A founder's note

Why I built Caddie.

I spent nine months building a B2B voice AI company. The tech worked — real conversations, clean data. The sales didn't. A hundred cold calls, SDRs, a new pitch, a pivot. The market moved slower than a bootstrapped company can wait. Funding ran out first.

So I did the thing founders hate admitting: I opened the job boards.

It was worse than I remembered. Four hundred new roles a day, maybe eight worth my time. My career doesn't fit one filter — AI, big data, marketplaces, SaaS, GameFi, eCommerce, Web3, infrastructure; founder, IC, teams of 40 at scale. No job title covers that. So every board showed me 5% of what mattered and buried it in noise. And applying well — actually reading the ad, judging fit, re-tailoring the CV, writing a letter that isn't slop — is an hour a role. Nobody has forty hours a week for that on top of interviews.

I'm a builder before I'm a candidate. So I built my caddie. A good caddie doesn't take the shot for you — it reads the course, tells you which holes are worth playing, and hands you the right club. Mine scouts every new posting, scores it against my actual career, and gets me from "just posted" to "applied" within hours — but only on the roles genuinely worth the swing. It never sends anything. Every line it drafts I can rewrite, and it learns from each correction. By now it writes like me.

Then I looked around. My feed, my chats, my old colleagues — everyone struggling in this market, fifty applications into silence. Meanwhile I kept getting interviews. Same CV. The difference was the caddie carrying my bag.

So I made it a product. No pivot deck, no vision slide — a tool I built because I needed it, shared with the people stuck in the same rough.

If you're mid-search right now: I know exactly what it feels like. That's the point.

Pixel-art portrait of Dmitry, founder of Caddie
— Dmitry

Grab your caddie.

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