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In this episode of The Unchecked-In Podcast, Bobby Marhamat sits down with Jacob Messina, CEO of Stayntouch, a cloud-native PMS helping hotels streamline operations and deliver exceptional guest experiences. Jacob shares insights from his journey across hospitality—from working in restaurants as a teen, to leading operations at Lowe’s Hotels and MCR Hotels, to now driving innovation in hotel technology. He dives into the real challenges hotel operators face with tech adoption, why independent hotels often outperform big brands in flexibility and guest experience, and how AI and automation can enhance—but not replace—the human touch in hospitality. What you’ll learn in this episode: How to approach hotel technology without fear of choosing the “wrong” system The balance between automation, AI, and personalized guest experiences Key operational processes that drive the biggest impact on staff and guest satisfaction Lessons learned from mistakes early in Jacob’s career and how they shaped his leadership The philosophy behind roadmap planning, prioritizing customer requests, and standardization Insights on change management and making technology actually work for your team TIMESTAMPS: 00:00 Introduction 00:28 Meet Jacob Messina 01:41 Cornell & Hospitality Roots 03:54 Independents vs Big Brands 04:53 How Hotels Make Tech Decisions 05:54 Biggest Screw-Up & 'Untouchables' 07:24 Roadmap Philosophy 09:03 Change Management Tech 10:32 Tech vs Human Touch 11:52 Leadership Superpower 13:18 Fixing Booking & Pre-Arrival 15:09 Vendor Partnerships & UX Wins 18:10 Advice to Young Jacob & Tech Adoption 23:00 Stayntouch & Final Thanks Links: Jacob on LinkedIn: / jacob-messina-b6361311 Company Website: https://www.stayntouch.com/ Connect with Bobby Marhamat: Website: https://bobbymarhamat.com/ Facebook: / bobbymarhamat LinkedIn: / bobbymarhamat Instagram: / bobbyhabanero AI Hotel Revenue Management Software | TakeUp TakeUp: https://takeup.ai/ LinkedIn: / takeup-ai Instagram: / takeupforhospitality Facebook: / takeupforhospitality YouTube: / @takeup-for-hospitality #hoteltechnology #hospitality #podcast #interviews6tvtv 1BNTVFQA8WKJJRZN