Craft Outreach

• "I am writing to express my interest in..."
• "I believe my skills would be a great fit for..."
• "I am a passionate and driven professional..."
• Anything that reads like it was generated by an LLM
• Generic templates with [Company Name] swapped in
• Overly formal, sycophantic, or salesy language
• Buzzword soup ("synergy", "leverage", "ecosystem")

Voice rules:

• First person, always
• Short sentences. Get to the point.
• One specific hook per message — not a laundry list of achievements
• Questions over statements. Curiosity over claims.
• Reference concrete things (a product feature, a blog post, a metric) — never vague platitudes
• No exclamation marks unless genuinely excited about something specific
• Never open with the recipient's name followed by a comma and a compliment ("Hi Sarah, I love what you're building at...")

Process

Given $ARGUMENTS as a company name:

Step 0: Resolve the Company Slug

Convert the company name to a slug (lowercase, hyphens for spaces, strip special characters). For example: "Native Instruments" becomes native-instruments.

Step 1: Read the Strategy and Context

Read ALL of these files. If any are missing, note it but continue with what's available.

Required (fail if missing):

• /Users/godzillaaa/Documents/WEB_PROJECTS/jobsearch/journey/strategies/{company-slug}.md — the outreach strategy

If the strategy file doesn't exist, STOP and tell the user: "No strategy found for {company}. Run /outreach-strategy {company} first."

Required context:

• /Users/godzillaaa/Documents/WEB_PROJECTS/jobsearch/journey/dossiers/{company-slug}.md — company dossier

Doug's assets (read all — you need these to write authentic messages):

• /Users/godzillaaa/Documents/WEB_PROJECTS/jobsearch/assets/LINKEDIN_PROFILE.md
• /Users/godzillaaa/Documents/WEB_PROJECTS/jobsearch/assets/CONTRA_PORTFOLIO.md
• /Users/godzillaaa/Documents/WEB_PROJECTS/jobsearch/assets/GITHUB_PROFILE.md
• /Users/godzillaaa/Documents/WEB_PROJECTS/jobsearch/assets/CLUTCH_REVIEWS.md
• /Users/godzillaaa/Documents/WEB_PROJECTS/jobsearch/assets/WITHSEISMIC_COMPREHENSIVE_CONTENT.md

Extract from the strategy:

• Target contact (name, title)
• Channel (LinkedIn, email, careers page, etc.)
• The angle/hook identified in the strategy
• Any proof-of-work ideas
• Timing and sequencing notes

Step 2: Draft the Initial Message

The format depends on the channel identified in the strategy.

LinkedIn Connection Request (300 character limit)

• Ultra-concise. One specific hook.
• No fluff, no pleasantries beyond "Hey"
• End with a question or observation, not an ask
• Count the characters. If over 300, cut ruthlessly.

LinkedIn DM (after connected)

• 3-5 sentences max
• Open with the specific hook from the strategy
• Reference one concrete thing about their company
• Connect it to one concrete thing from Doug's experience (with a real metric or outcome)
• End with a soft call-to-action — a question, not "can we schedule a call?"

Email

• Subject line: specific and intriguing. Never "Application for [Role]" or "Experienced Engineer Interested in [Company]"
• Good subject lines reference something specific: a product feature, a blog post, a problem they're solving
• Body: 4-6 sentences
• Same structure as LinkedIn DM but with slightly more room to breathe
• Include one link — a portfolio piece, demo, or relevant project that's directly relevant
• Sign-off: first name + one-line identifier (e.g. "Doug — growth eng, 3x exits, currently building automation tooling")

Careers Page Application

When applying through a careers page, produce TWO things:

Cover letter (3 short paragraphs max):

• Para 1: Why THIS company specifically. Reference something current — a recent launch, a blog post, a product decision. Show you've done homework.
• Para 2: What you bring. 2-3 specific results with metrics. No generic "I have X years of experience."
• Para 3: What you'd want to explore. Forward-looking, shows you've thought about their problems. Not a plea.

Direct message to hiring manager (in addition to the application):

• Follow the LinkedIn DM or Email format above
• Reference that you've applied, but lead with value, not "I just applied and wanted to follow up"
• The application is the baseline. The direct message is what gets you noticed.

Step 3: CV Tailoring Notes

Don't rewrite the full CV. Produce notes on how to customize it for this specific company:

• Lead with: Which role title / summary line to use
• Emphasize: Which 2-3 roles/projects are most relevant and why
• Key metrics: Which specific numbers to highlight (pulled from real data in the assets)
• Tech stack order: Which technologies to list first (match their stack)
• De-emphasize: What's less relevant here (e.g., for a music tech company, move generic SaaS work down; for a gaming company, lead with Patrianna)
• Keywords: Any specific terms from their job posting to mirror

Step 4: Portfolio Selection

From Doug's existing assets (Contra portfolio, GitHub, withSeismic content), select:

• 2-3 most relevant portfolio pieces for THIS company
• For each piece: one sentence explaining why it's relevant to their specific problems
• The actual URL to include in outreach

Selection criteria:

• Industry relevance (music tech company? Lead with creative/audio-adjacent work)
• Technical relevance (their stack matches the project's stack)
• Outcome relevance (they care about growth? Show growth results)
• Recency (prefer recent work unless older work is significantly more relevant)

Step 5: Follow-up Drafts

Write exactly 2 follow-up messages:

Follow-up 1 (Day 3-5):

• Brief — 2-3 sentences
• Adds new value. Don't just bump the thread.
• Share a thought, an observation about their product, a relevant link, or a quick insight
• Tone: helpful peer, not desperate applicant

Follow-up 2 (Day 7-10):

• Final message. 1-2 sentences.
• Graceful. Leaves the door open without pressure.
• Something like: "No worries if the timing's off — if things change down the line, I'd still be keen to chat about [specific topic]."
• Never guilt-trip, never "just checking in", never "I know you're busy"

Step 6: Write the Output

Create the outreach materials file. First, ensure the directory exists:

Create directory if needed: /Users/godzillaaa/Documents/WEB_PROJECTS/jobsearch/journey/outreach/

Write to: /Users/godzillaaa/Documents/WEB_PROJECTS/jobsearch/journey/outreach/{company-slug}.md

Use this format:

# {Company Name} — Outreach Materials

**Target:** {Name, Title}
**Channel:** {LinkedIn DM / Email / Careers Page / etc.}
**Strategy:** [journey/strategies/{company-slug}.md](../strategies/{company-slug}.md)
**Status:** Draft — Ready for Doug's review

---

## Initial Message

### LinkedIn Connection Request (if applicable)
> {Message text — must be under 300 characters}
> _{character count}_

### Primary Outreach
**Subject:** {For email only — the subject line}

> {The actual message text}

---

## CV Tailoring

- **Lead with:** {Role title / summary line}
- **Emphasize:** {Specific projects/metrics and why}
- **Key metrics:** {The numbers to highlight}
- **Tech stack order:** {Reordered for this company}
- **De-emphasize:** {What to move down or remove}
- **Keywords to mirror:** {Terms from their posting}

---

## Portfolio Links

1. **{Project Name}** — {One sentence: why it's relevant to this company} — {URL}
2. **{Project Name}** — {One sentence: why it's relevant to this company} — {URL}
3. **{Project Name}** — {One sentence: why it's relevant to this company} — {URL}

---

## Follow-up 1 (Day 3-5)
> {Message text}

## Follow-up 2 (Day 7-10)
> {Message text}

---

## Proof of Work (if applicable)
**What to build/reference:** {Description from strategy}
**How to present it:** {How to attach/link/reference in the message}
**Time investment:** {Estimated effort}

---

## Cover Letter (if careers page application)

{3-paragraph cover letter text}

---

*Generated {today's date} — These are drafts. Doug reviews and edits before sending.*

Step 7: Quality Check

Before finishing, verify:

1. Specificity test: Read every message. If you could swap in a different company name and it would still make sense, it's too generic. Rewrite.
2. Voice test: Read every message out loud (mentally). If it sounds like a cover letter template, a recruiter email, or an LLM wrote it, rewrite.
3. Length test: LinkedIn connection request under 300 chars. LinkedIn DMs under 5 sentences. Emails under 6 sentences. Follow-ups under 3 sentences. If over, cut.
4. Truth test: Every claim about Doug's experience must be backed by real data from the asset files. No exaggeration, no invention.
5. Cringe test: Would Doug be embarrassed to send this? Would the recipient roll their eyes? If yes, rewrite.

Important Guidelines

• EVERY message must be specific to this company. Zero generic content.
• Doug will review and edit before sending. Mark everything as drafts.
• The goal is to make the reader curious, not overwhelmed.
• Never lie or exaggerate. All claims must trace back to real data in the assets.
• Never include salary expectations in outreach.
• For agencies/consultancies, emphasize breadth and client diversity.
• For startups, emphasize scrappy builder mentality and startup exits.
• For music/gaming companies, lead with genuine domain passion and relevant side projects.
• Keep messages SHORT. Respect the reader's time. If in doubt, cut a sentence.
• The connection request is the hardest part. Spend the most time on it.
• Subject lines for email are the second hardest part. They determine open rates.
• Create the journey/outreach/ directory if it doesn't exist.