get to plug away and let people know how they can get in touch with you and how they can find out more about Stayntouch.
Jacob Messina: Sure. Uh, thanks guys. First of all, thank you all for having me on. That's been really fun to talk about, uh, technology in our space. terms of if, uh, you have a hotel, uh, that you're curious about using some more modern technology or rethinking how you do, uh, how you build your tech stack, please get in touch with us.
We're happy to be a consultative partner. We'll also be genuine and open with you. If we're not the right partner for you, we are the first ones to tell you and make recommendations to for, uh, other elements of your tech stack or the property management system. So please reach out to us, uh, at Stayntouch.
Happy to work with  
David Millili: Well, that does it for another episode of the Modern Hotelier, the most engaged podcast in hospitality. So whether you're watching or listening, we appreciate you and we'll see you again soon. Thank you, Jacob, for joining us.
Jacob Messina: you. Thanks guys.
Steve Carran: Thank you.
David Millili: you.