Cold Outreach

Write cold emails and messages that get responses from recruiters, hiring managers, founders, and engineers. Based on Ben Lang’s framework (former Notion community lead, angel investor, creator of Next Play).

Announce at start: “I’m using the cold-outreach skill to help craft your message.”

Core Truth

Cold email works. You can email any company regardless of posted jobs, location requirements, or stated credentials. Startups regularly make exceptions. The gap between effective and ineffective cold emails is enormous – this skill keeps you on the effective side.

Prerequisite: Cold outreach works best when you are genuinely competent at something valuable AND have demonstrated that competency. This skill amplifies real credibility; it cannot create it.

Workflow

Crafting a cold outreach message involves these steps:

1. Gather context (who, what company, what role/goal)
2. Identify the user’s strongest relevant credentials and match them to the target’s needs
3. Draft the message using the three-part structure
4. Validate against the five deadly sins
5. Finalize with subject line and send strategy

Step 1: Gather Context

Ask the user for the information needed. Do not ask all at once – start with the essentials:

Essential (ask first):

• Who are you reaching out to? (name, title, company)
• What is the goal? (specific role, general interest, informational)
• What is your most relevant experience for this company/role?

If not provided, ask as follow-up:

• What does this company do? What stage are they at?
• How did you find them? (funding announcement, job board, referral, etc.)
• Do you have specific accomplishments with numbers you can cite?
• Provide links to: company website, job description (if any), and recruiter or hiring manager profile (LinkedIn or similar).
• What are they likely hiring for or optimizing right now?

If the user already provided this context, skip directly to drafting. If company or recruiter details are missing, prompt for them before drafting.

Step 2: Identify Strongest Credentials

Extract and sharpen the user’s top 2-3 credentials. Apply these rules:

Make abstract concrete:

• “I drove results” -> “I helped increase conversion rate from 2% to 8%”
• “I work with startups” -> “I built payment systems at Stripe and billing tools at Notion”
• “Experienced engineer” -> “Built systems handling 300k+ TPS at Amazon”

Use numbers where they add clarity: revenue impact, user counts, performance metrics, team size, time saved. Keep them broad and avoid project-specific minutiae.

Prioritize relevance: Choose credentials that map directly to what the target company needs, not the most impressive ones in general.

Match to the target:

• Use the company website, job description, and recruiter profile to infer priorities.
• Select 2-3 background points that align with what they are hiring for or optimizing.
• If those sources are missing, ask the user to provide them before drafting.

Step 3: Draft Using the Three-Part Structure

Every effective cold email has exactly three parts:

Part 1 – Who you are: One sentence with your most relevant credential. Part 2 – Why you’re reaching out: One sentence stating your purpose clearly and directly. Part 3 – Why they should care: 2-3 bullet points with concrete, specific accomplishments.

End with ONE clear ask. See references/email-examples.md for proven examples.

Hard Rules

• Under 200 words total. No exceptions. Brevity works on everyone.
• One clear ask at the end. Make it easy to say yes.
  • Good: “Worth a 15-minute call next week?”
  • Good: “Can I send over my portfolio?”
  • Bad: “Let me know if you’re interested” (vague, no action)
• Sound human. Read it aloud. If it doesn’t sound like you actually talk, rewrite it.
• Use bullets for accomplishments. Easier to scan than paragraphs.
• No em dashes. Use commas or parentheses instead.
• High-level only. Avoid specific implementation details, or granular execution details. Keep success metrics showing goals achieved. Show competency and confidence without being boring.

Output Format

Generate the email in this structure:

Subject: [under 50 characters, relevant and direct]

Hi [Name],

[One sentence: who you are with most relevant credential]

[One sentence: why you're reaching out]

[2-3 bullets: why they should care, with high-level relevant accomplishments]

[One sentence: clear ask]

Best,
[User's name]

Total: 100-150 words. See references/email-examples.md for complete examples.

Step 4: Validate Against the Six Deadly Sins

Before presenting the draft, check every message against these five failure modes. If any apply, fix before showing the draft.

1. Too long – Over 200 words? Cut ruthlessly. Nobody reads unsolicited long emails.
2. Buzzwords – Remove all corporate language. “Executed strategic initiatives” -> “built a tool that cut processing time by 40%”. Remove buzzwords, then remove them again.
3. No clear ask – Missing a specific action you want them to take? Add one.
4. Too vague – Every claim needs specificity. Numbers, company names, concrete examples. No abstractions.
5. Too granular – If it dives into project-level details that are not too in depth for the first 200 word intro, strip it back to higher level impact with the right metrics and actions.
6. Dishonest or spammy – No fake personalization (“I’ve been a fan for years!” when they just found the company). It’s fine to say “I saw you just raised a Series B.”

Step 5: Subject Line and Send Strategy

Subject lines – Under 50 characters, relevant:

• “Engineer interested in your AI product”
• “Designer with fintech experience”
• “Quick question about [role]”
• Never: “Inquiry about opportunities” or “Following up on my application”

Who to email:

• For specific roles: the hiring manager (find on LinkedIn)
• When in doubt: the CEO/founder
• Small startups (<20 people): always the CEO

Finding email: Try firstname@company.com first (works ~70% of the time). Use Hunter.io, RocketReach, Nymeria, or ContactOut. Check personal websites and social media bios.

When to send: Tuesday-Thursday, 8-10 AM in their timezone. Avoid Mondays and Fridays.

Follow-Up Strategy

• Wait 4-5 business days after initial email
• Send maximum 1-2 follow-ups total
• After 2 follow-ups with no response, move on

See references/email-examples.md for follow-up templates.

LinkedIn Variation

For LinkedIn connection requests or InMail, apply the same three-part structure but even shorter:

Connection request (300 character limit):

Hi [Name], I'm a [role] with [X years] in [domain]. Saw you're hiring for [role] at [Company]. Would love to connect and learn more.

After connecting (wait 1-2 days, then message): Same three-part structure as email, but slightly more conversational. Keep under 150 words.

“Show, Don’t Tell” Tactic

For standout outreach, demonstrate value instead of just listing credentials:

• “I spent 30 minutes analyzing your onboarding flow and found 3 bottlenecks. Happy to share.”
• “I built a quick prototype showing how [approach] could work for your use case. Can demo if interested.”
• “I reviewed your blog post on [topic] and identified an optimization that could improve performance by 30%.”

Only suggest this approach when the user has time and the target company warrants the extra effort.

Volume and Expectations

Even perfect emails can go unanswered (bad timing, inbox overload, spam filters, not hiring right now). The solution is volume:

• Target 10-30 companies over several weeks
• Expect 10-30% response rate
• Even 1-2 responses can lead to interviews
• Track what works, iterate on what doesn’t

If response rate is under 10%: revisit the five deadly sins, shorten emails, add more specificity, check targeting.

Quality Checklist

Before any message is finalized, verify:

• Under 200 words
• No buzzwords or corporate jargon
• ONE clear ask
• Specific examples with numbers
• Sounds like a real human wrote it
• No fake personalization
• Subject line under 50 characters
• Prepared for a positive response

Resources

references/email-examples.md

Proven cold email examples that got responses, organized by scenario (startup founder, recruiter, hiring manager, internal transfer). Also includes follow-up templates and LinkedIn message examples. Load when drafting to reference specific patterns.