In this episode of The Mid-Market Multiplier, Chris Happ sits down with Todd Dooling, Chief Information Officer of Crow Holdings, to explore what practical AI leadership looks like inside a complex, growth-focused organization.

Todd shares his unique journey from application development to leading business technology, how Crow Holdings fosters a culture of empowerment, and why that matters to employees. The conversation also unpacks why incremental efficiency gains with AI will pay off significantly for companies in the long run, and what mid-market leaders must do to implement AI effectively, including securing top-down support to cultivating subject matter experts.

They also discuss the evolving impact of AI on workforce dynamics, and why curiosity, adaptability, and proactive learning will define the next generation of business leaders.

A must-listen for executives looking to move AI from experimentation to measurable impact.

In this episode of The Mid-Market Multiplier, we sit down with multi-time founder Kate Boyer as she shares the entrepreneurial journey behind building the Anatomie brand and the operating principles that helped her scale. Kate emphasizes that strong core values, grassroots marketing, and personal customer relationships are foundational to durable growth—and that speed in customer service is a direct signal of respect for the customer’s time. She describes entrepreneurship as a constant cycle of learning and adaptation, where leaders must stay agile as markets evolve.

Kate also makes a clear case for embracing technology, especially AI, as a competitive advantage for mid-market companies. She explains how AI can improve efficiency in areas like design, marketing, and customer engagement, enabling faster decisions and more responsive execution. 

Her advice to CEOs is practical: start small, focus on eliminating inefficiencies, and lead by example so teams feel confident adopting new tools. Throughout the conversation, she highlights curiosity and adaptability as the most important traits to hire for, noting that the easiest part of AI adoption is getting started—the real challenge is committing to it and scaling with consistency.

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.