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Why Most Enterprise AI Churns After The Pilot

Hakan Ozturk | The CS Café's avatar
Hakan Ozturk | The CS Café
Dec 26, 2025
∙ Paid

Kargo.ai just raised $42M Series B to scale enterprise deployments across global warehouses. (Source: BusinessWire)

This is not another “AI-powered” pitch deck story.

This is an execution story.

And that’s why it matters to Customer Success, especially if you’ve tried to prove CS impact without perfect data inside messy enterprise rollouts.

Most AI startups fail for one simple reason:

They sell intelligence. Customers need operational change.

Kargo’s round is interesting because it highlights what actually works when AI leaves the demo and hits real-world operations.


The Uncomfortable Truth About Enterprise AI

Most “enterprise AI” churns quietly.

Not because the model is bad.

Not because customers hate AI.

It churns because nothing around the model changes.

AI that doesn’t change workflows is just an expensive dashboard.

AI that doesn’t change behavior is just a science project, which is why teams that track success metrics leaders actually trust stop hiding behind activity.


The Hidden Moat No One Puts In The Deck

The moat is not the model. It’s the rollout.

Enterprise AI survives only when the vendor can turn a pilot into a repeatable deployment motion.

That is the whole game.


If you want this to be predictable, you need a deployment system, not “best effort CS.”

Below is the exact rollout framework, checklists, and templates to make AI expansion repeatable.

The Enterprise AI Deployment System That Prevents “Quiet Churn”

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