Every Fortune 500 CEO investing in AI right now faces the same brutal math. They’re spending $590-$1,400 per employee annually on AI tools while 95% of their corporate AI initiatives fail to reach production.
Meanwhile, employees using personal AI tools succeed at a 40% rate.
The disconnect isn’t technological—it’s operational. Companies are struggling with a crisis in AI measurement.
Three questions I invite every leadership team to answer when they ask about ROI from AI pilots:
- How much are you spending on AI tools companywide?
- What business problems are you solving with AI?
- Who gets fired if your AI strategy fails to deliver results?
That last question usually creates uncomfortable silence.
As the CEO of Lanai, an edge-based AI detection platform, I’ve deployed our AI Observability Agent across Fortune 500 companies for CISOs and CIOs who want to observe and understand what AI is doing at their companies.
What we’ve found is that many are surprised and unaware of everything from employee productivity to serious risks. At one major insurance company, for instance, the leadership team was confident they had “locked everything down” with an approved vendor list and security reviews. Instead, in just four days, we found 27 unauthorized AI tools running across their organization.
The more revealing discovery: One “unauthorized” tool was actually a Salesforce Einstein workflow. It was allowing the sales team to exceed its goals — but it also violated state insurance regulations. The team was creating lookalike models with customer ZIP codes, driving productivity and risk simultaneously.
This is the paradox for companies seeking to tap AI’s full potential: You can’t measure what you can’t see. And you can’t guide a strategy (or operate without risk) when you don’t know what your employees are doing.
‘Governance theater’
The way we’re measuring AI is holding companies back.
Right now, most enterprises measure AI adoption the same way they do software deployment. They track licenses purchased, trainings completed, and applications accessed.
