Twenty Years of Conversational AI: Lessons from the Field
Conversational AI has seen huge changes in the field, not least in the past 5 or so years. However, some of the most important lessons we can take from the developments only become visible over time. In an upcoming conference keynote at Beyond Boundaries, Alice Kerly will draw on more than twenty years of experience across academic research and enterprise delivery to explore what has genuinely changed in Conversational AI, what hasn’t, and what today’s leaders and practitioners can learn from the shifts in that time.
Alice’s career began in academia, completing a PhD focused on Conversational AI in Education. Her research involved building a virtual assistant integrated with an intelligent tutoring system, designed to help learners reflect on their progress. That early work combined language, psychology, and technology, long before terms like “conversation design” were widely used, and set the foundation for a career focused on how people actually interact with automated systems.
Since then, Alice has worked across the full lifecycle of Conversational AI, from strategy and team enablement through to design, implementation, and optimisation. Her experience spans a wide range of enterprise environments and technologies, including work with organisations such as HelloFresh, Samsung, and HP, as well as many others. Over that time, she has seen multiple waves of tooling, techniques, and hype come and go, alongside steady (and sometimes huge and rapid!) progress in what really enables assistants to deliver value at scale.
Beyond Boundaries Global Festival 2026 Speaker
In her talk, Alice will reflect on the evolution from early dialogue systems to today’s large language models, and what that progression reveals about the realities of building and running Conversational AI in production. Rather than focusing on technology alone, the keynote will centre on lessons that have remained consistent across two decades: the importance of outcomes over novelty, strong design discipline, effective governance, and robust analytics.
The session is aimed at both leaders and practitioners. Executives will gain a clearer perspective on how to steer through the hype, set realistic expectations, and make informed decisions about where new capabilities genuinely add value. Practitioners will hear practical insights grounded in real deployments, including where teams commonly struggle and how those challenges can be addressed.
At The CAI Company, this focus on evidence, outcomes, and operational reality underpins our approach to Conversational AI. Alice’s keynote reflects that same philosophy: looking beyond surface-level innovation to the careful, detailed and nuanced work of building assistants that succeed for both organisations and the people who use them.
Find out more about Beyond Boundaries and other events you can find The CAI Company team at.
