Rob Bernshteyn has lived the full arc of enterprise software. He started at Accenture when on-premises ruled, built Coupa into one of SaaS's defining platforms (leading it from its embryonic startup days to a multi-billion-dollar company), and now invests in what comes next at ICONIQ. In this fireside chat with Jason Busch, Rob traces that journey and makes the case that we're entering a radical new era of enterprise technology. One where AI doesn't just improve software but changes everything, starting with how we define it, how it's sold, who (and what) makes decisions, and what it's worth (to everyone from users to investors).