Enterprise technology leaders are entering a more demanding phase of artificial intelligence adoption, with attention shifting from experimentation toward the organizational, financial, and architectural changes required to deploy AI at scale.

That shift will be the focus at the CIO 100 Leadership Live Boston event on Sept. 24. Technology executives, investors, and industry leaders will examine how AI is changing transformation priorities, operating models, and the expectations placed on CIOs. Sign up to attend here.

While AI remains central to the technology leadership conversation, the management challenge now extends beyond selecting models or identifying use cases to harder questions surrounding the ability to achieve sustained value across the enterprise. Sessions throughout this one-day event will test whether organizations possess the data infrastructure, governance mechanisms, talent, processes, and financial discipline required to turn fast-moving technologies into sustainable business capabilities.

To this end, panels will examine how those issues affect enterprise architecture, transformation economics, AI in regulated environments, venture investment, and the priorities likely to shape CIO agendas over the next 12 to 24 months.

AI scale puts enterprise foundations under scrutiny

The morning program opens with the leadership demands surrounding technology-enabled business transformation.

Mona Bates, SVP and CIDO at BAE Systems; Sal Companieh, CIDO at Cushman & Wakefield; and Paul Hlivko, CIO of Optum Financial, will discuss how technology leaders navigate transformation while managing culture, talent, architecture, and changing operating models. The panel will draw on lessons from initiatives that succeeded and from initiatives that forced executives to reconsider their approach.

Jim Chilton, a five-time CIO who is now EVP of Enterprise Ventures at Southern New Hampshire University, is the author of the recently release book Enterprise Coherence in the Age of AI. He will explain why scaling AI requires coordination across business processes, data, governance, and people.

Those requirements have become increasingly critical as enterprises move from contained AI experiments toward technologies that operate across workflows, applications, and organizational boundaries. He will discuss how AI deployments are exposing weaknesses that organizations have tolerated for years, including fragmented data, redundant systems, inconsistent governance, and disconnected business processes.

Transformation economics move to the foreground

Technology modernization faces greater financial scrutiny this year. The “Return on Transformation: Time, Talent, and Tradeoffs” session will examine the costs that accumulate around major initiatives, including budget overruns, organizational resistance, and investments that fail to produce expected results.

Scott Gardner, CIO of MGX Beverage Group; Angelic Gibson, chief product and technology officer at ISG; and Afshean Talasaz, former SVP of strategic projects and innovation and CTDO at Colonial Pipeline, will examine how organizations respond when transformation programs run into those pressures.

Panelists will discuss whether organizations may need to modernize aging infrastructure, fund AI initiatives, strengthen cybersecurity, improve data environments, and maintain existing operations at the same time. Smaller discussion groups later in the morning will extend the conversation into AI-ready data infrastructure, workflow automation, and AI return on investment.

A Next CIO luncheon will turn to talent, focusing on the leadership and workforce requirements facing emerging technology executives. The program will examine skills gaps, technology hiring, leadership pipelines, and succession as organizations try to assemble teams capable of operating in a rapidly changing technology environment.

Governance, investment, and the next CIO agenda

The afternoon shifts toward the boundaries organizations are encountering as AI moves deeper into business operations.

Agam Upadhyay, SVP and CDIO at Vertex Pharmaceuticals, will examine AI adoption in healthcare and life sciences, where organizations face pressure to innovate while operating within significant regulatory, governance, security and risk constraints. He will address how enterprises can balance those requirements without letting either speed or control dominate technology strategy.

Rudina Seseri, founder and managing partner of Glasswing Ventures, will bring a different view of the AI market from the investment community. She will examine the movement of investment toward focused AI applications and the signals CIOs can use to distinguish potentially durable technologies from market hype.

Enterprise technology portfolios are expanding, which makes that perspective increasingly relevant. This session will explore how modern CIOs should evaluate a growing field of AI platforms, applications, and infrastructure providers.

Terry Carpenter, CIO of MIT Lincoln Laboratory; Jacqui Nevils, global CIO of Fresenius Medical Care; and Chad Wright, CIO of Boston Dynamics, will examine emerging priorities ranging from AI economics to organizational redesign.

Their discussion returns to the changing responsibilities of the CIO because the next stage of enterprise AI will require technology executives to make decisions across several dimensions at once. In the process, the panelists will describe the kinds of frameworks that can help determine which emerging technologies warrant investment, which legacy environments require modernization, how governance should evolve, where organizational structures need to change and how technology investments contribute to measurable business performance.