Disruption, data & the human touch: Hospitality tech insights from HITEC 2025
In Indianapolis, at HITEC 2025, one of the most candid and forward-thinking conversations on hospitality tech took place at a panel hosted by Cendyn. With industry leaders gathered to share their expertise, the discussion tackled integration issues, outdated systems, and operational hurdles that continue to challenge hoteliers across the globe.
Caryl Helsel, Founder & CEO of Dragonfly Strategists, brought her signature mix of sharp insight and practical strategy to the panel, highlighting the need for systems that support, not sabotage, great guest experiences. Caryl kicked off the session by reminding attendees that while technology may drive the industry forward, it should never come at the expense of personalization.
“If we’re not creating a better guest experience, then we’re just adding tools to be busy, not better.”
Outdated tech is a turn-off
One key takeaway echoed throughout the discussion: technology should serve the guest, not the other way around. Hospitality may be about warm welcomes and human connection, but technology underpins the entire guest journey. From streamlining check-ins to anticipating guest preferences, panelists noted that great technology often fades into the background, allowing service to shine.
Also emphasized was the importance of integrations that eliminate friction for staff. John Burns, President of Hospitality Technology Consulting, recalled a hotel school graduate swearing off a property management system (PMS) after an internship. Caryl shared a young relative’s story: after five months in a hotel job, he quit out of frustration with clunky and extremely antiquated systems at the front office.
The message was clear. Hotels can’t afford to alienate digitally savvy employees with green screens from the 1990s; however, it’s not just about upgrading tools, it’s about rethinking the entire approach.
Integration, not just installation
One standout example came from Michael Hirschler, Chief Growth Officer, from Staypineapple Hotels, who shared how his team used the pandemic as an opportunity to rethink, not just refresh, their entire approach to technology. By overhauling their tech stack with innovative property management and cloud-based CRM solutions, , along with strategic integration support from Dragonfly Strategists, they set the stage for more agile, personalized guest interactions and a streamlined experience for both guests and employees..
The panel also tackled the real-world challenges of implementation. Several shared stories of underutilized tech due to lack of training, lack of change management processes, siloed departments, or failure to align systems with actual workflows. “You can’t just buy a shiny new tool and expect it to solve old problems,” one noted. “It has to work for your team first.”
Caryl emphasized that success starts with vision: “What guest experience do you want to deliver? What do your employees need to support that?” From there, she explained, you map the tech, not the other way around. And change management is the linchpin. “If a hotel team doesn’t use it effectively or adopt the technology, it won’t matter how great the tech is – it will not provide ROI if it is not adopted and if best practices are not taught.”
CRM and PMS: Co-equal partners
The conversation moved into the power of CRM-driven personalization. Staypineapple now sends guests a post-booking welcome message that asks, “What brings you to Chicago?”
The results? Hundreds of heartfelt replies, from concert trips to food pilgrimages. The data flows through their CRM and into their PMS, giving staff the ability to create targeted, memorable touches, like themed cocktails for The Who concert-goers.
It’s a simple but powerful example of zero-party data in action, and a reminder that personalization doesn’t require a loyalty program, just curiosity and follow-through.
The AI elephant in the room
While the panel acknowledged the growing presence of AI in the industry, Caryl made a crucial point: “We’re not ready for it.”
Many hotels can’t ensure consistent, basic content across platforms, let alone feed accurate information to generative AI tools and Large Language Models (LLMs). Content needs to be in natural language and not marketing “speak”. For example, a hotel with a rooftop bar described it online as a "rooftop oasis.” Charming, but not keyword-aligned with how people search and natural language. If AI is the future, content optimization, reorganization, and delivery to agents are the required first steps.
Ricky Castoldi, CSO of Cendyn, highlighted a successful case where conversational AI reduced call center abandonment, and increased reservation conversions while more quickly responding to informational questions from callers. Still, panelists urged caution: AI must enhance the guest journey, not confuse or frustrate it.
Final thoughts: Change is possible, with the right partners
The message throughout the session was clear: change is hard, but necessary. Hoteliers must rethink rigid antiquated systems and invest in the long game. Panelists stressed that tech should never be deployed for its own sake. It must serve people, it must serve our guests, and it must serve strategy.
As Caryl reflected in the closing moments, “Hospitality is about creating moments of joy, comfort, and connection. Technology, when used with intention, can make those moments more consistent, accessible, and memorable.”
Dragonfly Strategists was proud to contribute to this forward-looking discussion, and we thank Cendyn for hosting this timely and important conversation. As the industry continues to evolve, it’s clear that the most impactful innovations will be those that put people, both guests and staff, at the heart of every strategy. If you’re ready to reimagine your hospitality tech strategy with people-first innovation, connect with Dragonfly Strategists to start the conversation.