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Job Hunting with Cowork: Drop a Job Description, Get a Tailored Resume and Cover Letter

User created a structured job-search folder with resume/cover-letter subfolders and a CLAUDE.md config. Drop in a job description and Cowork auto-analyzes the role, generates targeted .docx resume and cover letter

★☆☆ Beginner 15-30 min 13. Juni 2026
D
DrewGrgich @u/DrewGrgich

Job seeker sharing a structured Cowork workflow for resume/cover letter generation

Source
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Scenario

A job seeker needs to tailor resumes and cover letters for each application, but manual customization is time-consuming. The user set up a CLAUDE.md config in Cowork with personal info, work history, and core competencies — just paste a job description and Cowork generates the documents.

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Prompt

Set up a job search workspace in Cowork with this structure:
- /job-search/resumes/ (with example resumes)
- /job-search/cover-letters/ (with example cover letters)
- /job-search/CLAUDE.md (with my profile: name, career summary, education, experience, core competencies, key achievements)

When I paste a job description, automatically:
1. Analyze the role (company, title, requirements, technologies, values)
2. Create a targeted resume as .docx, referencing my examples for formatting
3. Create a targeted cover letter as .docx
4. Tailor language to mirror the job posting without sounding copied

Expected Result

Set up a paste-and-go job hunting workflow: 1. **Folder structure**: job-search/ with resumes/ and cover-letters/ subfolders containing examples 2. **CLAUDE.md config**: contains name, contact, career summary, education, experience, core competencies, quantifiable achievements 3. **Workflow**: paste job description → Cowork analyzes role requirements → generates targeted resume (.docx) → generates targeted cover letter (.docx) 4. **Smart tailoring**: adjusts language to mirror the posting's terminology without sounding copied **Result:** each application requires just pasting a JD — targeted resume and cover letter ready in minutes.

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Original Post

· 2026-06-13

I have been using Claude Cowork to assist in looking for new work. I created a job-search folder with a resumes sub-folder and a cover-letters sub-folder. I provided examples of my previous resumes and cover-letters in each folder. Here is the CLAUDE.md file in the root of the job-search folder. Edit the About You section below with your own details or have Claude interview you to get this filled out. To use this, navigate to the job-search folder with Claude Code or Cowork, and copy in a job description. Claude will use the information you've provided to create a targeted job description and resume for you to use as a starting point to apply for the job. The CLAUDE.md includes sections for: Purpose, About You, Career Summary, Education, Experience, Core Competencies, Key Achievements, and a Workflow section that tells Claude to analyze roles, create targeted resumes (.docx), and create targeted cover letters when you drop in a job description.