cold-outreach-sequence · diff
git:20260225.733acad to git:20260308.5724749
154 added, 134 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.
- Spray-and-pray templates don't work. 10 minutes of research + a specific reference = not cold anymore. This skill builds the second kind.
+ 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.
- ## Context Loading Gates
+ This skill helps you do the second thing.
- **Before writing any message, collect:**
+ ---
- - [ ] **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)
+ ## Mode
- **Research tool calls — run before writing:**
+ Detect from context or ask: *"One message, full sequence, or full outreach system?"*
- ```
- web_search('[Company] [Founder/Name] news 2026')
- web_search('[Company] funding recent')
- web_search('[Person name] [Company] LinkedIn')
- ```
+ | 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 |
- **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.
+ **Default: `standard`** — use `quick` if they give you one name and say "draft something." Use `deep` if they're building a repeatable outreach engine.
---
- ## Phase 1: Research & Signal Assessment
+ ## Before You Write a Single Message
- For each prospect, document findings before drafting:
+ The research is the work. Skip it and you'll sound like everyone else in their inbox.
- **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)
+ **For each prospect, find:**
- **Personalization tier assignment:**
+ - **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?
- | 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 |
+ **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.
+
---
- ## Phase 2: Sequence Generation
+ ## The Connection Request (LinkedIn)
- ### Connection Request (LinkedIn) — 300 chars max
+ You have 300 characters. Don't waste them on a pitch.
- **Formula:** `[Specific observation from research] + [Simple reason to connect]`
+ **The formula:**
+ > [Specific observation] + [Simple reason to connect]
- **Rules:**
- - No pitching
- - Prove you did research (name the signal)
- - One sentence, conversational
- - Never "I'd love to pick your brain"
+ **Examples:**
- **By signal type:**
- ```
- Recent funding: "Congrats on the Series A — the [investor] backing is a smart signal. Would love to connect."
+ > "Following [Company]'s growth — the [specific thing] is smart positioning. Would love to connect."
- Recent post: "Your post on [specific topic] resonated — been thinking the same thing. Happy to connect."
+ > "[Their recent post] resonated. Been thinking about the same thing. Happy to connect."
- News/launch: "Saw the [product] launch — [specific detail] is smart positioning. Would love 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 Accept — Wait 24-48 Hours)
+ ## First Message (After They Accept)
- **Formula:** `[Thanks] + [Bridge to relevance] + [Light value] + [Soft question]`
+ Wait 24-48 hours. Then:
- **Template:**
- ```
- Thanks for connecting. I work with [ICP description] on [specific outcome].
+ **The formula:**
+ > [Thanks] + [Bridge to relevance] + [Light value] + [Soft question]
- Curious — is [relevant function] something you own directly at [Company],
- or is that still founder-led?
+ **Example:**
- Happy to share what I'm seeing work at similar-stage companies either way.
- ```
+ > 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
+
---
- ### Follow-Up #1 (Day 7)
+ ## First Follow-Up (If No Response)
- **Formula:** `[Light nudge] + [New signal or angle] + [Easy out]`
+ Wait 5-7 days. Then:
- **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
+ **The formula:**
+ > [Light nudge] + [New value or angle] + [Easy out]
- **Template:**
- ```
- Bumping this up — came across [specific article/trend/insight] and
- thought of your situation at [Company].
+ **Example:**
- [One sentence on why it's relevant to them.]
+ > Bumping this up — know you're slammed. Came across [relevant thing] and thought of your situation at [Company]. Worth a look if helpful.
- Happy to share more if useful. If not, no worries.
- ```
+ **Or:**
- ---
+ > Following up — been seeing [trend] hit companies at your stage. Happy to share what's working if useful. If not, no worries.
- ### Follow-Up #2 (Day 14)
+ **The rules:**
+ - Don't just say "following up"
+ - Add something new
+ - Give them an easy out (takes the pressure off)
- Shift to email if LinkedIn hasn't converted, or try a different angle.
+ ---
- **Subject line options:**
- - "[Company]'s [function] as you scale"
- - "Saw your [post/news] — quick thought"
- - "Question about [specific thing they're doing]"
+ ## The Break-Up (Final Attempt)
- **Email structure:**
- ```
- [1-line hook tied to their specific situation]
+ Wait 7-10 days. Then move on gracefully:
- [2-3 sentences: why you're reaching out + one proof point]
+ **Example:**
- [Soft CTA — 1 sentence]
- ```
+ > 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
+
---
- ### Break-Up Message (Day 21)
+ ## Email Version
- ```
- I'll assume timing isn't right — totally get it.
+ Same principles, different format.
- 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].
+ **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]
- **Post-break-up action:** Add to 6-month re-engagement list with a resurface date.
+ [2-3 sentences: why you're reaching out + relevance]
- ---
+ [1 sentence: soft CTA]
- ## Phase 3: Self-Critique Pass (REQUIRED)
+ [Simple signature]
+ ```
- After generating the full sequence, evaluate:
+ **Example:**
- - [ ] 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?
+ ```
+ Subject: [Company]'s GTM as you scale
- Flag any issue: "The first message doesn't include a soft question — it reads as a pitch. Revised to invite dialogue."
+ Hey [Name],
- ---
+ Saw the [news] — congrats. [One specific observation].
- ## Pipeline Tracking Table
+ I work with growth-stage companies on [relevant thing]. Helped [similar company] with [specific result].
- Always output a tracking table for the batch:
+ Worth a quick chat to see if there's a fit?
- ```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 | — |
+ [Your name]
```
---
- ## Iteration Protocol
+ ## The Full Sequence Calendar
- 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
+ | 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 |
---
- ## Output Structure
+ ## Personalization Tiers
- ```markdown
- ## Outreach Sequence: [Prospect Name] — [Date]
+ Not everyone deserves 15 minutes of research. Here's how to think about it:
- ### Research Summary
- - Signal type: [news / post / company info / none]
- - Signal found: "[Specific detail]"
- - Personalization tier: [1/2/3]
- - Source: [URL or platform]
+ **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
- ### Sequence
+ The math: 10 highly personalized messages often beat 100 spray-and-pray.
- **Connection Request (LinkedIn):**
- [Text — max 300 chars]
+ ---
- **First Message (Day 1-2 after accept):**
- [Text]
+ ## What You Get Back
- **Follow-Up #1 (Day 7):**
- [Text]
+ A complete outreach doc for each prospect:
- **Follow-Up #2 (Day 14):**
- Platform: [LinkedIn / Email]
- Subject: [if email]
- [Text]
+ ```
+ # Outreach: [Prospect Name]
- **Break-Up (Day 21):**
- [Text]
+ ## Research
+ - Company: [stage, news, situation]
+ - Their likely pain: [what they're dealing with]
+ - Connection point: [what you'll reference]
- ### Pipeline Entry
- | Prospect | Company | Platform | Tier | Stage | Next Action | Resurface Date |
- |---|---|---|---|---|---|---|
- | [Name] | [Co] | [Platform] | [Tier] | Connection sent | Wait 24-48h | — |
+ ## Sequence
+ ### Connection Request:
+ [Your message]
- ### Self-Critique Notes
- [Any issues flagged + revisions made]
+ ### 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](https://brianrwagner.com)
---
*Skill by Brian Wagner | AI Marketing Architect | brianrwagner.com*