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.mdWhat 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.mdbefore writing messages - I read
./references/sequence-strategy.mdbefore 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.