Cold Outreach Sequence

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.

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.

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"

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

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)

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

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]

The Full Sequence Calendar

DayActionPlatform0Research + Connection requestLinkedIn1-2Accept → Wait 24h → First messageLinkedIn7Follow-up #1LinkedIn14Follow-up #2 or try emailLinkedIn/Email21Break-up messageSame

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.

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]

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" Need help building an outreach system that actually works? → Book a strategy call Skill by Brian Wagner | AI Marketing Architect | brianrwagner.com