How to Tailor Your Resume for Each Job Application (Without Spending Hours)
Tailoring a resume works. Everyone knows it works. The problem is the boring part: rewriting the same bullets again and again for job descriptions that are 80% identical.
I hit a point where I stopped applying for a bit and started building tools instead. Not because I love “productivity”. Because I hated the workflow.
This post is the workflow I wish I had earlier.
What “tailoring” really means (and what it doesn’t)
Tailoring is not lying. It’s translation.
If the job description says stakeholder management and your resume says worked with teams, you might be describing the same thing. But machines (and rushed humans) don’t always make that leap.
Your goal is simple: make it obvious that you’ve already done the kind of work they’re hiring for.
The manual workflow (still the best baseline)
If you do this by hand, do it like this:
- Copy the job description into a scratch doc.
- Highlight repeated words/phrases (tools, skills, responsibilities).
- For each highlighted phrase, find the closest thing you’ve done.
- Rewrite 3–6 bullets so the first half of the bullet contains the job’s wording.
- Stop. Don’t rewrite your whole life story for one application.
This takes time, but it’s reliable.
The common shortcut (LLM chat)
A lot of people paste the JD + their resume into a chat model and ask for a rewrite.
It can help, but watch out for two failure modes: - It invents achievements you didn’t do. - It rewrites everything into the same “corporate” voice.
If you use chat, add one rule to your prompt: “Do not invent facts. Only rephrase what’s already true.”
The faster workflow I built for myself
I wanted the speed of an LLM, but without the copy/paste mess and without signing up for yet another platform.
So I built Resume Tailor: https://deadsimpletools.com/resume-tailor
How it works: - Upload your resume PDF - Paste a job description (or link) - Get tailored bullets (and optionally a cover letter)
Privacy notes (because this matters to me): - No accounts. - No resume storage (processed in memory, then discarded). - IPs are stored only as hashes for rate-limiting/abuse prevention.
Core privacy logic is public here: https://github.com/midnightdim/resume-tailor-core
A quick reality check
Tailoring is worth doing, but it’s not magic. You still need: - A resume that’s already “close” to the role. - Real metrics/examples where possible. - A sane application strategy (fewer, better applications beats spray-and-pray).
If you try the workflow (manual or tool-assisted) and it still doesn’t move the needle, the issue is usually targeting, not wording.