The Future Of Less Work · 2026-06-16 · 28 min
Why are so many enterprise AI adoption projects failing? What happens when AI stops being a visible tool and becomes invisible infrastructure embedded directly into workflows? In this episode of The Future of Less Work , host Nirit Cohen sits down with Darren Kimura, CEO of AI Squared , to explore what he calls the “last mile” problem of enterprise AI transformation: the gap between successful AI pilots and actual operational change inside organizations. As companies race to deploy AI, Darren argues that the real challenge is no longer the models themselves. The bottleneck is integration, orchestration, governance, and redesigning workflows built for a pre-AI world. The conversation explores why organizations remain trapped between experimentation and transformation, how fragmented enterprise systems prevent AI from becoming operational at scale, and why simply adding AI tools on top of legacy processes rarely delivers the productivity gains leaders expect.
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