Resume Tailoring Skill

Priority hierarchy: See references/priority-hierarchy.md for conflict resolution.

Create compelling, tailored resumes that make it obvious you're the right candidate for a specific job.

File Structure

scripts/
  tailor-resume.md        # Resume tailoring subagent prompt

The profile template is at references/profile.md.

Data Directory

Resolve the data directory using references/data-directory.md.

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Workflow

Step 0: Check Prerequisites

Resolve the data directory, then check prerequisites per references/prerequisites.md. Resume is required; profile is strongly recommended. If the user proceeds without a profile, set a flag to present all assumptions for verification (see Step 3a below).

If $ARGUMENTS is a URL, continue to Step 1. Otherwise, ask for a job URL.

Step 1: Get Job Details

Accept a job URL from the user (from $ARGUMENTS or by asking).

Use Claude in Chrome MCP tools to fetch the job posting per references/browser-setup.md.

Parse and extract:

• Job title and level (IC vs. manager, seniority)
• Company name and what they do
• Responsibilities - what the job actually involves day-to-day
• Requirements - must-have qualifications
• Nice-to-haves - preferred qualifications
• Keywords - industry terms, tools, methodologies mentioned
• Team context - who they report to, team size, cross-functional partners
• Company stage/size indicators

Create a job folder at DATA_DIR/jobs/[company-slug]-[date]/ and save the parsed job posting to posting.md.

If the page can't be loaded or parsed, ask the user to paste the job description directly.

Step 2: Analyze Match

Before writing, map the candidate's experience to the job:

1. Level match: Confirm the candidate's experience level matches the role. A VP-level candidate applying for a Director role should lean on strategic impact. A Director applying for VP should emphasize scope and leadership growth.

2. Requirement mapping: For each job requirement, identify the strongest evidence from the work history profile:

   • Direct experience ("Led SEO strategy" → job asks for SEO experience)
   • Analogous experience ("Scaled marketplace from 1M to 10M users" → job asks for growth experience)
   • Transferable skills ("Managed 30-person team" → job asks for leadership)

3. Gap identification: Note any requirements where the candidate has no clear match. These should NOT be fabricated - instead, find adjacent experience that demonstrates capability.

4. Keyword alignment: Identify the job posting's language and terminology to mirror in the resume.

5. Compelling narrative: Determine the 2-3 sentence story of why this person is the obvious choice. What's the throughline?

Step 3: Generate Tailored Resume

Create the tailored resume following these principles:

Structure:

• Header: Name, contact info, LinkedIn (same as original)
• Summary/Profile: 2-3 sentences positioning the candidate specifically for THIS role. Not generic - reference the company and role context directly.
• Experience: All roles from the resume, but with bullet points rewritten, reordered, and selectively emphasized
• Skills: Reorganized to lead with what the job asks for
• Education: Same as original

Bullet point principles:

• Lead each role with the bullets most relevant to the target job
• Rewrite bullets to mirror the job posting's language where authentic
• Include metrics and quantified impact (from work history profile)
• Remove or de-emphasize bullets that aren't relevant to this specific role
• Add bullets from the work history profile that weren't on the original resume but ARE relevant to this job
• Each bullet should start with a strong action verb
• Each bullet should show: what you did → how you did it → what the impact was

Level-matching:

• For executive roles: emphasize strategy, P&L ownership, board interaction, team building, cross-functional leadership
• For director roles: emphasize program ownership, team management, operational excellence, stakeholder management
• For IC roles: emphasize hands-on execution, technical depth, individual contributions, collaboration

Writing rules (CRITICAL — target Flesch score above 90):

• Write like a sharp executive, not a language model. Short sentences. Plain words.
• Every sentence gets one idea. If a sentence has "and" connecting two unrelated clauses, split it.
• Never use emdashes. Use commas, periods, colons, semicolons, or parentheses instead.
• Vary sentence structure. Not every bullet should follow the exact same pattern.
• No preamble clauses. Bad: "Leveraging deep expertise in marketplace dynamics, led..." Good: "Led..."
• No stacking adjectives. Bad: "cross-functional, data-driven, customer-centric approach". Pick one.
• No filler phrases: "demonstrating ability to", "showcasing expertise in", "with a track record of", "needed to drive", "spanning", "leveraging", "utilizing"
• No compound noun piles: "AI-driven product opportunity identification and execution" — just say what you did
• Summaries must be 2-3 SHORT sentences. Each sentence under 20 words. No run-on sentences connecting multiple capabilities with commas and "and".

Strict accuracy rules (CRITICAL):

• ONLY use information explicitly stated on the resume or in the work history profile
• NEVER assume business model (B2B vs B2C), revenue type, or company stage unless stated
• NEVER infer scope beyond what's written (e.g., don't add "P&L ownership" if resume says "revenue targets")
• NEVER add responsibilities, skills, or functional areas the candidate didn't mention
• NEVER assume cross-functional partnerships that aren't listed
• When the resume is ambiguous, use conservative language or omit the detail entirely
• If you need to frame experience differently for the target role, only reframe what IS there, never invent what ISN'T

What NOT to do:

• Don't fabricate experience or skills the candidate doesn't have
• Don't use generic buzzwords that aren't backed by specific experience
• Don't make the resume longer than 2 pages
• Don't change job titles or dates
• Don't remove roles (gaps look suspicious)
• Don't assume anything about the candidate's business, scope, or responsibilities that isn't explicitly documented

Step 3b: Critique and Rewrite (MANDATORY — do this before presenting)

Before showing the resume to the user, review every line and fix AI-sounding writing. Go sentence by sentence and ask:

1. Is this sentence doing too much? If it has more than one comma-separated clause, split it into separate sentences or bullet points.
2. Would a real person say this? Read it out loud. If it sounds like a LinkedIn post or a ChatGPT response, rewrite it.
3. Is there filler? Cut any phrase that doesn't add information. "Demonstrating ability to identify and execute on AI-driven product opportunities from ideation through production" → "Built an AI product from idea to production."
4. Are there stacked buzzwords? "Cross-functional, data-driven, customer-centric leadership" → pick the one that matters for this job and give a concrete example.
5. Is the summary under control? Max 3 sentences. Each under 20 words. No sentence should list more than 2 things.

Common AI patterns to kill:

• "I combine X with Y, Z, and the W needed to..." → Split into separate statements
• "...demonstrating [abstract quality]" → Delete or replace with the actual result
• "...spanning [long list]" → Pick the most relevant 1-2 items
• "Led [action], [action], and [action] across [scope]" → One action per bullet
• Any bullet over 2 lines is probably trying to do too much — split it
• Gerund clauses tacked onto the end: "...delivering X while maintaining Y" → Two sentences

Test: After rewriting, re-read the summary and first 3 bullets. If any sentence takes more than one breath to read out loud, it's too long. Shorten it.

Output:

Save the tailored resume to DATA_DIR/jobs/[company-slug]-[date]/resume.md

Present the resume to the user with a brief explanation:

Here's your tailored resume for [Role] at [Company].

**Key changes I made:**
- [What was reordered/emphasized and why]
- [What bullets were rewritten and why]
- [What was added from your work history]

**The narrative:** [2-3 sentence pitch for why you're the right person]

The resume is saved to: DATA_DIR/jobs/[folder]/resume.md

Step 3a: Verify Assumptions (if no profile exists)

If no work history profile was available, present the user with a list of every assumption made:

Before we finalize, here are the assumptions I made. Please correct
any that are wrong:

1. [Company] - I assumed [X]. Is that right?
2. [Role scope] - I described your scope as [Y]. Accurate?
3. [Business model] - I framed this as [Z]. Correct?
...

Wait for the user to verify or correct before finalizing. Apply all corrections to the resume AND save them to DATA_DIR/profile.md so they persist.

Step 4: Iterate

Ask if the user wants to adjust anything:

• Tone (more technical, more strategic, more metrics-heavy)
• Emphasis (highlight certain roles or skills more)
• Length (condense to 1 page, expand detail in certain areas)
• Specific bullet points to rephrase

Apply changes and re-save.

Step 5: Update Profile (ALWAYS)

Every time the user corrects a factual detail, update DATA_DIR/profile.md immediately:

• Business model corrections (e.g., "Proficiently is B2C, not B2B")
• Scope corrections (e.g., "I had revenue targets, not P&L ownership")
• Responsibility corrections (e.g., "I didn't manage candidate workflows")
• Any other clarification about roles, teams, or accomplishments

This prevents the same mistakes on future resumes. If the profile is still a blank template, create a new one with whatever the user has told you so far. Use the structure from references/profile.md but fill in only what you know for certain.

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Response Format

Structure user-facing output with these sections:

1. Tailored Resume — the full resume text
2. Tailoring Notes — key changes made (reordered bullets, rewritten sections, added content from profile) and the narrative pitch
3. What's Next — suggest iterating on tone/emphasis, or writing a cover letter using the cover-letter skill