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Enterprise AI for Tech Leaders: From Strategy to Impact

Scale AI initiatives to deliver measurable enterprise ROI

Work Experience

Lead enterprise AI from strategy to execution

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.

15%

percentage increase in global GDP driven by AI adoption by 2035
Source: PwC

$ 45 billion

estimated reach of global Agentic AI market by 2030.
Source: Deloitte

93%

of employers expect generative AI to power innovation, automation, and learning within next five years.
Source: Amazon

An immersive, applied learning experience

In this eight-week online course, you will engage with practical frameworks for evaluating, prioritizing, and scaling enterprise AI initiatives. The learning experience focuses on real organizational contexts and helps you translate AI capabilities into accountable decisions around strategy, governance, workforce impact, and measurement.

Live, Instructor-Led Sessions

Immerse yourself in interactive sessions and practical insights led by UChicago instructors. Recordings of all live sessions are included to support the course learning flow.

Structured Learning Experience

Build depth through guided preparation and follow-up activities that reinforce live sessions and enterprise AI applications.

Capstone Presentation

Apply course frameworks through a hands-on capstone presentation focused on real-world enterprise AI challenges.

Course modules

  • 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

Capstone presentation

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

Meet your instructor

UCH - Faculty - David Thomas 
David Thomas 

VP, AI and Distinguished Engineer, Upside

Guest speakers

UCH - Faculty - James Janega
James Janega

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

UCH - Faculty - Justin Reock
Justin Reock

Deputy CTO at DX (getdx.com) 

Course features

UCH-icon-liveOnline
Live Online
UCH-icon-world-class-new
World-Class Instructors
UCH-icon-HandsOn
Hands-On Learning
UCH-icon-Capstone
Capstone Presentation

What you'll learn

  • 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.

Who is this course for?

  • 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 

Program calendar

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.

Certificate of completion

Certificate of completion

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.

Connect with a Program Advisor for a 1:1 Session

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.

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