Johnny Rodriguez
MAR 07, 2026
I reviewed 300 pitch decks using an AI workflow I built inside Claude Cowork.
What used to take around one hour of first-pass diligence now takes about two minutes.
This is the full setup guide I promised. No teaser. No gatekeeping. Everything — the prompts, the context structure, the scoring logic, the folder architecture — is in here.
If you follow all nine steps, you will have a fully automated deal intake pipeline running by the end of today.
Claude Cowork is a desktop application that runs Claude — Anthropic’s AI — directly on your computer. It connects to your local file system and can execute multi-step workflows automatically.
The difference from a regular AI chatbot is fundamental. A chatbot answers one question at a time. Cowork reads files, writes files, runs sequences of tasks, and does it without you being in the loop.
For deal flow, that distinction is everything.
Download it at claude.ai. A Claude Pro or Team subscription is required.
Most people who try using AI for deal diligence get mediocre results. They ask a general AI to “review this pitch deck” and get a generic, surface-level response.
That is not what this system does.
The value is not in a single prompt. It is in how the prompts, context, evaluation logic, and workflow are structured together to replicate the early diligence layer most VCs perform.
There are four layers that have to work together: