outreach

name	outreach
description	Draft a cold email or warm-intro-request message to a specific person at a target company. Produces applications/<app_id>/outreach/<slug>.md and logs a communication_sent event. Runs after company-research. Enforces the One-Take Rule — refuses to draft without a grounded decision from company.md. This is the highest-payoff channel per 2026 hiring research.

outreach

This skill drafts a cold email or warm-intro-request for a specific person at a target company. It is the highest-payoff channel per notes/research/2026-ai-hiring-shift.md: cost 3, payoff 5, top of the channel ranking along with warm intros and building in public. It replaces the cover letter for engineer-led startups where formal applications are negative signal.

Core rules (from research):

• Draft is 4-7 sentences, max 150 words. Longer than that and reviewers bounce.
• Must contain a One-Take: an opinionated observation grounded in a decisions[] entry from company.md.
• Must name a specific person. "Hey team" is garbage.
• Must include one concrete artifact link (a shipped project, a blog post, a repo). No link = no email.
• Must end with a concrete small ask (15 min call, or pointer to the right person), not "let me know if there's a fit."

---

When to invoke this skill

• Mason says "write a cold email to [company]"
• Mason says "draft outreach for [person at company]"
• cover-letter-writer refused to generate because the lane is OFF and recommended outreach instead
• Mason is chasing a target-companies.md entry where artifact_fit: strong and wants to open the conversation

Do not run this skill if:

• company.md does not exist → run company-research first
• company.md has zero grounded decisions → rerun company-research with more primary-source attempts
• Mason hasn't named a specific person and no people[] entry in company.md has enough context to target

---

Prerequisites

1. applications/<app_id>/ directory exists
2. applications/<app_id>/company.md exists with at least one grounded decision
3. profile/voice.md, profile/wins.md, profile/story.md
4. A specific target person, either named by Mason or picked from company.md people[]

---

The pipeline

1. Read inputs (targeted)

• applications/<app_id>/company.md — the decisions[] and people[] sections are the gold
• applications/<app_id>/role.md if it exists (not required — outreach can precede a formal role)
• profile/voice.md — full voice contract
• profile/wins.md — quotable lines
• profile/story.md — narrative arc

2. Pick the target person

If Mason named someone, use them. Otherwise pick from company.md people[], preferring in this order:

1. The founder or engineer who wrote one of the grounded decisions Mason has an opinion on
2. An engineer whose recent public writing shows priorities Mason can speak to
3. A founder whose podcast / blog / Twitter has revealed specific positions
4. A hiring manager named in the JD

Do not default to generic HR / recruiter contacts. The research is explicit: recruiter outreach is near the bottom of the channel ranking. If the only identifiable person is a recruiter, flag that and ask Mason whether to send anyway or wait for a better target.

3. Pick the One-Take

From company.md decisions[], pick the single grounded decision Mason has the strongest opinion on. This is the reason the email exists. If no grounded decision exists in company.md, refuse to draft.

4. Pick the artifact link

Pick ONE link to include. Priority order:

1. A shipped application-artifact for this specific company (if artifact_shipped event exists in data)
2. The most relevant project from profile/projects/ — usually VTR for production credibility, Staffclaw for reverse-engineering / platform work, SonicGen for audio / hand-written-code credibility
3. A relevant blog post Mason has written (once the fingerprinting deep-dive exists, that's the default anchor for every outreach)

Exactly one link. Not three. Not a portfolio dump.

5. Pick the ask

Two shapes, pick one:

• Call ask: "Is there 15 min next week to talk about [specific topic]?" — use when Mason has a direct connection to the person's work.
• Pointer ask: "Is there a better person on your team to talk to about [specific topic]?" — use when reaching a founder who isn't the direct hiring decision-maker.

Never "let me know if there's a fit." Never "would love to chat." Never "happy to jump on a call whenever."

6. Draft the email (4-7 sentences, 150 words max)

Structure:

1. Sentence 1 (opener) — direct, names a specific thing. Not "I hope this finds you well." Not "I'm reaching out because." Good openers: "I've been running your product on a collection of 10,000 historical letters and noticed X," "Read your essay on Y — the trade-off you mentioned in Z is..."
2. Sentences 2-3 (One-Take) — the opinionated observation. Grounded in a specific decision. Mason's actual take.
3. Sentences 4-5 (credibility) — one concrete thing Mason has shipped, with the artifact link. One real number.
4. Sentence 6-7 (ask) — the specific ask. Forward momentum.
5. Sign-off: "Mason"

No subject-line trickery. Subject should be 4-6 words, descriptive, not clickbait. Good: "Reaction to your GPUI essay," "Audio fingerprinting + Zed question." Bad: "Quick question," "Opportunity to connect."

7. Voice audit (blocking)

Against profile/voice.md, blocking violations:

• Any rule 15 LLM-vocab word (leveraged, delve, seamless, passionate, excited to, thrilled to, eager to, reaching out because, huge fan, reach out)
• "I hope this finds you well" / "I hope you are doing well"
• "I'd love to chat / jump on a call / connect"
• Any em-dash in a sentence
• Any hyphen compound adjective
• Any tilde, arrow, brand-name drop in prose
• Any self-deprecation
• Over 150 words total
• Missing the One-Take
• Missing the artifact link
• Missing the specific ask
• Generic "your company" / "your team" when the email should name something specific

8. The One-Take check (second pass)

• Could this sentence have been written about any other company? If yes, fail.
• Does it reference an essay every candidate references? If yes, fail.
• Does it carry Mason's opinion, not just a fact? If no, fail.
• Grounded in a company.md decision tagged grounded? If no, fail.

If any fail, rewrite. If after two rewrites the One-Take still fails, stop and tell Mason which grounded decision to use or which new primary source to research.

9. Write the file

Write to applications/<app_id>/outreach/<person_slug>.md. Structure:

---
to_name: <Full name>
to_role: <role>
to_email: <email if known, otherwise blank>
channel: <email | linkedin | twitter_dm>
one_take_source: <decision title from company.md>
artifact_link: <url>
drafted_at: <ISO date>
sent_at: <blank until Mason sends>
---

# Outreach to <Name> at <Company>

**Subject:** <4-6 word subject>

<body of email, 4-7 sentences>

Mason

---

## Reasoning

- **Person picked because:** <why them>
- **One-Take grounded in:** <decision, source URL from company.md>
- **Artifact link:** <url, what it proves>
- **Ask:** <call | pointer>

Do NOT log a communication_sent event yet. The event is logged only when Mason confirms he actually sent it.

10. Report to Mason

Under 200 words. Include:

• Path to the draft
• Target name + role
• The One-Take sentence, quoted verbatim
• Which artifact link you used and why
• The ask shape (call or pointer)
• Anything flagged during the voice audit or One-Take check
• Next action: "Confirm when sent and I'll log communication_sent"

---

Logging the send

When Mason confirms he sent the email, log:

cd ~/Workspace/job && pnpm log communication_sent --app_id=<app_id> --channel=email --to="<Name>" --summary="Cold outreach re: <one-take topic>" --message_ref=applications/<app_id>/outreach/<slug>.md

Then update the sent_at field in the outreach file's frontmatter.

---

Rules and guardrails

• Never draft without a grounded decision in company.md. Blocking.
• Never draft generic "Hey team" emails. Specific person required.
• Never exceed 150 words.
• Never include more than one artifact link.
• Never ask for a call without naming a specific topic.
• Never use LinkedIn connect-request template language. "I came across your profile" is banned.
• Never name-drop brand tools (Codex, Codex, Cursor) in the prose. Describe the work, not the tooling.
• Never apologize for Mason's background or hedge about experience.
• Respect the primary-source ladder indirectly: the One-Take should trace to something Mason or the research agent actually touched, not to something aggregated from Crunchbase.
• Do not mass-generate. This skill is one email at a time, one person at a time. The point is that each email is uniquely expensive to write.

---

What this skill does NOT do

• Does not send the email. Mason sends it.
• Does not log communication_sent until Mason confirms the send.
• Does not do company research. That's company-research.
• Does not write a cover letter. That's cover-letter-writer.
• Does not produce an artifact. That's application-artifact.
• Does not replace warm intros. If Mason has a warm intro path, use that first — outreach is for when the warm path doesn't exist.