Hospitality technology balances tradition with innovation – personal service with digital efficiency. Ryan Hamilton, co-founder of SalesAndCatering.com, represents a different approach to tech leadership.
While competitors race to claim AI dominance through marketing hype, Hamilton’s team has quietly integrated AI for years, creating practical solutions with tangible benefits. This methodical approach has earned him respect as a leader who honors both technological advancement and industry tradition.
As STS Cloud and ProposalPath evolve in an AI-enhanced world, Hamilton shows how established companies can embrace new technologies without losing their identity. In this conversation, we explore how his approach – valuing clarity, conviction, and service – creates an AI vision for hospitality that strengthens rather than diminishes the human element at its core.
Q/Ivana: While most tech executives are racing to make sweeping AI proclamations, your approach seems refreshingly deliberate. You’ve built platforms that have quietly transformed how thousands of hotels manage their sales operations. Now, as AI reshapes the technology landscape, I’m curious – how are you applying that same thoughtful philosophy to this new frontier?
A/Ryan: I’ve come to see AI as a journey we’re navigating collectively, not a destination we’re racing toward. The truth is, our team has been quietly integrating AI into our processes for years now. My business partner and our development team discovered early on that AI tools could enhance their coding workflows, creating space for deeper creative thinking.
What feels different now is the accessibility and maturity of the technology. We’re witnessing a convergence of possibility and practicality that opens doors for meaningful transformation—not just incremental improvement.
Q: That’s fascinating that you’ve been integrating AI tools behind the scenes for so long. How do you personally navigate your role in guiding the company through what many are calling an AI revolution?
A: I’m embracing my role as a translator between technological potential and human-centered application. In our company culture, where trust and clarity are foundational values, my responsibility is to ask the essential questions: How can AI remove unnecessary friction for our customers? Where can it genuinely enhance how we work together? How do we build with AI rather than around it?
This intentional approach ensures we don’t chase technology for its own sake but rather align these powerful tools with who we are and the value we create for our community.
Q: Let’s talk about implementation. How is your team currently using AI in their day-to-day operations?
A: We’re cultivating an organic integration strategy, allowing AI to flow naturally into areas where it creates immediate value. Our development team pioneered this approach, finding that AI tools could optimize their workflows and create space for deeper problem-solving.
Now we’re expanding this thinking across our entire ecosystem—from support to sales, marketing to operations. We’re identifying those small but powerful wins that compound over time—enhancing communication clarity, distilling complex data into actionable insights, and creating more impactful training resources.
What energizes me most is the absence of fear I see in our team. Instead, there’s genuine curiosity and enthusiasm. Everyone recognizes we’re learning together in this space. My role is to nurture this mindset that AI is a tool for elevating our collective capabilities, not replacing our essential human contributions.
Q: Your company’s flagship products, STS Cloud and ProposalPath, have become essential tools for hotel and venue sales teams. How do you envision AI enhancing these platforms?
A: This is where our purpose comes alive. Our platforms already empower sales teams to work with greater efficiency and effectiveness, so the question becomes: how can AI amplify this value in authentic ways?
We’re exploring capabilities that align with real user needs—like summarizing incoming RFPs to highlight key requirements, automatically populating proposal details based on historical patterns, suggesting contextually relevant content, and even adapting communication tone to resonate with different client personas.
The guiding principle is that these AI enhancements must feel intuitive and invisible. When we implement them correctly, users won’t marvel at the AI—they’ll simply notice their workflow becoming more fluid and their results more impressive. That’s the mark of technology that truly serves.
Q: You’ve often described your leadership approach as that of a “quiet builder.” How does this philosophy influence your AI strategy, especially in an environment where AI is often surrounded by hype and bold claims?
A: I believe the most transformative innovation happens quietly, in the background—creating value without demanding attention. That’s precisely our approach to AI integration.
We’re not interested in AI as a marketing buzzword or status symbol. We’re focused on delivering tangible benefits that make a real difference in people’s work lives. Success for us isn’t when someone marvels at our sophisticated use of AI—it’s when they simply express that their day became easier, their work more fulfilling, or their results more impressive.
This quiet builder mindset has guided us away from the pressure to be first-to-market and toward the discipline of getting it right. It’s the foundation that has made our platforms trusted, stable, and genuinely valuable, and it’s now shaping our thoughtful journey into the AI landscape.
Q: Looking ahead, what excites you most about the next phase of your AI journey?
A: What energizes me is that we’re at the beginning of discovering what’s possible. We’re already seeing meaningful value from our early implementations, and with the technology advancing so rapidly, I believe the next 12-24 months will bring exponential growth in how we can serve our community.
Our path forward is clear—continuous learning, staying open to new possibilities, nurturing our collective curiosity, and integrating AI in ways that honor our core values of being thoughtful, practical, and customer-focused.
This isn’t a passing trend or a checkbox for us; it’s a powerful capability we’re learning to master together—with our team and our customers as collaborative partners in the journey. That shared exploration is what makes this moment so full of possibility.
Q: Thank you for sharing these insights, Ryan. It’s refreshing to hear such a balanced perspective on AI – one that acknowledges both its transformative potential and the importance of purposeful implementation.
A: Thank you for this conversation. It’s truly an exciting time to be building in this space—not because of the technology itself, but because of the potential it holds to enhance how we serve and connect with one another. I’m deeply grateful to be on this journey with a dedicated team and a supportive customer community who share our vision for technology that elevates rather than replaces the human experience.
Ryan Hamilton’s approach to AI integration offers a refreshing blueprint for technology leadership in an era often dominated by hype cycles and quick-fix solutions. What stands out about his philosophy isn’t just what he’s building, but how he’s building it—with intention, patience, and a deep respect for the human element at the heart of hospitality.
For hospitality professionals and business leaders trying to make sense of AI, Hamilton offers a refreshing perspective: it’s not about replacing people or blindly chasing trends — it’s about using technology to support what we already do well, and taking thoughtful steps forward, one move at a time.
About Puzzle Partner
Puzzle Partner is a leading marketing consulting firm specializing in the hospitality and travel technology sector. Founded in 2014 and headquartered in Toronto, Canada, the company serves as a trusted advisor to innovative change-makers in the global hospitality and travel technology landscape.
With exceptional domain expertise, an influential industry network, and decades of collective experience, Puzzle Partner delivers customized marketing solutions that amplify brand visibility and drive sustainable growth. The firm’s team of experts possesses unparalleled understanding of the interplay between travel, hospitality, and wellness technology branding.
Over the past decade, Puzzle Partner has established a proven track record of helping clients outperform competitors, achieve profitable exits, expand into the Americas, and realize extraordinary business outcomes. The company maintains the highest level of client advocacy in the industry while transforming visionary companies into unforgettable brands through strategic storytelling, brand positioning, and innovative content marketing.
To learn more, visit puzzlepartner.co.
Lauren Ramesbottom
VP of Strategic Storytelling and Content
Puzzle Partner Ltd.
