Pipeline

Conversations with GTM peers who are actually filling pipeline right now—something you can use by Monday.

Why Does AI Prospecting Get Worse the Longer You Use It?

Why Your AI Gets Worse The Longer You Use It (with Jack Taubl from Ocean.io)

AI prospecting gets worse in long chats for two reasons: models are built to compact context, and vague prompts drift. Jack Taubl, Director of Sales at Ocean.io, explains both on Pipeline, along with his fixes. He works inside Claude projects, opens a fresh chat when an answer looks wrong, grounds projects in real files, and schedules daily briefings.

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