Resume Tailoring Skill

AI-powered resume generation that researches roles, surfaces undocumented experiences, and creates tailored resumes from your existing resume library.

Mission: Your ability to get a job should be based on your experiences and capabilities, not on your resume writing skills.

Table of Contents

• Overview
• Installation
• Prerequisites
• Quick Start
• Key Features
• Architecture
• Usage Examples
• Contributing
• License

Overview

This Claude Code skill generates high-quality, tailored resumes optimized for specific job descriptions while maintaining factual integrity. It goes beyond simple keyword matching by:

• Deep Research: Analyzes company culture, role requirements, and success profiles
• Experience Discovery: Surfaces undocumented experiences through conversational branching interviews
• Smart Matching: Uses confidence-scored content selection with transparent gap identification
• Multi-Format Output: Generates professional MD, DOCX, PDF, and interview prep reports
• Self-Improving: Library grows with each successful resume

Installation

Option 1: Install from GitHub (Recommended)

Clone the repository:

git clone https://github.com/varunramesh/resume-tailoring-skill.git ~/.claude/skills/resume-tailoring

Verify installation:

ls ~/.claude/skills/resume-tailoring

You should see: SKILL.md, research-prompts.md, matching-strategies.md, branching-questions.md, README.md 1.

Restart Claude Code (if already running)

Option 2: Manual Installation

Create the skill directory:

mkdir -p ~/.claude/skills/resume-tailoring

Download the files:

• Download all files from this repository
• Place them in ~/.claude/skills/resume-tailoring/

Verify installation:

• Open Claude Code
• Type /skills to see available skills
• resume-tailoring should appear in the list

Prerequisites

Required:

• Claude Code with skills enabled
• Existing resume library (at least 1-2 resumes in markdown format)

Optional but Recommended:

• WebSearch capability (for company research)
• document-skills plugin (for DOCX/PDF generation)
• 10+ resumes in your library for best results

Resume Library Setup:

Create a resumes/ directory in your project:

mkdir -p ~/resumes

Add your existing resumes in markdown format:

~/resumes/
├── Resume_Company1_Role1.md
├── Resume_Company2_Role2.md
└── Resume_General_2024.md

Quick Start

1. Invoke the skill in Claude Code:

"I want to apply for [Role] at [Company]. Here's the JD: [paste job description]"

2. The skill will automatically:

1. Build library from existing resumes
2. Research company and role
3. Create optimized template (with checkpoint)
4. Offer branching experience discovery
5. Match content with confidence scores (with checkpoint)
6. Generate MD + DOCX + PDF + Report
7. Optionally update library

3. Review and approve:

• Checkpoints at key decision points
• Full transparency on content matching
• Option to revise or approve at each stage

Files

• SKILL.md - Main skill implementation
• research-prompts.md - Company/role research templates
• matching-strategies.md - Content scoring algorithms
• branching-questions.md - Experience discovery patterns
• README.md - This file

Key Features

🔍 Deep Research

• Company culture and values
• Role benchmarking via LinkedIn
• Success profile synthesis

💬 Branching Discovery

• Conversational experience surfacing
• Dynamic follow-up questions
• Surfaces undocumented work

🎯 Smart Matching

• Confidence-scored content selection
• Transparent gap identification
• Truth-preserving reframing

📄 Multi-Format Output

• Professional markdown
• ATS-friendly DOCX
• Print-ready PDF
• Interview prep report

🔄 Self-Improving

• Library grows with each resume
• Successful patterns reused
• New experiences captured

Architecture

Phase 0: Library Build (always first)
↓
Phase 1: Research (JD + Company + Role)
↓
Phase 2: Template (Structure + Titles)
↓  [CHECKPOINT]
Phase 2.5: Experience Discovery (Optional, Branching)
↓
Phase 3: Assembly (Matching + Scoring)
↓  [CHECKPOINT]
Phase 4: Generation (MD + DOCX + PDF + Report)
↓  [USER REVIEW]
Phase 5: Library Update (Conditional)

Design Philosophy

Truth-Preserving Optimization:

• NEVER fabricate experience
• Intelligently reframe and emphasize
• Transparent about gaps

Holistic Person Focus:

• Surface undocumented experiences
• Value volunteer work, side projects
• Build around complete background

User Control:

• Checkpoints at key decisions
• Options, not mandates
• Can adjust or go back

Usage Examples

Example 1: Internal Role Transfer

USER: "I want to apply for Principal PM role in 1ES team at Microsoft.
Here's the JD: [paste]"

RESULT:
- Found 29 existing resumes
- Researched Microsoft 1ES team culture
- Featured PM2 Azure Eng Systems experience
- Discovered: VS Code extension, AI side projects
- 92% JD coverage, 75% direct matches
- Generated tailored resume + interview prep report

Example 2: Career Transition

USER: "I'm a TPM transitioning to ecology PM. JD: [paste]"

RESULT:
- Reframed "Technical Program Manager" → "Program Manager, Environmental Systems"
- Surfaced volunteer conservation work
- Identified graduate research in environmental modeling
- 65% JD coverage with clear gap analysis
- Cover letter recommendations provided

Example 3: Career Gap Handling

USER: "I have a 2-year gap from starting a company. JD: [paste]"

RESULT:
- Included startup as legitimate role
- Surfaced: fundraising, product development, team building
- Framed gap as entrepreneurial experience
- Generated resume showing initiative and diverse skills

Usage Patterns

Internal role (same company):

• Features most relevant internal experience
• Uses internal terminology
• Leverages organizational knowledge

External role (new company):

• Deep company research
• Cultural fit emphasis
• Risk mitigation

Career transition:

• Title reframing
• Transferable skill emphasis
• Bridge domain gaps

With career gaps:

• Gaps as valuable experience
• Alternative activities highlighted
• Truthful, positive framing

Testing

See Testing Guidelines section in SKILL.md

Run tests:

cd ~/.claude/skills/resume-tailoring
# Follow test procedures in SKILL.md Testing Guidelines section

Key test scenarios:

• Happy path (full workflow)
• Minimal library (2 resumes)
• Research failures (obscure company)
• Experience discovery value
• Title reframing accuracy
• Multi-format generation

Contributing

Contributions are welcome! Please follow these guidelines:

1. Fork the repository
2. Create a feature branch: git checkout -b feature/amazing-feature
3. Make your changes:

• Update SKILL.md for implementation changes
• Add tests if applicable
• Update README if architecture changes

1. Commit with descriptive messages: git commit -m "feat: add amazing feature"
2. Push to your fork: git push origin feature/amazing-feature
3. Open a Pull Request

Before submitting:

• Run regression tests (see Testing section in SKILL.md)
• Ensure all phases work end-to-end
• Update documentation

Troubleshooting

Skill not appearing:

• Verify files are in ~/.claude/skills/resume-tailoring/
• Restart Claude Code
• Check SKILL.md has valid YAML frontmatter

Research phase failing:

• Check WebSearch capability is enabled
• Skill will gracefully fall back to JD-only analysis

DOCX/PDF generation failing:

• Ensure document-skills plugin is installed
• Skill will fall back to markdown-only output

Low match confidence:

• Try the Experience Discovery phase
• Consider adding more resumes to your library
• Review gap handling recommendations

License

This project is licensed under the MIT License - see the LICENSE file for details.

Acknowledgments

• Built for Claude Code skills framework
• Designed with truth-preserving optimization principles
• Inspired by the belief that job opportunities should be based on capabilities, not resume writing skills

Support

• Issues: GitHub Issues
• Discussions: GitHub Discussions

Roadmap

• Cover letter generation integration
• LinkedIn profile optimization
• Interview preparation Q&A generation
• Multi-language resume support
• Custom industry templates