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.

Hillary Folkvord is the Founder of Lady H, a lifestyle and consulting brand focused on hospitality, entrepreneurship, and mentorship. She is the owner and operator of boutique hotels, including RSVP Motel, Farmers Daughters Cafe, and The Cottages at Bigfork, located in Montana. With over 17 years of experience in hospitality, she has expertise in property development, branding, revenue strategy, and independent hotel operations. Hillary also advises emerging hoteliers on marketing, financial management, and building guest-centered hotel brands.

Great hospitality isn't just about a beautiful lobby or a high nightly rate. It's about creating a place that feels intentional, local, and memorable while still making the numbers work. So how do you build boutique hotels that are both deeply guest-centered and financially successful?

Drawing from her experience as a boutique hotelier, Hillary Folkvord explains that it starts with story and place. For her, every property has a narrative, whether it's a nostalgic lakeside retreat or a funky roadside motel, and her job is to bring that story to life through design, partnerships, and guest experience. When that sense of authenticity is clear and consistent, the right guests find you, return, and turn a thoughtfully built brand into a sustainable business.

In this episode of The Lights On Podcast, Kin Sio is joined by Hillary Folkvord, Founder of Lady H, to discuss building guest-centered boutique hotels that perform. They explore turning local partnerships into real revenue, playing the OTA game strategically, and using storytelling to differentiate each property. Hillary also shares advice on hiring the right experts and knowing when to invest in revenue management and marketing.

Kin Sio is the CEO of Lights On, a company specializing in digital marketing and revenue management for independent hotels and resorts. He grew up in Macau and transitioned from a successful tech career to entrepreneurship after acquiring Lights On in early 2025. Drawing on his background in technology and hospitality, Kin helps small hotel businesses optimize pricing, distribution, and their online presence. He leads his team with a focus on data-driven strategies that increase visibility and drive revenue growth for clients.

In the hospitality industry, where competition is fierce and guest expectations are higher than ever, how can smaller hotel owners compete with the big players?

For Kin Sio, the answer lies in modernizing the way smaller hotels operate. He explains that many hotel operators are unaware of the powerful tools available to optimize pricing, manage distribution, and refine marketing strategies. Kin believes that even the smallest hotels can dramatically increase their profits by implementing smarter, data-driven decisions — something that was once only accessible to larger chains.

In this episode of The Lights On Podcast, Kin Sio, CEO of Lights On, is interviewed by Chad Franzen of Rise25 to discuss modernizing hotel operations and maximizing revenue. Kin explains how integrating revenue management principles and digital marketing can help small hotels thrive, the importance of leveraging technology to streamline operations, and how even boutique hotels can benefit from corporate-level strategies.