Cold Outreach

---
name: cold-outreach
description: "Builds personalized cold email and DM outreach sequences with research-backed personalization, multi-touch follow-up cadence, subject line formulas, and response-handling scripts for every outcome. Use when an entrepreneur, freelancer, or agency owner needs to reach prospects they have no prior relationship with — for sales, partnerships, collaborations, or client acquisition."
allowed-tools: Read Write Glob
metadata:
  author: matthewhitcham
  version: "1.0"
---

# Cold Outreach

## When to Use This Skill

Use this skill when you need to:
- Reach out to prospects you have never spoken to before (cold sales, partnerships, sponsorships)
- Build a multi-email or multi-DM sequence with planned follow-ups
- Personalize outreach beyond "Hi {first_name}" using real prospect research
- Handle replies systematically — positive, objection, rejection, or silence
- Convert a list of target companies/people into a ready-to-send outreach campaign

**DO NOT** use this skill for warm introductions, existing client communication, or mass newsletter blasts. This is for targeted, one-to-one cold outreach only.

---

## Core Principle

EVERY COLD MESSAGE MUST PROVE YOU DID YOUR HOMEWORK — GENERIC OUTREACH GETS DELETED, PERSONALIZED OUTREACH GETS REPLIES.

---

## Phase 1: Research and Personalize

Before writing a single word, build a personalization brief for each prospect (or prospect type). No brief, no sequence.

### The Personalization Framework

For each prospect, identify these three elements:

1. **Trigger Event** — something recent and specific that makes your outreach timely
2. **Identified Pain** — a problem they likely have based on their role, company stage, or public signals
3. **Credibility Bridge** — why YOU are the right person to help (shared context, relevant result, mutual audience)

### Where to Find Trigger Events

| Source | What to Look For |
|--------|-----------------|
| LinkedIn posts | New role, product launch, hiring spree, content they published |
| Company blog/news | Funding round, expansion, rebrand, new feature |
| Podcast appearances | Stated goals, challenges they mentioned publicly |
| Job postings | Roles they are hiring for reveal internal priorities |
| Social media | Complaints, celebrations, questions in their niche |

### Personalization Brief Template

Present this to the user before writing the sequence:

```
## Prospect Brief

**Prospect:** Sarah Chen, Head of Growth at Launchpad SaaS
**Trigger event:** Just raised Series A ($8M) — posted about it on LinkedIn 5 days ago
**Identified pain:** Scaling outbound pipeline post-funding (hiring 3 SDRs per their job board)
**Credibility bridge:** You helped 2 other post-Series-A startups build outbound systems that generated 40+ qualified meetings/month
**Tone match:** Direct, data-driven (her LinkedIn posts are metrics-heavy)
```

**GATE: Do not proceed to Phase 2 until the user confirms or adjusts the personalization brief.**

---

## Phase 2: Write the Sequence

Default sequence is **3 emails over 7 days**. This is the highest-performing cadence for cold outreach to busy decision-makers.

### Email 1: The Opener (Day 1)

**Goal:** Prove relevance, spark curiosity, earn a reply.

**Structure:**
1. **Personalized hook** (1 sentence referencing trigger event)
2. **Pain acknowledgment** (1-2 sentences connecting trigger to a likely challenge)
3. **Credibility proof** (1 sentence with a specific result)
4. **Low-friction CTA** (1 question — not "book a call")

**Length:** 60-90 words. Shorter is better.

**Example — B2B SaaS sales:**

Subject: your SDR hiring spree

```
Hi Sarah,

Saw Launchpad just closed your Series A — congrats. Hiring 3 SDRs
tells me outbound pipeline is the priority right now.

We helped Crestline (also post-Series-A, similar ACV) go from 12
to 47 qualified meetings per month within 60 days — without adding
headcount beyond one SDR.

Would it be useful to see the exact playbook we used?

— James
```

**Example — Freelance/agency pitch:**

Subject: the onboarding bottleneck

```
Hi Marcus,

Noticed your agency just landed the Greenfield Hotels account — nice win.
When agencies take on enterprise clients like that, onboarding SOPs
usually become the first bottleneck.

I built the client onboarding system for Ridgeway Digital (12-person agency,
similar size) — cut their onboarding time from 3 weeks to 5 days.

Worth a 15-minute look at how it worked?

— Dana
```

### Email 2: The Follow-Up (Day 3)

**Goal:** Add value, not pressure. Give them a reason to reply that is different from Email 1.

**Structure:**
1. **Quick callback** (1 sentence — "Circling back on my note about X")
2. **New value angle** (share a resource, insight, or relevant data point they can use regardless of whether they hire/buy)
3. **Restate CTA** (same low-friction ask, slightly rephrased)

**Length:** 40-70 words. Even shorter than Email 1.

**Example — B2B SaaS follow-up:**

Subject: re: your SDR hiring spree

```
Hi Sarah,

Quick follow-up — I put together a one-page breakdown of the 3 outbound
channels that worked best for post-Series-A SaaS companies this year
(spoiler: LinkedIn voice notes outperformed cold calls 2:1).

Happy to send it over either way. Would that be useful?

— James
```

**Example — Freelance/agency follow-up:**

Subject: re: the onboarding bottleneck

```
Hi Marcus,

Following up — I wrote a short teardown of the 5 most common places
agency onboarding breaks down at the enterprise level. Might save your
team some headaches with Greenfield regardless.

Want me to send it your way?

— Dana
```

### Email 3: The Breakup (Day 7)

**Goal:** Create closure. Polite finality often triggers a response from prospects who meant to reply but did not.

**Structure:**
1. **Acknowledge silence** (1 sentence — no guilt, no passive aggression)
2. **Restate value in one line** (the single strongest reason to reply)
3. **Give them an easy out** (explicitly say it is fine to say no)

**Length:** 30-50 words. The shortest email in the sequence.

**Example — B2B SaaS breakup:**

Subject: closing the loop

```
Hi Sarah,

I know pipeline-building after a raise is all-consuming, so I will
keep this short: if doubling qualified meetings without doubling
headcount is on your radar this quarter, I would love 15 minutes.

If the timing is off, no worries at all — just say the word.

— James
```

**Example — Freelance/agency breakup:**

Subject: closing the loop

```
Hi Marcus,

Totally understand if onboarding is not the fire right now. If it
becomes one down the line, I am an email away.

Either way, no hard feelings — good luck with the Greenfield launch.

— Dana
```

**GATE: Present the full 3-email sequence to the user. Do not finalize until the user approves the tone, length, and CTA approach.**

---

## Phase 3: Subject Line Formulas

Use one formula per email. Do not get creative with subject lines — clarity beats cleverness in cold outreach.

### Proven Formulas

| Formula | Structure | Example |
|---------|-----------|---------|
| **Lowercase specific** | their [specific thing] | your SDR hiring spree |
| **Pain + context** | the [pain point] at [company event] | the onboarding bottleneck |
| **Mutual connection** (only if real) | [Name] suggested I reach out | Alex Park suggested I reach out |
| **Quick question** | quick question about [topic] | quick question about outbound |
| **Result teaser** | [number] [result] in [timeframe] | 47 meetings in 60 days |
| **Re: original** | re: [original subject] | re: your SDR hiring spree |

### Subject Line Rules

- **ALL LOWERCASE** for the first email (mimics a casual, personal note)
- **NEVER use** ALL CAPS, exclamation marks, or emoji in subject lines
- **NEVER use** "Just checking in" or "Following up" as standalone subjects
- **Keep under 7 words** — mobile inboxes truncate after 35-40 characters
- **Re: prefix** is acceptable for follow-ups in the same thread

---

## Phase 4: Response Handling Scripts

After the sequence is sent, prospects reply in one of four ways. Provide a response script for each.

### Positive Reply ("Interested, tell me more")

**Goal:** Move to a call or next step immediately. Do not oversell in the reply.

```
Hi Sarah,

Great to hear — I will keep this brief.

The fastest way to see if this fits: a 15-minute call where I walk
you through exactly what we did for Crestline and you can judge
if it maps to Launchpad's setup.

Here are a few times that work on my end: [2-3 specific times].
Or grab whatever works for you here: [scheduling link].

Talk soon,
James
```

### Objection ("Sounds interesting but [concern]")

**Goal:** Validate the concern, reframe with proof, re-extend the offer.

Common objections and responses:

**"We already have something in place"**
```
Totally makes sense — most teams at your stage do. Out of curiosity,
are you seeing the volume you need from it? The reason I ask is that
Crestline had an outbound motion too, but it was producing 12 meetings/month
vs. their target of 40. Happy to compare notes if useful, zero pressure
if not.
```

**"Not in the budget right now"**
```
Completely understand — budget post-raise is allocated fast. For what
it is worth, our model with Crestline was performance-based (we only
got paid on meetings that showed up). If that kind of structure would
make the math easier, happy to walk through it.
```

**"Send me more info"**
```
Absolutely — I put together a one-page overview with the Crestline
case study and how the process works. Attached here.

After you have had a chance to skim it, would a quick 15-minute call
make sense to see if it fits your setup?
```

### Rejection ("Not interested")

**Goal:** Leave the door open gracefully. No arguing, no convincing.

```
Appreciate you letting me know, Sarah — I would rather hear a clear no
than chase. If outbound pipeline ever moves up the priority list,
I am easy to find.

Good luck with the Series A growth push.

— James
```

### No Response (After Full Sequence)

**Goal:** Archive, do not keep emailing. Revisit only if a new trigger event appears.

**NEVER send a fourth email in the same sequence.** If all 3 emails get no response:

1. Mark the prospect as "sequence completed — no reply"
2. Set a reminder to check for new trigger events in 60-90 days
3. Only re-engage if there is a genuinely new reason (new funding, new role, company pivot)

---

## Phase 5: DM Variant (LinkedIn / Twitter / Instagram)

When the user wants DM outreach instead of email, adapt the sequence with these rules:

### DM vs Email Differences

| Element | Email | DM |
|---------|-------|-----|
| Length | 60-90 words (opener) | 30-50 words (opener) |
| Tone | Professional-casual | Conversational |
| CTA | "Would it be useful to..." | "Mind if I send over..." |
| Follow-ups | 2 follow-ups | 1 follow-up only |
| Subject line | Required | Not applicable |
| Formatting | Paragraphs | Short lines, no paragraphs |

### DM Sequence: 2 Messages Over 5 Days

**DM 1: The Opener (Day 1)**

```
Hey Sarah — congrats on the Series A. Noticed you are
hiring SDRs which usually means outbound is the focus.

We helped a similar post-Series-A SaaS go from 12 to 47
qualified meetings/mo in 60 days. Mind if I send a quick
breakdown of how?
```

**DM 2: The Follow-Up (Day 5)**

```
Hey Sarah — no worries if the timing is off. I put together
a quick teardown of what is working in outbound for post-raise
SaaS companies. Happy to share it either way — just say the word.
```

**DO NOT send a third DM.** Two unanswered DMs is the hard limit on direct message platforms.

---

## Delivery and File Output

When the sequence is complete, present it in a structured format:

1. **Personalization brief** at the top
2. **Full email/DM sequence** with send dates labeled
3. **All 4 response scripts** (positive, objection, rejection, silence)
4. **Subject lines** listed separately for easy copying

If the user provides a file path or asks to save, write the complete sequence to a single file:

```
outreach/
└── [prospect-name]-sequence.md
```

Include a **pre-send checklist** at the end of every delivered sequence:

```
## Pre-Send Checklist

- [ ] Every email references a REAL trigger event (not fabricated)
- [ ] Prospect name and company name are correct in every email
- [ ] No "just checking in" or "hope you are doing well" filler
- [ ] CTA is a question, not a demand
- [ ] Emails are under 90 words each
- [ ] Subject lines are under 7 words, all lowercase for opener
- [ ] Nothing promises results you cannot deliver
- [ ] No false claims about mutual connections
```

---

## Anti-Patterns

**NEVER do these in cold outreach:**

- **"Just checking in"** — this communicates "I have nothing new to say." Every follow-up must add new value.
- **"I hope this email finds you well"** — filler that signals a mass blast. Delete it.
- **Mass-blast language** — "Dear Sir/Madam," "To whom it may concern," or anything that sounds like it went to 500 people.
- **Lying about mutual connections** — "Our mutual friend suggested..." when there is no mutual friend. This destroys trust permanently.
- **Paragraph walls** — anything over 4 lines without a break gets skimmed or skipped.
- **Multiple CTAs** — asking them to book a call AND check out your website AND download a resource. One ask per email.
- **Apology openers** — "Sorry to bother you" or "I know you are busy" — these lower your status and give them permission to ignore you.
- **Fake urgency** — "Only 2 spots left" or "This week only" in a cold email is transparent and damages credibility.
- **Attaching files in Email 1** — cold emails with attachments trigger spam filters. Save attachments for replies.

---

## Recovery

- **No trigger event found:** Ask the user for more context about the prospect. Check the company careers page, recent press, or social posts. If nothing surfaces after 3 searches, use a role-based pain point instead (e.g., "Most Heads of Growth at Series A companies struggle with...").
- **User has no credibility proof or case study:** Use a framework-based approach instead — offer to share a methodology or insight rather than a result. Example: "I put together a framework for..." instead of "We helped X achieve Y."
- **User wants to outreach to a list of 10+ prospects:** Build one master sequence template with personalization slots clearly marked, then show the user how to customize each slot per prospect. Do not write 10 fully unique sequences — that does not scale.
- **Prospect replies with hostility:** Provide a brief, professional close: "Understood — appreciate your time. Removing you from my list." Do not engage further.
- **If 3 personalization research attempts fail** (no public info, no trigger events, no LinkedIn presence): **Stop and reassess.** This prospect may not be reachable via cold outreach. Recommend the user find a warm introduction path or choose a different prospect.

---

## Quick Reference: Sequence Timing

| Touch | Channel | Day | Length | Goal |
|-------|---------|-----|--------|------|
| Email 1 | Email | Day 1 | 60-90 words | Prove relevance, earn a reply |
| Email 2 | Email | Day 3 | 40-70 words | Add new value |
| Email 3 | Email | Day 7 | 30-50 words | Create polite closure |
| DM 1 | LinkedIn/Twitter | Day 1 | 30-50 words | Start conversation |
| DM 2 | LinkedIn/Twitter | Day 5 | 30-50 words | Final follow-up |