Jacob Messina is the CEO of Stayntouch, a leading hospitality technology firm that provides cloud-based property management systems (PMS) for hotels. Under his leadership since 2022, Stayntouch has achieved record growth and become one of the fastest-adopted PMS platforms in the industry, enabling hotel clients to implement new systems in as little as 48 to 72 hours. Jacob's diverse hospitality background began at age 15 in frontline restaurant and hotel roles, later building Loews Hotels' digital marketing practice from scratch and overseeing technology for 150+ properties at MCR Hotels.

Jacob Messina, CEO of Stayntouch, breaks down how a cloud PMS built by former hoteliers cuts implementation from months to days and staff training from weeks to about an hour. He explains why distribution is the most overlooked revenue function for independent hotels and what to do about it.

Before leading Stayntouch, Jacob spent six months at Loews Hotels manually merging guest profiles in Opera V5. Forty hours a week of clicking through multiple screens for a task that should have been automated. That experience shaped his view of what hotel technology should do: give time back to the people using it, not create more work.

At MCR Hotels, he oversaw technology across 150-plus properties. When a soft brand inspection failed a week before opening, his team had to stand up an entire independent tech stack in eight days. Stayntouch made it work. That scramble became the catalyst for productizing fast implementations. Today, Stayntouch can get a hotel live in 48 to 72 hours.

Three principles drive the company under Jacob's leadership. First, customer support where you talk to a real person within seconds. No phone tree, no callback queue. Second, 1,200-plus integrations offered at no cost, with a fully open API for anything not yet connected. Third, intuitive design that gets a new front desk agent checking guests in within an hour, even if they've never worked in a hotel.

One counterintuitive decision stands out: Stayntouch deliberately slowed its release cycle from every two weeks to every four to six weeks. Not because development couldn't keep pace, but because hoteliers are already tracking updates from six to eight other systems. Shipping faster than operators can absorb creates waste, not value.

On distribution, Jacob's advice is straightforward. Stack your channels from lowest to highest cost of acquisition. If you know what you're paying Booking.com, put a portion of that spend toward driving direct bookings instead. In OTA-heavy markets like Hawaii, that channel shift is where the margin lives.

The conversation also covers ancillary revenue. Stayntouch's upsell module is included free in the PMS subscription and runs inside the mobile check-in flow. Guests can upgrade based on room attributes and local experiences. Jacob points to Castle and MacNaughton in Hawaii as groups that have made this work by investing in clear room-type definitions and content that tells the story of what makes each property worth the upgrade.