As AI redefines the IT landscape, leaders face growing pressure to modernize their infrastructure, optimize workflows, and maintain oversight over increasingly intelligent systems. In this episode of The Hitchhiker’s Guide to IT, host Michelle Dawn Mooney welcomes Jeff Hagins, CTO of Contextual.io, for a deep dive into how AI is transforming IT operations, infrastructure, and automation strategies.

With over four decades in technology leadership—including roles as CTO, CIO, and startup founder—Jeff shares practical insights on what’s changing, what’s not, and what IT leaders must prioritize in the age of AI. From modernizing IT service management and incident response, to managing risk and compliance in hybrid cloud environments, Jeff unpacks the real opportunities—and challenges—of AI-powered IT.

Key topics include:

• How AI is reshaping IT operations, infrastructure, and incident management
• The risks of over-automation and the need for continuous human oversight
• Best practices for scaling AI-driven workflows across hybrid and multi-cloud environments
• Why “small wins” matter more than big bets in successful AI adoption
• The role of contextual intelligence in delivering smarter automation
• How to prepare IT teams for the long game—without overhyping short-term change

Whether you're a CIO planning your AI roadmap or an engineer navigating the shifting tech stack, this episode delivers essential guidance for building future-ready IT environments—grounded in real-world experience.