caboodle design
caboodle design · resource
A walkthrough for setting up a Cowork system that scans job boards for you every morning and helps you tailor application materials to each role. Build it once, run it daily.
This is a three-layer setup. Master files keep both layers honest. The scan keeps you informed without doomscrolling LinkedIn. The tailoring pass keeps applications high-quality without starting from a blank page each time.
| Layer | When | Effort |
|---|---|---|
| Master files | Build once, update quarterly | High upfront, then low |
| Scheduled scan | Runs daily on its own | Zero after setup |
| Tailoring pass | On-demand per role | 5 minutes per role |
You could automate this too — have the scheduled task auto-generate materials for every flagged role. Don't. You want to read the JD yourself before deciding it's worth applying to. Auto-applying is a fast path to pattern-matched rejection and burned reputation with companies you actually care about.
Before automating anything, you need clean source-of-truth files. Set these up first — the scheduled scan and the tailoring pass both point back here.
Create a plain .txt version and a .docx version. No columns, no graphics, no fancy fonts. Times New Roman or Calibri. This is what gets parsed by applicant tracking systems and what most automated screeners read.
If you want a designed version for portfolio links or hiring managers who'll actually look at it, build that as a separate HTML or PDF. Keep it visually distinct from the ATS version.
Pick one folder on your computer where everything lives — master resume, branded versions, headshots, and tailored versions per company. Pointing Claude at one folder makes the whole workflow simpler.
# one folder. everything inside. job-search/ ├── master/ │ ├── resume-master.docx # human-friendly source │ ├── resume-ats.txt # plain text for screeners │ └── resume-branded.pdf # optional, designed ├── assets/ │ └── headshot.jpg └── tailored/ └── [company-name]/ ├── resume-[company].docx └── coverletter-[company].docx
The folder isn't decorative. When you ask Claude to tailor a resume, it reads from master/ and writes to tailored/[company]/. One folder, predictable paths, no copy-paste between apps.
This is the piece that does morning research while you're still drinking coffee. In Cowork, ask: "Create a scheduled task that scans job boards for me every weekday at 8am." Cowork will load its schedule skill and walk you through it. The output is a SKILL.md file containing your brief.
Six sections. Be specific — the more specific the brief, the less noise comes back.
| Section | What to include |
|---|---|
| 1. Context | Who you are, what you're looking for. Title types, remote vs. hybrid, contract vs. full-time. Be picky here. |
| 2. Comp floor | A hard filter. Pick a number for hourly contract and a number for full-time salary. Anything below gets filtered out, even if skills match. |
| 3. Skills inventory | Your tools, methodologies, and certifications. Claude uses this to assess fit on each role it finds. |
| 4. Credibility signals | Past clients, employers, or projects worth name-dropping. Helps Claude flag a "strong match" vs. a generic listing. |
| 5. Pipeline exclusion | Roles already applied to or mid-application. Without this, you'll see the same three jobs every morning. Update as your pipeline changes. |
| 6. Search strategy | Exact job titles, boards to hit (LinkedIn, Indeed, Glassdoor, Built In, niche sites), what to capture per role, and the output format you want. |
Add this line to your brief: "Take read-only actions. Research and report only. Do not apply, message, or send anything on my behalf." This keeps the scheduled run safely in research mode. You decide what to act on.
Tell it to keep updates short and direct. Say no to corporate fluff if you don't want it. The brief is where you set tone for everything that comes back — including how the scan reports to you each morning.
When the morning scan flags a role you want to pursue, this is the next step. For each role, you'll generate two files — a tailored resume and a tailored cover letter — both saved as .docx to your folder.
Open Cowork and say something like:
# paste the JD or share the link Here's a JD I want to pursue. Tailor my master resume and write a cover letter for it. [paste JD or link]
Pulls out keywords, required skills, nice-to-haves, and tone signals.
Most relevant experience moves to the top. Bullets get rephrased to match the JD's language without lying about what you did.
If the JD says "learner-centered curriculum," the resume says "learner-centered curriculum." Helps with both ATS keyword matching and the human read.
Hook tied to one specific thing about the company, body that maps your experience to their needs, clear close.
Filenames include the company name so they're easy to find later — e.g. resume-acme.docx, coverletter-acme.docx.
Before you start tailoring, set up your Cowork preferences so output sounds like you, not like Claudette. Words to avoid, tone, formatting habits. The voice rules do heavy lifting on every cover letter.
Walk through these in order. The first four are one-time setup. The last two are the daily and per-role rhythm you'll settle into.
.txt and .docx).From here: the scan keeps you informed. The tailoring pass keeps quality high. Master files keep both honest. Update the master quarterly, and the rest of the system stays sharp.