The AI hiring wave is over.
Companies hired AI teams in 2024-2025 like they were collecting Pokemon cards.
Head of AI. VP of AI Strategy. Chief AI Officer.
Most didn’t know what these people would actually do.
I watched 12 portfolio companies make this mistake. They hired AI expertise before defining AI problems.
Behind closed doors, these expensive hires spent months in meetings. Talking about “AI transformation roadmaps” and “machine learning pipelines.”
Meanwhile, the sales team was still manually qualifying leads.
Customer service was drowning in tickets.
Operations was burning cash on repetitive tasks.
The real AI opportunity was sitting right there. Unglamorous. Unnoticed.
Here’s what I learned from the companies that got it right:
They didn’t hire AI people first.
They identified their most painful manual processes first.
Then they found people who could automate those specific problems.
The best AI hires weren’t the ones with fancy titles.
They were the ones who saved the company 40 hours a week in the first month.
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Writing at the intersection of AI, capital, and the future of the human job market – sharing mylife lessons, reflections, and honest takes from the founder-investor’s seat.
