open-to-work

name

open-to-work

description

A complete, self-contained job-search pipeline for ANY user. Onboards once — building resume, fact pack, voice, and styling files from a resume, LinkedIn/portfolio, or quick interview. After that it tailors your resume to any job (truthfully, never fabricating), builds a one-page DOCX + PDF, runs an ATS scoring loop twice, writes a cover letter in your voice, answers application questions, and can fill/upload the form in the browser. Scans job boards on a schedule, preps for interviews (prep kit, mock, debrief), drafts outreach to recruiters or hiring managers, and tracks every application in a standing pipeline ledger with follow-ups, thank-yous, and offer-negotiation help — all feeding one self-improving library. Use for anything job-search related — onboarding, tailoring, cover letters, ATS scoring, applying, scanning, interview prep or debrief, outreach, tracking applications, negotiating offers, or any time they paste a job posting. If there's a chance this is a job-search task, load it.

Open To Work

A full job-search loop in one self-contained skill: scan → shortlist → tailor → ATS-score → cover letter + application answers → browser fill/upload. It works for any user because all personal content lives in the user's own user-library/ files, which the skill builds during onboarding. Nothing about any specific person is hardcoded.

There are four entry paths. Pick based on the request and on whether the user is already onboarded.

• A. ONBOARDING — builds the user-library. Runs on first use, or when the user says "set me up / onboard me / customize me", or whenever the user-library is missing or empty.
• B. RUN — the tailor-and-apply pipeline for a specific job. Runs once the user-library exists and the user brings a job description (or picks one from a scan).
• C. PREP — interview preparation for a role the user already applied to (or is about to interview for), plus post-interview debrief that grades a real interview transcript against the prep and feeds the lessons back. Runs when the user says they "got an interview", asks to "prep", "practice", or "get ready" — or afterward, "debrief that interview / how did I do / review my interview". Best invoked in the same chat where the application was built — the strategy doc and JD are already in context — but works standalone too. See C. PREP below.
• D. OUTREACH — a direct, personal note (email or LinkedIn) to the recruiter or hiring manager, to pull a strong application out of the pile. Runs when the user asks to "reach out", "email the hiring manager/recruiter", "find their email", or do "cold outreach" — and is offered proactively at the end of a strong tier-1 RUN. Gated to genuinely strong-fit roles. See D. OUTREACH below.

The one rule that overrides everything

Never fabricate experience. Every word on the resume, in the cover letter, and in the application answers must trace to the user's real background as recorded in their user-library/fact-pack.md and base_resume.md, or to something they say in the conversation. Tailoring means reordering, reframing, and resurfacing real experience to match a role — never inventing employers, titles, metrics, skills, tools, or projects. When the ATS step asks for something the user can't truthfully claim, you do not add it; you flag it. A higher score earned by a lie is worthless and collapses in an interview.

Everything you write follows the house writing standard

All copy this kit produces — résumé bullets, the cover letter, application answers, outreach notes, prep-kit framing — should read like the user wrote it, not like an AI. references/writing-standards.md is the advisory house style: the structural tells of machine-written prose (anaphora, the "not X, it's Y" false-negative, antithesis, asyndeton, rhetorical-question transitions, clever comparative endings, staccato fragments), the positive habits that read as human, and how the standard flexes by format (a résumé bullet is terse and fragment-normal; a cover letter flows). Hold it in mind while drafting so output adheres by construction — it's a writing habit, not a post-hoc scoring gate. It never overrides the two rules above it: voice.md (the user's actual voice) wins any conflict, and nothing it suggests excuses fabricating.

The library is a living system — improve it on every pass

The user-library is not a static file you only read. It's a self-improving record that should get richer and more accurate every time the user works with the kit. The truthfulness rule and the enrichment habit are two sides of the same coin: you never invent a fact to fill a gap, but you always capture a real one when it surfaces.

Across every mode, stay alert for material that belongs in the library but isn't there yet, and for entries that have gone stale:

• a real metric the user mentions in chat that a fact-pack bullet was missing;
• a story they tell (a conflict, a failure, a 0→1 win) not yet in fact-pack.md;
• a new role, title, or tool they reference that post-dates the base resume;
• a recurring hard-gap worth noting as a standing pattern, or one that's now closed because they've gained the experience;
• a refined preference (a domain they're done with, a role shape they keep picking) that should update scanner_config.json;
• a gap with no prepared framing that prep should add.

How to capture, safely:

1. Only ever record what the user actually stated or confirmed. Never infer a fact into the library to make an answer or score better. A fillable gap (a missing number the user knows) → ask. A genuine gap (no domain experience) → leave it logged as-is; don't nag about what can't truthfully change.
2. Batch it at the end, never mid-task. Don't interrupt a tailoring or prep flow to do bookkeeping. Collect candidate additions and handle them in the close-out step of each mode.
3. Respect the enrichment mode in profile.json → library_enrichment.mode:
   • confirm (default) — list the candidate additions at the end and ask before writing anything. Trust comes first; the user should always know what's in their library.
   • silent — auto-write the clearly-true, unambiguous additions, then briefly note what you saved ("added that 40% metric to your Zoom entry"). Still pause to confirm genuinely ambiguous ones. The never-fabricate rule is absolute in both modes.
4. Keep base_resume.md clean. Enrich it only with confirmed durable facts (a new role, a real metric) — never with role-specific tailoring from a single RUN.

Track the pipeline — one standing ledger

Where the library captures who the user is, the user-library/applications.json ledger captures where every role stands — applied, reached out, interviewing, heard back — and what's owed next. Every mode updates it in its close-out (RUN logs an application, OUTREACH logs a note, PREP logs an interview, the debrief logs the outcome), so the user can ask "what's still open?" or "who do I owe a follow-up?" and get a real answer. The full schema and the per-mode update rules are in references/application-tracker.md. It's the same discipline as the library: agent- maintained plain JSON, written at close-out (not mid-task), under library_enrichment.mode, recording only what actually happened. Thank-yous, status nudges, and offer-negotiation briefs hang off it — see references/followup-and-negotiation.md.

This skill needs Cowork or Claude Code — not a plain chat

The full system only works in an environment with a persistent filesystem, a shell, and (for the power features) scheduled tasks and browser control — i.e. Claude Cowork or Claude Code. This is not optional polish; several core pieces silently fail without it, and a user who runs this in a regular claude.ai/Claude-app chat will get a convincing conversation with nothing real behind it. Be honest about this up front rather than letting them discover it after onboarding.

What depends on the environment:

• The persistent user-library/ — onboarding's entire premise is "build it once, reuse it forever." A plain chat has no folder that survives between conversations, so nothing actually saves; the library evaporates when the chat ends.
• The bundled Python scripts — generate_resume.py (DOCX), export_pdf.py (LibreOffice → PDF), page_count.py, and job_scanner.py need a shell to run. No shell, no real DOCX/PDF, no scan.
• Scheduled scans need scheduled tasks; browser fill and the LinkedIn/Wellfound pass need the Claude for Chrome extension on an agentic surface.

In a plain chat the skill can still talk — discuss strategy, draft a cover letter or answers as throwaway text — but it cannot save a library, produce files, score with the real scripts, scan, or apply. If you detect you're in an environment without a usable filesystem/shell, say so before onboarding (see Step A0) so the user can switch to Cowork or Claude Code instead of building a library that won't persist. Never narrate ✓ Saved … for writes you cannot actually perform.

Where the user-library lives

The user-library is a user-library/ folder in the user's working folder (the folder they've connected, or wherever their job-search files live) — NOT inside the installed skill bundle, which may be read-only. The bundle ships a user-library/NOT_ONBOARDED.md marker as the seed.

Detect first-run: at the start of any job task, check for the user's user-library/ with filled files (profile.json, base_resume.md, fact-pack.md, voice.md, format.json). If it doesn't exist, is empty, or still contains NOT_ONBOARDED.md, go to ONBOARDING — starting with the Step A0 welcome below. Otherwise go to RUN (or the scanner). If you're unsure where the working folder is, ask the user, or create user-library/ in the folder you have access to.

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A. ONBOARDING — build the user-library

The point is to capture, once, everything the pipeline needs so every later run is fast. Be warm and efficient; don't interrogate.

Step A0 — First-run welcome & overview (always do this first)

Before anything, confirm the environment can actually run the full system. The kit needs a persistent filesystem (a library that survives between conversations), a shell (to run the bundled scripts), and — for the power features — scheduled tasks and browser control. That means Claude Cowork or Claude Code. Be careful here: a regular claude.ai/Claude-app chat with code execution on has a temporary sandbox that looks writable but is wiped when the conversation ends — so "can I write a file right now?" is not a sufficient test. It would pass in plain chat and then silently lose the whole library.

So determine the surface honestly:

• If you can tell you're on an agentic surface with a persistent working folder (Cowork or Claude Code — you have a connected/working directory the user returns to, not just an ephemeral sandbox), proceed.
• If you're in a plain chat (no persistent working folder across sessions, even if a temporary sandbox exists, or you genuinely can't tell), say so before onboarding in one short message: the full kit — saving a reusable library, generating the DOCX/PDF, scanning, and applying — needs Claude Cowork or Claude Code. In a regular chat you can only talk through strategy or draft throwaway text that won't persist. If unsure which surface you're on, ask the user (e.g. "Are you running me in Cowork or Claude Code, or a regular Claude chat?") rather than assuming. Offer the lighter help, but recommend they re-open the skill in Cowork or Claude Code for the real thing.

Do not proceed into onboarding and pretend-save a library that will vanish, and never narrate ✓ Saved … for a write that won't persist. Only continue past this point once you've confirmed a genuinely persistent place to write.

On the very first run (the library is missing/empty or NOT_ONBOARDED.md is still present), before asking anything else, give the user a short, friendly orientation so they know what they're installing and what it will need from them. Keep it to a tight, skimmable message — a couple of short paragraphs or a compact list, not a wall of text — covering:

1. What this skill does. The full loop, in one breath: it learns your background once, then for any job you target it tailors your resume (truthfully — never inventing experience), builds a polished one-page DOCX + PDF, ATS-scores it twice, writes a cover letter in your voice, answers the application questions, can fill and upload the application in your browser (stopping before Submit), and can scan job boards on a schedule to surface new matching roles.

2. What you'll provide (in onboarding, next). Whatever you have — an uploaded resume, a LinkedIn/portfolio link, or just a guided Q&A — plus a few things only you know: real metrics and stories, any genuine personal hooks to companies or domains, an honest list of gaps, and a writing sample so the voice matches yours. This builds your private library (profile.json, base_resume.md, fact-pack.md, voice.md, format.json).

3. The two power features worth turning on (don't undersell these — they're where most of the leverage is, and they need a little setup, so actively walk the user toward them rather than mentioning them in passing):

   • Automated job scanning on a schedule. Runs twice a day (or your cadence) and surfaces a ranked shortlist of new matching roles — including a logged-in browser pass over LinkedIn and Wellfound alongside the keyless job-board APIs, so you're not limited to boards with a public API. You'll configure your search (roles, levels, locations, comp floor, the role shape and priority vs. hard-no domains, companies to watch) and pick a schedule.
   • Browser fill & upload. At the end of an application run, it can open the form in your browser, fill the standard fields from your profile, upload your tailored résumé + cover letter into the right slots, drop in your drafted answers, and stop before Submit for you to review.

   Both of these use the Claude for Chrome extension (for the browser pass and the form fill) and a logged-in browser session. Tell the user this up front so they can install it — these aren't afterthoughts, they're the difference between a one-shot document generator and a standing job-search engine. You'll prompt them to set both up right after the library is built (Step A3).

4. Where your data lives & privacy. Everything personal stays in your own user-library/ files in your working folder, on your machine — nothing is baked into the skill or shared by installing it.

5. Dependencies (mention briefly). Python 3.8+, the python-docx package, LibreOffice for PDF export, and poppler (pdfinfo/pdftotext, for the page check

   • ATS text extraction — pypdf is an auto-fallback); the scanner itself is pure standard library. The Claude for Chrome extension powers the scheduled browser pass and the form fill/upload. Running python3 <skill_dir>/scripts/selfcheck.py verifies dependencies and the scanner's core logic in one shot — do this once after install, and after editing any script.

6. Where it runs (state this plainly). The full system runs in Claude Cowork or Claude Code — it needs a persistent place to keep your library and a shell to build your documents. In a regular Claude chat it can still talk through strategy and draft text, but it can't save your library or generate real files. If they're already in Cowork/Code, a quick "you're in the right place" is enough; if not, point them there before going further.

Then tell them what happens next and hand off to Step A1 to begin — e.g. "Ready to set up your library? It takes ~5 minutes if you have a resume to upload, or ~20 for a fuller guided version — and once it's built I'll get you set up with automated scanning and browser apply. Which would you prefer?" Don't wait for a separate "go" if they've already asked to be onboarded — flow straight from the overview into the Quick-vs-Thorough choice.

Step A1 — Offer Quick vs. Thorough

Ask the user which they'd prefer (use the question tool if available):

• QUICK (~5 min) — best if they upload a resume. Parse it, then ask only the gaps. Produces a solid library.
• THOROUGH (~20 min) — a fuller guided interview. Produces a richer fact pack and a more precise voice capture. Best if there's no resume or they want the strongest output.

Accept any starting material: an uploaded resume file, a pasted LinkedIn or portfolio URL/text, or pure guided Q&A. Parse whatever they give first and only ask for what's genuinely missing.

The full question banks for both depths are in references/onboarding-interview.md — read it and follow the matching set.

Step A2 — Produce the library files

Write these into the user's user-library/ folder. Each has a template in references/ — read the template, then fill it from what you gathered. Strip nothing into them but the user's real information.

• profile.json — name, contact, links, location, work authorization, sponsorship need, comp target/floor, and the standard application-form answers. Template: references/profile-template.json.
• base_resume.md — their master resume in the exact markdown format generate_resume.py consumes. Template: references/base_resume-template.md.
• fact-pack.md — roles with real metrics; signature stories (including a "deviated from standard process" story, which most applications ask a version of); genuine personal hooks/passions; the reusable elevator pitch; recurring narrative threads; differentiators; and an honest list of gaps. Template: references/fact-pack-template.md.
• voice.md — their writing voice, captured from a writing sample if they have one, else from how they answer. Template (with the capture method): references/voice-template.md.
• format.json — letterhead/styling tokens (name font, body font, accent color, text/muted/rule colors) so the output reflects them, not a fixed design. Template: references/format-template.json.

Step A3 — Set up automation & browser apply (strongly recommended — prompt for it)

This is the step that turns the kit from a document generator into a standing job-search engine. Don't present it as a throwaway "optional" — actively walk the user through it and explain what each piece buys them. Use the question tool if available. Cover all three of the following; if the user declines any, that's fine — note it and tell them they can turn it on later by saying "set up scanning" or "set up browser apply."

A3a — Build the scanner config. Gather the config the template asks for and write it into user-library/scanner_config.json (template: references/scanner_config.template.json):

• target roles/levels and (optionally) a precise role_title_regex;
• acceptable locations + home_terms, and whether to require remote-or-home;
• comp_target/comp_floor (and whether to admit unleveled roles when comp clears the floor);
• signal_keywords (role-fit themes) and shape_signals (the role shape they most want — founding / first-hire / 0→1 / generalist — edit the example list);
• tier1_keywords/tier2_keywords as example priority domains (non-exhaustive — an unlisted domain stays neutral) and exclude_keywords as the hard-no list;
• max_age_days (recency window), deep_read_threshold (default 50), result_cap;
• any companies to watch (find and verify their Greenhouse/Lever/Ashby board slugs), or leave watchlist_enabled: false for discovery-only.

Present these as user-configurable with sensible defaults — the tier/keyword and watchlist lists are examples, not a fixed whitelist. Also write an empty user-library/seen_postings.json containing {"seen": []} and an empty user-library/applications.json containing {"applications": []} (the pipeline ledger — see references/application-tracker.md).

A3b — Create the recurring schedule (offer it directly, with a default). Don't just mention that scheduling exists — propose it: "I'll set this to scan twice a day (~8am and ~4pm your time) and send you a ranked shortlist — sound good, or want a different cadence?" Then create the scheduled task using the ready-made prompt in references/scanner-scheduled-task.template.md (it already wires up the full flow: the logged-in LinkedIn/Wellfound browser pass, the keyless API aggregators, two-stage scoring, the live-status check, and the canonical-ATS lookup). Confirm their timezone. See the Scanner & Scheduling section for the run mechanics.

A3c — Set up the Claude for Chrome extension (the key enabler — prompt for it). Two of the best features depend on it, so explicitly ask the user to install it and confirm it's connected:

• the logged-in browser pass over LinkedIn and Wellfound in the scheduled scan (these have no keyless API — the browser pass is the only way to include them, and it needs the user signed in to those sites in their browser);
• the browser fill & upload at the end of an application run.

Walk them to it: "Install the Claude for Chrome extension and stay signed in to LinkedIn/Wellfound — that lets me scan those two and fill out applications for you. Want to do that now?" If they install it, confirm it connects. If they skip it, note that LinkedIn/Wellfound won't be scanned and applications will be hand-off-to-them rather than auto-filled — and that they can add it anytime.

A3d — Set up interview recording (offer it; apply the consent logic). The debrief step — which turns every real interview into sharper prep — requires a written transcript. Setting up a transcription tool now means the user is ready to capture from interview one.

Before recommending, check consent tier from profile.json → location (or ask):

• Location known, one-party consent state (not CA, CT, FL, IL, MD, MA, MI, MT, NH, OR, PA, WA — most states fall here, including CO and the majority of the US): recommend Meetily directly. It's free, open-source, runs and transcribes locally (no audio leaves the device, no bot joins the call), and exports clean plain text. Walk them to it: "I'd recommend setting up Meetily for recording interviews — it's free, totally local, and makes the debrief possible. Want to do that now?"
• Location known, two-party consent state (CA, CT, FL, IL, MD, MA, MI, MT, NH, OR, PA, WA — or equivalent in another country): almost never raise this unprompted. If the topic comes up, surface it once with the caveat first and leave it: "Quick note: [state] requires all parties to consent to a recording. If you disclose it at the start of the call and get agreement, Meetily is a good free option — but that disclosure is on you." Don't push; don't repeat.
• Location unknown: ask before recommending — "One useful thing to set up is a transcription tool for debriefing interviews later. What state (or country) are you in? That affects whether recording is fair game or requires disclosing it to the other party." Once they answer, apply the appropriate path above.

Save the tool name (e.g. "meetily") or null if they skip, and the derived consent_tier ("one_party", "two_party", or null) to profile.json → interview_recording. These fields drive the prep-session close-out reminder and the debrief consent note.

A3e — Set the library-enrichment mode (quick, one question). Explain in a line that the kit keeps their library improving over time — when a real metric, story, or preference surfaces during a run, it can save it so every future application and prep gets sharper. Ask how they want that handled and write it to profile.json → library_enrichment.mode:

• Confirm (default) — "I'll ask before saving anything new to your library."
• Silent — "I'll auto-save clearly-true additions and just tell you what I saved (and still check with you on anything ambiguous)."

Note that either way it only ever saves things they actually said — it never invents or guesses a fact. Default to confirm if they don't care.

Step A4 — Confirm back, then finish

Read back a concise confirmation: identity, the roles captured, the personal hooks and the deviated-from-process story, the honest gap list, and a 2–3 sentence pastiche in the captured voice ("does this sound like you?"). Adjust from their reaction. Then delete user-library/NOT_ONBOARDED.md so first-run won't re-trigger, and summarize what's now live: that they can paste a job description to tailor an application; whether scanning is scheduled (and when); and whether browser apply is ready (Chrome extension connected) or still needs the extension. Name anything they skipped and how to turn it on later.

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B. RUN — tailor an application for a specific job

Mirrors a proven pipeline, reading the user's library. Tailor → build DOCX → export PDF → enforce one page → ATS loop ×2 → coordinated cover letter + application answers → report → (optional) browser apply.

The split is deliberate: the fiddly, error-prone mechanics (building the .docx, PDF conversion, page counting, letterhead) are handled by deterministic scripts so they come out identical every time. The parts that need judgment — what to emphasize, which ATS recommendations to act on, whether a claim is true, and the writing — stay with you.

Prerequisites

• Full JD text is required. If given only a URL, fetch it and confirm you have the real responsibilities and qualifications. If the fetch is thin or blocked, ask the user to paste the posting. Don't infer the role from a company name.
• The user-library exists (else onboard first). Identify the company name from the JD — it drives the file names.

Naming convention

Working files in the user's working folder; <Name> = the user's name (no spaces), <Company> = the company TitleCased, <company> lowercase:

• Resume working markdown: resume_<company>.md
• Cover-letter working markdown: coverletter_<company>.md
• Deliverables: Resume_<Name>_<Company>.docx / .pdf, and CoverLetter_<Name>_<Company>.docx

Path note for the scripts

Run scripts from <skill_dir>/scripts/. Always pass the user's library files so nothing is hardcoded:

--profile <working>/user-library/profile.json
--format  <working>/user-library/format.json

Step 1 — Strategy + tailor (judgment)

Read user-library/fact-pack.md and user-library/base_resume.md. Analyze the JD against them: strongest alignment, real gaps, the positioning angle. Then create resume_<company>.md by copying base_resume.md and editing the copy — never edit the base; it must stay clean for the next role.

Tailor through the levers the format supports: the title line (highest-impact single change — match the role's language), the summary (lead with the most relevant angle — always in first person; see the two hard rules below), experience lines (reorder and reword for keyword alignment, never invent), skills (reorder so JD-relevant terms lead), and projects (reorder/lightly reword). Keep the section order and density of the base.

When rewording any prose — the summary especially, and bullet phrasing — follow references/writing-standards.md, calibrated to résumé register: bullets are terse and metric-led (a bullet is allowed to be a fragment), but avoid the résumé-specific tells — every bullet opening the same way, buzzword padding, and a summary written in abstract "results-driven professional" AI-speak. Lead with concrete outcomes.

The summary is first-person and yours — two hard rules. (1) Voice. Write it as the user actually talks — first person ("I'm a product designer; for 10 years I've…"), never the detached third-person/persona register ("Product designer with 10+ years…", "Designs end-to-end experiences…", "Prototypes and ships…", "raises the bar for the teams around him"). Bare third-person verb openers and any he/she/him/her pointing at the user are the tell — the summary should read as genuinely the user, not a dossier about them. voice.md governs the exact register. (2) No trait-mirroring. Echoing the JD's nouns/keywords (design systems, MCP, retrieval, evals, Figma plugin, the domain) is correct and good for ATS — do it. Echoing the JD's adjectives / behavioral / "who you are" trait language ("holds a point of view in a critique", "pragmatic about where AI pays off", "comfortable being the senior IC", "it just works", "keeps people in control") lightly reworded is the tell — it makes the résumé read as reverse-engineered for one posting. The test for every summary line: would the user write this sentence if they had never seen this posting? If it exists only because the JD said it, cut it or rewrite it to something true and durable. (Run lint_copy.py summary resume_<company>.md to catch the mechanical version of both.)

Step 2 — Build the DOCX (deterministic)

Do not hand-roll a renderer. The whole visual design lives in the script:

python3 <skill_dir>/scripts/generate_resume.py \
  --input resume_<company>.md \
  --output Resume_<Name>_<Company>.docx \
  --profile <working>/user-library/profile.json \
  --format  <working>/user-library/format.json

(Optional company logo: --logo logos/<company>.png --logo-height 38.)

Step 3 — Export the PDF (deterministic)

python3 <skill_dir>/scripts/export_pdf.py "<working>/Resume_<Name>_<Company>.docx"

Step 4 — Enforce the page target (deterministic check, judgment fix)

python3 <skill_dir>/scripts/page_count.py "<working>/Resume_<Name>_<Company>.pdf" \
  --max-pages <format.json max_pages, default 1>

The target is one page for most roles; pass the user's format.json max_pages so longer-format fields (academic CV, federal, senior/technical) aren't force-trimmed to one. If it reports more than the target, it prints exactly what spilled past it. Trim the smallest amount that fixes it (tighten the longest wrapped lines first, drop the least JD-relevant skill terms) in resume_<company>.md, then re-run Steps 2→3→4 until it's within target.

Optional parse-safety check. Confirm the PDF extracts cleanly the way an ATS parser reads it (catches a styled header — e.g. a logo table — scrambling extraction order):

python3 <skill_dir>/scripts/lint_copy.py parse "<working>/Resume_<Name>_<Company>.pdf" \
  --expect "<Name>" "EXPERIENCE" "SKILLS"

Summary voice check (advisory). Confirm the summary reads as first-person and isn't mirroring the JD's trait language:

python3 <skill_dir>/scripts/lint_copy.py summary "<working>/resume_<company>.md"

Step 5 — ATS loop, run it TWICE (judgment inside a fixed loop)

Use the self-contained rubric in references/ats-rubric.md. Run the whole sub-loop two full rounds. Each round: score the current resume against the full JD → triage each gap through the truthfulness filter (soft gap → reword/surface it truthfully; hard gap → do NOT fix; record it for the report) → apply edits to resume_<company>.md and re-run Steps 2→3→4 so docx, pdf, and the one-page guarantee stay in sync. Length is fixed at one page — every addition needs a trim. Capture both scores and the specific changes; Round 2 scores what Round 1 produced.

Step 6 — Coordinated writing pass: cover letter + application questions

Runs after the resume is locked, drawing on the same role analysis. Cover letter (a file) and answers to open-ended application questions (delivered in chat) come from one coordinated effort — plan them as a single set so the user's stories and metrics don't collide across them.

First, load the user's voice. Read user-library/voice.md and hold it in mind for every sentence — the whole point is that the letter sounds like them, not like generic AI cover-letter voice. Then read references/cover-letter-playbook.md for the universal craft rules: the opener hierarchy (genuine personal connection if real > elevator pitch > never a thesis cold open), the anti-staccato rhythm rule (flowing sentences whose clauses connect — clipped fragments-for-effect are the #1 machine-written tell), naming honest gaps plainly, and the coordinated evidence-distribution plan across the letter and every answer. Also hold references/writing-standards.md — the full house style — so the letter and every answer avoid the structural AI tells while you draft them, not after.

Ground every claim in user-library/fact-pack.md; the never-fabricate rule applies in full. Scan for open-ended application questions both in the JD text and — if you have browser access — in the application form itself (most ATS hide essay questions behind the Apply button). List the questions you found before answering.

Write the letter, save it as coverletter_<company>.md (frontmatter + body paragraphs — see the format in scripts/build_cover_letter.py), then render it:

python3 <skill_dir>/scripts/build_cover_letter.py \
  --input coverletter_<company>.md \
  --output "CoverLetter_<Name>_<Company>.docx" \
  --format  <working>/user-library/format.json \
  --profile <working>/user-library/profile.json

This reuses the resume's exact design tokens so the letter is a visual match. Keep it to one page, ~3–5 tight paragraphs (verify with export_pdf + page_count if unsure). As an advisory pass, you can run lint_copy.py prose <coverletter_<company>.md> to surface the structural AI tells from writing-standards.md — judge each flag against the user's voice; never auto-rewrite a clean, true line. Output the application answers directly in chat, copy-paste-ready — a markdown heading with the exact question text and the answer beneath — never as a file. If you found no open-ended questions and couldn't see the form, say so and remind the user to check the form for hidden questions.

Step 7 — Report & enrich the library

Give a tight summary: Round 1 score + changes; Round 2 score + changes; final score; Deliberately skipped (every recommendation declined because it would require fabricating experience — a feature, not an apology); the cover-letter angle/hook and any honest gap named; which application questions you found (and whether any may be hidden behind the form); and the three deliverable paths. Then share the files (via present_files if available, else give the paths).

Then enrich the library (per "The library is a living system" up top). Look back over the run for anything true that surfaced and isn't captured yet: a real metric the user mentioned that a bullet was missing, a story they told in chat, a tool or role newer than the base resume, or a hard-gap that recurred and is worth logging as a pattern. Handle it per profile.json → library_enrichment.mode — in confirm mode, list the candidates and ask before writing; in silent mode, save the clearly-true ones and note what you saved. Only ever record what the user actually said. Keep base_resume.md clean — durable facts only, never this role's tailoring.

Update the tracker. Log this role in user-library/applications.json — status (applied if submitted, else prepared), the deliverable paths, JD/apply links, ATS, and tier — per references/application-tracker.md. This is what lets the user later ask "what's still open?"

If this is a strong tier-1 fit, offer outreach (see D. OUTREACH). When the user has a genuine hook to this company/role/domain — a real passion, a near-exact experience match — a personal note to the recruiter or hiring manager is the natural next step, and it's strongest right now while everything's in context. Offer to draft it. On a weaker (tier-2/3) fit with no genuine hook, don't push it — just mention it's available if they have a personal angle worth playing.

Step 8 — Apply in the browser (optional)

If the user wants you to fill/upload the application, follow references/browser-autofill.md. The essentials:

• Apply on the canonical ATS, not a profile-only aggregator. Some sources (e.g. Wellfound, LinkedIn Easy Apply) only transmit the user's profile with no file upload — so the tailored résumé and cover letter can't be attached. When a role was found on one of those, first search for the same posting on the company's real ATS (Greenhouse / Ashby / Lever) or careers page and apply there. Profile-only is the fallback when no canonical posting exists.
• Stage the final PDFs into the agent's writable outputs/working folder (never a read-only dir, Drive/Dropbox cross-origin picker, or the native OS dialog — only the outputs→file_upload path works), open each application in its own tab, fill standard fields from profile.json, upload résumé then cover letter (re-find each file input right before each upload; verify the filenames landed in the correct slots after).
• Some ATS forms have no cover-letter slot and/or no open-ended essay questions. That's fine — the cover letter is always a standalone deliverable the user can email or hand to a recruiter, so produce it regardless of whether the form accepts it.
• Leave genuine user-judgment fields for the human — never auto-answer or auto-agree to: relocation-willingness questions, "have you used before" questions, terms/consent checkboxes, and the final Submit. Fill what you can verify from profile.json, then stop before Submit for the user to review — unless they've explicitly authorized you to submit.

---

C. PREP — get ready for the interview

The loop doesn't end at "applied." When the user lands an interview, this turns the same context the application was built from — the JD, the positioning strategy, the fact pack, the honest gap list — into a focused prep kit, and (if they want) runs a mock interview. The advantage over generic interview advice is continuity: the prep emphasizes the exact strengths you positioned on and defends the exact gaps you logged, so the user walks in consistent with the application that got them the call.

Tell the user the best way to invoke this: from the same chat where the application was built, the JD and strategy are already in context, so prep is sharpest there. If they're in a fresh chat, that's fine — reconstruct from the library and ask them to paste the JD (and the company/role if unclear).

Prerequisites

• The user-library exists (else onboard first — though prep can run thin if they just want quick practice).
• The role. Ideally the original JD + the strategy/tailoring notes from the RUN. If this is a fresh chat, ask for the JD and company; pull everything else from fact-pack.md, base_resume.md, and the tailored resume_<company>.md if it's still around.

Step P1 — Ask how they want to prep (unless they've said)

If the user hasn't already specified, ask (use the question tool if available) which they want — they can pick more than one:

• Prep kit — a single written brief they can read on their phone before walking in. The default; fast and high-value.
• Mock interview — an interactive practice loop where you play the interviewer, ask questions, and give feedback after each.
• Both — build the kit first, then run the mock off it.

Also ask what round this is if it's not obvious, because it reshapes everything: recruiter screen (tight pitch, comp positioning, logistics, "why this company"), hiring-manager / behavioral (STAR stories mapped to competencies, gap defense), panel / cross-functional (stakeholder stories, breadth, working style), portfolio / case review (which work to lead with, how to narrate decisions and tradeoffs — for design/eng/PM), technical / take-home (scope, what "good" looks like, how to talk through tradeoffs), or final / executive / skip-level (vision, trajectory, culture-add, smart questions upward). Default to a hiring-manager behavioral round if they don't know.

The full prep playbook — what goes in the kit, how to map stories, how to run the mock loop, and round-by-round emphasis — is in references/interview-prep.md. Read it and follow it.

Step P2 — Build the prep kit (if chosen)

Following references/interview-prep.md, assemble a tailored brief with these parts, drawn from the JD + strategy + library (not generic advice):

1. Company & role refresher — what the company does, recent context worth knowing, and a plain-language read of what this role actually owns and is measured on. If you have web access and the company may have had recent news/funding/launches, do a quick check so the user isn't blindsided; otherwise work from the JD.
2. Your angle — the positioning the application led with, restated as the through line to hold across every answer.
3. Strengths to emphasize — the 3–5 strongest alignments between their background and this role, each with the proof point ready.
4. Gaps to manage — the honest gaps logged during the application (and any new ones the JD implies), each with a prepared, non-defensive framing. These are the "questions you're afraid of"; rehearse them most.
5. Story bank, mapped — their signature stories from fact-pack.md mapped to the competencies this role screens for, so they know which story answers which likely question. Include the "deviated from standard process" story (commonly asked) and at least one conflict/failure story.
6. Predicted questions — the behavioral and role-specific questions this posting is most likely to generate, each with a one-line angle (and which mapped story to reach for). Not a generic bank — derived from the JD's responsibilities and the gaps.
7. Questions to ask them — tiered by interviewer (recruiter vs. hiring manager vs. skip-level/exec), because asking the right person the right thing reads as seniority. Include 1–2 that surface real red flags about the team or role.
8. Logistics & comp — their target/floor from profile.json, how to deflect an early comp question, and any format specifics (who they're meeting, how long).

Deliver the kit as chat text by default (readable on a phone), or as a file if the user asks for something to keep. Keep it tight and scannable — this is a pre-interview brief, not a dossier.

Step P3 — Run the mock interview (if chosen)

Run it as a real interactive loop, per references/interview-prep.md: play the interviewer for the chosen round, ask one question at a time, wait for the user's answer, then give brief, specific feedback (what landed, what to tighten, whether they reached for the right story) before the next question. Calibrate difficulty to the round. Pull from the predicted-questions list and lean into the gap questions, since those are where people most need reps. After ~6–10 questions (or when they call it), give a short overall read: strongest answers, the 2–3 things to fix, and any story that still needs sharpening. Never invent facts about the user to fill an answer — if they fumble a story, help them reshape their real material, not a better fictional one.

Step P4 — Close out & enrich the library

Point them back to whichever piece they didn't use yet ("want the mock now?" / "want the written kit to review later?"), and remind them prep is sharpest from the application chat next time. Log the upcoming interview on the role's applications.json record (round + date, status: interviewing) per references/application-tracker.md.

Then enrich the library (per "The library is a living system" up top). Prep is one of the richest sources of new material: stories the user told better out loud than they're written in the fact pack, a failure or conflict story that wasn't logged, a gap framing they worked out during the mock that's worth saving, or a metric they recalled mid-answer. Capture it per profile.json → library_enrichment.mode (confirm vs. silent), recording only what they actually said. If the library was thin where it mattered — a sparse story bank, no failure story, gaps with no prepared framing — name it so fact-pack.md is stronger before the next round.

Recording reminder — one line, at the natural close. At the end of the prep kit delivery or the mock wrap — whichever is the last substantive exchange — add a brief note based on profile.json → interview_recording:

• Tool is set (e.g. "meetily") → always include a one-liner: "Don't forget to start [tool] before the call." One sentence, nothing more.
• Tool is null, consent_tier one_party → offer once if it fits: "If you haven't set up a transcription tool, it's worth doing before this one — makes the debrief possible. Meetily is free." Skip if they've declined before.
• Tool is null, consent_tier two_party → omit the reminder entirely. If they ask about recording, surface the all-party-consent caveat once and leave it with them.
• Tool is null, consent_tier null → one sentence at most: "If you're in a one-party-consent state, Meetily is free and worth setting up before the call." Don't ask the location question here — that belongs in setup (A3d), not a close-out.

Keep this minimal: the user is heading into an interview, not starting a new task. If the session ended without a clear closing signal (the user just stopped responding), the natural injection point was the last substantive message you sent — the kit delivery or mock wrap — so it should have been included there.

Step P5 — Debrief the real interview (after it happens)

Prep gets the user ready; the debrief is how the kit learns from how it actually went. Runs when the user comes back from a real interview and wants to review it — "debrief that interview", "how did I do", "review my interview". Best run in the same chat as the prep, where the prep kit and predicted questions are already in context.

This requires a written transcript (Meetily recommended, but any accurate transcript works — Otter, the call platform's own captions, or a clean manual transcription). The debrief grades what actually happened against the prep; a from-memory recap is too lossy and biased by the user's own impression to be useful, so the kit does not reconstruct a debrief from recollection. No transcript, no debrief — say that plainly and point them at the capture setup for next time (in references/interview-prep.md).

When the user has a transcript:

1. Consent note (once, tiered). Apply the same logic as A3d: check profile.json → interview_recording.consent_tier. For one_party, a brief "on you to have had the legal basis" line is enough, said once. For two_party, it matters more — ask plainly whether they disclosed the recording before it started, then proceed regardless of the answer (don't withhold the debrief, but make sure they know). For null, surface the question: "Was this recorded in a state where only your consent is needed, or do all parties need to agree?" Then save the tier. Don't moralize; don't repeat.
2. Synthesize against the prep kit, per references/interview-prep.md: which predicted questions actually came up (and which the prep missed), how each answer landed, where they reached for the right story vs. fumbled, which gaps got probed and whether the prepared framing held, and anything notable in how the interviewer reacted or where the conversation cooled or warmed.
3. Deliver a tight learning report: strongest answers, the 2–3 highest-leverage fixes, and specific lines or stories to tighten — concrete and quotable from the transcript, never generic interview advice.
4. Enrich the library (per "The library is a living system"). The debrief is the single richest signal the kit gets, because it's real performance, not rehearsal: flag underperforming stories for reshaping, add questions the prep didn't predict to the bank for next time, and rewrite gap-framings that didn't hold. Capture per the user's library_enrichment.mode, recording only what the transcript actually shows. This is the compounding loop — every real interview makes the next prep sharper.
5. Update the tracker and offer a thank-you. Mark the interview debriefed with a one-line outcome in applications.json, and — since it's within the ~24-hour window — offer to draft the post-interview thank-you (specific to this conversation, in the user's voice). Both per references/followup-and-negotiation.md and references/application-tracker.md.

Setup for capturing the transcript (Meetily, both call types, speakerphone tips) is in references/interview-prep.md.

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D. OUTREACH — reach the human directly

An application goes into a pile; a personal note to the right human can pull it out. This builds that note — but only when the fit is genuine, because outreach works because it's real. Best run as the next step after a strong RUN (the JD, strategy, and tailored materials are right there), but works standalone too ("help me reach out to the hiring manager at X").

Full method — finding the person, deducing the email, the subject-line formula, the body arc, the LinkedIn variant, and the guardrails — is in references/outreach-playbook.md. Read it and follow it. The essentials:

• Tier-gate it. Outreach is for tier-1, genuinely strong-fit roles — where the user has a real passion, near-exact experience match, or personal hook. On tier-1, recommend it proactively and draft it without being asked. On tier-2/3 with no genuine hook, don't push it; offer only if asked, and be honest it's weaker without a real connection. Never manufacture a passion or connection to justify a note. (Pull the tier from the scan score if there is one; judge fit from the fact pack if standalone.)
• Two methods: email preferred, LinkedIn fallback. Email when the address is findable and the user's willing; LinkedIn (shorter, no subject line) when the email can't be found/verified or they'd rather not cold-email. On a strong tier-1 role, prepare both.
• Find a real named person (hiring manager for "why I'm a fit," recruiter for "is this live / please flag my app") via LinkedIn research — never invent a name.
• Deduce the email honestly — hunter.io in the browser or pattern inference from a known company address; flag whether it's verified or just deduced (deduced may bounce), and never present a guess as confirmed.
• Write it in the user's voice (voice.md + the cover-letter playbook's craft rules + references/writing-standards.md), grounded in fact-pack.md. The subject-line formula and body arc in the playbook are an adaptable pattern, not a fill-in template — shape them to the individual's voice, material, and prep. A true single hook beats three stretched ones. The danger here is sounding like cold AI outreach, so the structural tells matter doubly: no asyndeton lists, no "Here's why I'm perfect for this," lead with a genuine specific.
• Deliver copy-paste-ready; never auto-send. The human always presses send on something genuinely personal. (A reviewed Gmail draft is fine if they ask; the human still sends.)
• Enrich the library afterward with any genuine new hook that surfaced, per the enrichment mode, and log the outreach on the role's applications.json record (method, who, email-confidence, date) per references/application-tracker.md.

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Scanner & Scheduling (optional)

A config-driven scanner surfaces new matching roles and feeds them into RUN. It does broad market discovery across keyless aggregators (Remotive, RemoteOK, Arbeitnow, Jobicy; Adzuna optional) plus an optional Greenhouse/Lever/Ashby watchlist. Everything it filters/scores on lives in user-library/scanner_config.json.

Run a scan now (on a machine with network):

python3 <skill_dir>/scripts/job_scanner.py --config <working>/user-library/scanner_config.json

Two-stage scoring (don't deep-read everything). The script is the cheap Stage-1 card pass: it scores every role 0–100 from the listing and flags deep_read: true/false against deep_read_threshold (default 50). The agent does Stage 2 by hand only on flagged cards — open the JD, do a live-status check (drop 404s / "no longer accepting"), extract real comp + scope, re-score, and for a profile-only find (Wellfound/LinkedIn/Built In) search for the canonical ATS "Apply at" link. Scoring is calibrated so domain is non-exhaustive (an unlisted domain is neutral; only exclude_keywords drop a role) and role-shape/baseline can carry a well-shaped role over the bar with no domain match.

Scheduled & unattended runs can't use bash networking, so the agent web-fetches each source. Full procedure, the browser pass (LinkedIn, Wellfound, Built In), and the ready-made scheduled-task prompt are in references/scheduling.md and references/scanner-scheduled-task.template.md — default cadence twice daily (~8am/4pm local). Postings dedupe via seen_postings.json so nothing repeats. From a shortlisted role the user drops into RUN.

Built In (tech/startup users). builtin.com is a strong board for tech/startup roles with good national-remote and metro coverage. It's JavaScript-rendered (no clean public API), so it runs in the browser pass alongside LinkedIn/Wellfound — NOT the API aggregator pass. Tech-field users should include it; non-tech users can skip it. See references/scheduling.md for the URL pattern and save format. The script picks up fetched/builtin__<label>.json and fetched/builtin-<region>__<label>.json files automatically through the same pipeline as other browser sources.

Resilience — best-effort aggregators and incremental persistence (important). The scanner is designed so a single failure doesn't wipe the run:

• Aggregator failures are skipped, not fatal. If a source fails, times out, returns non-JSON, or is blocked, it's logged in sources_failed and the run continues. HARD RULE: never route aggregator JSON through the browser/JS-eval as a fallback. The browser pass over the user's boards is primary; aggregators are a best-effort bonus.
• Incremental persistence. The script writes intermediate artifacts to a phases/ directory (next to shortlist_latest.json) as each stage completes: phases/normalized_<source>__<label>.json (rows per source), phases/scored_candidates.json (all survivors after card scoring), phases/deep_read_queue.json (roles flagged for Stage 2), and phases/digest_latest.json (the final shortlist). A mid-run connection drop is recoverable from whatever phase completed last, rather than losing the whole run.
• Deep-read stays scoped. Stage 2 covers ONLY roles above deep_read_threshold. As the tracker grows, per-run weight stays bounded.

Tab cleanup (browser pass). After delivering the digest, close every tab the browser pass opened this run (search tabs + JD deep-read tabs) using tabs_close_mcp. Track tab IDs as you open them; only close tabs opened this run. A failed close is noted but must not block the run. Leave the user's own tabs untouched.

Scan reactions are preference signal — feed them back. When the user reacts to a shortlist ("not interested in crypto," "more founding roles," "too junior"), offer to refine scanner_config.json per the enrichment mode — only encoding preferences they actually expressed.

---

Why the script/judgment split (so future-you doesn't undo it)

The scripts exist because docx building, PDF conversion, page counting, and letterhead styling are deterministic and were re-derived by hand every time before they existed — slow and inconsistent. They now run identically every run, and read the user's profile.json + format.json so they carry no one's identity in code. Everything left in these instructions is genuine judgment: the tailoring, the truthfulness filter, the trim decisions, which ATS recs to honor, and — above all — writing in the user's actual voice. Don't push judgment into scripts (they can't tell truth from plausible fiction, and they can't write like the user) and don't pull mechanics back into prose (you'll reinvent them under time pressure).

Bundled scripts

• scripts/generate_resume.py — resume markdown → polished one-page .docx. Parametrized by profile.json (identity) + format.json (fonts/colors).
• scripts/export_pdf.py — DOCX → PDF via LibreOffice headless (faithful render).
• scripts/page_count.py — prints PAGES: n; on overflow prints the page-2+ text so you trim deliberately.
• scripts/build_cover_letter.py — cover-letter markdown → .docx using the resume's design tokens, so letter and resume match. Renders only — words are yours.
• scripts/job_scanner.py — config-driven scanner: broad discovery across keyless remote-job aggregators (Remotive/RemoteOK/Arbeitnow/Jobicy, Adzuna optional) plus an optional Greenhouse/Lever/Ashby watchlist, plus browser-pass sources (LinkedIn, Wellfound, Built In, manual). Card-level (Stage 1) scoring with a recency gate, non-exhaustive domain tiers, role-shape signals + baseline, and a deep_read flag per result. --print-urls and --input-dir support the unattended web-fetch flow. Incremental persistence to phases/ means a mid-run drop is recoverable. Aggregator failures are skipped (never routed through the browser as a fallback).
• scripts/lint_copy.py — advisory linter: prose flags the structural AI tells from writing-standards.md; summary flags a résumé summary that isn't first-person or that mirrors the JD's trait language; parse checks a resume PDF extracts cleanly for ATS parsing. Surfaces issues for judgment; never rewrites.
• scripts/selfcheck.py — post-install/edit health check: compiles the scripts, reports dependencies (python-docx / LibreOffice / poppler / pypdf), and asserts the scanner's core logic (incl. the word-boundary exclude behavior) against a built-in fixture.

Bundled references

references/onboarding-interview.md (Quick + Thorough question sets) · references/profile-template.json · references/base_resume-template.md · references/fact-pack-template.md · references/voice-template.md · references/format-template.json · references/cover-letter-playbook.md · references/ats-rubric.md · references/browser-autofill.md · references/scheduling.md · references/scanner_config.template.json · references/scanner-scheduled-task.template.md · references/interview-prep.md · references/outreach-playbook.md · references/writing-standards.md · references/application-tracker.md · references/followup-and-negotiation.md