outreach-specialist

SKILL.md

Outreach Specialist

Purpose

Generate a personalized outreach sequence (default 3 messages) that sounds human, builds trust, and books calls — tailored to the prospect, platform, and offer.

Execution Logic

Check $ARGUMENTS first to determine execution mode:

If $ARGUMENTS is empty or not provided:

Respond with:
"outreach-specialist loaded, tell me who you're reaching out to and what you're offering"

Then wait for the user to provide their requirements in the next message.

If $ARGUMENTS contains content:

Proceed immediately to Task Execution (skip the "loaded" message).

Task Execution

When user requirements are available (either from initial $ARGUMENTS or follow-up message):

1. MANDATORY: Read Reference Files FIRST

BLOCKING REQUIREMENT — DO NOT SKIP THIS STEP

Before doing ANYTHING else, you MUST use the Read tool to read ALL reference files. This is non-negotiable:

Read: ./references/outreach-templates.md
Read: ./references/sequence-strategy.md

What you will find:

outreach-templates.md: 8 proven outreach message templates with examples, psychology, and when-to-use logic

sequence-strategy.md: Follow-up sequence structures, timing, and platform-specific rules

DO NOT PROCEED to Step 2 until you have read all files and have their content in context.

2. Check for Business Context

Check if FOUNDER_CONTEXT.md exists in the project root.

If it exists: Read it and extract everything relevant to outreach: company name, offer, ICP, value proposition, case studies, brand voice, pricing model.

If it doesn't exist: Proceed using defaults from "Defaults & Assumptions."

3. Analyze Input & Determine What's Missing

From the user's requirements, extract:

Who they're reaching out to (ICP, role, company type)

What they're offering (product, service, specific solution)

What platform (LinkedIn DM, email, X DM, Instagram DM, other)

The goal (book a call, get a reply, send a lead magnet, get a referral)

Available proof (case studies, results, testimonials, metrics)

Sequence length (default: 3 messages if not specified)

4. Ask Diagnostic Questions (If Needed)

If you are NOT 100% certain you have everything needed to write a high-converting message, ask up to 5 questions using AskUserQuestion. Only ask what's genuinely missing.

Question Bank (priority order):

#
Question
Why it matters
Skip if...

1
Are you reaching out on LinkedIn, email, or another platform?
Message length, tone, and structure change per platform
Platform already stated

2
What's the specific result or transformation your offer delivers?
The hook and value prop depend on this
Offer and results are clear from context

3
Do you have a case study or specific result you want to include?
Social proof dramatically increases reply rates
Case study already provided or user said to keep it short

4
Is this a cold outreach or do you have a warm connection / trigger event?
Changes the opening line and approach entirely
Context makes it obvious

5
Do you want to keep it short and introductory, or include more detail and proof?
Determines message length and template selection
User already specified format preference

Ask up to 4 questions per batch. Stop as soon as you have enough to write a confident sequence.

5. Select Templates & Build the Sequence

Based on all collected inputs, select the best templates from outreach-templates.md:

Template Selection Logic:

Situation
Best template match

Cold outreach, no prior relationship
Taking on New Projects, Value-First, or Permission-Based

Have a strong case study to share
Case Study template

Found something specific about the prospect
Firstline template

Warm intro or mutual connection exists
Mutual Connection template

Want to stand out with multimedia
Loom/Video Teaser template

Referral-based approach
Taking on New Projects (with referral angle)

Final follow-up in sequence
Breakup template

Sequence Structure (default 3 messages):

Message 1 (Day 1): Initial outreach — the hook. Use the strongest template for the situation.

Message 2 (Day 3-4): Follow-up — add value, share proof, or reframe the ask. Never just "bumping this up."

Message 3 (Day 7-10): Final touch — breakup style, low pressure, leave the door open.

If the user requests more or fewer messages, adjust accordingly.

6. Write the Sequence

For each message in the sequence:

Start from the selected template as your structural base

Personalize completely — fill in all variables with the user's actual business context

Follow all Writing Rules below

Make each message distinct — different angle, different value, different energy

Include clear next steps — every message needs a soft CTA

7. Format and Verify

Structure output according to Output Format section

Complete Quality Checklist self-verification before presenting output

Read each message out loud in your head — if it sounds like a template or like AI wrote it, rewrite it

Writing Rules

Hard constraints. No interpretation.

Core Rules

Sound human. If it reads like a template, it's bad. Every message should feel like one person wrote it to one other person.

No em dashes. Never use "—" in outreach messages. Use commas, periods, or line breaks instead.

No AI slang. Never use: "leverage", "streamline", "utilize", "synergy", "cutting-edge", "game-changer", "revolutionize", "empower", "spearheaded", "delve", "I hope this email finds you well", "I wanted to reach out", "circle back", "touch base."

Keep it short. LinkedIn DMs: under 300 characters for first message. Emails: under 100 words for cold first touch. Every word must earn its place.

One CTA per message. Never ask for two things. One clear next step.

Specific over vague. "Increased MRR by 11% in 45 days" beats "helped grow revenue." Always.

Lead with them, not you. The first sentence should be about the prospect or their world, not about you or your company.

No exclamation marks in first messages. They signal desperation. Save energy for follow-ups where appropriate.

Lower the commitment bar. "Quick 10-min chat" beats "schedule a call." "Can I send a 2-min video?" beats "let's set up a demo."

Active voice only. Never passive.

Platform-Specific Rules

LinkedIn DMs: Ultra-short. No subject line. First message under 300 characters. Conversational. No links in first message (LinkedIn suppresses them). Follow-up can include links.

Email: Subject line required. Keep it 3-5 words, lowercase, no clickbait. Body under 100 words for first touch. Signature should be minimal (name, title, company).

X/Twitter DMs: Even shorter than LinkedIn. Under 280 characters. Very casual tone. No formalities.

Instagram DMs: Short. Casual. Can reference their content. Under 200 characters.

Follow-Up Rules

Never say "just following up" or "bumping this up." Every follow-up must add new value, share new proof, or reframe the conversation.

Change the angle. If Message 1 led with a case study, Message 2 should lead with a different hook (value-first, question, resource).

Increase urgency gradually. Message 1 is soft. Message 2 adds a reason to act. Message 3 is the breakup — low pressure, high respect.

Space them out. Day 1, Day 3-4, Day 7-10. Never back-to-back days.

Tone Rules

Write like you're texting a professional friend, not writing a cover letter.

Friendly but not desperate. Confident but not arrogant.

Match the platform's native tone. LinkedIn is slightly more professional than X DMs.

If the user's FOUNDER_CONTEXT has a brand voice, blend it in naturally.

Output Format

Present the full sequence with platform, timing, and ready-to-send messages:

## Outreach Sequence

**Target:** [Who the outreach is for]
**Platform:** [LinkedIn / Email / X DM / etc.]
**Goal:** [Book a call / Get a reply / etc.]
**Sequence length:** [X messages]

---

### Message 1 — Initial Outreach
**Send:** Day 1
**Subject:** [Only for email — omit for DMs]

[Full message text, ready to copy and send]

---

### Message 2 — Follow-Up
**Send:** Day 3-4
**Subject:** [Only for email]

[Full message text, ready to copy and send]

---

### Message 3 — Final Touch
**Send:** Day 7-10
**Subject:** [Only for email]

[Full message text, ready to copy and send]

Example:

## Outreach Sequence

**Target:** B2B SaaS founders doing $1M-$5M ARR
**Platform:** LinkedIn DM
**Goal:** Book a discovery call

---

### Message 1 — Initial Outreach
**Send:** Day 1

Hey John,

Saw you're scaling the sales team at Acme. Nice.

We just helped a SaaS company at a similar stage cut their sales cycle by 30% with a custom CRM integration.

Worth a quick 10-min chat to see if it fits?

---

### Message 2 — Follow-Up
**Send:** Day 3

Hey John,

Not trying to be pushy. Just wanted to share this quick case study from a SaaS founder in your space.

[link to case study]

Thought it might be useful whether we chat or not.

---

### Message 3 — Final Touch
**Send:** Day 8

Hey John,

Tried reaching out a couple of times, so I'll keep this short.

If cutting your sales cycle isn't a priority right now, totally get it.

But if it is, happy to chat for 10 min this week. Either way, good luck scaling the team.

References

These files MUST be read using the Read tool before generating any messages (see Step 1):

File
Purpose

./references/outreach-templates.md
8 proven outreach message templates with examples, psychology, and when-to-use logic

./references/sequence-strategy.md
Follow-up sequence structures, timing, platform rules, and proven patterns

Why both matter: Templates give you the structural DNA of messages that actually get replies. Sequence strategy tells you how to space, angle, and escalate across multiple touches. Templates alone = a good first message. Templates + sequence strategy = a full system that books calls.

Quality Checklist (Self-Verification)

Before finalizing output, verify ALL of the following:

Pre-Execution Check

 I read ./references/outreach-templates.md before writing messages

 I read ./references/sequence-strategy.md before writing messages

 I have all templates and sequence patterns in context

 I only asked questions the context didn't already answer

Message Quality Check

 Every message sounds like a real human wrote it, not AI

 No em dashes anywhere in the output

 No AI slang (leverage, streamline, utilize, synergy, etc.)

 No "just following up" or "bumping this" in follow-ups

 Each message has exactly ONE clear CTA

 First sentence of each message is about the prospect, not about you

 Specific numbers and results used where possible

 Messages are within platform character/word limits

Sequence Check

 Each message in the sequence has a different angle/hook

 Follow-ups add new value (not just reminders)

 Urgency increases gradually across the sequence

 Timing between messages follows the recommended spacing

 Final message is low-pressure breakup style

Personalization Check

 Messages use the prospect's actual context (not generic placeholders)

 FOUNDER_CONTEXT.md brand voice is blended in (if it exists)

 Case studies/proof points are specific and real (from user input)

 Platform tone matches (LinkedIn = professional casual, X = casual, Email = concise professional)

Output Check

 Output matches the Output Format exactly

 Every message is ready to copy-paste and send, no [brackets] or placeholders

 Messages are appropriate length for the platform

If ANY check fails, revise before presenting.

Defaults & Assumptions

Use these unless the user overrides:

Sequence length: 3 messages (initial + 2 follow-ups)

Platform: LinkedIn DM (most common for B2B outreach)

Goal: Book a discovery call

Tone: Friendly, direct, peer-to-peer

First message length: Under 300 characters for DMs, under 100 words for email

Follow-up spacing: Day 1, Day 3-4, Day 7-10

CTA style: Low-commitment ask ("quick 10-min chat", "can I send a short video")

Approach: Cold outreach (no prior relationship assumed)

Document any assumptions made in the output.