Cold Outreach Sequence

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name: cold-outreach-sequence description: Build personalized cold outreach sequences for LinkedIn and email. Use when someone needs to reach prospects, warm up cold leads, or build a systematic outreach engine. Covers research, connection requests, follow-ups, and conversion.

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Cold Outreach Sequence

Here's what I've learned about cold outreach: the word "cold" is the problem.

If you're sending messages to strangers who've never heard of you, with templates you copied from some guru — yeah, that's cold. And it doesn't work.

But if you've done even 10 minutes of research, found something specific about them, and have a genuine reason to reach out? That's not cold. That's just... reaching out.

This skill helps you do the second thing.

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Before You Write a Single Message

The research is the work. Skip it and you'll sound like everyone else in their inbox.

For each prospect, find:

Recent news — Funding, launches, hires, press

What they're posting about — Their content tells you what they care about

Their likely pain — Given their role and stage, what's keeping them up?

Your connection point — What can you genuinely comment on?

Where to look:

Their LinkedIn activity (posts, comments, shares)

Company news (Crunchbase, TechCrunch, press releases)

Their website (about page, blog, careers)

Podcasts they've appeared on

Time investment: 10-15 minutes per high-value prospect.

This is what separates you from spam.

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The Connection Request (LinkedIn)

You have 300 characters. Don't waste them on a pitch.

The formula: > [Specific observation] + [Simple reason to connect]

Examples:

> "Following [Company]'s growth — the [specific thing] is smart positioning. Would love to connect."

> "[Their recent post] resonated. Been thinking about the same thing. Happy to connect."

> "Congrats on [news]. Impressive trajectory."

The rules:

No pitching. At all.

Be specific (prove you looked)

Keep it human

No "I'd love to pick your brain"

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First Message (After They Accept)

Wait 24-48 hours. Then:

The formula: > [Thanks] + [Bridge to relevance] + [Light value] + [Soft question]

Example:

> Thanks for connecting. I've been working at the intersection of [relevant area] — [one-line credibility]. > > Curious if you have someone owning [relevant function] as you scale, or if that's still founder-led? > > Either way, happy to share what I'm seeing work in the space.

The rules:

Still not a hard pitch

Demonstrate relevance, not desperation

Ask a question that invites dialogue

Offer value without strings attached

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First Follow-Up (If No Response)

Wait 5-7 days. Then:

The formula: > [Light nudge] + [New value or angle] + [Easy out]

Example:

> Bumping this up — know you're slammed. Came across [relevant thing] and thought of your situation at [Company]. Worth a look if helpful.

Or:

> Following up — been seeing [trend] hit companies at your stage. Happy to share what's working if useful. If not, no worries.

The rules:

Don't just say "following up"

Add something new

Give them an easy out (takes the pressure off)

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The Break-Up (Final Attempt)

Wait 7-10 days. Then move on gracefully:

Example:

> I'll assume timing isn't right — totally get it. If [relevant pain point] becomes a priority down the road, happy to reconnect. Best of luck with [specific thing they're working on].

The rules:

No guilt trips

No "just checking in one last time"

Leave with class

They may come back later

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Email Version

Same principles, different format.

Subject lines that work:

"[Company]'s marketing as you scale"

"Saw your [post/news] — quick thought"

"[Mutual connection] suggested I reach out"

"Question about [specific thing they're doing]"

Structure:

[1-line hook tied to them]
[2-3 sentences: why you're reaching out + relevance]
[1 sentence: soft CTA]
[Simple signature]

Example:

Subject: [Company]'s GTM as you scale
Hey [Name],
Saw the [news] — congrats. [One specific observation].
I work with growth-stage companies on [relevant thing]. Helped [similar company] with [specific result].
Worth a quick chat to see if there's a fit?
[Your name]

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The Full Sequence Calendar

| Day | Action | Platform | |-----|--------|----------| | 0 | Research + Connection request | LinkedIn | | 1-2 | Accept → Wait 24h → First message | LinkedIn | | 7 | Follow-up #1 | LinkedIn | | 14 | Follow-up #2 or try email | LinkedIn/Email | | 21 | Break-up message | Same |

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Personalization Tiers

Not everyone deserves 15 minutes of research. Here's how to think about it:

Tier 1 — Top 10 prospects: Full research, fully custom messages Tier 2 — Next 20: Template with personalized opener Tier 3 — Volume: Template with minimal customization

The math: 10 highly personalized messages often beat 100 spray-and-pray.

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What You Get Back

A complete outreach doc for each prospect:

# Outreach: [Prospect Name]
Research
Company: [stage, news, situation]
Their likely pain: [what they're dealing with]
Connection point: [what you'll reference]
Sequence
Connection Request:
[Your message]
First DM:
[Your message]
Follow-up #1:
[Your message]
Break-up:
[Your message]

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What Kills Outreach

❌ "I'd love to pick your brain" ❌ "Can I get 15 minutes of your time?" ❌ Long paragraphs about yourself ❌ Immediate pitch in connection request ❌ Same message to everyone ❌ Following up every 2 days ❌ "Hope this finds you well"

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Need help building an outreach system that actually works? → Book a strategy call

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*Skill by Brian Wagner | AI Marketing Architect | brianrwagner.com*