An Operator’s Perspective
Twenty-five years of enterprise transformation.
Now applied to AI.
Rich Steele has spent a career at the fault line, driving transformations that bridge the gap between what a company decides to do and executing the work. That gap showed up in different forms across financial services and healthcare: post-merger integration, platform development, and the organizational strain that transformational change creates.
AI-driven transformation is reproducing that same gap, faster than most enterprises expected. The organizations finding traction aren't the ones with the most aggressive deployment timelines. They're the ones that treated adoption as an organizational problem before a technology problem, building the governance, execution discipline, and organizational change management maturity that determine whether a capability actually changes how work gets done.
That perspective shapes both his advisory work at ESG and what he teaches in the graduate classroom at the University of Denver.
About Rich
Rich is currently Enterprise AI Practice Leader at Execution Specialists Group (ESG), where he works with advisory teams and client leadership to treat AI as the enterprise transformation it is, not a technology project. That perspective comes from more than 25 years in senior PMO leadership roles at Charles Schwab, DaVita, and JPMorgan Chase, plus earlier years in solution architecture and application development. He's also an Adjunct Associate Professor at the University of Denver, teaching graduate-level courses in AI enterprise strategy and agile project management, and holds master's degrees in Education and Political Science from The Ohio State University.
The tools change. The fault line doesn't.
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