Jacob Messina, Stayntouch

Jacob Messina became CEO of Stayntouch in April 2023 after six months as interim leader. Prior to that he had been senior vice
president of technology and innovation at MCR Hotels, the third-largest hotel
operator in the United States and the parent company of Stayntouch.

Stayntouch provides a suite of hospitality solutions
including a cloud-based property management system, payment processing, a
booking engine, a channel manager and a guest-facing kiosk. The company works
with independent hotels, major chains and management companies and ownership groups.

In your prior role as senior vice
president of technology and innovation at MCR Hotels, you oversaw 150
technology solutions, including Stayntouch, across more than 150 properties. How
did that prior experience as a Stayntouch customer shape your perspective when
you became CEO?

It definitely has in pretty meaningful
ways. … I represent how a customer is thinking about our product, using our product
and also what they are expecting from our team. … My career has been on the
owner-operator side from a technology perspective, so I’m kind of like the perfect
customer. And I often think, when I see our marketing, our sales efforts, would
this have worked on me? And sometimes we have to make adjustments to what we’ve
been doing historically and make sure that we are talking to customers in the right
way, providing the right level of detail and technical information where it makes
sense as well.


Bethesda, Maryland

What has been the most challenging part of your time as CEO?

We have a lot of priorities within the
company. So a lot of it is how do we take a step back and make sure we are doing
things really well. … We made some changes to our delivery structure so instead
of doing sprints every two weeks and pushing new product, we actually moved to three
to four weeks. It allows us to have a much higher level of confidence in the
quality of work we’re doing, and we’ve actually seen that it has improved our product
philosophy because we have more eyes on every item going out the door. 

The hospitality industry is often
criticized for being too slow – or too cautious – about implementing new
technology. Why do you think that is?

Slow would be generous. I do feel that
we’ve really kind of missed the boat on new technology in the hospitality
space. Our systems that we use for the most part to run and operate hotels are
archaic. We’ve had a couple companies – some of my competitors – that have
really held things back by having on-premise systems that are really not moving
the needle. 

I was with a hotel company for 10
years at the start of my career, and our property management system was
upgraded every two to three years. I could be looking for a small piece of functionality
that was three years away, and I knew I couldn’t do anything about it. And that
was a really frustrating feeling, to know there was optimization and I could be
doing better business and being more profitable but the technology wasn’t there
for us. So I think the velocity that companies are getting by moving to the
cloud is great. 

Beyond the technology itself, does innovation
require a different mindset?

Yes, it’s about priorities within a
company too. Here’s an example. When I was with MCR, the group I ran was
technology and innovation. At other companies that’s a traditional IT group. We
never referred to ourselves as IT, we wouldn’t allow other teams to refer to us
as IT because it has a bit of a stigma. These are just people that do break
fixes, they are not part of driving revenue. And if you think of your technology as just IT and only
think of it when it breaks, you are leaving money on the table.

There were opportunities where we would take over an independent hotel, not
change the physical layout or the way they sold the property, but we would
change and update every system within their tech stack and drive additional
profitability for the property. So if you think of technology and IT groups as
a profit center potentially and a way to drive more to the bottom line, that’s
a much better way. And then you start getting the budgets to be successful
there, instead of just how many tickets did they close, that kind of thing.

How important is it to have startups in the space to push
things forward?

We do need innovation in our space, but innovation just for
the sake of innovation is not helpful. You need to find the balance of taking
what’s worked for some of these legacy companies and adding new spin to it. It’s
no secret that Stayntouch was born out of a group that left [Oracle] Opera
about 10 years ago. And one of the things we’ve done is we’ve focused almost
all of our attention on our differentiating factors from Opera. It’s how do we
have top-notch and above customer support. … We have free integrations, unlike
the business practices of Oracle Opera, and it’s really about that partnership,
it’s not a transactional relationship to us.  

still needs to be fixed when it comes to hotel technology systems?

I don’t think we have enough time. There’s
a lot that still needs to get fixed. The piece that’s just starting and is really
exciting to me is taking down the barriers of entry to the market, which is
great, and the barriers for people to be working together.


If you think of your technology as just IT and only think of it when it breaks, you are leaving money on the table.

Jacob Messina – Stayntouch

One of the core
things we work on at Stayntouch are integrations with partners. That is
something that has really been lacking in the space – really well built, advanced
integrations between systems so information can flow really easily. Too many
times hotels are really faced with this [decision of] I either need to buy an expensive
product to make something integrated or they are limited with only working with
two or three vendors. You can’t build a tech stack that is going to be right
for you and right for your business with just being limited to two to three

You’ve had roles both leading tech and
innovation for a hotel company and now leading a technology provider. If you
were a hotelier, what would be your priorities when it comes to technology?

My answer here may be a little surprising.
I wouldn’t say you need to evaluate each area of your tech stack. Or as the CEO
of a property management system you’d think I’d say, “Put in a different PMS.”
It’s really that if you treat the vendors in your tech stack in a transactional
way, and you think of them only as vendors that sell you a product, you are
leaving money on the table. If you invest in the partnership side of this, if
you build relationships with them, not only will you get better customer
support, but if something breaks like it always does in our industry … they’ll
be on the phone for you when it does. … And if you don’t receive that level of
collaboration back from your partner, that’s when it’s time to look for a new

The online travel agenices are focusing on driving loyalty to their brands – what’s the best way for
hotels to compete with that to drive their own direct bookings? 

The major brands have very powerful
and, frankly, expensive loyalty programs. Our customers with Stayntouch tend to be
independents and chains as well. Where they have seen success is building the
relationships one on one with customers. A lot of it happens when they get the customer
into their property. I think part of it is to be able to put technology to the
side and be able to have those interactions. So instead of clicking away at a
keyboard because you need to create a reservation and then update it 12
different times, it’s really where automation and technology can make that
three clicks and now you can have a conversation [with the guest]. … It is
important that information then is easily stored in systems to be referenced
and utilized later. It’s kind of that marriage of technology and the personal connection.

What about attribute-based selling? It’s
something we’ve been hearing about for years, but implementations have been
slow. What is Stayntouch doing in regard to ABS?

We do have a major release that’s
coming out in the middle of Q2 this year, which will allow for full attribute-based
selling in our product. … We’re taking each individual room and de-coupling the
features of it. Hotels for the longest time have built everything based on
categories – and it’s been a problem because as a consumer, I don’t really know
what the difference between the standard, deluxe and premium is. … We’ve gone
into our own nomenclature, which is not customer friendly. The way this product
works is you can set it so that each individual room is a set of feature sets. It’s
toggle-ons – different view types, different floor types, high floor/low floor,
near the elevator or not. … Where I think it’s really important, though, is you
don’t need a person to be managing this for every request – you build it once,
it pulls from real-time inventory, and then it’s doing all of this behind the
scenes and not having to be done with a lot of manual intervention. 

How is Stayntouch using generative artificial intelligence, and how do you think
this technology will be most impactful for hospitality in the future?

We use AI quite a bit behind the scenes, but we are very cautious
about bringing it to our customer-facing pieces of the product. It’s used quite
often in our engineering, regression testing, quality assurance. … For customer
facing, we really do not believe in putting a step between our customers
speaking to us, such as using AI for support chats. … Part of that is because
we have not seen AI get to a place yet where it can answer complex hospitality questions
better than our team and faster. … Our customers are reaching out to us when they
need help at the front desk and there’s a line growing – that’s not when AI is
going to help them in the process.

That being said, where we see a lot of
opportunity is around automation. Already today within our platform we’ve built
AI in to do automated room assignments using preferences from guests. So if the
guest is a repeat customer, with one click it will assign them to the room they
stayed in last time or use their preferences to find the right room for them. … I’m very excited about where AI is going, and I know we will have more
front-facing or customer-facing applications.  

Stayntouch received a $48 million Series B investment in December – does
that create pressure on your business? And how are you using that funding? 

It does not put pressure on the business. We did spend a lot
of time on fundraising. We had opportunities to do it much faster, but we
really wanted to find the right partner. And we were able to do that with Sixth
Street. They believe in our vision. They believe in how we are growing and how we
are going to continue to grow. With the investment … it means we get to expand
the team in a lot of meaningful ways. We are rebuilding our team and doubling
down on existing investments in Europe. … It also allows every element of our
team to receive more resources. … Part
of where we really see ourselves focusing is how do we stay nimble. … It’s a big
differentiator for us. 

Do you have any plans for mergers and acquisitions? 

That is definitely within our plans now. We don’t look to do
a ton of deals, but we’ll probably look to do between one to two deals per year,
maybe two to three. … We want to make sure we are expanding in meaningful ways. … We don’t believe in reinventing the wheel. If there are great tools and solutions
out there, we want to one, partner with them and two, if it makes sense for
them to join the Stayntouch organization, we would love that.

More from our CEO Spotlight series …

PhocusWire talks to leaders across the digital travel landscape.


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