CEO Spotlight: Jacob Messina of Stayntouch

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.

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.  

What 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

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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 vendors.

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 one. 

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.