Subscribe
Share
Share
Embed
The Unchecked-In goes beyond a traditional podcast—it’s a raw, unfiltered space where independent hotel owners get real about what it actually takes to survive, grow, and stay sane in the hospitality business.
The Unchecked-In will explore critical themes in independent hospitality, including:
Revenue Optimization Strategies: How small properties can compete with larger chains through smart pricing and positioning
Guest Experience Innovation: Creating memorable stays that drive loyalty and word-of-mouth marketing
Technology Integration: Leveraging AI and automation to streamline operations without losing the personal touch
Succession Planning: Preparing the next generation of hospitality leaders and ensuring business continuity
Market Positioning: Standing out in a crowded marketplace dominated by large chains and vacation rental platforms
Each episode will feature candid conversations with successful property owners, industry experts, and hospitality innovators who are pushing boundaries and creating exceptional guest experiences. From family-run bed and breakfasts to boutique glamping retreats, the podcast will showcase the diverse landscape of independent hospitality.
The Unchecked-In Podcast #08: Overcoming Challenges in Hotel Tech Adoption | with Jacob Messina, CEO of Stayntouch
===
Jacob Messina: People often get scared by technology decisions, whether it's am I gonna pick the wrong vendor or the wrong partner and the wrong system to use and, and it often stops them from even starting the process. You should always be thinking about what are the areas that I want to be improving, whether in, in my guest experience or my operations, and how can technology help and enable that? So that should be an always on type of conversation, either internally or externally.
Bobby Marhamat: Hi everyone. Thanks for listening to another episode of The Unchecked In Podcast where we get real with the people actually running independent hotels or in the industry, technology. Anything adjacent to the industry. No fluff, no filter, just a win. Screw ups, and lessons that they wish someone told them sooner. I'm Bobby Marhamat.
And today I am here with Jacob Messina, the CEO of Stayntouch. Jacob is one of the most interesting people I've had a chance to read about and now talk to. Um, he is one of those leaders who's lived both sides of hospitality. He came through the hotel world, spent a decade at Lowe's hotels and e-commerce and performance marketing, then moved into digital operations and technology leadership at MCR hotels since 2022.
He is now leading Stay in Touch a cloud native PMS built around helping hotel teams run smarter operations and deliver a better guest experience. Jacob, really happy to have you here. Um, really welcome to the show and really excited to kinda dig in.
Jacob Messina: Thanks for having me on. Appreciate it, poppy.
Bobby Marhamat: Absolutely. What did I miss? Anything I miss about your bio that you wanna make sure everyone
Jacob Messina: knows? I dunno that, that was pretty, uh, pretty good. I was, uh, remembering things about myself. It's been a minute and I'm getting old
Bobby Marhamat: and I talked fast, so hopefully you got it all. We
Jacob Messina: got a lot to go through today, so.
Bobby Marhamat: Yeah, exactly. Exactly. So we're gonna start with. School, uh, you went to Cornell Hotel School, your grad, you started in restaurants as a teenager, by the way. I started in restaurants as well. So I know kind of all the world lessons that we learned, but what's one lesson from those early days that you, uh, still shapes you and, and what you do today?
Jacob Messina: I honestly, um, getting started on the restaurant side of the business I thought was really, uh, important and it has shaped a lot of, uh, I think who I am today and like how I lead and things. It, it is a truly grueling and, and difficult area of the service industry and hospitality. It, it's something I encourage, uh, you know, anyone.
You know, any area of restaurants and not hotels and a service line level employee, um, understanding that, you know, uh, you know, working nights, weekends away from your family, uh, it takes a different kind of person and it takes a different kind of industry to make sure those people can be successful.
It's not, uh, what you see on Top Chef, uh, where you get to cook, cook a different thing every day. In fact, it's. It's more like, how can you cook the same thing a hundred times a day as close, uh, close to perfect as possible. So, uh, yeah, definitely an interesting way to get started.
Bobby Marhamat: Yeah, I mean, it's one of those things, uh, you know, my son's 11, but I told him when he is 14 and a half, I think that's a legal age now, uh, he has to go, his first job has to be in a restaurant.
I mean, you learn. The good and the bad, and it's to your point, um, it's one of those things where you really cut your teeth and, and understand hospitality and, and servicing people and customer service and all the good stuff, so, absolutely.
Jacob Messina: Yeah. A funny little, uh, story there. On my first day working in a commercial kitchen, I was the assistant to the apprentice, uh, and we were executing this really complex, uh, dish that in involved, uh, a, a deli slicer and slicing apples paper thin, uh, al.
Spare the gruesome details. Let sage, ooh, let's say I got promoted to, uh, you know, uh, apprentice, uh, that day. Uh, she didn't. Oh
Bobby Marhamat: man.
Jacob Messina: Well, but, um, you know, it was, uh, it was illegal to use a meat slicer at 16 in the state of New York at that time. So then
Bobby Marhamat: it should be. Yeah. That's crazy.
Jacob Messina: Yeah. But they promoted on day one.
Bobby Marhamat: Yeah, a hundred percent. A hundred percent. I mean, you, so the interesting part, uh, I, there's a lot of interesting parts about your bio, but one of the interesting parts is you've learned, you've worked really inside some big hotel brands as well, large management companies. Now you lead one of the, you know, the, the larger main, uh, hotel tech companies, uh, servicing hotels.
What's something independent hotel owners don't realize? They actually do better than some of the big, big boys and girls, if you will, that are out there.
Jacob Messina: I think, uh, the really easy one for me is just around flexibility and how they interact with their, um, with their customers and, uh, with their hotel guests.
Being able to let, uh, your employees shine through in their individualness, I think is really, uh, undervalued. Especially brands being, um, you know, more and more cookie cutter, uh, harder to differentiate between some of these sub-brands that, you know, independent hotels have so much ability to really. Kind of take some of those rules away and let people shine and, and that's what hospitality really did best at.
So
Bobby Marhamat: yeah, it's, it's definitely a people business for sure.
Jacob Messina: Mm-hmm.
Bobby Marhamat: Um, so as you, you actually learned kind of on, on the other side as well, uh, when you were, you know, on the operator side at Lowe's and MCR, like as you kind of first. Crossed over to be the CEO of stay in touch and like got on the tech side.
What surprised you the most about, you know, how really technology, hotel decisions are ma hotel tech decisions are made, uh, inside hotels.
Jacob Messina: Um, I think one of the things that really surprises me on that front is, um, how often people are looking for just a single, they're trying to solve one problem where they should be trying to solve many, um, and they don't realize that, oh, I have these five or six operational issues that are, you know, it's either.
Legacy systems that aren't helping me or really, uh, empowering my employees and they try to fix one thing when they really need to be thinking, all right, I need a strategy and a plan in place to cross these five things off the list. Um, it's not as simple as just, oh, switch out this one system with another, uh, and it's all gonna be successful.
Bobby Marhamat: No. Totally, totally agree. Totally agreed. And you brought up, you brought up with a me grinder, but let's talk about a screw up, a screw up that, you know, kinda you made maybe earlier in your career that you, you know, you thought was the right move at the time, but now as you kinda look back, you're like, Hey, I wish I would've done this differently.
Share, share, share your most favorite story.
Jacob Messina: Um, I, you know, there's one from. Early days of working, uh, at stay in touch. Um, you know, at, just after I'd come over. So I was a, a customer of stay in touch, uh, before I came over as the CEO. And we had an opportunity with a, um, a customer of stay in touch to expand pretty rapidly.
And they gave us this list of, uh, eight or nine things that they needed us to do. And, um, I. Disrupted our roadmap. I said, all right, we're gonna put everything on pause. We're gonna do these nine things and expand with this customer. And it was a learning for me, not just in the two months we lost to doing the development work, uh, but how much time we lost in switching time between, you know, uh, means coming off of their existing projects and then having to come back onto them.
It probably set us back about five or six months, uh, at the end of it. Um, we ended up taking a really big step back and we came up with this concept called Untouchables, which we have generally between seven and nine of them per year. And these are, uh, projects that are locked into time. Um, I'm not allowed to change it.
Uh, I present them to our board every year at the beginning of the year. Um, so not even, uh, uh, not even the c CEO's able to change, uh, are these gonna get done in the year, which makes it easier to communicate with our internal and external stakeholders.
Bobby Marhamat: Jacobs, do you think about, like your, your philosophy around what you just shared was super interesting, what your philosophy around like road mapping, that balance of like how much you have to kind of lean into customer's request versus like create some of that innovation path for them.
What is your philosophy around that?
Jacob Messina: Yeah, I think balance is probably the nicest way to put it. It's a, uh, a war I would say in a lot of ways in terms of. Uh, competing priorities. There's never enough resources. Um, you know, we are a community platform, so I, I always look towards when we get customer requests.
Is this serving one customer? Is it serving all customers? And does it help us support kind of the things that we do differently at stand? Honestly, if we get customer requests that align with the things that we think are really important to build and um, are things that we can differentiate ourselves with.
Those go to the top of the list very quickly. We also like work through, and we, we do spend a lot of time with our customers understanding how they're using the system. Um, 'cause if we just try to put a roadmap, uh, on paper without talking to customers, it, it'll never match up with what their priorities are either.
Bobby Marhamat: Yeah, I think about that very, very similarly. We have a 80% rule, so things have to hit at least an 80% mark around hitting and serving at least 80% of what our customer requests before something hit hits the roadmap. So, I'm with you there. I
Jacob Messina: think an an important piece there too is we try to allow for bandwidth.
You know, if you go in Jan one and you're already a hundred percent committed, uh, you're gonna end up trying to do 150 things and you know, it's to try to lead that. Does that always happen? No, but you know, you try, uh, try art each year at it.
Bobby Marhamat: Yeah, you gotta try at it for sure. A hundred percent. A hundred percent.
You know, one of the things that, that I, I talk to a lot of operators about is tech. Like, they come in with certain requests and they think tech can solve all problems. It can solve a lot of problems. But as you think about, you know, high level from your seat, as you think about hospitality and owners and using technology, what's one problem that you've heard in hospitality that you really don't think is, is a problem that technology can, can help solve?
Jacob Messina: Um, let's see. You know, I, I'm, uh, if, if I can, I'll take the first part of that question.
Bobby Marhamat: Yeah, absolutely. Yeah.
Jacob Messina: Um, I think one of the things is that people, especially on the operator side, having been there, you think you buy a new system and it solves the problem and. What I find is that people spend, um, too much time focused some, uh, on the tech and not enough on the change.
And you know, you can have the best technology and pick the perfect, uh, partner and vendor, but if you don't invest the time into the change management process. It, it's guaranteed it's going to fail. Yeah. And whether that bringing your own team and stakeholders along for it, it's planning for, um, you know, the bumps that are in the road.
You know, we all know that hospitality is, uh, an imperfect business. Uh, hospitality technology isn't done immune to that either. So make sure you plan for, um. Plan for issues occurring and how you're gonna recover from them, uh, as opposed to trying to think it's all gonna be this, you know, kind of magic bullet of, oh, I buy a new system and it works on day one and everything, it solves all the problems.
Bobby Marhamat: All my problems. No, a hundred percent. Yeah, a hundred percent. And hospitality too, like what, what is your philosophy around, again, you've been on both sides of the coin as we know, like what's their philosophy around the right use of technology within a. You know, property versus kind of that, you know, that that human touch that has to, has to come a long way in creating that experience, if you will.
Jacob Messina: Yeah. You know, it's, um, it's interesting across like the portfolio of stay in Touch customers. We have such a wide breadth, you know, of, uh, hotel, uh, types of hotels. We have properties that are entirely automated, uh, and extremely tech forward, uh, in that sense. And, you know, tech facing, uh, with customers and then ones that really lean into the purely hu uh, kind of human touch side.
I think technology plays a role, obviously in both. I think that even when you're delivering an automated experience, there's still ways for your brand and, uh, hospitality to shine through. So I always encourage, um, you know, our customers of how do we, uh, how do you use our technology and others, um, to enable hospitality, not get in the way of it.
Um, you know, that could be something as simple as, alright, a process, uh, of a check-in, used to take nine clicks and someone is. Staring at a screen, now they're able to make eye contact and have a conversation. Um, you know, it can be simple things like that, but freeing up your employees to get back to hospitality, I think is important.
Bobby Marhamat: Totally agreed. Uh, and reading your background, you talked a lot about curiosity, asking the que the right questions and a lot of questions as a leadership superpower. Can you share a moment where, you know, asking the right question really changed the direction of a, of a project or decision?
Jacob Messina: Uh, yeah, sure.
Um, I. You know, something when we, uh, kind of back to the roadmap conversation, you know, um, we've got an amazing team, uh, of product leads as well as an engineering team that sits, uh, alongside them. And, um, often when we are brainstorming and thinking about what we are gonna build in a year, I often challenge the team or, you know, I try to push them on like, I would say, why us?
Um, you know, why should we be doing this, you know, and building this 'cause it, you know, if, if we're gonna decide to build something, we wanna do it right. Uh, but there's an investment we make by doing that time and resources. Absolutely. So I always think, you know, what are we gonna add that someone else couldn't?
And, and part of that is not just 'cause we don't wanna just copy others, but I, I really don't believe in reinventing the wheel if we can avoid it. Yeah. Um, I'd rather partner, uh, you know, with great partners like yourselves, um, you know, to do the things that we're not good at or that we don't do today.
This, you know, just copying and building the same thing as others that doesn't help advance, uh, the industry or operators either.
Bobby Marhamat: Yeah, absolutely. Totally agreed. Yeah, you, yeah. You wanna keep best, best in breed. Yeah. Best in breed, for sure. Um, as you think about, you know, independent operators, now imagine, um, you're, you're running Jacob's Hotel, it's a 75 room independent hotel.
What's the one operational process you'd really focus on that you think creates the most downstream pain when it's, when it's broken?
Jacob Messina: Um, I only one. Uh,
Bobby Marhamat: or, or sure. Or multiple or multiple. However many you got.
Jacob Messina: You know? Um, I think, well, I'm gonna cover two, but they're like adjacent to Yeah,
Bobby Marhamat: sure.
Jacob Messina: So, uh, I would say, um, you gotta get the booking process right.
And I think an important piece of that is setting expectations. Um, you know, whether that's within your website, the content you have, making sure it's up to date. Um, you know, I, I recently had an experience, a, a, a negative hospitality experience, which I don't have all that often, thankfully. Um, and at the end of the day, I, you know, I walked away from this experience and was like, what went wrong here?
And I came back and, you know, I, I realized that the, the website had just set. A false expectation. It was actually like a great hotel of great things, but, uh, you know, it, it was a different, uh, than what had been communicated. But I think if you can really nail your, um, your pre-arrival experience, and that's all the way from the booking, uh, components so people know what they're, uh, should be expecting in communication leading up.
Um, this is, I've seen this as a challenge for a lot of hoteliers where you get a booking and then you don't communicate with the guest until they check in or maybe the day before.
Bobby Marhamat: Yeah. A
Jacob Messina: lot you could be doing leading up to that, uh, both in a planning phase and again, setting those expectations of what your experience and your product is like.
And then I think that has, you know, the most downstream impact. 'cause if someone is coming in knowing what your brand looks like and feels like, you know, it's gonna lead to a more seamless experience.
Bobby Marhamat: Absolutely. And what do you think WW with that question, like, what do you think from a perspective of, if you think about, again, that balance of the use of tech within a location, right?
Versus that human touch. Like what does, what does that balance look like for you as, as your, you know, as an independent hotel owner and as a group, maybe owner? You know, if, if you're, if you own multiple hotels,
Jacob Messina: just in terms of like the amount of tech or like, yeah. Okay.
Bobby Marhamat: Exactly. And how you, how do you choose the tech?
Jacob Messina: I don't think there's one size that fits all in this. Uh, you know, like I mentioned, some hotels, their, their model is based on being more tech enabled or tech forward.
Bobby Marhamat: Yeah, for
Jacob Messina: sure. I think the reality is hospitality from a technology perspective has been underserved for multiple decades. So there's a lot of catching up that we're doing there.
When I evaluate vendor or like, uh, you know, uh, technology that we're gonna be using, I, I try to look at it too. Um, more than just the technology itself or just the product. Um, you know, our teams are gonna be working with their teams. Um, and, you know, especially when I was on the hotel side. It needed to be more of a partnership.
Mm-hmm. They needed to understand what we were looking to accomplish and, uh, you know, they were gonna be part of it to get there. Um, you know, whether it was at Lowe's or other, uh, other brands, um, you, you always have too few resources or teams too small to accomplish anything, always.
Bobby Marhamat: Yep.
Jacob Messina: If you really do partner with your technology vendors and make them kind of part, uh, a part of the team with shared goals and shared accomplishments, wins and losses, um, I, I've always found that to be a really successful way to get more out of a technology vendor, um, than to just really look at it as a transactional, uh, type of relationship.
Bobby Marhamat: You all, uh, you know, stay in touch, you sit right at the intersection of a guest experience and back of house operations. Right. What's, what's a small change you've seen operators make that's really had a, a larger impact on both, you know, staff and guest satisfaction?
Jacob Messina: You know, I think, uh, when I look at systems like the ones that I grew up with, uh, they were really difficult to use.
I mean, my first hotel job, I won't, um. Yeah, I was working front desk, uh, at the Afinia Beekman Tower. I won't mention what property management system they used. Uh, but it was a legacy on-premise system and, you know, I was 17, 18 years old and new to hospitality. I didn't know what a DR was or, uh, you know, uh, all the three letter codes that you needed to, uh, memorize, things like that.
And I remember this fear that I had of interacting with guests as a result of that. Not because of the interaction with the customer, but the interaction with the systems themselves. So I find that um, investing in intuitive and easy to use systems and easy to train on systems is really important. De definitely.
And we have such a, you know, and we are an industry with extremely high turnover. So the easy to train is really important because, um, you know, just when you do that initial rollout, you have to assume that a year, two year, three years, it, it's really a train the trainer type approach. And you need to have that buy-in with the team.
Bobby Marhamat: Absolutely. Um, one, one magical question that, that I wanna get a magical answer to is if you could sit down with yourself 10 to 15 years ago, early in your career, what's one piece of advice you'd give the, the younger Jacob on how to, you know, really save time, money, burnout in this industry?
Jacob Messina: Uh, you know, I remember in the early days of, uh, my career, like when I moved into like corporate, uh, life and, uh, working at Lowe's Hotels, and there was a time, you know, I started there as an intern and, uh, ended up, I, I worked there for 10 years in various roles. Uh, thankfully not an intern for all 10 years.
Um, I remember sitting there and wish like, oh, I wish I was part of that meeting and if only I had, uh, more meetings and, uh. Believe me, the, the meetings come, uh, whether you like it or not. That's fine. So, uh, you know, I I, it was a time when I, I always was sitting on, uh, you know, at the early days sitting on the outside hoping to be in the room and realizing that that will, that will come later on, uh, whether you like it or not.
Yeah. So, yeah,
Bobby Marhamat: no, for sure. For sure, for sure. Awesome. My, my, my last question here for you, um, because we're out of time here, is. You know, as you look at, um, really tech adoption and how some maybe independent hotels or groups struggle with it, um, how would you, what's, what's your like step-by-step kind of approach?
And I know I'm put you on the spot right now, so like, what's your step-by-step approach of like, how you look at that, think about that and really kind of maneuver that technology roadmap within a location very seamlessly?
Jacob Messina: Yeah. Um. I think people often get scared by technology decisions, whether it's am I gonna pick the wrong vendor?
Or the wrong partner and the wrong system to use and, and it often stops them from even starting the process. So the advice I would give from the get go is you should always be thinking about what are the areas that I wanna be improving, whether in, in my guest experience or my operations, and how can technology help and enable that?
So that should be an always on type of conversation, either internally or externally. Um, I'm a big believer in standardization. I think it helps. Uh, uh, you know, uh, whether you're a single operator, um, that is trying to, you know, build standards across, uh, your multiple teams. But even more so, like we work with a lot of management groups and brands, and any opportunity that you can build, standardized, uh, you know, uh, processes and, uh, build outs, it makes the, um, it makes the ability to.
To change much faster and better, uh, with higher quality results. So I, I'm a big believer standardized where you can, um, you know, I, I would say if you can get 70% standardized and then focus all, all your creativity on the next 30%, um, that's always really been my approach there.
Bobby Marhamat: I'm gonna have to squeeze in a, a mini question too.
So how do you standardize, how do you standardize, like, like how do you think about AI in, in this, in the world of standardization? Like how do you lead into that or not lead into that as, as you're gonna, you know, in building your technology roadmap and stack within a a location?
Jacob Messina: Wow. And here I thought I was gonna get through a podcast without talking about it.
No, I, uh, you know, I think AI is a great enabler and it, it, it's, uh, it's exciting how many, how, uh, open it's created in terms of like, the ability to create new products and systems and things like that. Um, I always look towards what's the end goal. Uh, whenever I think about, um, you know, I, I'm a real believer in not using AI for the sake of ai.
So, um, especially when it comes to hotel operations, I think about it, automation and efficiency. That to me is the end goal when you're thinking about how do you build, uh, or how do you choose and how do you implement the right technology or ai. So I look at it as how does an enhanced experience and how do we implement it in a way that, um, you know, a task that used to take five minutes now takes two.
Um, I, I find that it's, you know, there are some, but it's rare in a hospitality when interacting with guests. You're gonna automate that entire experience, and that's a very type of product. So don't try to just, um. Remove technology entirely, but how do you make things more efficient at each step using uh, you know, natural language processing and all sorts of things there with ai, you know, that's a real big focus for us.
Bobby Marhamat: It's absolutely, absolutely. I think there's a lot of value add. It was actually interesting. I was staying at a, a property recently and I'm, I'm with you. Like that balance is super important. They had a, uh, you room service, a voice activation type module that would talk to you and it was like,
Jacob Messina: yeah,
Bobby Marhamat: it was weird.
Like, are you listening to everything else I'm saying? You know, the right use of technology for sure at the right time and being able to give guests that, that choice of like how to lean into that. So you still have that guest experience that's, uh, that's really high.
Jacob Messina: Tim,
Bobby Marhamat: absolutely. Well, Jacobs, thank you so much.
If, if people wanted to check, check you out, or, you know, check out, uh, stay in touch, where do they, where do they go?
Jacob Messina: Uh, just, uh, come to our website, stay in touch.com. Uh, you know, anyone can always reach out to me either via LinkedIn or email. Uh, always happy to talk about hotel tech.
Bobby Marhamat: Awesome. Amazing. Thank you so much again for your time today.
Jacob Messina: Great. Thanks Bobby.
Bobby Marhamat: Absolutely.