
Scale AI initiatives to deliver measurable enterprise ROI
AI is reshaping products, platforms, and operations across industries, and the gap between organizations that capture real value and those that stall at the pilot stage is widening rapidly. Tech leaders who can scale AI at the enterprise level, translate it into measurable business impact, and navigate risk, governance, and workforce transformation will set the pace for their industries, not chase it.
The evolving enterprise AI landscape and major shifts in recent years
How AI-driven change compares to prior technology adoption cycles
The role of technical leaders in shaping enterprise AI direction
The modern AI ecosystem, where generative and agentic AI fit, and key model types
Representative AI use cases across enterprise functions
Connecting model capabilities to practical business problems
Common patterns that slow or derail AI initiatives
Technical, organizational, and cultural sources of friction
Framing risks and challenges so they can be surfaced and addressed
How AI changes roles, skills, and expectations for teams
Patterns of technology adoption across early adopters, the majority, and laggards
Leadership communication and collaboration with HR and people leaders
Identifying promising tasks and workflows for generative and agentic AI support
Differentiating between task assistance, augmentation, and deeper automation
Assembling an initial portfolio of AI initiatives aligned with enterprise goals
Navigating the J-curve by understanding why metrics often decline before improving during AI adoption, and how to set expectations with stakeholders
Principles for choosing meaningful success metrics at different stages of AI adoption
How measurement evolves as AI initiatives move from pilots to scaled deployment
Understanding why performance metrics may initially decline before improving, and how to set realistic expectations with stakeholders
Approaches for assessing internal initiatives and external AI offerings
Key categories of risk introduced by enterprise AI
Governance structures and acceptable use guidelines for AI programs
High-level views of technical and process guardrails that enable responsible experimentation
Participants step into the role of a newly appointed CTO at a tech company struggling to integrate AI into its operations. Drawing on the knowledge, skills, and frameworks they have learned in the course, they design a practical roadmap to guide AI adoption and execution.
Using provided organizational context, including qualitative survey inputs and workflow analyses that highlight operational bottlenecks, they produce a capstone deliverable that includes:
A categorized workstream analysis identifying high-value opportunity areas
A focused project brief outlining the initial initiative to pursue and the rationale behind it, including opportunity cost considerations
A multi-stage plan to improve adoption and traction across teams
A prioritized backlog of additional AI opportunities beyond the initial initiative
A draft internal communication, such as a Slack post, announcing and framing the transition
The course concludes with structured presentations demonstrating how AI pilots can be translated into accountable, scalable programs aligned with organizational goals

VP, AI and Distinguished Engineer, Upside

Chief Executive Officer of Clarity Group and Adjunct Professor at The University of Chicago Booth School of Business

Deputy CTO at DX (getdx.com)
Evaluate the strategic and organizational implications of Generative AI for enterprise value creation and competitiveness.
Assess major Generative AI model types and align them with enterprise use cases across key business functions.
Identify and address the technical, organizational, and human headwinds that limit AI adoption, including overconfidence and jagged intelligence, non-determinism, vendor lock-in, and employee resistance.
Analyze workforce and talent implications of AI, including evolving competencies and leadership communication.
Apply generative and agentic AI to decompose jobs, workflows, and tasks to determine where work can be assisted, augmented, or automated.
Prioritize AI initiatives and develop a practical enterprise AI roadmap that balances ambition and feasibility.
Apply course frameworks through a Capstone Project integrating strategy, technology, talent, measurement, and governance.
Technology executives, including CTOs and CIOs, defining and guiding enterprise AI strategy, investment, and scale
Mid- to senior-level technical leaders and enterprise architects, evaluating, designing, and governing AI-enabled systems across the organization
IT strategists and digital or AI-transformation leaders, translating AI capabilities into coordinated, enterprise-wide initiatives
Technology consultants, advising organizations on enterprise AI strategy, implementation, and readiness
Date | Time | |
|---|---|---|
Live Online Session 1 | June 29, 2026 | 9:00 am-10:30 am CST |
Live Online Session 2 | July 6, 2026 | 9:00 am-10:30 am CST |
Live Online Session 3 | July 13, 2026 | 9:00 am-10:30 am CST |
Live Online Session 4 | July 20, 2026 | 9:00 am-10:30 am CST |
Live Online Session 5 | July 27, 2026 | 9:00 am-10:30 am CST |
Live Online Session 6 | August 3, 2026 | 9:00 am-10:30 am CST |
Live Online Session 7 | August 10, 2026 | 9:00 am-10:30 am CST |
Note: Session dates and timings are subject to change.
Participants who successfully complete the course will receive credentials certifying completion from the University of Chicago, including a digital badge, and become part of the UChicago network.
Note: Certificates and digital badges are issued in the name used during program registration. Images are for illustrative purposes and may be updated at the discretion of the University of Chicago.
Didn't find what you were looking for? Schedule a call with one of our Program Advisors or call us at +1 315 810 9499.
Starts on