DM4419/caddie-ai

caddie-ai

An open-source tool I built for my own job search, then tidied up to share with friends going through the same thing.

Applying to a lot of roles gets repetitive: read the posting, decide if it's worth it, then retailor your CV and cover letter. caddie-ai takes the first pass at that. It scans job boards, scores how well each role fits your CV, and drafts a tailored CV, cover letter, and screening answers. You review, edit, and send everything yourself — it never submits anything on its own.

It runs entirely on your own machine, and it learns from the edits you make, so over time its drafts land a little closer to your voice.

The name: like a golf caddie, it reads the course and hands you the right club. You still take every swing.

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Contents

• Why · The system at a glance · Screenshots
• The learning loop — the part that compounds
• How fit is evaluated (JD ↔ your CV)
• How it sources jobs · How drafting works
• Architecture · Setup · Settings reference
• Safety & privacy · Roadmap · Tech stack

Why

Applying well is slow: read the JD, judge whether it's worth your time, then rewrite your CV and cover letter to match — for every single role. caddie-ai automates the judgement and the first draft, where an LLM genuinely helps, and keeps the human firmly in the loop for everything that carries risk (what you send, where you send it).

It runs entirely on your machine. Your CV, your application history, and your API key never leave it.

The system at a glance

caddie-ai is a closed loop, not a one-shot generator. Four engines feed each other, and the output of your own judgement is captured and fed back in:

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