Jason Giles began his career at the dawn of the commercial internet, when a new technology cracked a door open and curiosity mattered more than credentials. He was early enough to watch the dot-com crash unfold firsthand, discovering that technological disruption rarely replaces human judgment, it changes where it’s needed most.
Today, after more than two decades leading design at Microsoft, DirecTV, Ticketmaster, and now UserTesting, Jason sees the same patterns emerging with AI. The excitement, uncertainty, fear of missing out, and rapid acceleration all feel remarkably familiar.
In this talk, Jason draws on lessons from the internet’s formative years to explore why AI doesn’t diminish the value of designers it raises the premium on judgment. As AI compresses days of design and research into seconds, the real competitive advantage shifts from producing work to knowing what good work looks like, what questions to ask, and which decisions still require human discernment.
The session concludes with an extended Q&A, focused on the questions that matter most to the audience.