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.

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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).

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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):

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:

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:

1. Start from the selected template as your structural base
2. Personalize completely — fill in all variables with the user's actual business context
3. Follow all Writing Rules below
4. Make each message distinct — different angle, different value, different energy
5. 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

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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.

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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]

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

[Full message text, ready to copy and send]

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

[Full message text, ready to copy and send]

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### 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

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### 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?

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### 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.

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### 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.

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References

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

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.

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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.

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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.