Four steps, one loop: find → score → draft → learn. The more you use it, the better it writes.
Caddie checks 500+ job boards and company career pages — the big aggregators plus the ATS boards companies actually post on first (Greenhouse, Lever, Ashby and friends).
The first scan covers the last 7 days. After that it only picks up what's new. You never open a job board again.
Every role gets a score from 0 to 100 against your real career — not keyword matching. A role can score 90 even if the ad never uses your exact job titles.
And you see why: which requirements you match, which are a stretch, which you genuinely don't have. Every claim quotes the job ad word-for-word, so you can check it yourself.
One click. Caddie researches the company first, then drafts the whole pack: tailored CV, cover letter, and answers to the actual screening questions from the application form.
Because the research comes first, the whole pack tells one coherent story — same angle in the CV, the letter, and the answers. Everything is a draft. Nothing is ever sent.
Every line in the pack shows what changed and why — tap any highlighted line to see the original text and the reasoning. Don't like a line? Rewrite it in place, or reject it.
You approve the pack sentence by sentence. Nothing goes out that you didn't sign off. And where a fact is missing, you get a visible placeholder — never an invention.
I'm writing because you're building workflow AI for ops teams — the exact thesis I spent two years on at my own startup.
I haven't managed a PM team directly, but I've led three cross-functional squads end to end and would step into that with the team size you'd want me to own.
was: “I have lots of management experience.” · why: name the real gap, then bridge it honestly — tap any highlight to accept, rewrite, or reject.Here's the compounding part: every edit you make trains your Caddie. Rewrite a line — it learns your voice. Skip a role and say why — it stops showing you that kind of role. Rate a score up or down — the ranking sharpens.
Your corrections become standing rules that shape every future draft and every future shortlist. The first pack is decent. The tenth sounds like you wrote it.
Caddie drafts and fills; you review and send every application yourself.
Where something's missing it leaves a visible placeholder — not a fabrication.
Every tailored change shows its original text and the reason; the job ad is quoted verbatim.
Caddie reads the course and hands you the club. The shot is always yours.