cold-outreach-sequence · diff
git:20260308.5724749 to git:20260308.1c3e1fe
135 added, 141 removed. Audit A to A.
---
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.
---
# 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.
+ Spray-and-pray templates don't work. 10 minutes of research + a specific reference = not cold anymore. This skill builds the second kind.
---
## Mode
Detect from context or ask: *"One message, full sequence, or full outreach system?"*
| Mode | What you get | Best for |
|------|-------------|----------|
| `quick` | 1 connection request + 1 follow-up for a single prospect | Testing an angle, one-off outreach |
| `standard` | Full 4-touch sequence for a single prospect | Active pipeline, individual targets |
| `deep` | Multi-prospect sequence system + A/B variants + tracking framework | Launching an outreach campaign |
**Default: `standard`** — use `quick` if they give you one name and say "draft something." Use `deep` if they're building a repeatable outreach engine.
---
- ## Before You Write a Single Message
-
- The research is the work. Skip it and you'll sound like everyone else in their inbox.
+ ## Context Loading Gates
- **For each prospect, find:**
+ **Before writing any message, collect:**
- - **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?
+ - [ ] **Prospect name and company** — full name, company, role/title
+ - [ ] **Research signals** — run tool calls first (see below); do not write without them
+ - [ ] **Sender positioning** — what does the sender do, for whom, with what result? (Use `positioning-basics` output if available)
+ - [ ] **Platform** — LinkedIn DM, email, or both?
+ - [ ] **Batch size** — how many prospects? (determines tier assignment)
- **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
+ **Research tool calls — run before writing:**
- **Time investment:** 10-15 minutes per high-value prospect.
+ ```
+ web_search('[Company] [Founder/Name] news 2026')
+ web_search('[Company] funding recent')
+ web_search('[Person name] [Company] LinkedIn')
+ ```
- This is what separates you from spam.
+ **Personalization constraint:** Do not write a Tier 1 message without a named specific signal from research. If search yields 0 signals, default to Tier 3 and say so explicitly.
---
- ## The Connection Request (LinkedIn)
-
- You have 300 characters. Don't waste them on a pitch.
-
- **The formula:**
- > [Specific observation] + [Simple reason to connect]
-
- **Examples:**
+ ## Phase 1: Research & Signal Assessment
- > "Following [Company]'s growth — the [specific thing] is smart positioning. Would love to connect."
+ For each prospect, document findings before drafting:
- > "[Their recent post] resonated. Been thinking about the same thing. Happy to connect."
+ **Signal types (ranked by message strength):**
+ 1. Recent news event (funding, launch, hire, press) → strongest signal
+ 2. Recent LinkedIn post activity → strong signal
+ 3. Company stage/growth data → medium signal
+ 4. Role + industry awareness only → weak signal (Tier 3)
- > "Congrats on [news]. Impressive trajectory."
+ **Personalization tier assignment:**
- **The rules:**
- - No pitching. At all.
- - Be specific (prove you looked)
- - Keep it human
- - No "I'd love to pick your brain"
+ | Research Result | Tier | Approach |
+ |---|---|---|
+ | Named signal (news + post + context) | Tier 1 | Fully custom, reference signal in every message |
+ | Company info + role context | Tier 2 | Template + personalized opener |
+ | No signals found | Tier 3 | Volume template, minimal customization |
---
- ## First Message (After They Accept)
-
- Wait 24-48 hours. Then:
-
- **The formula:**
- > [Thanks] + [Bridge to relevance] + [Light value] + [Soft question]
+ ## Phase 2: Sequence Generation
- **Example:**
+ ### Connection Request (LinkedIn) — 300 chars max
- > 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.
+ **Formula:** `[Specific observation from research] + [Simple reason to connect]`
- **The rules:**
- - Still not a hard pitch
- - Demonstrate relevance, not desperation
- - Ask a question that invites dialogue
- - Offer value without strings attached
+ **Rules:**
+ - No pitching
+ - Prove you did research (name the signal)
+ - One sentence, conversational
+ - Never "I'd love to pick your brain"
- ---
+ **By signal type:**
+ ```
+ Recent funding: "Congrats on the Series A — the [investor] backing is a smart signal. Would love to connect."
- ## First Follow-Up (If No Response)
+ Recent post: "Your post on [specific topic] resonated — been thinking the same thing. Happy to connect."
- Wait 5-7 days. Then:
+ News/launch: "Saw the [product] launch — [specific detail] is smart positioning. Would love to connect."
+ ```
- **The formula:**
- > [Light nudge] + [New value or angle] + [Easy out]
+ ---
- **Example:**
+ ### First Message (After Accept — Wait 24-48 Hours)
- > Bumping this up — know you're slammed. Came across [relevant thing] and thought of your situation at [Company]. Worth a look if helpful.
+ **Formula:** `[Thanks] + [Bridge to relevance] + [Light value] + [Soft question]`
- **Or:**
+ **Template:**
+ ```
+ Thanks for connecting. I work with [ICP description] on [specific outcome].
- > Following up — been seeing [trend] hit companies at your stage. Happy to share what's working if useful. If not, no worries.
+ Curious — is [relevant function] something you own directly at [Company],
+ or is that still founder-led?
- **The rules:**
- - Don't just say "following up"
- - Add something new
- - Give them an easy out (takes the pressure off)
+ Happy to share what I'm seeing work at similar-stage companies either way.
+ ```
---
- ## The Break-Up (Final Attempt)
+ ### Follow-Up #1 (Day 7)
- Wait 7-10 days. Then move on gracefully:
+ **Formula:** `[Light nudge] + [New signal or angle] + [Easy out]`
- **Example:**
+ **Constraint:** Do NOT write "following up" with nothing new. Add one new piece:
+ - A relevant article or trend
+ - A related insight you recently had
+ - A connection to something they posted
- > 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].
+ **Template:**
+ ```
+ Bumping this up — came across [specific article/trend/insight] and
+ thought of your situation at [Company].
- **The rules:**
- - No guilt trips
- - No "just checking in one last time"
- - Leave with class
- - They may come back later
+ [One sentence on why it's relevant to them.]
+ Happy to share more if useful. If not, no worries.
+ ```
+
---
- ## Email Version
+ ### Follow-Up #2 (Day 14)
- Same principles, different format.
+ Shift to email if LinkedIn hasn't converted, or try a different angle.
- **Subject lines that work:**
- - "[Company]'s marketing as you scale"
+ **Subject line options:**
+ - "[Company]'s [function] as you scale"
- "Saw your [post/news] — quick thought"
- - "[Mutual connection] suggested I reach out"
- "Question about [specific thing they're doing]"
- **Structure:**
+ **Email structure:**
```
- [1-line hook tied to them]
-
- [2-3 sentences: why you're reaching out + relevance]
+ [1-line hook tied to their specific situation]
- [1 sentence: soft CTA]
+ [2-3 sentences: why you're reaching out + one proof point]
- [Simple signature]
+ [Soft CTA — 1 sentence]
```
- **Example:**
+ ---
- ```
- Subject: [Company]'s GTM as you scale
+ ### Break-Up Message (Day 21)
- Hey [Name],
+ ```
+ I'll assume timing isn't right — totally get it.
- Saw the [news] — congrats. [One specific observation].
+ If [relevant pain point] becomes a priority down the road, happy to reconnect.
+ Best of luck with [specific thing they're working on based on research].
+ ```
- I work with growth-stage companies on [relevant thing]. Helped [similar company] with [specific result].
+ **Post-break-up action:** Add to 6-month re-engagement list with a resurface date.
- Worth a quick chat to see if there's a fit?
+ ---
- [Your name]
- ```
+ ## Phase 3: Self-Critique Pass (REQUIRED)
- ---
+ After generating the full sequence, evaluate:
- ## The Full Sequence Calendar
+ - [ ] Does every message reference the specific signal from research, or are they generic?
+ - [ ] Is the connection request under 300 characters?
+ - [ ] Does the first message ask a question (invite dialogue) rather than pitch?
+ - [ ] Does follow-up #1 add something genuinely new, or is it just "following up"?
+ - [ ] Does the break-up message reference something specific about their situation?
+ - [ ] Did I correctly assign the personalization tier, or am I over-personalizing a Tier 3 prospect?
- | 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 |
+ Flag any issue: "The first message doesn't include a soft question — it reads as a pitch. Revised to invite dialogue."
---
- ## Personalization Tiers
-
- Not everyone deserves 15 minutes of research. Here's how to think about it:
+ ## Pipeline Tracking Table
- **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
+ Always output a tracking table for the batch:
- The math: 10 highly personalized messages often beat 100 spray-and-pray.
+ ```markdown
+ | Prospect | Company | Platform | Tier | Sent Date | Response | Stage | Next Action | Resurface Date |
+ |---|---|---|---|---|---|---|---|---|
+ | [Name] | [Co] | LinkedIn | 1 | [date] | — | Connection sent | Wait 24-48h | — |
+ | [Name] | [Co] | Email | 2 | [date] | — | First email sent | Follow-up Day 7 | — |
+ ```
---
- ## What You Get Back
+ ## Iteration Protocol
- A complete outreach doc for each prospect:
+ After each response (or non-response), ask:
+ - Did the connection request get accepted? If low acceptance rate → revise the observation line
+ - Did the first message get a reply? If no → was the question soft enough, or did it feel like a pitch?
+ - Did follow-ups get ignored? If yes → try a different angle or acknowledge the silence directly
- ```
- # Outreach: [Prospect Name]
+ ---
- ## Research
- - Company: [stage, news, situation]
- - Their likely pain: [what they're dealing with]
- - Connection point: [what you'll reference]
+ ## Output Structure
- ## Sequence
- ### Connection Request:
- [Your message]
+ ```markdown
+ ## Outreach Sequence: [Prospect Name] — [Date]
- ### First DM:
- [Your message]
+ ### Research Summary
+ - Signal type: [news / post / company info / none]
+ - Signal found: "[Specific detail]"
+ - Personalization tier: [1/2/3]
+ - Source: [URL or platform]
- ### Follow-up #1:
- [Your message]
+ ### Sequence
- ### Break-up:
- [Your message]
- ```
+ **Connection Request (LinkedIn):**
+ [Text — max 300 chars]
- ---
+ **First Message (Day 1-2 after accept):**
+ [Text]
- ## What Kills Outreach
+ **Follow-Up #1 (Day 7):**
+ [Text]
- ❌ "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"
+ **Follow-Up #2 (Day 14):**
+ Platform: [LinkedIn / Email]
+ Subject: [if email]
+ [Text]
- ---
+ **Break-Up (Day 21):**
+ [Text]
- **Need help building an outreach system that actually works?**
- → [Book a strategy call](https://brianrwagner.com)
+ ### Pipeline Entry
+ | Prospect | Company | Platform | Tier | Stage | Next Action | Resurface Date |
+ |---|---|---|---|---|---|---|
+ | [Name] | [Co] | [Platform] | [Tier] | Connection sent | Wait 24-48h | — |
+
+ ### Self-Critique Notes
+ [Any issues flagged + revisions made]
+ ```
---
*Skill by Brian Wagner | AI Marketing Architect | brianrwagner.com*