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Every company buys AI tech.
Few make it work at scale.

90% of enterprises are running AI experiments, but only 22% see real financial returns. The gap is not the technology—it is governance, integration, and the discipline to turn pilots into defensible operating capability.

ENTERPRISE AI FAILURE POINTS

Eight systemic areas where AI at scale underperforms.

Click any card to inspect the hard data.

MY PRACTITIONER'S PERSPECTIVE

Why I work on solving these.

When you look at these eight areas, it becomes clear why so many enterprise AI initiatives stall: these are the foundational friction points that determine whether AI scales or stays an expensive experiment.

This is precisely why I focus my work here.

While generative AI introduces unique technical complexities, its core structural hurdles (governance, security, change management, and data readiness) are fundamental challenges that occur during any once-in-a-generation technological shift.

My last three years inside Electronic Arts leading AI product and engineering teams don't stand alone. They build on a 22-year foundation of navigating exactly these kinds of enterprise disruptions and landing deployments successfully. Long before LLMs, directing audited identity infrastructure at Visa or leading global commercial platform transformations at EA taught me the same underlying truth: scaling technology is ultimately a discipline of governance, workflow redesign, data, and organizational change.

I care about these failure points because the playbook for enterprise AI at scale isn't being invented from scratch. It is being adapted by seasoned practitioners who have led large-scale enterprise transformations before.

NOTES FROM THE TRENCHES

Perspectives from the field.

The Yes-Man You Won't Fire
The Yes-Man You Won't Fire

Jun 30, 2026

How AI sycophancy triggered a 42-state OpenAI subpoena, documented "AI psychosis," and a severe new enterprise safety crisis.

Read More on Substack
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Interested in comparing notes?

I'm always open to thoughtful conversations with enterprise leaders, builders, investors, and others working through the realities of AI at scale.

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