resume-tailor

name

resume-tailor

description

Tailor an existing resume to one or several job descriptions with visible confidence scoring, structured reframing, and positioning help. Triggers on "tailor my resume", "update my resume for this job", "resume to job", "match resume to JD", "resume multiplier", "three resume versions", "multiple job descriptions", "resume keywords", "ATS alignment", "position my experience", "reframe my resume", or pasting JDs alongside a resume.

Resume Tailor — JD-Driven Resume Tailoring + Positioning

Token Economy

Apply token-economy whenever this skill would otherwise trigger broad exploration, repeated file reads, multi-file scans, or heavy reference loading.

• Load only the phase, reference, or script needed for the current step.
• Prefer targeted search and line-range reads over whole-file slurping.
• Batch independent tool calls and keep narration/results tight.
• If the task is tiny or the file set is already known, apply the relevant patterns inline instead of loading extra material.

Walks the user through a phased resume-tailoring session: JD analysis → matching pass with confidence scores → optional gap discovery → positioning pass → output. Truth-preserving — the skill selects, emphasizes, and reframes existing experience; it never fabricates.

Mission

A person's ability to get a job should be based on their actual experience, not on their resume-writing skills. This skill closes that gap by making alignment auditable (visible scores), bringing out undocumented experience (branching interview), and calibrating tone/level to the target role — without inventing anything.

Before Starting

Ask the user for:

1. Resume source — path to their canonical resume (markdown preferred; DOCX/PDF fine, converted in-memory) OR pasted text.
2. Job description — URL, file path, or pasted text. If it is a LinkedIn URL, prefer tools/jd-prep/jd_prep.py to capture jd.md. If it is another URL, fetch it with the host's available web tool. If fetch fails, ask the user to paste the JD text and keep the URL for jd.md.
3. Target outcome — "drop-in replacement bullets", "full rewrite", or "just show me gaps". Default: tailored resume + keyword coverage report. Cover letters are opt-in only — see Phase 5 §4 and Principle 8. Do not offer one unless the user has explicitly asked.

If any piece is missing, ask once. Don't proceed with half the inputs.

If no resume exists yet: offer to run Phase 3 (discovery) first to generate source bullets from scratch, then return to Phase 1 with the drafted material as the "resume".

If the user pastes multiple JDs: choose the correct path:

• If the user asks to compare roles, rank fit, or decide which roles to pursue, route to jd-screener.
• If the user explicitly asks for multiple tailored resume versions from one resume (resume multiplier, 3 versions, tailor this resume to these JDs), run Multi-JD Mode below for 2-5 JDs.
• Otherwise, pick one JD and defer the others. Full file-writing and DOCX export remain one-JD-at-a-time.

Multi-JD Mode - Resume Multiplier

Use only when the user provides one resume and 2-5 job descriptions and explicitly wants separate tailored versions in one pass. This mode produces truth-preserving text drafts and comparative fit notes; it does not write final files unless the user later selects one version for the standard Phase 1-5 flow.

Workflow:

1. Parse each JD into title, company, must-haves, nice-to-haves, keywords, level signals, and differentiators.
2. Build one shared fact inventory from the resume. Every tailored bullet must trace back to this inventory.
3. For each JD, produce:
   • tailored headline/summary
   • reordered experience emphasis
   • rewritten bullets using the JD's language where truthful
   • de-emphasized or removed material, with reason
   • significant gaps the cover letter or interview must address
4. After all versions, compare:
   • strongest fit
   • biggest gap
   • highest-risk keyword mismatch
   • recommended role to tailor fully first

Rules:

• Do not invent, inflate, or imply experience not present in the resume.
• Keep materially important experience visible somewhere unless the user explicitly wants a shorter version.
• Use numbers only when present in the source resume or supplied by the user.
• Mark each risky reframe as verify.
• If one JD needs a materially different resume architecture, recommend running the standard single-JD flow for that role.

---

Phase 1 — JD Analysis

Produce a structured job profile before touching the resume. Output format, action codes, and extraction heuristics live in references/jd-analysis.md — load it now. Also load references/role-archetypes.md so the JD is classified into the right resume-story type before weights and bullet rewrites begin.

Output to user (checkpoint) — in this order:

1. JD recap — title, company, seniority, comp, work mode, industry. Then a bulleted 3-6 line summary of what the role actually does (responsibilities + must-haves in plain language, not JD-parroted). This anchors the user in the JD before they evaluate weights.
2. Weighted focus areas (weights sum to 1.0) — tied explicitly to JD recap items so the user can see why each area got its weight
3. Must-have keywords vs. nice-to-haves (ATS tier)
4. Seniority signals + scope signals (team size, ownership, budget)
5. Cultural signals (what kind of operator do they want?)
6. Archetype selected + resume story to foreground + what to downplay
7. Action-code plan per focus area: LEAD_WITH / EMPHASIZE / QUANTIFY / DOWNPLAY
8. Hiring risk — single sentence. "What is the hardest thing this person has to do, that most candidates with the right keywords can't actually do?" Format and examples in references/jd-analysis.md §"Hiring Risk". This artifact is required before any cover-letter drafting can begin in Phase 5 — it is the antecedent for the cover letter's P1 "specific bet" clause and prevents the draft from drifting into resume narration.

Rationale for JD-first ordering: Users often can't evaluate whether a weight is right without re-anchoring in the JD content. Placing the JD recap immediately above the weights means the user sees the evidence and the derived profile together, without scrolling back to the JD file.

YOE cutoff check (honest-scoping): if the JD specifies a years-of-experience requirement (e.g. "8+ years", "12+ years required"), compute the earliest plausible role start year for the resume: current_year - (YOE + ~3 grace). Any role on the resume starting more than that window back becomes a truncate-or-summarize candidate in Phase 2. Hiring managers reading a 25-year tenure for an 8-YOE role read it as overqualified, not as bonus. See references/jd-analysis.md §"YOE Cutoff".

Ask: "Does this profile match how you read the role? Anything I over- or under-weighted?" Wait for confirmation before Phase 2.

---

Phase 2 — Matching Pass

For each bullet and role in the resume, assign a confidence band vs. the JD profile and propose a reframe if appropriate. Rubric + four reframing strategies are in references/matching-rubric.md — load it. Also load shared/communication-principles.md — reframed bullets must lead with the conclusion, stay in plain language, and serve the reader (hiring manager / ATS), not the author. If the target role is Head/VP/executive level, also load references/executive-bullets.md so bullet rewrites surface decisions, tradeoffs, governance, and leverage rather than just implementation.

Anti-fabrication mechanic — copy master, then diff. The Phase 2 working baseline is a literal copy of the canonical resume, not a draft regenerated from memory of the user's experience. Reframes are diffs against that copy: each change names the strategy used (Keyword Alignment / Emphasis Shift / Abstraction Level / Scale Emphasis) and traces back to a specific bullet in the copied source. If a proposed reframe has no antecedent in the copied master, it is fabrication, not reframing — route to Phase 3 discovery instead.

Output to user (checkpoint):

• Per-bullet table: Current → Band → Reframed → Strategy used
• Roll-up counts: # DIRECT / TRANSFERABLE / ADJACENT / WEAK / GAP
• Proposed reorderings within sections (lead with highest-confidence)

For resumes >15 bullets: present results one role at a time and get confirmation before moving to the next role. Dumping 30-bullet tables at once overwhelms the checkpoint.

Ask: "Which reframes feel true? Any I'm stretching too far? Any bullets you want to remove entirely?" Apply the user's corrections before Phase 3.

---

Phase 3 — Gap Discovery (Conditional)

Skip if: <3 GAP/WEAK items AND all must-have keywords have DIRECT or TRANSFERABLE coverage — unless the user explicitly asks "what else should I include?" or similar, in which case always run.

Otherwise, surface the gaps and run a branching discovery interview to find undocumented experience. Branch taxonomy (A–E) and question banks are in references/discovery-interview.md — load it.

Output to user:

• Each gap → 2–3 targeted questions
• When the user answers, convert into a candidate bullet at a realistic band
• Any claim that can't be substantiated → flag as a real gap; route to positioning or cover-letter. Never invent.

Then fold new bullets into the matching pass and update the roll-up.

---

Phase 4 — Positioning

Always runs. This is where the skill's second promise lives. Covers headline/summary, narrative arc, level calibration, and gap handling. Load references/positioning.md, shared/communication-principles.md, references/writing-quality.md, references/headline-library.md, and references/summary-patterns.md — the "I help" framing (principle 6) applies directly to headlines and summaries; audience-centered focus (principle 1) drives the narrative arc; the headline and summary libraries keep the prose specific instead of generic.

Output to user (checkpoint):

• Headline options (2–3) at different angles, with the framing choice shown
• Narrative arc — current vs. target, with the delta named
• Level calibration — is the language at, above, or below target seniority? Evidence required.
• Gap handling plan — per visible gap: resume / cover letter / interview

Ask: "Which headline angle? Does the narrative match how you want to be perceived?"

---

Phase 5 — Output

Final deliverables. Format details, ATS tips, and optional DOCX export are in references/output-formats.md. Load references/templates/README.md, references/writing-quality.md, references/resume-bullet-bans.md, and references/resume-qa.md now — the template file captures the user's canonical resume + cover-letter layout, heading style, date format, and DOCX style source; the other references keep the prose specific, ban low-signal bullet patterns, and force a final coherence pass. Every Phase 5 output must follow those conventions unless the user explicitly deviates.

Template-compliant markdown is mandatory. Resume markdown must use pandoc custom-style divs for the name (::: {custom-style="Title"} ... :::) and headline (::: {custom-style="Subtitle"} ... :::), ALL-CAPS H1 section headers (# SKILLS, # EXPERIENCE, # EDUCATION), plain-text H2 role headings (## Company, Location - Title, no italics), and MONTH YYYY - PRESENT date lines. Do NOT write the name as # Name or add a ## Summary heading — both break the template's style mapping. Cover letters use the top-block format in references/templates/README.md (bold name, city/phone/email, ordinal date, recipient block, Dear ..., body, Regards,, bold signature name).

Output path: all files go to ~/Documents/resumes/<Company>/ (one folder per target company). See references/output-formats.md §0.

Required step before any file write: walk the user through the assembled resume section by section (header/summary, each role, tail sections) for approval. See references/output-formats.md §3.5. Cover letters get the same treatment paragraph-by-paragraph, and must also clear both review tiers:

• §6.1 mechanical pre-ship checks (sentence-subject sequence per paragraph, proper-noun cross-check, prestige-density count, hiring-risk anchor present in P1, structural diff against canonical baseline, closing-line standalone read, §5/§5a/§5b sweep). Each check produces a printed one-line output; fail conditions trigger a rewrite, not a "ship anyway".
• §6.2 hiring-manager perspective review dispatched to a fresh Sonnet subagent with ONLY the JD, the draft, and the Phase 1 hiring-risk sentence — no resume, no baseline, no philosophy doc. Same-context review by the drafting model systematically under-flags problems the drafter has rationalized.

Both tiers live in references/cover-letter-review.md §6. Surface the §6.1 evidence and the §6.2 verdict to the user before file-write so they can override or revise.

Required Phase 1 artifact for cover letters: the Phase 1 hiring-risk sentence (Phase 1 output item #8) is the antecedent for P1's "specific bet" clause. Do not begin cover-letter drafting unless that sentence exists. If the user requests a cover letter and the hiring-risk sentence was not produced in Phase 1 (e.g. Phase 5R review-only path skipped Phase 1), produce it now from the JD before drafting.

Voice corpus + canonical baseline + structural template — when drafting a cover letter: load references/voice-corpus.md, references/cover-letter-review.md, and references/templates/cover-letter-structural-template.md before drafting. The canonical structural baseline is ~/Documents/resumes/Summer_Rae_CoverLetter.md — always load it as the voice example. The annotated structural template (references/templates/cover-letter-structural-template.md) captures the 4-paragraph shape with per-paragraph rules and variants — always load it as the skeleton. The voice corpus at ~/Documents/resumes/_voice-corpus/{originals,successful}/ supplements with proven-by-interview letters when available. NEVER pull voice from per-company folders even if endorsed in-session — that compounds AI cadence across drafts. If the corpus is empty, baseline + structural template alone are sufficient.

Drafting model — Sonnet (latest): cover letters must be drafted with the latest Claude Sonnet. If the orchestrator is Opus or another model, dispatch the draft to a subagent via the Agent tool with model: "sonnet" and pass: (a) the JD, (b) ~/Documents/resumes/Summer_Rae_Resume.md as the resume, (c) ~/Documents/resumes/Summer_Rae_CoverLetter.md as the voice example, (d) references/templates/cover-letter-structural-template.md as the paragraph-shape skeleton, and (e) the philosophy + tone + hard rules from references/cover-letter-review.md §A. The cover-letter-review contract applies regardless of which model drafts.

Post-interview promotion: when the user reports an interview/screen/offer signal for an application that has a letter on disk ("I got an interview at X", "X invited me to a phone screen", "X moved me forward", "X made me an offer"), offer to promote ~/Documents/resumes/<X>/cover-letter.md to ~/Documents/resumes/_voice-corpus/successful/<YYYY-MM-DD>-<X>-cover-letter.md. Promotion is a copy (not symlink), frozen at success-time. Do not promote on application-submitted, auto-acks, or in-session endorsement. See references/voice-corpus.md §"Promotion Trigger".

Defaults:

1. Tailored resume (markdown, ready to copy-paste or convert)
2. Keyword coverage report — must-haves + nice-to-haves hit/missed
3. jd.md — source URL + captured date + full JD text. Required in every company folder so the tailored outputs remain legible months later. See references/output-formats.md §0.1.
4. Cover letter draft — opt-in only. Do NOT offer, pre-announce, or auto-draft a cover letter at the end of Phase 5. Produce resume + keyword coverage + jd.md only. Draft a cover letter exclusively when the user explicitly requests one ("draft a cover letter", "write me a letter for this", etc.). The default closing prompt does NOT mention cover letters — its absence is what prevents an unwanted draft from being produced unprompted.
5. Connection message — opt-in only. Same rules as cover letters. Produce a ~300-character LinkedIn DM aimed at a recruiter, hiring manager, or referrer ONLY when the user explicitly asks ("draft a connection message", "write me a LinkedIn DM for this", "outreach to the recruiter"). Spec lives in references/connection-message.md. Output path: ~/Documents/resumes/<Company>/connection-message.md.

No change log. What was reframed and why is a conversation artifact, not a deliverable — if the skill itself should behave differently next time, that's a session-learnings update to the skill, not a file for the user.

Offer: "Want me to convert to DOCX or iterate on any section?"

---

Phase 5R — Review Mode (Critique an Existing Letter)

Use when the user has already drafted a cover letter (or resume bullet set) and wants targeted critique without redrafting. Triggers: "review my cover letter", "critique this draft", "what would you change?", "don't rewrite it, just tell me what's weak".

Mode contract — what Review Mode does NOT do:

• Does NOT redraft. The user owns the prose; Review Mode produces feedback.
• Does NOT rewrite paragraphs into "improved" versions unless the user explicitly asks for a rewrite of a specific paragraph.
• Does NOT silently apply voice from _voice-corpus/ — Review Mode evaluates against the user's voice, not toward AI cadence.

Workflow:

1. Inputs: the draft (paste or path) + the JD (URL, file, or paste). If no JD, ask once; without it the review is blind.
2. Quick JD scan: load references/jd-analysis.md and produce a compact JD profile (no full Phase 1 checkpoint — this is a critique pass, not a tailoring session).
3. Load review references: references/cover-letter-review.md (anti-patterns + opener rules), shared/communication-principles.md (audience-centered, lead-with-conclusion). For resume-bullet review, also references/matching-rubric.md and references/writing-quality.md.
4. Output (single checkpoint, no phase chain):
   • Strengths (2-4 bullets) — what's working, with the specific phrase quoted and why it lands
   • Targeted issues (per paragraph or per bullet) — quote the exact text, name the rule it violates, suggest a direction (not a rewrite). Example: "P2 opens with I led enterprise AI delivery at Govini... — candidate-focused per cover-letter-review §1. Direction: lead with the company's pain, then your evidence."
   • Anti-pattern hits — explicit list of any §5 anti-patterns triggered
   • Mechanical pre-ship checks (per cover-letter-review §6.1): sentence-subject sequence per paragraph, proper-noun cross-check, prestige-density count, hiring-risk anchor in P1, structural diff against canonical baseline, closing-line standalone read, anti-pattern sweep. Print evidence for each — flag any that fail.
   • Hiring-manager perspective review (per cover-letter-review §6.2): dispatch a fresh Sonnet subagent with ONLY the JD, the draft, and the Phase 1 hiring-risk sentence. Surface the subagent's verdict verbatim. If §6.1 caught structural failures the user agrees to revise, optionally defer §6.2 until after the revise.
5. Close: "Want me to rewrite any paragraph you flag, or leave the draft entirely yours?" Wait for explicit per-paragraph rewrite request before producing replacement prose.

Narrow-scope-only refinement rule: broad revision requests ("rewrite this to be better," "tighten the whole letter," "make it more compelling," "improve the flow") produce over-revisions that erase the candidate's voice. When the user asks for broad refinement, push back before drafting: "Want me to (a) flag specific spots to revise, (b) rewrite one paragraph you name, or (c) do an errors-only pass that preserves all phrasing?" Wait for the user to choose scope. Never silently broad-revise — that is the failure mode the named refinement patterns exist to prevent.

Named refinement patterns (user-triggered, per-paragraph):

When the user asks for targeted refinement after the initial review, use these named patterns. Each operates on one paragraph at a time, preserves the rest of the draft, and respects §A philosophy + §5 anti-patterns.

• Personalization pass. Trigger: "add the company project", "tie this to their X", "make this specific to them". Rewrite the named paragraph to reference one verified company project, product, or moment (§4 verification required — never invent) and connect it directly to one concrete element of the candidate's experience. One reference, one connection — don't stack.
• Critique pass. Trigger: "what sounds generic", "what reads like a press release", "what would a hiring manager skip". Critique-only mode: name 2-4 spots that read as filler, press-release cadence, or hiring-manager skim-bait. Quote the exact phrase, name the failure mode, suggest a direction — do NOT rewrite unless the user then asks for a rewrite of a specific flagged spot.
• Tone calibration pass. Trigger: "what's the tone", "does this sound desperate / formal / confident / arrogant", "calibrate the tone". Label the current tone in one word first (e.g. desperate, deferential, boastful, confident, flat, warm) — show the user what you heard before suggesting a shift. Then propose a one-paragraph rewrite toward the target tone if the user names one, or recommend a target if they didn't. Do not rewrite the whole letter — single-paragraph shift only.

Why this mode exists: the default Phase 1-5 chain assumes the user wants a tailored draft. When the user wants critique, the chain over-produces — it rewrites material that should stay theirs. Review Mode is the "I want a sharp editor, not a ghostwriter" path.

Post-write verification (when this skill's own files are edited): after any Edit to references/*.md or SKILL.md in this skill, Read the written file and grep for the inserted anchor text. Do not trust the Edit tool's success signal alone — on hosts where ~/.claude/skills/resume-tailor/ is not a symlink to claude_code/claude-skills/resume-tailor/, edits can land in a stale copy while the canonical repo stays clean. Verify in the canonical path at /Users/summerrae/claude_code/claude-skills/resume-tailor/ (or the host's equivalent).

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Principles

1. Truth-preserving. Select, emphasize, reframe — never fabricate. A reframe must be defensible from the user's actual experience.
2. Visible scoring. Every recommendation shows its confidence band and strategy. No black-box rewrites.
3. Collaborative, not autopilot. Every phase ends with a checkpoint. The user edits, vetoes, and corrects before the next phase runs.
4. Solo-user scope. One person and one canonical resume. Default to one JD at a time. Multi-JD Mode is allowed only for explicit 2-5 JD resume-multiplier requests and produces comparative drafts, not final file-writing or DOCX export.
5. Minimum viable dependencies. Pure markdown by default. Optional DOCX via pandoc with the template reference docs in references/templates/. If pandoc is unavailable, stop at reviewed markdown instead of inventing another render path. No bun/node/React required.
6. Gap handling is disclosure, not manufacturing. Visible gaps go to cover letters or discovery prompts — never filled with invented content.
7. Communication principles apply. Resumes are author-to-audience writing. Audience-centered focus, lead with the strongest evidence, simple plain-language bullets, no ego residue. Load shared/communication-principles.md before Phase 2 matching and Phase 4 positioning — the bullet-level and headline-level decisions are where these principles bite hardest. Run the §9 sameness-detector pass before shipping any resume or cover-letter draft — tailored resumes are a prime sameness offender (generic verbs, interchangeable bullets, cover-letter openers swappable across candidates). Apply the generic-swap test bullet-by-bullet and paragraph-by-paragraph: if swapping the company name leaves the line still working, it's too generic.
8. Cover letters are opt-in only. The default Phase 5 deliverable set is resume + keyword coverage + jd.md. Cover letters are produced only on explicit user request — never offered proactively, never pre-announced, never drafted as a "while I'm at it" addition. The closing prompt deliberately omits cover-letter language so the user has to raise it.
9. Final prose must not sound templated. Lists and tables are for analysis checkpoints only. Headlines, summaries, and cover letters must read like authored prose with a governing idea, specific evidence, and no buzzword stacking. Load references/writing-quality.md before writing them.
10. Voice templates come from the corpus, not from per-company folders. When drafting a cover letter, voice cues come ONLY from ~/Documents/resumes/_voice-corpus/{originals,successful}/. Never read prior letters from ~/Documents/resumes/<other-companies>/cover-letter.md as voice templates — those letters either failed, are in flight, or were endorsed in-session without an interview signal, and pulling voice from them compounds AI cadence. See references/voice-corpus.md.

Professional Help Boundary

This skill helps with resume content and positioning for a specific role. It does not replace professional help for:

• Sustained job-search distress, burnout, or imposter-spirals → therapist or EAP. If the session surfaces acute distress — job-loss anxiety, panic, depressive ideation, or compulsive rewriting driven by anxiety rather than fit — pause the tailoring and say so directly. The resume can wait.
• Career direction at large (whether to apply, whether to change fields, longer-term strategy) → licensed career coach.
• Salary negotiation strategy → licensed career coach or negotiation specialist.
• Legal questions (visa sponsorship, non-competes, discrimination claims, termination disputes) → employment attorney.

When the conversation drifts into any of those, name the limit and suggest the appropriate professional before continuing with resume work.