Tailoring a resume is easy. Not lying is the hard part

Ask a language model to make a resume fit a job description and it will do it immediately, cheerfully, and with a confidence that should worry you. It will add the tool you have never used, because the posting asked for it. It will promote you half a level, because the posting is for a senior role. It will turn “helped with” into “led”. None of this requires a bad model. It is what “make this fit” means if nobody has told the model what it is not allowed to do.

That matters more in a job search than in almost any other writing task, because the document is going to be read back to you in an interview. A line you never wrote, about work you never did, is a question you cannot answer. I have watched that happen to people. It is a bad ten seconds and it ends the conversation.

The check that had to exist before the generator did

So this week’s main piece of work was not the cover letter generator, even though that is the flashier thing on the list. It was the fit check that sits beside it.

The fit check reads a posting against your profile and reports two things. The first is obvious and every competitor has some version of it: the requirements in the posting that your profile does not cover. The second is the one I actually built this for: where your own documents have overreached. If the resume claims something the profile does not support, the check names it and shows you the line.

A tool that only tells you what to add will keep adding until you are unrecognizable. The useful half is being told what you have already stretched.

The other half of the design is that edits travel in the right direction. When the fit check makes you realize you left something out — a tool, a certification, a project — you can push that back into the profile, not just into this one resume. The profile is the master record. Everything else is generated from it. Fix it once, and every future document is better.

Cover letters that read the tailored resume

The cover letter generator works off the resume already tailored to that job, rather than off the raw profile. That ordering is deliberate. A cover letter’s job is to say the thing the resume cannot — why this role, why now, what the bullet points do not explain. It cannot do that if it is working from the same undifferentiated pile the resume started from, and it should never introduce a claim the resume does not make.

Also this week

The government job sites — federal and all fifty states — went into Find Jobs as their own tab. They are consistently the least spammy listings on the internet and nobody aggregates them well. The Help Center opened with seven tutorials, and eight guides went up. The browser extension got a one-click sign-in so capturing a posting does not mean pasting an API token by hand.

And a hardening pass went through authentication, the AI layer, and email: no provider errors leaking to the client, no email bodies in production logs, tokens hashed at rest. None of that is visible to anyone. It is the part of the work that is only noticed when it was skipped.