It's Personal Stories, A Hospitality Podcast

Jacob Messina, CEO, Stayntouch, interviewed by Rachel Humphrey

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Jacob shares how an early love of video games led to a career in technology and the hospitality industry. He discusses why trust is critical in leadership, reflects on his own leadership evolution and philosophies, and why anticipating and learning from challenges is more important than being perfect. Jacob also talks about cooking as a form of self care and why relationships matter in an industry that seems so large but is really so small.

Rachel Humphrey:

Good afternoon. I am Rachel Humphrey with its Personal Stories. We are a nonprofit dedicated to empowering personal success in the hospitality industry. And today I'm really excited to be joined by Jacob Messina, the CEO first. Stay in touch. Jacob, welcome to the program.

Jacob Messina:

Thank you for having me, Rachel. Appreciate it.

Rachel Humphrey:

We are gonna jump right in. Everyone knows who listens to the series regularly, knows that I absolutely love how unique everybody's path to leadership is within the hospitality industry. That no two have to mirror one another, but you yet can have this very distinct path to leadership. So tell us a little bit about yourself and a little bit about your path to leadership and how you got to where you are today.

Jacob Messina:

Sure. So let's see. I'm Jacob Macina, EO of Stay Touch. I've been in the role for about three years but my background is really more on the hotel side of things. Before coming over to running a software company I've always. Been really interested in software and technology. And I would say that what got me interested in hospitality, it's a little unique. It started with computer games at an early age. Games like the Sims and Rollercoaster Tycoon where you're managing large scale operations, but also you have to think in, manage complex people's interests, likes, behaviors and things like that. And I really enjoyed these types of games growing up and was challenged at an early age by my parents of how do you apply these type of things to like a career, what or an industry. And that's what brought me originally actually to restaurants. And I got my start working in restaurants at about like the age of 16 in New York City. I'm a native New Yorker. And I very quickly, over a couple years learned that working in restaurants is more of a passion than it was a career for me. It's a really grueling and difficult life and I have a ton of appreciation for all the people that work in the food service industry. But I realized at that point hospitality was really a career and a passion of mine. And I switched over to the hotel side. And where I got to get my hands dirty, working front desk in in a couple hotels in in New York City. And that was really the start of my hotel career and went on from there.

Rachel Humphrey:

I love the tie to video games, so for anyone who's out there with kids who are playing and they wonder what will that ever lead to? Now they have a prime example of that.

Jacob Messina:

Yeah, there's lots of good lessons you can learn from them. So

Rachel Humphrey:

yeah. One of the things that I think that is. Interesting thing with your journey is that you assumed the CEO role from an interim CEO role and a role I actually held at one point in my career as well. I'm curious for you if you think that you lead differently with an interim CEO title than you do the CEO title, but then also from the role you had. Prior to becoming the interim CEO, maybe what type of leadership changes you made to lead differently with those different career titles?

Jacob Messina:

Yeah. When I started at Stay in Touch as the interim CEO it was at my first time, first CEO role still is. And I would say that there was definitely a bit of a learning curve there in terms of finding my specific leadership style. More so just. Making sure that the way that I operated in other roles was gonna work at this scale. This was, I went from managing a team of, I think 12 to a team of about 150 or 130, and we grew to 150. And part of that was understanding could I have the same level of connection with a larger team that I wouldn't get to see every day? And, we, I have employees in 18 countries today. What I found is that it does scale because it's a mixture of just understanding people at more of, just than an employee level, understanding what's their motivations, what makes them tick as humans. I really try to understand that before having any kind of conversations or working with people. So that definitely was in that interim into full-time CEO and being a permanent position. Before that, my role was a bit different. I was not leading a software company. I was leading technology for the third largest owner and operator of hotels in the us. So I was actually a customer of stay in touch before I came over to run the organization. So that's been a very interesting mindset change to bringing that customer led knowledge base to this company and really being able to run things through that lens and what our customers are asking for and have been in their shoes. And understand what's affecting them on a daily basis.

Rachel Humphrey:

I like the self-awareness to see can I scale how I know that I am a leader in one sense, and then applying it to another, and then probably the satisfaction and realizing that it does, because it's a way that's leading that's very genuine to you. And so to be able to grow that as. The number of people that you were overseeing grew as well? It's interesting to me ways that I have grown as I've watched and conducted a lot of these interviews. One of the things that's been really eye-opening for me is how many leaders in our industry describe themselves as curious. And it was a word that I would not have used, but I have found. Over the last couple years that it seems to be one of the threads that runs through a lot of our industry leadership. I'm wondering if you think that you are a curious person, the types of things you're curious about, and then maybe what's one thing today professionally or personally that you're curious about?

Jacob Messina:

I would definitely describe myself as a curious person. It's what has propelled me in my career from an early early age. I was at a company for a while where through a series of events I had multiple different bosses. They either left the organization or. Were asked to move on and I really was able to rise just by taking on responsibility without being asked. And part of that was I was just curious to learn and curious to do things differently and to try to do things better. And then, upper management would circle back six months later and be like, oh, did we ever fill that role? And they're like oh, that that intern seems to have stepped up and is doing it. And that's how I really was able to progress. So I would say it's really been a driving thing. Force in a lot of what I do and how I got to where I am today is just remaining curious. Asking questions is probably the most powerful thing that you can do, not just as a leader, but in any role. If someone, I've always had a rule that if someone can't under it can't explain the why we do something the way we do. That generally means that they don't understand what they're working on or what the path to success is gonna be. I've always you have to be respectful.'cause sometimes it can sound a little or come off a little bit challenging, but if you do it in the right way, it's all constructive and you can build and learn a lot from that. Definitely a curious person across all traits.

Rachel Humphrey:

And do I remember you told me that you actually ask when you're interviewing others for open roles about their curiosity?

Jacob Messina:

Yeah. Hopefully. I won't give this away to too many people, but I do ask two questions on every interview. So I ask tell me about something you're curious about, and I also ask, tell me about something you failed and time you failed and something you learned from it. Those are my two major interview questions.

Rachel Humphrey:

I have a question sticking with the curiosity theme, just a second. When you ask that of candidates,'cause now you have an important role in hiring, what are you looking to tell from that question? You've decided this is an important enough one that I'm gonna be able to make perhaps a decision based on that question. What are you looking for?

Jacob Messina:

I'm looking for it. It's generally a question people aren't expecting. Both questions are ones that people aren't expecting. So it's more about how people come to a conclusion. So when I ask about curious, it's either what is someone passionate about? I'm always looking for something. And it could be I hope it's something completely unrelated to technology or hospitality but it helps people open up a bit in terms of things outside of their career or work life. And then, the second part of that on the question about tell me something you failed at and what you learned from it. It, that one's a little bit of a trick question. Everyone focuses on what did I fail at and trying to make it not sound terrible when the reality is I don't really care what they say at that point. I'm listening to what did you learn from it? And if you don't learn from your mistakes, that's a number one red flag for me.

Rachel Humphrey:

Excellent. No, absolutely. Sticking with the idea of leadership, we have a lot of people who say I was born to lead and we have others who say, even today, I'm not sure I would consider myself a leader. When you think about the term leadership, was that something that. When you entered the industry, you could see yourself being in a leadership position one day, or were there pivotal moments along the way where it went for you? You know what? I'm actually part of a leadership team now, or I lead this organization today.

Jacob Messina:

Yeah, and it's a great question. I honestly never really saw myself as a leader in the early stages of my career. I thought of myself as a really strong individual contributor and one that was able to work really well with a lot of different people and different working styles. But I did think of myself. Not as a leader or in the early stages, mostly because I didn't, it wasn't a muscle that I got to flex very often in the early stages of my career, or I didn't think I did. And I realized I was wrong. I didn't realize how much actual leadership and management I was doing, even in the early stages. At one point I was managing three or four third party agencies each of which had six to eight people assigned to our account for a hotel company I worked at. And I realized that I was leading this and I had to create motivation and inspiration project management across these different orgs. And while they weren't employees, they didn't directly report to me. There was an element of leadership from that. And I didn't realize it in the moment, but I was learning those skills. And, for so long I thought of it just as, oh, I didn't have direct reports, so I wasn't leader when in reality it was really the relationships I had at this large scale organization that I could be a leader just by working with other groups in the company and helping them be successful or, removing roadblocks so that they could do other things. There was a lot of leadership that I gained from that, or skills that I ended up using in a leadership career later.

Rachel Humphrey:

I really like the evolution of that as well as to how you saw yourself and then when that. Self-perception started to change how the skills came along with it. You have an interesting background. You mentioned in technology, and we are in an industry that it is critically important that we stay either on top of or even ahead of growing trends and technology seems to change faster. Then any of us can stay abreast of it. Where do you turn for continuous growth to make sure that you know what's going on in the industry, what's going on in your field specifically, and that you as a company are meeting the industry where it's at or even leading the industry into where you're going.

Jacob Messina:

Yeah. It's definitely a tricky one, especially as I've taken steps further away from the end customer or client, and that's one that I really focus and try to spend as much time as I can with our customers to understand, listen, what are the challenges that they're running into? I find so often, and I was often in this position when I was on the other side and a customer of many technology products, people were building things that didn't apply to me. And, they thought it was this amazing innovation and it felt really flat. So I, coming from that background I really do spend time with our customers learning, listening, spending time with their teams and understanding how they're using. Technology'cause it's off very often. It's not how, the product was ever designed or the team at a company thinks it's being used. So to make sure that you're really understanding and in the weeds to a degree so you can gain a lot of perspective from that.

Rachel Humphrey:

Is that the same advice you would give to your team or rising leaders within the industry who you want to make sure continuing to invest in themselves or in their own growth from a really, a substantive matter standpoint.

Jacob Messina:

I, I would, I don't think you can lead from an ivory tower. You need to understand how everyone is working both together and in their own individual roles. How their how they relate to and leverage technology on a daily basis. Because we often have these preconceived notions, every technology company thinks that everyone's adopting all elements of their product. When in reality they may miss an area or miss a release and things like that. And that can really affect how they leverage your product. So I think it's really important to take a step down every now and then and make sure that you are spending time, in the trenches and understand what other people are going through and,'cause it's not, it's often not what you think.

Rachel Humphrey:

I like that. You mentioned that you had been in your current role for about three years now, and I wanna focus really only on the last 12 months or so. Tell me one lesson that you've learned or one of the biggest lessons that you've learned in the last 12 months, and how or if it will impact your leadership evolution moving forward.

Speaker 3:

Let's see. Something I have learned in the last 12 months, I.

Jacob Messina:

I would say everything takes longer than you think it's going to. And it's something that you know it was that and try not to be a perfectionist. It's something I'm definitely not but it's something that I've been coaching a lot of our teams around, instead of trying to do things perfectly the advice I give is plan for when things go wrong. I'd rather people and our team spend time understanding how this could go sideways and be prepared for that. And I think that is an incredibly important part of any, product or project that people don't spend enough time on. Everyone wants to get it right. But in the reality of hospitality is that it's incredibly complex and nothing goes right the first time. So it's better to be prepared for when things are gonna go down a difficult direction and be prepared for them, have contingencies in place, and to protect your downside than to try to do it perfectly the first time. And I think you win a lot of respect with your customers and clients and, other people that you work with, colleagues by being prepared in those situations as opposed to just hoping it goes perfectly and then being disappointed when it doesn't.

Rachel Humphrey:

I'm gonna ask you a follow up to that in a second, but I'm gonna tell you that's interesting that you just mentioned that because that's actually how I lead when I know that I need buy-in from a lot of different stakeholders. Okay? I try to anticipate why are they not going to want whatever I want to happen, and then how do I be prepared to address that? So it sounds like a similar. Strategy here. But my follow up question is actually, do you follow that own advice? So are you able to say, okay I'm not seeking perfection, I'm seeking to anticipate all of the ways it may not be perfect, and then how am I gonna navigate it?

Jacob Messina:

I'm a big advocate for this, and I do follow this advice to the point where, my sales team sometimes get mad. Me when I am part of sales pitches or meeting with new customers. I often tell people, this, no technology project has gone exactly perfectly. There's always a hiccup. There's always something. There's always something that happens in your business that we need to be prepared for. We are the team that's gonna be there for you when things get difficult, as opposed to the team that's gonna come in here and say everything's gonna work a hundred percent on day one. That's unrealistic. So you need to be authentic and not just pretend everything works right out of the box. It's, you wanna pick a team that's gonna be with you when it doesn't, so

Rachel Humphrey:

I like the way of modeling too, what you're telling the rest of your team, if you're able to do that as leader, especially those of us with. Perfectionist tendencies that can be hard to step away from. But that's actually a perfect segue. So when things don't go perfectly, let's talk about overcoming obstacles for a second. One of the, no one reaches any level of leadership without having challenges or obstacles along the way. What is the approach you use when you do maybe have some challenges, things that don't go your way, and then is there any particular example you can think of that maybe you learned, you talked about when things go wrong, when you're interviewing people. What did you learn from it? What is maybe a challenge that you came across that you took a big lesson away from at the end of the day?

Jacob Messina:

Yeah, this ties in well with my own interview question, and I would be it would be embarrassing if I didn't have an answer to that within this. No, I, for me it's about it, everyone fails many times in their career. Many times in a week we fail at things. There's micro moments of that too. So I do try to take a step back at the end of every week and say not just what could I have done better? It's more what could I have done differently to achieve a different outcome? Difficult to be regimented about this and to find the time. But when I'm able to, I take a step back and try to understand what did I learn and what could I have done differently in this previous week, month, or period of time? I've had periods in my career and going back to, what are the things that I've failed on one time, a long time ago now, I took on far too many projects that I was not in control of. I was in charge of executing against them, and it was a scope of work that I wasn't fully bought into and I didn't have control over. And as a result, the expectation that had been set at the company. Didn't match with the scope of work with the external parties we were working with. So we had this huge e even if executed perfectly, everyone was gonna be disappointed or underwhelmed. And I realized at that point that I, the failure, there was a failure to communicate very early in a stage of a new relationship, both internally and externally. So that's one thing that I really work at, is when we're embarking on a new project. Talk to the customer and talk to your own teams about what are we trying to achieve here and why?

Rachel Humphrey:

I love that from a communication standpoint as well, because I think one of the things that I have found challenging is not saying out loud what's in my head, assuming everybody knows what I know, and so then people start questioning things. I'm like, wait, but you know all that, and it really doesn't. Work out that way'cause they don't know all of

Speaker 3:

that. Yeah.

Rachel Humphrey:

I wanna turn our attention now to mentors and allies and champions and talk about the importance of having people that are there to bounce ideas off of, to overcome obstacles with, to. Be a hype squad, whatever type of support system, but also in this industry as you've had new roles, new opportunities where you look to for guidance. So talk a little bit about the role of mentors and champions maybe in your experience, and then how do you try to do that for others at this point in your career?

Jacob Messina:

Yeah, I, I would say throughout my career I've had some spec, I've had amazing bosses. I've had ones that I was not on the same page with. And what I've really boiled that down to in terms of where I was able to see myself be successful is around trust. When I had trust with. The person I reported to and with my team I and now to look back on those teams that were really built and surrounded by trust. I look back and I can see how much more work product I was able to accomplish.'cause I wasn't worried about CYA or just, am I stepping on toes. We were all moving the same direction and even if we didn't agree, we trusted each other to really have the company's interests in mind. The team's interests at mind, at heart, sorry. And. That was really remarkable to me is just to see how much more I could get done by that. So then, when I think about how I build teams now, it's really goes down to how can I build trust quickly with people, which can be very difficult today, especially in remote environments. Stay in touch as a remote company I make a point of trying to see all my direct reports as often as possible. I travel quite a bit so on the road and whatever I can get to see them so it can. Be difficult to build those bonds and that trust, but making sure that you have regular check-ins and people understand that, again, it's okay to fail. It's as long as you learn from it build from it onto the next project is really important There.

Rachel Humphrey:

It's interesting'cause the word trust seems so basic and it's understanding, but really such an important way for you both to recognize how much that trusting relationship impacted your overall productivity or your overall success in your role and now how you're able to pay that forward with your team. You just mentioned traveling a lot to see your team and so I learned a long time ago that if I say work life balance, it's gonna get people very unbalanced. The question, question in and of itself. But I am curious over the years maybe how you are able with a demanding career, with a demanding travel schedule of finding some sort of harmony between your professional career and your personal life, and maybe how that's changed over time or throughout different roles.

Jacob Messina:

Yeah, I definitely wouldn't be the first one to tell you that I have this fully figured out. Definitely an evolution that happens over time. And we all have ebbs and flows of when we're good at the work-life balance and when we're not. What I really do try to focus on I love to cook and it's something that I find really rejuvenating. One, because I, I. Am unable to do cook simply, even when I'm cooking, just for me and my wife, I end up cooking for 10, 12 people. So I love to cook and it I get very fixated on it and I wanna do the best possible, so it forces me to put my phone down. And that is a really rare. Thing to be just fully focused on a task at hand like that. And it does allow me to disconnect. So I know when I'm unbalanced, cooking is the first thing I stop doing. I can just see it in my schedule and I have to like, remind myself that it's important to get back to the things you enjoy. Also a very difficult thing to do well. Traveling and on the road in hotels is maintaining cooking and doing that. Part of it is pushing ourself to explore new locations and while I'm traveling and not just, working while on the road constantly.

Rachel Humphrey:

It's interesting that you say that about cooking because one of the things that I have learned over the last couple years is that self-care means different things to different people. And for some people it may be physical exercise or fresh air, that other types of things. But for others there are simple acts that are. A form of self-care. And for you with cooking, it's interesting to see both that the absence of it is a sign for you that you are out of balance, but also that part of the reason that it becomes such a big part of your harmony is putting your phone down and that the relationship between,'cause lots of people will stand in the kitchen with the phone and still be trying to muster up a meal here or there. So it's interesting to see. How, what a role that, that love of cooking plays for you? As far as awareness goes, but also in the disconnect, which is nice to see.

Jacob Messina:

Yeah, and I would say part of that is because I'm also not a recipe chef, so I'll get an inspiration and then it is a creative exercise for me as well because it's more like, Ooh, I have a little bit of this, or What if I tried it this way this time? So it does make me flex the the creative side of how do I keep improving or learning something new there.

Rachel Humphrey:

I love that. One of my favorite questions, Jacob, to ask always is advice to our younger selves. And the reason I love it so much is I think we are all works in progress, whether it's our personal journey, our professional, our leadership journeys. So looking back on that little kid playing video games or at whatever age you want, graduating from college, whatever it may be. What is one of the pieces of advice you would tell your younger self, either about how things turned out for you today or maybe about something you wish you had known then that might've helped in your journey?

Jacob Messina:

I think the advice I would give is it's about how important relationships are. And I'm not saying just like networking or anything like that it's identifying people that you can work really closely with and you can ident, you can build trust with. And that can be people you work really closely with or that maybe you have something in common with, it could be a third party colleagues at other companies as well. But invest in those relationships early and continue to and really put aside the time to be helping others. When you go out of your way for someone and it's completely unexpected, it's something that they will remember. It's some, it's the beginning of a relationship that can have paid dividends for many years or decades to come. We have a very unique industry in the sense that it's very large, but also tiny at the same time. And I'm always blown away by. How many people from early stages in my career remember a project I worked on or a presentation I gave, and then that had an impact on how something they learned and were able to apply later in their careers too. So I would say go, really spend the time and dedicate time to helping others, even if it doesn't even if it's not for an immediate return or you're working with them directly, but it will pay dividends for sure.

Rachel Humphrey:

I love the concept of investing in relationships too. It's such a different concept than networking or just building relationships, but if you invest in those relationships, you never know how or why or when they are going to come back. So I love that advice. We are wrapping up on time here and we've certainly covered a lot of ground, but thinking about. The motto of its personal stories, which is empowering personal success. Is there any one piece of final advice that you'd like to share with our audience?

Jacob Messina:

Rachel, I think you said it really well in one of your earlier questions. And I would go back to that about curiosity. It is something that helps you constantly learn and it never stops. So if there's any advice I could give that has helped me in my career it's to be. Curious to learn from others and to try to incorporate that into your daily life. But to never stop asking questions. So that, that would be the advice I would give to as many people that are willing to listen,

Rachel Humphrey:

I love that. Jacob, I'm really thrilled that you decided to join me a little bit today, getting to know a little bit more about you and your leadership journey. But thank you so much for joining the program today and sharing everything with us.

Jacob Messina:

Great. Thanks Rachel. It was a pleasure.

Rachel Humphrey:

To our audience out there. We hope you've enjoyed our time today with Jacob, and you can head on over to its personal stories.com to hear from over 200 other hospitality industry leaders who have likewise shared their personal journeys and their leadership insights as well. And have a good afternoon.