September 2, 2025 • 26 mins
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.
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Episode Transcript
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Rachel Humphrey (00:02):
Good afternoon.
I am Rachel Humphrey with itsPersonal Stories.
We are a nonprofit dedicated toempowering personal success in
the hospitality industry.
And today I'm really excited tobe joined by Jacob Messina, the
CEO first.
Stay in touch.
Jacob, welcome to the program.
Jacob Messina (00:17):
Thank you for having me, Rachel.
Appreciate it.
Rachel Humphrey (00:20):
We are gonna jump right in.
Everyone knows who listens tothe series regularly, knows that
I absolutely love how uniqueeverybody's path to leadership
is within the hospitalityindustry.
That no two have to mirror oneanother, but you yet can have
this very distinct path toleadership.
So tell us a little bit aboutyourself and a little bit about
your path to leadership and howyou got to where you are today.
Jacob Messina (00:42):
Sure.
So let's see.
I'm Jacob Macina, EO of StayTouch.
I've been in the role for aboutthree years but my background is
really more on the hotel side ofthings.
Before coming over to running asoftware company I've always.
Been really interested insoftware and technology.
And I would say that what got meinterested in hospitality, it's
a little unique.
(01:03):
It started with computer gamesat an early age.
Games like the Sims andRollercoaster Tycoon where
you're managing large scaleoperations, but also you have to
think in, manage complexpeople's interests, likes,
behaviors and things like that.
And I really enjoyed these typesof games growing up and was
challenged at an early age by myparents of how do you apply
(01:24):
these type of things to like acareer, what or an industry.
And that's what brought meoriginally actually to
restaurants.
And I got my start working inrestaurants at about like the
age of 16 in New York City.
I'm a native New Yorker.
And I very quickly, over acouple years learned that
working in restaurants is moreof a passion than it was a
career for me.
It's a really grueling anddifficult life and I have a ton
(01:46):
of appreciation for all thepeople that work in the food
service industry.
But I realized at that pointhospitality was really a career
and a passion of mine.
And I switched over to the hotelside.
And where I got to get my handsdirty, working front desk in in
a couple hotels in in New YorkCity.
And that was really the start ofmy hotel career and went on from
there.
Rachel Humphrey (02:06):
I love the tie to video games, so for anyone
who's out there with kids whoare playing and they wonder what
will that ever lead to?
Now they have a prime example ofthat.
Jacob Messina (02:16):
Yeah, there's lots of good lessons you can
learn from them.
So
Rachel Humphrey (02:19):
yeah.
One of the things that I thinkthat is.
Interesting thing with yourjourney is that you assumed the
CEO role from an interim CEOrole and a role I actually held
at one point in my career aswell.
I'm curious for you if you thinkthat you lead differently with
an interim CEO title than you dothe CEO title, but then also
(02:41):
from the role you had.
Prior to becoming the interimCEO, maybe what type of
leadership changes you made tolead differently with those
different career titles?
Jacob Messina (02:54):
Yeah.
When I started at Stay in Touchas the interim CEO it was at my
first time, first CEO role stillis.
And I would say that there wasdefinitely a bit of a learning
curve there in terms of findingmy specific leadership style.
More so just.
Making sure that the way that Ioperated in other roles was
gonna work at this scale.
(03:14):
This was, I went from managing ateam of, I think 12 to a team of
about 150 or 130, and we grew to150.
And part of that wasunderstanding could I have the
same level of connection with alarger team that I wouldn't get
to see every day?
And, we, I have employees in 18countries today.
What I found is that it doesscale because it's a mixture of
(03:35):
just understanding people atmore of, just than an employee
level, understanding what'stheir motivations, what makes
them tick as humans.
I really try to understand thatbefore having any kind of
conversations or working withpeople.
So that definitely was in thatinterim into full-time CEO and
being a permanent position.
Before that, my role was a bitdifferent.
(03:55):
I was not leading a softwarecompany.
I was leading technology for thethird largest owner and operator
of hotels in the us.
So I was actually a customer ofstay in touch before I came over
to run the organization.
So that's been a veryinteresting mindset change to
bringing that customer ledknowledge base to this company
and really being able to runthings through that lens and
(04:16):
what our customers are askingfor and have been in their
shoes.
And understand what's affectingthem on a daily basis.
Rachel Humphrey (04:24):
I like the self-awareness to see can I
scale how I know that I am aleader in one sense, and then
applying it to another, and thenprobably the satisfaction and
realizing that it does, becauseit's a way that's leading that's
very genuine to you.
And so to be able to grow thatas.
The number of people that youwere overseeing grew as well?
(04:44):
It's interesting to me ways thatI have grown as I've watched and
conducted a lot of theseinterviews.
One of the things that's beenreally eye-opening for me is how
many leaders in our industrydescribe themselves as curious.
And it was a word that I wouldnot have used, but I have found.
Over the last couple years thatit seems to be one of the
threads that runs through a lotof our industry leadership.
(05:07):
I'm wondering if you think thatyou are a curious person, the
types of things you're curiousabout, and then maybe what's one
thing today professionally orpersonally that you're curious
about?
Jacob Messina (05:18):
I would definitely describe myself as a
curious person.
It's what has propelled me in mycareer from an early early age.
I was at a company for a whilewhere through a series of events
I had multiple different bosses.
They either left theorganization or.
Were asked to move on and Ireally was able to rise just by
taking on responsibility withoutbeing asked.
(05:40):
And part of that was I was justcurious to learn and curious to
do things differently and to tryto do things better.
And then, upper management wouldcircle back six months later and
be like, oh, did we ever fillthat role?
And they're like oh, that thatintern seems to have stepped up
and is doing it.
And that's how I really was ableto progress.
So I would say it's really beena driving thing.
Force in a lot of what I do andhow I got to where I am today is
(06:02):
just remaining curious.
Asking questions is probably themost powerful thing that you can
do, not just as a leader, but inany role.
If someone, I've always had arule that if someone can't under
it can't explain the why we dosomething the way we do.
That generally means that theydon't understand what they're
working on or what the path tosuccess is gonna be.
(06:23):
I've always you have to berespectful.
'cause sometimes it can sound alittle or come off a little bit
challenging, but if you do it inthe right way, it's all
constructive and you can buildand learn a lot from that.
Definitely a curious personacross all traits.
Rachel Humphrey (06:38):
And do I remember you told me that you
actually ask when you'reinterviewing others for open
roles about their curiosity?
Jacob Messina (06:45):
Yeah.
Hopefully.
I won't give this away to toomany people, but I do ask two
questions on every interview.
So I ask tell me about somethingyou're curious about, and I also
ask, tell me about something youfailed and time you failed and
something you learned from it.
Those are my two major interviewquestions.
Rachel Humphrey (07:01):
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 youlooking to tell from that
question?
You've decided this is animportant enough one that I'm
gonna be able to make perhaps adecision based on that question.
What are you looking for?
Jacob Messina (07:21):
I'm looking for it.
It's generally a question peoplearen't expecting.
Both questions are ones thatpeople aren't expecting.
So it's more about how peoplecome to a conclusion.
So when I ask about curious,it's either what is someone
passionate about?
I'm always looking forsomething.
And it could be I hope it'ssomething completely unrelated
to technology or hospitality butit helps people open up a bit in
(07:43):
terms of things outside of theircareer or work life.
And then, the second part ofthat on the question about tell
me something you failed at andwhat you learned from it.
It, that one's a little bit of atrick question.
Everyone focuses on what did Ifail at and trying to make it
not sound terrible when thereality is I don't really care
what they say at that point.
I'm listening to what did youlearn from it?
(08:04):
And if you don't learn from yourmistakes, that's a number one
red flag for me.
Rachel Humphrey (08:08):
Excellent.
No, absolutely.
Sticking with the idea ofleadership, we have a lot of
people who say I was born tolead and we have others who say,
even today, I'm not sure I wouldconsider myself a leader.
When you think about the termleadership, 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
(08:30):
along the way where it went foryou?
You know what?
I'm actually part of aleadership team now, or I lead
this organization today.
Jacob Messina (08:38):
Yeah, and it's a great question.
I honestly never really sawmyself as a leader in the early
stages of my career.
I thought of myself as a reallystrong individual contributor
and one that was able to workreally well with a lot of
different people and differentworking styles.
But I did think of myself.
Not as a leader or in the earlystages, mostly because I didn't,
(09:02):
it wasn't a muscle that I got toflex very often in the early
stages of my career, or I didn'tthink I did.
And I realized I was wrong.
I didn't realize how much actualleadership and management I was
doing, even in the early stages.
At one point I was managingthree or four third party
agencies each of which had sixto eight people assigned to our
account for a hotel company Iworked at.
(09:24):
And I realized that I wasleading this and I had to create
motivation and inspirationproject management across these
different orgs.
And while they weren'temployees, they didn't directly
report to me.
There was an element ofleadership from that.
And I didn't realize it in themoment, but I was learning those
skills.
And, for so long I thought of itjust as, oh, I didn't have
(09:46):
direct reports, so I wasn'tleader when in reality it was
really the relationships I hadat this large scale organization
that I could be a leader just byworking with other groups in the
company and helping them besuccessful or, removing
roadblocks so that they could doother things.
There was a lot of leadershipthat I gained from that, or
skills that I ended up using ina leadership career later.
Rachel Humphrey (10:09):
I really like the evolution of that as well as
to how you saw yourself and thenwhen that.
Self-perception started tochange how the skills came along
with it.
You have an interestingbackground.
You mentioned in technology, andwe are in an industry that it is
critically important that westay either on top of or even
(10:29):
ahead of growing trends andtechnology seems to change
faster.
Then any of us can stay abreastof it.
Where do you turn for continuousgrowth to make sure that you
know what's going on in theindustry, what's going on in
your field specifically, andthat you as a company are
meeting the industry where it'sat or even leading the industry
(10:50):
into where you're going.
Jacob Messina (10:52):
Yeah.
It's definitely a tricky one,especially as I've taken steps
further away from the endcustomer or client, and that's
one that I really focus and tryto spend as much time as I can
with our customers tounderstand, listen, what are the
challenges that they're runninginto?
I find so often, and I was oftenin this position when I was on
(11:12):
the other side and a customer ofmany technology products, people
were building things that didn'tapply to me.
And, they thought it was thisamazing innovation and it felt
really flat.
So I, coming from thatbackground I really do spend
time with our customerslearning, listening, spending
time with their teams andunderstanding how they're using.
Technology'cause it's off veryoften.
(11:34):
It's not how, the product wasever designed or the team at a
company thinks it's being used.
So to make sure that you'rereally understanding and in the
weeds to a degree so you cangain a lot of perspective from
that.
Rachel Humphrey (11:47):
Is that the same advice you would give to
your team or rising leaderswithin the industry who you want
to make sure continuing toinvest in themselves or in their
own growth from a really, asubstantive matter standpoint.
Jacob Messina (12:01):
I, I would, I don't think you can lead from an
ivory tower.
You need to understand howeveryone is working both
together and in their ownindividual roles.
How their how they relate to andleverage technology on a daily
basis.
Because we often have thesepreconceived notions, every
technology company thinks thateveryone's adopting all elements
(12:22):
of their product.
When in reality they may miss anarea or miss a release and
things like that.
And that can really affect howthey leverage your product.
So I think it's really importantto take a step down every now
and then and make sure that youare spending time, in the
trenches and understand whatother people are going through
and,'cause it's not, it's oftennot what you think.
Rachel Humphrey (12:42):
I like that.
You mentioned that you had beenin your current role for about
three years now, and I wannafocus really only on the last 12
months or so.
Tell me one lesson that you'velearned or one of the biggest
lessons that you've learned inthe last 12 months, and how or
if it will impact yourleadership evolution moving
(13:03):
forward.
Speaker 3 (13:06):
Let's see.
Something I have learned in thelast 12 months, I.
Jacob Messina (13:14):
I would say everything takes longer than you
think it's going to.
And it's something that you knowit was that and try not to be a
perfectionist.
It's something I'm definitelynot but it's something that I've
been coaching a lot of our teamsaround, instead of trying to do
things perfectly the advice Igive is plan for when things go
wrong.
I'd rather people and our teamspend time understanding how
(13:38):
this could go sideways and beprepared for that.
And I think that is anincredibly important part of
any, product or project thatpeople don't spend enough time
on.
Everyone wants to get it right.
But in the reality ofhospitality is that it's
incredibly complex and nothinggoes right the first time.
So it's better to be preparedfor when things are gonna go
(14:01):
down a difficult direction andbe prepared for them, have
contingencies in place, and toprotect your downside than to
try to do it perfectly the firsttime.
And I think you win a lot ofrespect with your customers and
clients and, other people thatyou work with, colleagues by
being prepared in thosesituations as opposed to just
hoping it goes perfectly andthen being disappointed when it
(14:22):
doesn't.
Rachel Humphrey (14:23):
I'm gonna ask you a follow up to that in a
second, but I'm gonna tell youthat's interesting that you just
mentioned that because that'sactually how I lead when I know
that I need buy-in from a lot ofdifferent stakeholders.
Okay?
I try to anticipate why are theynot going to want whatever I
want to happen, and then how doI be prepared to address that?
So it sounds like a similar.
Strategy here.
But my follow up question isactually, do you follow that own
(14:47):
advice?
So are you able to say, okay I'mnot seeking perfection, I'm
seeking to anticipate all of theways it may not be perfect, and
then how am I gonna navigate it?
Jacob Messina (14:58):
I'm a big advocate for this, and I do
follow this advice to the pointwhere, my sales team sometimes
get mad.
Me when I am part of salespitches or meeting with new
customers.
I often tell people, this, notechnology project has gone
exactly perfectly.
There's always a hiccup.
There's always something.
There's always something thathappens in your business that we
need to be prepared for.
(15:18):
We are the team that's gonna bethere for you when things get
difficult, as opposed to theteam that's gonna come in here
and say everything's gonna worka hundred percent on day one.
That's unrealistic.
So you need to be authentic andnot just pretend everything
works right out of the box.
It's, you wanna pick a teamthat's gonna be with you when it
doesn't, so
Rachel Humphrey (15:38):
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 uswith.
Perfectionist tendencies thatcan be hard to step away from.
But that's actually a perfectsegue.
So when things don't goperfectly, let's talk about
overcoming obstacles for asecond.
One of the, no one reaches anylevel of leadership without
(16:00):
having challenges or obstaclesalong the way.
What is the approach you usewhen you do maybe have some
challenges, things that don't goyour way, and then is there any
particular example you can thinkof that maybe you learned, you
talked about when things gowrong, when you're interviewing
people.
What did you learn from it?
What is maybe a challenge thatyou came across that you took a
(16:20):
big lesson away from at the endof the day?
Jacob Messina (16:23):
Yeah, this ties in well with my own interview
question, and I would be itwould be embarrassing if I
didn't have an answer to thatwithin this.
No, I, for me it's about it,everyone fails many times in
their career.
Many times in a week we fail atthings.
There's micro moments of thattoo.
So I do try to take a step backat the end of every week and say
(16:44):
not just what could I have donebetter?
It's more what could I have donedifferently to achieve a
different outcome?
Difficult to be regimented aboutthis and to find the time.
But when I'm able to, I take astep back and try to understand
what did I learn and what couldI have done differently in this
previous week, month, or periodof time?
I've had periods in my careerand going back to, what are the
(17:05):
things that I've failed on onetime, a long time ago now, I
took on far too many projectsthat I was not in control of.
I was in charge of executingagainst them, and it was a scope
of work that I wasn't fullybought into and I didn't have
control over.
And as a result, the expectationthat had been set at the
company.
Didn't match with the scope ofwork with the external parties
(17:27):
we were working with.
So we had this huge e even ifexecuted perfectly, everyone was
gonna be disappointed orunderwhelmed.
And I realized at that pointthat I, the failure, there was a
failure to communicate veryearly in a stage of a new
relationship, both internallyand externally.
So that's one thing that Ireally work at, is when we're
embarking on a new project.
(17:49):
Talk to the customer and talk toyour own teams about what are we
trying to achieve here and why?
Rachel Humphrey (17:54):
I love that from a communication standpoint
as well, because I think one ofthe things that I have found
challenging is not saying outloud what's in my head, assuming
everybody knows what I know, andso then people start questioning
things.
I'm like, wait, but you know allthat, and it really doesn't.
Work out that way'cause theydon't know all of
Speaker 3 (18:11):
that.
Yeah.
Rachel Humphrey (18:12):
I wanna turn our attention now to mentors and
allies and champions and talkabout the importance of having
people that are there to bounceideas off of, to overcome
obstacles with, to.
Be a hype squad, whatever typeof support system, but also in
this industry as you've had newroles, new opportunities where
(18:34):
you look to for guidance.
So talk a little bit about therole of mentors and champions
maybe in your experience, andthen how do you try to do that
for others at this point in yourcareer?
Jacob Messina (18:46):
Yeah, I, I would say throughout my career I've
had some spec, I've had amazingbosses.
I've had ones that I was not onthe same page with.
And what I've really boiled thatdown to in terms of where I was
able to see myself be successfulis around trust.
When I had trust with.
The person I reported to andwith my team I and now to look
(19:09):
back on those teams that werereally built and surrounded by
trust.
I look back and I can see howmuch more work product I was
able to accomplish.
'cause I wasn't worried aboutCYA or just, am I stepping on
toes.
We were all moving the samedirection and even if we didn't
agree, we trusted each other toreally have the company's
(19:30):
interests in mind.
The team's interests at mind, atheart, sorry.
And.
That was really remarkable to meis just to see how much more I
could get done by that.
So then, when I think about howI build teams now, it's really
goes down to how can I buildtrust quickly with people, which
can be very difficult today,especially in remote
(19:51):
environments.
Stay in touch as a remotecompany I make a point of trying
to see all my direct reports asoften as possible.
I travel quite a bit so on theroad and whatever I can get to
see them so it can.
Be difficult to build thosebonds and that trust, but making
sure that you have regularcheck-ins and people understand
that, again, it's okay to fail.
It's as long as you learn fromit build from it onto the next
(20:13):
project is really importantThere.
Rachel Humphrey (20:16):
It's interesting'cause the word trust
seems so basic and it'sunderstanding, but really such
an important way for you both torecognize how much that trusting
relationship impacted youroverall productivity or your
overall success in your role andnow how you're able to pay that
forward with your team.
You just mentioned traveling alot to see your team and so I
(20:39):
learned a long time ago that ifI say work life balance, it's
gonna get people veryunbalanced.
The question, question in and ofitself.
But I am curious over the yearsmaybe how you are able with a
demanding career, with ademanding travel schedule of
finding some sort of harmonybetween your professional career
and your personal life, andmaybe how that's changed over
(21:01):
time or throughout differentroles.
Jacob Messina (21:04):
Yeah, I definitely wouldn't be the first
one to tell you that I have thisfully figured out.
Definitely an evolution thathappens over time.
And we all have ebbs and flowsof when we're good at the
work-life balance and when we'renot.
What I really do try to focus onI love to cook and it's
something that I find reallyrejuvenating.
One, because I, I.
(21:24):
Am unable to do cook simply,even when I'm cooking, just for
me and my wife, I end up cookingfor 10, 12 people.
So I love to cook and it I getvery fixated on it and I wanna
do the best possible, so itforces me to put my phone down.
And that is a really rare.
Thing to be just fully focusedon a task at hand like that.
(21:45):
And it does allow me todisconnect.
So I know when I'm unbalanced,cooking is the first thing I
stop doing.
I can just see it in my scheduleand I have to like, remind
myself that it's important toget back to the things you
enjoy.
Also a very difficult thing todo well.
Traveling and on the road inhotels is maintaining cooking
and doing that.
Part of it is pushing ourself toexplore new locations and while
(22:07):
I'm traveling and not just,working while on the road
constantly.
Rachel Humphrey (22:12):
It's interesting that you say that
about cooking because one of thethings that I have learned over
the last couple years is thatself-care means different things
to different people.
And for some people it may bephysical exercise or fresh air,
that other types of things.
But for others there are simpleacts that are.
A form of self-care.
And for you with cooking, it'sinteresting to see both that the
(22:34):
absence of it is a sign for youthat you are out of balance, but
also that part of the reasonthat it becomes such a big part
of your harmony is putting yourphone down and that the
relationship between,'cause lotsof people will stand in the
kitchen with the phone and stillbe trying to muster up a meal
here or there.
So it's interesting to see.
(22:55):
How, what a role that, that loveof cooking plays for you?
As far as awareness goes, butalso in the disconnect, which is
nice to see.
Jacob Messina (23:04):
Yeah, and I would say part of that is because I'm
also not a recipe chef, so I'llget an inspiration and then it
is a creative exercise for me aswell because it's more like,
Ooh, I have a little bit ofthis, or What if I tried it this
way this time?
So it does make me flex the thecreative side of how do I keep
improving or learning somethingnew there.
Rachel Humphrey (23:23):
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 muchis I think we are all works in
progress, whether it's ourpersonal journey, our
professional, our leadershipjourneys.
So looking back on that littlekid playing video games or at
whatever age you want,graduating from college,
(23:43):
whatever it may be.
What is one of the pieces ofadvice you would tell your
younger self, either about howthings turned out for you today
or maybe about something youwish you had known then that
might've helped in your journey?
Jacob Messina (23:58):
I think the advice I would give is it's
about how importantrelationships are.
And I'm not saying just likenetworking or anything like that
it's identifying people that youcan work really closely with and
you can ident, you can buildtrust with.
And that can be people you workreally closely with or that
maybe you have something incommon with, it could be a third
party colleagues at othercompanies as well.
(24:20):
But invest in thoserelationships early and continue
to and really put aside the timeto be helping others.
When you go out of your way forsomeone and it's completely
unexpected, it's something thatthey will remember.
It's some, it's the beginning ofa relationship that can have
paid dividends for many years ordecades to come.
We have a very unique industryin the sense that it's very
(24:43):
large, but also tiny at the sametime.
And I'm always blown away by.
How many people from earlystages in my career remember a
project I worked on or apresentation I gave, and then
that had an impact on howsomething they learned and were
able to apply later in theircareers too.
So I would say go, really spendthe time and dedicate time to
(25:05):
helping others, even if itdoesn't even if it's not for an
immediate return or you'reworking with them directly, but
it will pay dividends for sure.
Rachel Humphrey (25:13):
I love the concept of investing in
relationships too.
It's such a different conceptthan networking or just building
relationships, but if you investin those relationships, you
never know how or why or whenthey are going to come back.
So I love that advice.
We are wrapping up on time hereand we've certainly covered a
lot of ground, but thinkingabout.
The motto of its personalstories, which is empowering
(25:35):
personal success.
Is there any one piece of finaladvice that you'd like to share
with our audience?
Jacob Messina (25:42):
Rachel, I think you said it really well in one
of your earlier questions.
And I would go back to thatabout curiosity.
It is something that helps youconstantly learn and it never
stops.
So if there's any advice I couldgive that has helped me in my
career it's to be.
Curious to learn from others andto try to incorporate that into
your daily life.
(26:02):
But to never stop askingquestions.
So that, that would be theadvice I would give to as many
people that are willing tolisten,
Rachel Humphrey (26:08):
I love that.
Jacob, I'm really thrilled thatyou decided to join me a little
bit today, getting to know alittle bit more about you and
your leadership journey.
But thank you so much forjoining the program today and
sharing everything with us.
Jacob Messina (26:22):
Great.
Thanks Rachel.
It was a pleasure.
Rachel Humphrey (26:24):
To our audience out there.
We hope you've enjoyed our timetoday with Jacob, and you can
head on over to its personalstories.com to hear from over
200 other hospitality industryleaders who have likewise shared
their personal journeys andtheir leadership insights as
well.
And have a good afternoon.
Good afternoon.
I am Rachel Humphrey with itsPersonal Stories.
We are a nonprofit dedicated toempowering personal success in
the hospitality industry.
And today I'm really excited tobe joined by Jacob Messina, the
CEO first.
Stay in touch.
Jacob, welcome to the program.
Jacob Messina (00:17):
Thank you for having me, Rachel.
Appreciate it.
Rachel Humphrey (00:20):
We are gonna jump right in.
Everyone knows who listens tothe series regularly, knows that
I absolutely love how uniqueeverybody's path to leadership
is within the hospitalityindustry.
That no two have to mirror oneanother, but you yet can have
this very distinct path toleadership.
So tell us a little bit aboutyourself and a little bit about
your path to leadership and howyou got to where you are today.
Jacob Messina (00:42):
Sure.
So let's see.
I'm Jacob Macina, EO of StayTouch.
I've been in the role for aboutthree years but my background is
really more on the hotel side ofthings.
Before coming over to running asoftware company I've always.
Been really interested insoftware and technology.
And I would say that what got meinterested in hospitality, it's
a little unique.
(01:03):
It started with computer gamesat an early age.
Games like the Sims andRollercoaster Tycoon where
you're managing large scaleoperations, but also you have to
think in, manage complexpeople's interests, likes,
behaviors and things like that.
And I really enjoyed these typesof games growing up and was
challenged at an early age by myparents of how do you apply
(01:24):
these type of things to like acareer, what or an industry.
And that's what brought meoriginally actually to
restaurants.
And I got my start working inrestaurants at about like the
age of 16 in New York City.
I'm a native New Yorker.
And I very quickly, over acouple years learned that
working in restaurants is moreof a passion than it was a
career for me.
It's a really grueling anddifficult life and I have a ton
(01:46):
of appreciation for all thepeople that work in the food
service industry.
But I realized at that pointhospitality was really a career
and a passion of mine.
And I switched over to the hotelside.
And where I got to get my handsdirty, working front desk in in
a couple hotels in in New YorkCity.
And that was really the start ofmy hotel career and went on from
there.
Rachel Humphrey (02:06):
I love the tie to video games, so for anyone
who's out there with kids whoare playing and they wonder what
will that ever lead to?
Now they have a prime example ofthat.
Jacob Messina (02:16):
Yeah, there's lots of good lessons you can
learn from them.
So
Rachel Humphrey (02:19):
yeah.
One of the things that I thinkthat is.
Interesting thing with yourjourney is that you assumed the
CEO role from an interim CEOrole and a role I actually held
at one point in my career aswell.
I'm curious for you if you thinkthat you lead differently with
an interim CEO title than you dothe CEO title, but then also
(02:41):
from the role you had.
Prior to becoming the interimCEO, maybe what type of
leadership changes you made tolead differently with those
different career titles?
Jacob Messina (02:54):
Yeah.
When I started at Stay in Touchas the interim CEO it was at my
first time, first CEO role stillis.
And I would say that there wasdefinitely a bit of a learning
curve there in terms of findingmy specific leadership style.
More so just.
Making sure that the way that Ioperated in other roles was
gonna work at this scale.
(03:14):
This was, I went from managing ateam of, I think 12 to a team of
about 150 or 130, and we grew to150.
And part of that wasunderstanding could I have the
same level of connection with alarger team that I wouldn't get
to see every day?
And, we, I have employees in 18countries today.
What I found is that it doesscale because it's a mixture of
(03:35):
just understanding people atmore of, just than an employee
level, understanding what'stheir motivations, what makes
them tick as humans.
I really try to understand thatbefore having any kind of
conversations or working withpeople.
So that definitely was in thatinterim into full-time CEO and
being a permanent position.
Before that, my role was a bitdifferent.
(03:55):
I was not leading a softwarecompany.
I was leading technology for thethird largest owner and operator
of hotels in the us.
So I was actually a customer ofstay in touch before I came over
to run the organization.
So that's been a veryinteresting mindset change to
bringing that customer ledknowledge base to this company
and really being able to runthings through that lens and
(04:16):
what our customers are askingfor and have been in their
shoes.
And understand what's affectingthem on a daily basis.
Rachel Humphrey (04:24):
I like the self-awareness to see can I
scale how I know that I am aleader in one sense, and then
applying it to another, and thenprobably the satisfaction and
realizing that it does, becauseit's a way that's leading that's
very genuine to you.
And so to be able to grow thatas.
The number of people that youwere overseeing grew as well?
(04:44):
It's interesting to me ways thatI have grown as I've watched and
conducted a lot of theseinterviews.
One of the things that's beenreally eye-opening for me is how
many leaders in our industrydescribe themselves as curious.
And it was a word that I wouldnot have used, but I have found.
Over the last couple years thatit seems to be one of the
threads that runs through a lotof our industry leadership.
(05:07):
I'm wondering if you think thatyou are a curious person, the
types of things you're curiousabout, and then maybe what's one
thing today professionally orpersonally that you're curious
about?
Jacob Messina (05:18):
I would definitely describe myself as a
curious person.
It's what has propelled me in mycareer from an early early age.
I was at a company for a whilewhere through a series of events
I had multiple different bosses.
They either left theorganization or.
Were asked to move on and Ireally was able to rise just by
taking on responsibility withoutbeing asked.
(05:40):
And part of that was I was justcurious to learn and curious to
do things differently and to tryto do things better.
And then, upper management wouldcircle back six months later and
be like, oh, did we ever fillthat role?
And they're like oh, that thatintern seems to have stepped up
and is doing it.
And that's how I really was ableto progress.
So I would say it's really beena driving thing.
Force in a lot of what I do andhow I got to where I am today is
(06:02):
just remaining curious.
Asking questions is probably themost powerful thing that you can
do, not just as a leader, but inany role.
If someone, I've always had arule that if someone can't under
it can't explain the why we dosomething the way we do.
That generally means that theydon't understand what they're
working on or what the path tosuccess is gonna be.
(06:23):
I've always you have to berespectful.
'cause sometimes it can sound alittle or come off a little bit
challenging, but if you do it inthe right way, it's all
constructive and you can buildand learn a lot from that.
Definitely a curious personacross all traits.
Rachel Humphrey (06:38):
And do I remember you told me that you
actually ask when you'reinterviewing others for open
roles about their curiosity?
Jacob Messina (06:45):
Yeah.
Hopefully.
I won't give this away to toomany people, but I do ask two
questions on every interview.
So I ask tell me about somethingyou're curious about, and I also
ask, tell me about something youfailed and time you failed and
something you learned from it.
Those are my two major interviewquestions.
Rachel Humphrey (07:01):
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 youlooking to tell from that
question?
You've decided this is animportant enough one that I'm
gonna be able to make perhaps adecision based on that question.
What are you looking for?
Jacob Messina (07:21):
I'm looking for it.
It's generally a question peoplearen't expecting.
Both questions are ones thatpeople aren't expecting.
So it's more about how peoplecome to a conclusion.
So when I ask about curious,it's either what is someone
passionate about?
I'm always looking forsomething.
And it could be I hope it'ssomething completely unrelated
to technology or hospitality butit helps people open up a bit in
(07:43):
terms of things outside of theircareer or work life.
And then, the second part ofthat on the question about tell
me something you failed at andwhat you learned from it.
It, that one's a little bit of atrick question.
Everyone focuses on what did Ifail at and trying to make it
not sound terrible when thereality is I don't really care
what they say at that point.
I'm listening to what did youlearn from it?
(08:04):
And if you don't learn from yourmistakes, that's a number one
red flag for me.
Rachel Humphrey (08:08):
Excellent.
No, absolutely.
Sticking with the idea ofleadership, we have a lot of
people who say I was born tolead and we have others who say,
even today, I'm not sure I wouldconsider myself a leader.
When you think about the termleadership, 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
(08:30):
along the way where it went foryou?
You know what?
I'm actually part of aleadership team now, or I lead
this organization today.
Jacob Messina (08:38):
Yeah, and it's a great question.
I honestly never really sawmyself as a leader in the early
stages of my career.
I thought of myself as a reallystrong individual contributor
and one that was able to workreally well with a lot of
different people and differentworking styles.
But I did think of myself.
Not as a leader or in the earlystages, mostly because I didn't,
(09:02):
it wasn't a muscle that I got toflex very often in the early
stages of my career, or I didn'tthink I did.
And I realized I was wrong.
I didn't realize how much actualleadership and management I was
doing, even in the early stages.
At one point I was managingthree or four third party
agencies each of which had sixto eight people assigned to our
account for a hotel company Iworked at.
(09:24):
And I realized that I wasleading this and I had to create
motivation and inspirationproject management across these
different orgs.
And while they weren'temployees, they didn't directly
report to me.
There was an element ofleadership from that.
And I didn't realize it in themoment, but I was learning those
skills.
And, for so long I thought of itjust as, oh, I didn't have
(09:46):
direct reports, so I wasn'tleader when in reality it was
really the relationships I hadat this large scale organization
that I could be a leader just byworking with other groups in the
company and helping them besuccessful or, removing
roadblocks so that they could doother things.
There was a lot of leadershipthat I gained from that, or
skills that I ended up using ina leadership career later.
Rachel Humphrey (10:09):
I really like the evolution of that as well as
to how you saw yourself and thenwhen that.
Self-perception started tochange how the skills came along
with it.
You have an interestingbackground.
You mentioned in technology, andwe are in an industry that it is
critically important that westay either on top of or even
(10:29):
ahead of growing trends andtechnology seems to change
faster.
Then any of us can stay abreastof it.
Where do you turn for continuousgrowth to make sure that you
know what's going on in theindustry, what's going on in
your field specifically, andthat you as a company are
meeting the industry where it'sat or even leading the industry
(10:50):
into where you're going.
Jacob Messina (10:52):
Yeah.
It's definitely a tricky one,especially as I've taken steps
further away from the endcustomer or client, and that's
one that I really focus and tryto spend as much time as I can
with our customers tounderstand, listen, what are the
challenges that they're runninginto?
I find so often, and I was oftenin this position when I was on
(11:12):
the other side and a customer ofmany technology products, people
were building things that didn'tapply to me.
And, they thought it was thisamazing innovation and it felt
really flat.
So I, coming from thatbackground I really do spend
time with our customerslearning, listening, spending
time with their teams andunderstanding how they're using.
Technology'cause it's off veryoften.
(11:34):
It's not how, the product wasever designed or the team at a
company thinks it's being used.
So to make sure that you'rereally understanding and in the
weeds to a degree so you cangain a lot of perspective from
that.
Rachel Humphrey (11:47):
Is that the same advice you would give to
your team or rising leaderswithin the industry who you want
to make sure continuing toinvest in themselves or in their
own growth from a really, asubstantive matter standpoint.
Jacob Messina (12:01):
I, I would, I don't think you can lead from an
ivory tower.
You need to understand howeveryone is working both
together and in their ownindividual roles.
How their how they relate to andleverage technology on a daily
basis.
Because we often have thesepreconceived notions, every
technology company thinks thateveryone's adopting all elements
(12:22):
of their product.
When in reality they may miss anarea or miss a release and
things like that.
And that can really affect howthey leverage your product.
So I think it's really importantto take a step down every now
and then and make sure that youare spending time, in the
trenches and understand whatother people are going through
and,'cause it's not, it's oftennot what you think.
Rachel Humphrey (12:42):
I like that.
You mentioned that you had beenin your current role for about
three years now, and I wannafocus really only on the last 12
months or so.
Tell me one lesson that you'velearned or one of the biggest
lessons that you've learned inthe last 12 months, and how or
if it will impact yourleadership evolution moving
(13:03):
forward.
Speaker 3 (13:06):
Let's see.
Something I have learned in thelast 12 months, I.
Jacob Messina (13:14):
I would say everything takes longer than you
think it's going to.
And it's something that you knowit was that and try not to be a
perfectionist.
It's something I'm definitelynot but it's something that I've
been coaching a lot of our teamsaround, instead of trying to do
things perfectly the advice Igive is plan for when things go
wrong.
I'd rather people and our teamspend time understanding how
(13:38):
this could go sideways and beprepared for that.
And I think that is anincredibly important part of
any, product or project thatpeople don't spend enough time
on.
Everyone wants to get it right.
But in the reality ofhospitality is that it's
incredibly complex and nothinggoes right the first time.
So it's better to be preparedfor when things are gonna go
(14:01):
down a difficult direction andbe prepared for them, have
contingencies in place, and toprotect your downside than to
try to do it perfectly the firsttime.
And I think you win a lot ofrespect with your customers and
clients and, other people thatyou work with, colleagues by
being prepared in thosesituations as opposed to just
hoping it goes perfectly andthen being disappointed when it
(14:22):
doesn't.
Rachel Humphrey (14:23):
I'm gonna ask you a follow up to that in a
second, but I'm gonna tell youthat's interesting that you just
mentioned that because that'sactually how I lead when I know
that I need buy-in from a lot ofdifferent stakeholders.
Okay?
I try to anticipate why are theynot going to want whatever I
want to happen, and then how doI be prepared to address that?
So it sounds like a similar.
Strategy here.
But my follow up question isactually, do you follow that own
(14:47):
advice?
So are you able to say, okay I'mnot seeking perfection, I'm
seeking to anticipate all of theways it may not be perfect, and
then how am I gonna navigate it?
Jacob Messina (14:58):
I'm a big advocate for this, and I do
follow this advice to the pointwhere, my sales team sometimes
get mad.
Me when I am part of salespitches or meeting with new
customers.
I often tell people, this, notechnology project has gone
exactly perfectly.
There's always a hiccup.
There's always something.
There's always something thathappens in your business that we
need to be prepared for.
(15:18):
We are the team that's gonna bethere for you when things get
difficult, as opposed to theteam that's gonna come in here
and say everything's gonna worka hundred percent on day one.
That's unrealistic.
So you need to be authentic andnot just pretend everything
works right out of the box.
It's, you wanna pick a teamthat's gonna be with you when it
doesn't, so
Rachel Humphrey (15:38):
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 uswith.
Perfectionist tendencies thatcan be hard to step away from.
But that's actually a perfectsegue.
So when things don't goperfectly, let's talk about
overcoming obstacles for asecond.
One of the, no one reaches anylevel of leadership without
(16:00):
having challenges or obstaclesalong the way.
What is the approach you usewhen you do maybe have some
challenges, things that don't goyour way, and then is there any
particular example you can thinkof that maybe you learned, you
talked about when things gowrong, when you're interviewing
people.
What did you learn from it?
What is maybe a challenge thatyou came across that you took a
(16:20):
big lesson away from at the endof the day?
Jacob Messina (16:23):
Yeah, this ties in well with my own interview
question, and I would be itwould be embarrassing if I
didn't have an answer to thatwithin this.
No, I, for me it's about it,everyone fails many times in
their career.
Many times in a week we fail atthings.
There's micro moments of thattoo.
So I do try to take a step backat the end of every week and say
(16:44):
not just what could I have donebetter?
It's more what could I have donedifferently to achieve a
different outcome?
Difficult to be regimented aboutthis and to find the time.
But when I'm able to, I take astep back and try to understand
what did I learn and what couldI have done differently in this
previous week, month, or periodof time?
I've had periods in my careerand going back to, what are the
(17:05):
things that I've failed on onetime, a long time ago now, I
took on far too many projectsthat I was not in control of.
I was in charge of executingagainst them, and it was a scope
of work that I wasn't fullybought into and I didn't have
control over.
And as a result, the expectationthat had been set at the
company.
Didn't match with the scope ofwork with the external parties
(17:27):
we were working with.
So we had this huge e even ifexecuted perfectly, everyone was
gonna be disappointed orunderwhelmed.
And I realized at that pointthat I, the failure, there was a
failure to communicate veryearly in a stage of a new
relationship, both internallyand externally.
So that's one thing that Ireally work at, is when we're
embarking on a new project.
(17:49):
Talk to the customer and talk toyour own teams about what are we
trying to achieve here and why?
Rachel Humphrey (17:54):
I love that from a communication standpoint
as well, because I think one ofthe things that I have found
challenging is not saying outloud what's in my head, assuming
everybody knows what I know, andso then people start questioning
things.
I'm like, wait, but you know allthat, and it really doesn't.
Work out that way'cause theydon't know all of
Speaker 3 (18:11):
that.
Yeah.
Rachel Humphrey (18:12):
I wanna turn our attention now to mentors and
allies and champions and talkabout the importance of having
people that are there to bounceideas off of, to overcome
obstacles with, to.
Be a hype squad, whatever typeof support system, but also in
this industry as you've had newroles, new opportunities where
(18:34):
you look to for guidance.
So talk a little bit about therole of mentors and champions
maybe in your experience, andthen how do you try to do that
for others at this point in yourcareer?
Jacob Messina (18:46):
Yeah, I, I would say throughout my career I've
had some spec, I've had amazingbosses.
I've had ones that I was not onthe same page with.
And what I've really boiled thatdown to in terms of where I was
able to see myself be successfulis around trust.
When I had trust with.
The person I reported to andwith my team I and now to look
(19:09):
back on those teams that werereally built and surrounded by
trust.
I look back and I can see howmuch more work product I was
able to accomplish.
'cause I wasn't worried aboutCYA or just, am I stepping on
toes.
We were all moving the samedirection and even if we didn't
agree, we trusted each other toreally have the company's
(19:30):
interests in mind.
The team's interests at mind, atheart, sorry.
And.
That was really remarkable to meis just to see how much more I
could get done by that.
So then, when I think about howI build teams now, it's really
goes down to how can I buildtrust quickly with people, which
can be very difficult today,especially in remote
(19:51):
environments.
Stay in touch as a remotecompany I make a point of trying
to see all my direct reports asoften as possible.
I travel quite a bit so on theroad and whatever I can get to
see them so it can.
Be difficult to build thosebonds and that trust, but making
sure that you have regularcheck-ins and people understand
that, again, it's okay to fail.
It's as long as you learn fromit build from it onto the next
(20:13):
project is really importantThere.
Rachel Humphrey (20:16):
It's interesting'cause the word trust
seems so basic and it'sunderstanding, but really such
an important way for you both torecognize how much that trusting
relationship impacted youroverall productivity or your
overall success in your role andnow how you're able to pay that
forward with your team.
You just mentioned traveling alot to see your team and so I
(20:39):
learned a long time ago that ifI say work life balance, it's
gonna get people veryunbalanced.
The question, question in and ofitself.
But I am curious over the yearsmaybe how you are able with a
demanding career, with ademanding travel schedule of
finding some sort of harmonybetween your professional career
and your personal life, andmaybe how that's changed over
(21:01):
time or throughout differentroles.
Jacob Messina (21:04):
Yeah, I definitely wouldn't be the first
one to tell you that I have thisfully figured out.
Definitely an evolution thathappens over time.
And we all have ebbs and flowsof when we're good at the
work-life balance and when we'renot.
What I really do try to focus onI love to cook and it's
something that I find reallyrejuvenating.
One, because I, I.
(21:24):
Am unable to do cook simply,even when I'm cooking, just for
me and my wife, I end up cookingfor 10, 12 people.
So I love to cook and it I getvery fixated on it and I wanna
do the best possible, so itforces me to put my phone down.
And that is a really rare.
Thing to be just fully focusedon a task at hand like that.
(21:45):
And it does allow me todisconnect.
So I know when I'm unbalanced,cooking is the first thing I
stop doing.
I can just see it in my scheduleand I have to like, remind
myself that it's important toget back to the things you
enjoy.
Also a very difficult thing todo well.
Traveling and on the road inhotels is maintaining cooking
and doing that.
Part of it is pushing ourself toexplore new locations and while
(22:07):
I'm traveling and not just,working while on the road
constantly.
Rachel Humphrey (22:12):
It's interesting that you say that
about cooking because one of thethings that I have learned over
the last couple years is thatself-care means different things
to different people.
And for some people it may bephysical exercise or fresh air,
that other types of things.
But for others there are simpleacts that are.
A form of self-care.
And for you with cooking, it'sinteresting to see both that the
(22:34):
absence of it is a sign for youthat you are out of balance, but
also that part of the reasonthat it becomes such a big part
of your harmony is putting yourphone down and that the
relationship between,'cause lotsof people will stand in the
kitchen with the phone and stillbe trying to muster up a meal
here or there.
So it's interesting to see.
(22:55):
How, what a role that, that loveof cooking plays for you?
As far as awareness goes, butalso in the disconnect, which is
nice to see.
Jacob Messina (23:04):
Yeah, and I would say part of that is because I'm
also not a recipe chef, so I'llget an inspiration and then it
is a creative exercise for me aswell because it's more like,
Ooh, I have a little bit ofthis, or What if I tried it this
way this time?
So it does make me flex the thecreative side of how do I keep
improving or learning somethingnew there.
Rachel Humphrey (23:23):
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 muchis I think we are all works in
progress, whether it's ourpersonal journey, our
professional, our leadershipjourneys.
So looking back on that littlekid playing video games or at
whatever age you want,graduating from college,
(23:43):
whatever it may be.
What is one of the pieces ofadvice you would tell your
younger self, either about howthings turned out for you today
or maybe about something youwish you had known then that
might've helped in your journey?
Jacob Messina (23:58):
I think the advice I would give is it's
about how importantrelationships are.
And I'm not saying just likenetworking or anything like that
it's identifying people that youcan work really closely with and
you can ident, you can buildtrust with.
And that can be people you workreally closely with or that
maybe you have something incommon with, it could be a third
party colleagues at othercompanies as well.
(24:20):
But invest in thoserelationships early and continue
to and really put aside the timeto be helping others.
When you go out of your way forsomeone and it's completely
unexpected, it's something thatthey will remember.
It's some, it's the beginning ofa relationship that can have
paid dividends for many years ordecades to come.
We have a very unique industryin the sense that it's very
(24:43):
large, but also tiny at the sametime.
And I'm always blown away by.
How many people from earlystages in my career remember a
project I worked on or apresentation I gave, and then
that had an impact on howsomething they learned and were
able to apply later in theircareers too.
So I would say go, really spendthe time and dedicate time to
(25:05):
helping others, even if itdoesn't even if it's not for an
immediate return or you'reworking with them directly, but
it will pay dividends for sure.
Rachel Humphrey (25:13):
I love the concept of investing in
relationships too.
It's such a different conceptthan networking or just building
relationships, but if you investin those relationships, you
never know how or why or whenthey are going to come back.
So I love that advice.
We are wrapping up on time hereand we've certainly covered a
lot of ground, but thinkingabout.
The motto of its personalstories, which is empowering
(25:35):
personal success.
Is there any one piece of finaladvice that you'd like to share
with our audience?
Jacob Messina (25:42):
Rachel, I think you said it really well in one
of your earlier questions.
And I would go back to thatabout curiosity.
It is something that helps youconstantly learn and it never
stops.
So if there's any advice I couldgive that has helped me in my
career it's to be.
Curious to learn from others andto try to incorporate that into
your daily life.
(26:02):
But to never stop askingquestions.
So that, that would be theadvice I would give to as many
people that are willing tolisten,
Rachel Humphrey (26:08):
I love that.
Jacob, I'm really thrilled thatyou decided to join me a little
bit today, getting to know alittle bit more about you and
your leadership journey.
But thank you so much forjoining the program today and
sharing everything with us.
Jacob Messina (26:22):
Great.
Thanks Rachel.
It was a pleasure.
Rachel Humphrey (26:24):
To our audience out there.
We hope you've enjoyed our timetoday with Jacob, and you can
head on over to its personalstories.com to hear from over
200 other hospitality industryleaders who have likewise shared
their personal journeys andtheir leadership insights as
well.
And have a good afternoon.
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