Outreach Specialist

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):

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

---

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):

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.

Outreach Message Templates

8 proven outreach templates. Each one has a specific use case, structure, psychology, and example. Select templates based on the situation, then personalize completely.

---

Template 1: Taking on New Projects

When to use: Cold outreach when you want a soft, referral-style approach. Works on any platform. Great for agencies and service providers.

Psychology: Asking "know anyone?" is less threatening than asking for a meeting directly. It gives the prospect an easy out while still planting the seed. Most people who respond will refer themselves.

Structure:

Hey [name],

We're taking on new projects for [offer].

Know anyone who might benefit?

[percentage] referral fee.

Cheers!

Example:

Hey Sarah,

We're taking on new projects for custom AI agents and workflow automation.

Know anyone who might benefit?

15% referral fee.

Cheers!

Platform fit: LinkedIn, Email, X DM Best for: Service businesses, agencies, freelancers

---

Template 2: Case Study

When to use: When you have a strong, specific result to share. Best for prospects who are data-driven and need proof before engaging.

Psychology: Leading with a third-party result feels less salesy than pitching directly. The case study does the selling. Ending with "do you know someone" keeps the pressure low.

Structure:

Hey [name],

My [agency/company] helps [ICP] [achieve the desired goal] with [solving pain point].

Last month, we [specific case study with numbers].

Do you know someone who might benefit from this?

Thanks!

Example:

Hey John,

My agency helps B2B software companies ship enterprise features faster with less engineering overhead.

Last month, we built a white-label analytics dashboard for a B2B SaaS team. Costed 20% less than if their core engineers built it.

Do you know someone who might benefit from this?

Thanks!

Platform fit: Email, LinkedIn Best for: Anyone with a recent win or measurable result to show

---

Template 3: Firstline (Personalized Observation)

When to use: When you found something specific about the prospect (bad reviews, outdated website, social media gap, hiring signals, recent news). The most effective cold template when done right.

Psychology: The personalized first line proves you did research. It signals effort. Prospects respond because the message clearly isn't mass-sent.

Structure:

Hey [name],

[Specific observation about their business].

We just helped [company] [achieve specific result].

Can I send you a quick video explaining more?

Example:

Hey John,

Saw a couple of bad Google reviews on your page so wanted to see if I can help.

We just helped Acme rank #1 on ChatGPT and increased their MRR by 11% in 45 days.

Can I send you a quick video explaining more?

Platform fit: LinkedIn, Email, X DM Best for: Highly targeted outreach where you've done research on the prospect

---

Template 4: Mutual Connection

When to use: When you share a mutual connection, attended the same event, are in the same community, or follow the same thought leader. Warm intros convert 5-10x better than cold.

Psychology: Name-dropping a mutual connection builds instant trust. The prospect's guard drops because you're no longer a stranger. Even a shared community or event works.

Structure:

Hey [name],

[Mutual connection / shared context] mentioned you might be dealing with [pain point].

We just wrapped a project doing [specific result] for [similar company].

Worth a quick 10-min chat?

Example:

Hey Mike,

We're both in the SaaS Growth community and I saw your post about struggling with churn.

We just helped a B2B SaaS company cut churn by 18% in 60 days with a custom onboarding flow.

Worth a quick 10-min chat to see if something similar could work for you?

Platform fit: LinkedIn, Email Best for: Warm-ish outreach, community-based selling, conference follow-ups

---

Template 5: Loom / Video Teaser

When to use: When you want to stand out in a crowded inbox. Record a short 1-2 min video showing something specific about their business (an audit, a suggestion, a quick win). Send the link.

Psychology: A personalized video is impossible to fake at scale. It signals extreme effort and care. Prospects watch because curiosity wins. The "no pitch" framing removes resistance.

Structure:

Hey [name],

Made a quick 2-min video breaking down [specific thing about their business].

[link]

No pitch, just thought it'd be useful.

Example:

Hey Lisa,

Made a quick 2-min video breaking down 3 things I'd change on your landing page to increase conversions.

[loom link]

No pitch, just thought it'd be useful.

Platform fit: Email, LinkedIn (link in follow-up, not first DM) Best for: High-value prospects worth the extra effort. Agency owners, consultants, coaches.

Note: On LinkedIn, don't include links in the first DM. LinkedIn suppresses messages with links. Use this as a follow-up or switch to email.

---

Template 6: Value-First

When to use: When you notice something specific about their business and can offer a quick, actionable suggestion for free. You lead with value before asking for anything.

Psychology: Giving before asking triggers reciprocity. The prospect feels like they owe you something. Even if they don't reply, they remember you. If your suggestion is actually good, you've demonstrated competence without a pitch.

Structure:

Hey [name],

Noticed [specific observation about their business].

Quick thought - [one actionable suggestion].

We did this for [company] and [specific result].

Happy to share more if useful.

Example:

Hey David,

Noticed your checkout page has 6 form fields. That's usually where 30-40% of drop-offs happen.

Quick thought - cutting it to 3 fields and adding a progress bar could bump your conversion by 15-20%.

We did this for an ecom brand last month and their checkout rate went from 2.1% to 3.4%.

Happy to share more if useful.

Platform fit: Email, LinkedIn Best for: Consultants, agencies, anyone who can spot quick wins in a prospect's business

---

Template 7: Permission-Based

When to use: When you want to be respectful of the prospect's time and let them opt in. Works especially well for senior decision-makers who get bombarded with pitches daily.

Psychology: Asking for permission flips the dynamic. Instead of pushing, you're inviting. Senior prospects respect this because it shows awareness of their time. The "no pressure" line removes the last barrier to replying.

Structure:

Hey [name],

We help [ICP] [achieve result] without [common objection or pain].

Would it be okay if I sent over a quick breakdown of how it works?

No pressure either way.

Example:

Hey Rachel,

We help DTC brands scale to $50K/mo in ad spend without burning through creative every 2 weeks.

Would it be okay if I sent over a quick breakdown of how it works?

No pressure either way.

Platform fit: LinkedIn, Email, X DM Best for: C-suite outreach, high-ticket offers, senior decision-makers

---

Template 8: Breakup / Last Touch

When to use: As the final message in any sequence. Also works as a standalone re-engagement message for prospects who went cold.

Psychology: The breakup message works because of loss aversion. When you signal you're about to stop reaching out, the prospect feels the potential loss of the opportunity. It also shows confidence: you're not desperate, you have other prospects.

Structure:

Hey [name],

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

If [solving their pain point] isn't a priority right now, totally get it.

But if it is, happy to chat for 10 min this week.

Either way, wishing you the best!

Example:

Hey Tom,

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

If cutting your customer acquisition cost isn't a priority right now, totally get it.

But if it is, happy to chat for 10 min this week.

Either way, wishing you the best with the launch!

Platform fit: LinkedIn, Email Best for: Final message in any sequence. Re-engaging cold prospects.

---

Template Selection Quick Reference

Outreach Sequence Strategy

How to structure multi-message outreach sequences that get replies and book calls. Based on patterns from top cold outreach practitioners including Client Ascension methodology and proven B2B outreach frameworks.

---

Core Principle: Every Message Must Earn Its Place

A follow-up is NOT a reminder. If your follow-up says "just checking in" or "bumping this up," delete it and start over. Each message in the sequence must:

1. Introduce a new angle, new proof, or new value 2. Feel like a standalone message (not dependent on the previous one being read) 3. Lower the commitment bar progressively 4. Sound like a different conversation, not a repeated one

---

The 3-Message Sequence (Default)

This is the standard structure. Use it unless the user asks for more or fewer messages.

Message 1: The Hook (Day 1)

Purpose: Open the conversation. Make them curious enough to reply.

Rules:

• Lead with them, not you
• One specific hook (case study, observation, referral angle, or value-first)
• Soft CTA: "Worth a quick chat?" or "Can I send more info?"
• Keep it the shortest message in the sequence

Best templates: Taking on New Projects, Firstline, Case Study, Permission-Based

Message 2: The Value Add (Day 3-4)

Purpose: Give them a reason to engage even if Message 1 didn't land.

Rules:

• Do NOT reference Message 1 ("just following up on my last message")
• Add new value: share a resource, case study, quick tip, or insight
• Can include a link (to a Loom, case study, or article)
• Slightly longer than Message 1 is okay
• CTA can be slightly more direct: "Want me to break this down for you?"

Best templates: Value-First, Loom / Video Teaser, Case Study (different angle)

Message 3: The Breakup (Day 7-10)

Purpose: Create urgency through loss aversion. Last touch, low pressure.

Rules:

• Acknowledge you've reached out before (briefly)
• Give them an easy out: "If this isn't a priority, totally get it"
• One final, low-pressure CTA
• Keep it the most casual message in the sequence
• End on a positive note regardless

Best template: Breakup / Last Touch

---

The 5-Message Sequence (Extended)

For email campaigns or when the user wants a longer drip. Space messages further apart.

---

The Single Message (One-Shot)

Sometimes the user just needs one killer message. In this case:

• Pick the single best template for the situation
• Make it slightly more complete than a sequence opener
• Include both the hook AND the proof in one message
• Keep the CTA clear and low-commitment

---

Platform-Specific Sequence Rules

LinkedIn DM Sequences

• First message: No links. LinkedIn suppresses messages with URLs. Keep it under 300 characters.
• Second message: Can include a link (Loom, case study, article). Can go slightly longer.
• Third message: Short breakup. Under 200 characters is fine.
• Connection request note: If you're not connected yet, the connection request IS your first message. Keep it under 300 characters. Then the sequence starts after they accept.
• Timing: If they viewed your profile after Message 1, send Message 2 sooner (Day 2 instead of Day 3-4).

Email Sequences

• Subject lines: 3-5 words, lowercase, no clickbait, no emojis. Examples: "quick question", "thought about your team", "re: [their company]", "[mutual connection] mentioned you"
• Follow-up subjects: Can reply to the same thread (no new subject) or use a fresh subject. Fresh subject = higher open rate. Same thread = less inbox clutter.
• Signature: Minimal. Name, title, company, one link (website or calendar). No quotes, no banners, no social icons.
• Timing: Tuesdays through Thursdays, 8-10am in the prospect's timezone. Avoid Mondays and Fridays.

X / Twitter DM Sequences

• Max 2 messages. Three feels like spam on X.
• Keep it ultra-casual. No "Hey [name]," formality. Just dive in.
• Reference their content. "Saw your tweet about X" is the best opener on this platform.

Instagram DM Sequences

• Max 2 messages. Same as X.
• React to a story first if possible. It warms the conversation before your pitch.
• Very casual. Instagram is the most informal platform.

---

Follow-Up Angle Rotation

Never use the same angle twice in a sequence. Rotate through these:

---

Timing Rules

Never send two messages on the same day. It looks desperate.

If they reply at any point, stop the sequence and have a real conversation. Do not send the next pre-written message.

---

Subject Line Formulas (Email Only)

Keep subject lines short, lowercase, and curiosity-driven. No clickbait.

---

What Makes Outreach Fail

Avoid these at all costs:

1. Talking about yourself first. "Hi, I'm John from Acme Agency and we..." Nobody cares. Lead with them. 2. Being vague. "We help companies grow" means nothing. Be specific about who, what, and how much. 3. Sounding like AI. If the message has em dashes, "leverage," "streamline," or "I hope this finds you well," it's going straight to trash. 4. Writing too much. If your first cold message is longer than 5 sentences, cut it in half. 5. No social proof. Claims without evidence get ignored. One case study beats ten claims. 6. Generic follow-ups. "Just following up" is the fastest way to get archived. 7. Weak CTA. "Let me know if you're interested" is weak. "Worth a 10-min chat this week?" is direct. 8. Sending on weekends. Business outreach on Saturday = ignored on Monday morning.