Tailoring your resume, cover letter, and thank-you note (plain version)

Engineer version: ../technical/document-generation.md

When you apply to a job by hand, you probably take your standard resume, read the job posting, and rework things: a headline that matches the role, a summary aimed at what they're asking for, a section that lines up each thing they want with something you've actually done, and bullet points re-angled toward the job. Then you write a cover letter in your own voice, and after an interview, a thank-you note.

WorkWingman does all of that for you — using your own Claude, on your machine — and it only ever works from what's actually in your profile.

What it produces

• A tailored resume: a role-matched headline, a rewritten summary, a "why this role" section matching the job's requirements to your real experience, and bullets re-angled toward the job.
• A cover letter in your voice.
• A thank-you note (email + a shorter LinkedIn version) after an interview.

It never makes things up

This is the important part. The app is only allowed to reshuffle and re-emphasize what you've already told it. It is not allowed to invent an employer, a job title, a date, a degree, a school, a certification, or a skill you don't have — and it keeps your honest hedges exactly as you wrote them (things like "proposed, not yet adopted" or "did not sit for the exam").

To make sure, there's an automatic honesty check. After Claude writes a draft, the app scans it for any company, school, degree, or year that isn't already in your profile. If it finds even one made-up detail, it throws that draft away and falls back to a plain, safe version instead. A fabrication can't reach you.

Using your own Claude

The app uses the Claude you're already signed into on your computer — it doesn't need a separate key, and it never signs in or sets anything up on your behalf. If Claude isn't installed or you're not signed in, the app quietly falls back to a plain deterministic draft, so document generation always works, even offline. If anything goes wrong or takes too long, it falls back the same way.

How the tailored resume gets uploaded

The tailored resume is saved as a real Word (.docx) file. When you approve the documents for a job and the app later fills out that job's application, it attaches that tailored file in the "upload documents" section — but only for that one job. Other jobs still use your standard resume until you tailor and approve documents for them too. Nothing is ever submitted without your review.

Thank-you notes

After an interview, the app can draft a thank-you email and a shorter LinkedIn message in your voice. It only mentions things you actually logged about that interview — what went well, a question you want to follow up on, common ground you noted. It won't claim a topic went well, or reference a question, that you didn't record. And like everywhere else in WorkWingman, it only writes the draft — you send it yourself.