Ken Stillwell, CFO and COO at Pega, says most enterprise AI business cases fund a label rather than a specific capability — and that the gap shows up later, on the P&L. He and Greg Kihlström get into what financial discipline around AI actually looks like.
“AI” is not a budget category. A rules engine, a predictive model, and a system that acts on its own carry different costs, risks, and payback periods. Stillwell on making teams say which one they’re asking for.
The benefit gets modeled; the operational change doesn’t. Where AI business cases reliably break down, and what tells you a case is going to miss before you fund it.
Scaling a pilot is a coherence problem, not a technology problem. What it takes to let many teams decide faster without the enterprise ceasing to behave like one company — and who owns that.
About Ken Stillwell
As Chief Operating Officer and Chief Financial Officer, Ken Stillwell is responsible for finance, investor relations, legal, facilities, information technology, Pega Cloud, global client support, and business operations, overseeing more than one thousand employees globally. His leadership has been central to Pega’s transformation to an as-a-Service business through Pega’s Cloud transition. Recognized as incisive, transparent, clear, and empathetic, his opinions and counsel are sought after by peers, clients, and media. Ken is a regular contributor to numerous industry publications regarding financial and operational leadership.
Ken has nearly 30 years of financial leadership experience in high-growth organizations in the technology sector. He is a graduate of the University of Pittsburgh, where he earned his undergraduate degree in business and economics, and the University of South Carolina, where he earned a Master’s in accounting and finance. Ken is also a certified public accountant.
———- Resources ———-
Pega delivers the platform to reimagine, run, and evolve the processes and decisions an enterprise can’t afford to get wrong. We combine AI with proven architecture to keep mission-critical operations governed, scalable, and continuously adaptable. Since 1983, the world’s largest organizations have trusted Pega to turn transformation ambition into durable results.
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