Booking the Future: PMS, AI, and the War on Clunky Software with Lodgify's CEO

In this episode, Zach sits down with Shaun Shirazian, CEO of Lodgify, for an unfiltered conversation about what’s next in hospitality tech—and what’s not changing. Shaun shares how a meaningful moment on a San Diego balcony more than a decade ago sparked his passion for short-term rentals, and how that guest connection still drives his work building tools for small operators around the globe.

We unpack Lodgify’s long-standing mission to “arm the underdogs” by empowering independent hosts and managers with the same technology advantages as the big players. Shaun draws a clear line between his upbringing as the son of immigrants, his experience at companies like Intuit and PipeDrive, and the deep conviction that great tech should level the playing field for the little guys.

But this episode isn’t just philosophical—it’s tactical. Shaun offers a refreshingly honest take on:

• Why switching PMSs still feels painful, and what needs to change.

• How Lodgify is navigating its role as both OTA partner and direct booking champion.

• What’s holding back the direct booking experience (hint: it’s not just UX).

• How the best future software will be invisible—delivering outcomes, not dashboards.

We also talk AI, and Shaun shares why Lodgify is entering what he calls its “13-year-old growth spurt,” a new chapter he’s dubbed Lodgify 2.0. Think: fewer clunky interfaces, more Stripe-like booking flows, and a relentless focus on what hosts have always cared about—trust, time savings, and more bookings.

This one’s for the rebels, the brand builders, and anyone who’s ever screamed at a janky checkout page and thought, “There has to be a better way.”

Behind the Stays is brought to you by Journey — a first-of-its-kind loyalty program that brings together an alliance of the world’s top independently owned and operated stays and allows travelers to earn points and perks on boutique hotels, vacation rentals, treehouses, ski chalets, glamping experiences and so much more.

Your host is Zach Busekrus, Head of the Journey Alliance. If you are a hospitality entrepreneur who has a stay, or a collection of stays with soul, we’d love for you to apply to join our Alliance at journey.com/alliance.