I Had ChatGPT Scrape Job Postings Relevant to Me and Even Companies Don’t Know What They Want With AI

The Setup

I’m sure you’ve asked the question “but like. HOW do I use AI?” to yourself before. If you develop apps, code, blah blah blah, yes, it’s straight forward. Use these tools to build things for you a la this site. But what else? When your job is inherently human-centric (i.e. strategy, sales, lifecycle marketing, etc.) what do you mean?

What I Asked ChatGPT To Look For

I had ChatGPT look up job listings that were relevant to all the resumes I’ve uploaded and job descriptions I’ve shared in my 2026 job search project (did I mention I was looking for a job?) and had it categorize sentiment behind AI usage across all the job descriptions.

What Showed Up In The Job Postings

• 44% just mentions “Uses AI” with no other context (huh?)
• 32% mentioned using AI in a way that increases productivity
• 16% doesn’t mention it at all
• AND ONLY 8% MENTIONS USING AI IN AN ACTUALLY MEANINGFUL WAY Like a genuinely thoughtful AI integration tied to data architecture, decisioning systems, real-time personalization.

The Weird (and honestly, quite annoying) Part

Very few postings actually described operationally meaningful AI systems work.

My Current Takeaway

Most companies haven’t had an honest conversation about what AI can actually do for them. We are convoluting earnings with productivity and are prioritizing the wrong things, especially in marketing.

AI has the ability to unlock real-time personalization at a massive scale if you have the right foundation in place, however most companies will fear uprooting their foundation or getting a closer look underneath the hood because of what they might find. And I get it. Doing that means rebuilding underlying data and orchestration infrastructure and that work is expensive, politcally difficult, and often exposes years of technical and operational debt which is the opposite of what the shareholders want, but the result is a negative feedback loop where leadership defaults to safer, shareholder-friendly productivity theater instead.

So to all these companies currently hiring: have you had this honest conversation yet? What do you really want from AI?