The Mid-Market Multiplier

In this episode of The Mid-Market Multiplier, we sit down with Dina Belon-Sayre, President of StayPineapple, to explore how AI is reshaping the future of hospitality. From hyper-personalized guest experiences to smarter operations and more agile decision-making, AI is opening new doors for mid-market hotel brands ready to innovate.Dina shares how StayPineapple thinks about customer delight, the role of data in crafting bespoke stays, and why mid-market hotel chains are uniquely positioned to scale with AI-driven insights. We dive into practical examples of how AI can enhance guest journeys—from booking to post-stay engagement—and how leaders can build a roadmap that multiplies both loyalty and revenue.Whether you're in hospitality or leading transformation in any mid-market sector, this conversation is a masterclass in using AI to elevate experience, efficiency, and growth.