The Enterprise AI Mistake Most Companies Will Regret

Joel McKelvey, VP of Product Marketing at Glean, shares why the enterprises winning with AI right now aren't the ones chasing the latest model—they're the ones who got their context layer right first. He explains why AI has moved from experimentation to company-wide production almost overnight, and why the biggest mistake enterprises are making is one they'll only recognize in hindsight.

Key Takeaways

Why the model you're running matters far less than the context you're feeding it

How to think about AI ROI across three levels: individual, team, and organization

What actually breaks employee trust in AI agents

Why being model-agnostic is the best future-proof decision

How fear of AI disappears quickly once employees get firsthand experience of a productivity win

Guest Bio:

Joel McKelvey is VP of Product Marketing at Glean, where he helps organizations turn AI initiatives into practical, metrics-driven business transformation. He brings more than 30 years of experience across engineering, marketing, and strategy, with deep expertise in AI, machine learning, analytics, and data architectures. His work focuses on how enterprises move from experimentation to execution using AI agents, enterprise search, and trusted data foundations to improve productivity, decision-making, and customer and employee experiences.

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About this Show:

The Brave Technologist is here to shed light on the opportunities and challenges of emerging tech. To make it digestible, less scary, and more approachable for all!