December 8, 2025
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.
It's not 'what could AI do?' It's 'what do I not want to do?' Let's get rid of that.
Dina is a multifaceted hospitality industry leader committed to crafting meaningful and thoughtful guest experiences. As President of Staypineapple Hotels, a distinguished boutique hotel brand, she provides strategic guidance to shape the brand's trajectory.
Dina's influence extends beyond the boardroom, as she is widely acknowledged as a leader and mentor in her field. Her remarkable achievements include being honored with the prestigious Top 50 Women Leaders in Hospitality award in 2024 and 2025, as well as being featured in The Boutique Hotelier's 2025 Women in Hotels and Power List of Industry Titans 2024, a testament to her exemplary contributions and leadership in the sector.
Beyond her role, Dina has actively contributed to the industry's knowledge base. Her insights and expertise have found expression in multiple publications and podcasts focusing on leadership, technology, and the unique nature of boutique hotels. Through her thought leadership, she continues to shape conversations and drive positive change within the industry.
Chris Happ is the CEO of VirtuousAI, where he’s pioneering a new era of execution for mid-market businesses with BAIO—the world’s first Business Automation, Intelligence & Outcomes platform. A serial entrepreneur and seasoned technology leader, Chris has spent his career transforming how companies operate, scale, and win with data.
Driven by a deep understanding of the challenges mid-sized businesses face, Chris launched VirtuousAI to close The Execution Gap, the costly distance between a company’s strategic goals and its ability to deliver. Under his leadership, VirtuousAI is redefining how businesses compete in the AI era: not by outspending the giants, but by out-executing them. His mission is to empower mid-market leaders to move faster, work smarter, and achieve measurable outcomes that drive sustainable growth.
Before founding VirtuousAI, Chris built and exited multiple successful ventures at the intersection of finance, supply chain, and enterprise software. His background blends deep operational knowledge with a visionary approach to automation and business intelligence, making him a trusted voice on the future of work, data, and strategic AI.
