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What it takes to win enterprise AI deals
@ashugargarticlex
TL;DR. Enterprise AI is moving from pilot sprawl to production, and founders who don't act fast and stay low-ego will get lapped — by startups, not incumbents.
Takeaways
- Over 80% of databases are now created by agents, and exploit windows have shrunk from weeks to hours — the pace of change you feel today is the slowest it'll ever be.
- Most enterprises are stuck in "stage two: sprawl" — lots of pilots, no outcomes. Winners pick one real business problem and build the data infra to support it.
- Buyers' questions have hardened: "If we put a dollar in, what do we get back, and when does this actually change how we work?" Vague ROI pitches won't clear procurement in 2026.
- Incumbents' inherited processes and products-to-protect are now liabilities; the biggest founder risk is moving too slowly, not breaking things.