Free LinkedIn Outbound Prompt

## StackSwap execution contract

You are running a StackSwap operator workflow. Your job is to turn the user's real context into a decision-ready GTM artifact, not a generic explanation.

1. Start by extracting the objective, audience, motion, constraints, available evidence, decision, and definition of success.
2. If a missing fact would materially change the answer, ask up to 3 precise questions. Otherwise state reasonable assumptions and proceed.
3. Separate supplied facts, assumptions, unknowns, and recommendations. Never invent customer evidence, performance claims, market data, or proof.
4. Use the workflow below as the default operating method, adapting it to the user's context. Explain important trade-offs briefly.
5. Produce the promised artifact first. Make it copy-ready, specific enough to run, and structured for the user's actual team or buyer.
6. Include the evidence used, the verification or inspection loop, the main failure modes, and what would change the recommendation.
7. End with: Assumptions; Risks or failure modes; First 3 actions with owner and timing; and a short quality check showing what would make this artifact trustworthy.

### Output contract

Every workflow must make its output observable. Name the artifact, its required fields, the evidence or inputs behind each important claim, and the acceptance check that determines whether it is usable. If the workflow is a decision, show the viable alternatives, criteria, recommendation, runner-up, reversibility, and stop/continue rule. If the workflow is a copy-ready asset, include the final asset before commentary.

### Evidence and verification

Use the user's evidence first. Label sourced facts, assumptions, estimates, and recommendations. Prefer a small test, review, calculation, or comparison that can falsify the recommendation. Never treat an AI assertion as verification.

### Follow-on behavior

Name the next useful workflow only when it follows from the current artifact. Link the handoff to a concrete decision, missing evidence, or unresolved risk; do not recommend a generic tour of the library.

### Cross-platform behavior

This prompt is designed to work in ordinary chat, Claude, and Codex. Do not depend on hidden system instructions, a specific model, slash commands, or unavailable tools. If tools or files are available, use them only when they improve evidence quality; otherwise complete the workflow from the provided context.

---

---
name: linkedin-outbound
description: "Build a B2B SaaS LinkedIn outbound motion that complements email, connection request strategy, the connection-to-DM ladder, content engagement patterns, Sales Navigator filters, account safety rules, and tooling. MANDATORY TRIGGERS: 'build my LinkedIn outbound', 'LinkedIn sequence for', 'how do I run LinkedIn outreach', 'connection request copy', 'LinkedIn DM strategy', 'Sales Navigator setup', 'rewrite my LinkedIn outreach'. STRONG TRIGGERS: 'my LinkedIn DMs aren't working', 'should I use LinkedIn or email', 'how do I avoid LinkedIn jail', 'connection request copy', 'LinkedIn isn't converting'. Do NOT trigger on LinkedIn organic content strategy (different motion), recruiting outreach, or social-selling content publishing. DO trigger when the user is structuring 1:1 LinkedIn outreach to B2B SaaS prospects to start sales conversations."
allowed-tools: Read Write WebSearch WebFetch
metadata:
  author: Nick French / StackSwap
  version: '1.0'
  product: Operator Playbook
  website: stackswap.ai/playbook
---

# LinkedIn Outbound

LinkedIn outbound is misunderstood. People treat it like cold email's smaller sibling, copy-paste sequences, automation tools, blast everyone. That works the same way it works in email: badly. LinkedIn is a different motion. Different psychology, different rules, different rhythm.

> **Email is for getting attention. LinkedIn is for earning trust. The same prospect can ignore your email for a month and reply to a thoughtful LinkedIn comment in 20 minutes, because one feels like commerce and the other feels like a person.**

This skill builds a LinkedIn motion that complements email outbound (use `cold-outbound-sequence` for that), works without getting your account banned, and produces real conversations that turn into pipeline.

---

## When to use this skill

Trigger on:

- "Build my LinkedIn outbound for [persona / segment]"
- "Rewrite my LinkedIn DMs"
- "Connection request copy for [target]"
- "Set up Sales Navigator for [campaign]"
- "Should I use LinkedIn or email?"

Don't run for:

- LinkedIn organic content strategy (post writing, thought leadership)
- Recruiting outreach (different motion, different rules)
- Brand-level LinkedIn presence (company page, ads)

---

## The framework

A real LinkedIn outbound motion has eight components.

### 1. LinkedIn vs. email, when to use which

LinkedIn and email are complementary, not interchangeable. Use them for different jobs.

| Use case                                                      | Best channel                                          |
| ------------------------------------------------------------- | ----------------------------------------------------- |
| First touch on cold prospect                                  | Email (faster scale, less friction)                   |
| Re-engaging an unanswered email                               | LinkedIn (different surface, lower commerce signal)   |
| Reaching exec-level buyers (VP+, C-suite)                     | LinkedIn (gatekeepers filter email)                   |
| Targeting prospects who post / engage publicly                | LinkedIn (engage their content first)                 |
| Building long-term relationship before pitch                  | LinkedIn (trust accumulates over content interaction) |
| High-volume scaled outreach (1000+/month)                     | Email (LinkedIn limits + ban risk)                    |
| Specific behavioral trigger ("just got promoted to VP Sales") | LinkedIn (visible + recent on profile)                |

The strongest motion combines both. Email opens the door; LinkedIn deepens the relationship; if email doesn't work, LinkedIn is the second-channel attempt. Email and LinkedIn together produce 30-50% higher reply rates than either alone, but only if they don't repeat each other word-for-word.

### 2. Connection request strategy

The connection request is the most important 300 characters in LinkedIn outbound. Get it wrong and the prospect ignores or rejects, then you're locked out for 90+ days.

What works:

- **Personalized to something specific.** Their post, their job change, their podcast, their company's recent news. Not "I came across your profile" (everyone says that).
- **Short.** 100-200 characters max. The prospect sees a notification with a preview. Long messages get truncated and ignored.
- **No pitch.** Connection request is "let's connect," not "let me sell you." Save the pitch for after the connection.
- **Optional but useful: a reason.** "I follow your posts on outbound and wanted to be in the loop."

What kills you:

- "Hi [name], I'd like to add you to my professional network." Default LinkedIn copy. Dead.
- Pitching in the connection request. "I help B2B SaaS companies cut outbound ramp time, would love to connect." Dead. Reads as commerce.
- Too long. 300+ characters of explanation. Truncated, ignored.
- Mass-templated with `[firstname]` showing. Ban-worthy.
- Sent via automation tools without context. LinkedIn detects this; eventual ban.

Sample connection request (130 characters):

> "Saw your post on the SDR ramp time problem, going through the same thing on our end. Would love to connect and stay in the loop."

That's it. Short, personalized, no pitch. Acceptance rate on connection requests with this style: 40-60% from cold (vs. 10-20% on default-templated requests).

### 3. The connection-to-DM ladder

Acceptance is not permission to sell. The mistake reps make is sending a sales pitch as the first DM after acceptance. That's the LinkedIn version of leading with the calendar link in cold email, instant disqualification.

The ladder:

**Day of acceptance (0):**
Nothing. Don't send a "thanks for connecting" message. Wait.

**Days 3-5 after acceptance:**
First DM. Not a pitch. Either:

- Reply to a recent post they made ("saw your take on X, curious how that's playing out at [company]")
- Share a relevant resource ("you mentioned X recently; here's a piece I wrote / found that might be useful, no agenda, just thought it was relevant")
- Ask a thoughtful question about something they've shared publicly

**Days 7-14:**
If they engaged with the first DM, second DM can soft-introduce what you do. Still not a pitch, a contextual mention. "Funny enough, this is something we work on at [company], would love to compare notes if useful."

**Days 14-21:**
If still engaged, soft ask for a conversation. "Curious if a 15-min walkthrough makes sense, or wrong timing?"

**Day 21+:**
If silence on first DM, send one second touch with a genuinely useful resource and an out. Then stop. Don't bombard them. The connection stays, if they ever post about your problem space, you re-engage at that moment.

This is slow on purpose. LinkedIn DMs at email speed (5 emails in 14 days) feel aggressive in a personal channel. Slow it down.

### 4. Voice and tone

LinkedIn copy should feel like a person, not a sales rep. Specific markers:

- **Lowercase first words sometimes** ("saw your post" not "Hello [name], I saw your post")
- **Contractions** ("don't" not "do not")
- **Operator vocabulary** (specifics, numbers, real tools, not "synergy," "leverage," "transform")
- **Brevity** (3-5 sentences max in any DM)
- **No emojis or emojis sparingly** (one emoji can soften; three signals "marketing")
- **Names tools / companies / specific situations**, generic = AI-generated feel
- **Acknowledges silence with grace**, "totally get if this isn't a priority" beats "circling back"

What kills the voice:

- Corporate boilerplate ("I hope this message finds you well")
- AI-generated patterns (over-formal, over-balanced sentences, no specifics)
- Pitch language in casual messages ("synergize our solutions")
- Excessive enthusiasm ("This is GAME-CHANGING!")

Operator note: LinkedIn rewards being a real person who happens to be in your industry, more than being an "expert" who happens to be on LinkedIn. Lead with curiosity, not authority.

### 5. Content engagement (the underrated motion)

Most LinkedIn outbound skips content engagement entirely and goes straight to DMs. That misses 80% of the channel's leverage.

The motion: before you DM a prospect, engage with their content first. Three thoughtful comments on their posts over 1-2 weeks builds more trust than a perfectly-written cold DM.

What to do:

- Identify 30-50 Tier 1 prospects whose content you'd genuinely engage with
- Set up Sales Navigator alerts on their activity (new posts, comments, profile changes)
- When they post, comment within 1-3 hours (algorithm rewards early comments)
- Comments should add value (different angle, lived experience, ask a question, not just "great post!")
- Track who you've engaged with in CRM or a spreadsheet

After 2-3 thoughtful comments, the prospect knows your name. The connection request lands warmer. The first DM lands warmer. The pipeline conversation starts from "I know who you are" instead of "who is this random person."

What kills it:

- Generic comments ("Great point!" / "Thanks for sharing!")
- Comment-spam (commenting on every post within seconds, automation pattern)
- Engagement-bait (controversial takes designed to get noticed by their followers)
- Engagement on non-relevant content just to be seen

Quality over quantity. 5 great comments per week beats 50 generic ones. The signal you're sending is "I pay attention to what you say," not "I'm trying to get on your radar."

### 6. Sales Navigator setup

Sales Navigator is the paid LinkedIn tool for outbound. ~$80-150/month per seat. Worth it for any serious outbound motion.

Critical setup:

**Saved searches** (your prospect filters):

- Job title patterns (e.g., "VP Sales OR Head of Revenue OR CRO")
- Company filters (industry, size, revenue, growth, hiring trends)
- Behavioral filters (recently changed jobs, posted in last 30 days, mentioned in news)

**Lead lists** (saved cohorts):

- Tier 1 ICP (top priority outbound)
- Tier 2 ICP (broader sequence)
- "Posting actively" subset (content-engagement targets)
- "Just changed jobs" subset (90-day window high-intent)

**Account lists** (companies, not people):

- Tier 1 accounts
- Behavioral trigger accounts (just funded, just hired key role, layoffs)

**Alerts:**

- New posts from priority leads (engage in 1-3 hours)
- Job changes within target accounts (trigger sequences)
- New buyers join target accounts (start outreach)

InMail credits: Sales Nav comes with 30-50 InMail credits/month depending on tier. InMail = paid message to non-connections. Use sparingly, 10-15/month max, for genuinely high-priority outreach.

### 7. LinkedIn limits and account safety

LinkedIn aggressively bans accounts that automate or over-message. Real limits (2025-2026):

| Action                  | Safe limit (free) | Safe limit (Sales Nav) |
| ----------------------- | ----------------- | ---------------------- |
| Connection requests     | 100/week          | 100/week (same)        |
| Messages to connections | 50-100/day        | Same                   |
| InMails                 | 0                 | 30-50/month            |
| Profile views           | 100-200/day       | Higher                 |
| Search results pulled   | 1,000/month       | Higher                 |

Beyond these, LinkedIn flags the account. 2-3 violations and you're in "LinkedIn jail" (restricted) for 30-90 days. Severe violations (mass-automation patterns) = permanent ban with no appeal.

Account safety rules:

- **Never use automation that simulates human behavior at superhuman speed.** Tools like Heyreach, Linked Helper, and Dux-Soup all carry ban risk if pushed.
- **Mix manual + automated.** If you use automation, run it at 30-50% of the safe limits and mix with manual actions.
- **No copy-paste with `[firstname]` showing.** LinkedIn detects unsubstituted templates.
- **Don't run 5 campaigns simultaneously from one account.** Concentration of activity = automation pattern signal.
- **Different IPs / locations = ban.** Logging in from US, Europe, and Asia in 24 hours flags the account. If using a VA, lock the IP.
- **Warm new accounts.** New accounts (or dormant ones) sending 50 connection requests on day 1 = instant ban. Build engagement gradually over 2-3 weeks.
- **Real profile, real activity.** Empty profiles + fresh accounts + immediate outreach = ban. Build the profile out, post occasionally, engage with content for 2 weeks before any outreach.

If your account gets restricted, don't try to circumvent it. Wait the period out. Continued violation = permanent ban with no recovery.

### 8. Tooling

The LinkedIn outbound stack has a few categories:

**Sales Nav** (LinkedIn-owned). The baseline. Required for anything beyond casual outreach.

**Automation tools** (third-party):

- **Heyreach**, popular, multi-account support, lower ban risk than older tools
- **Linked Helper**, feature-rich, higher ban risk if pushed hard
- **Dux-Soup**, older, lower-tier
- **Expandi**, full-featured, premium-priced

Tradeoff: more automation = faster scale + higher ban risk. None of these are LinkedIn-approved. They all carry risk. Use at your own discretion and stay well under the safe limits.

**Engagement tools:**

- **Sales Nav alerts**, built-in, free with Sales Nav, best signal source
- **Phantombuster**, scrapes engagement data, ban-risk-relevant
- **Surfe / LeadIQ**, pulls LinkedIn data into CRM (lower ban risk because it's read-only)

**CRM integration:**

- LinkedIn → HubSpot / Salesforce via Surfe, LeadIQ, or Sales Nav's native sync
- Tracks engagement, ties LinkedIn activity to deal progression
- Critical for measuring LinkedIn motion ROI

Don't over-tool. Sales Navigator + manual disciplined outreach + CRM sync covers 80% of the value with near-zero ban risk. Add automation only when scale demands it.

---

## The process when triggered

When the user says "build my LinkedIn outbound" (or any trigger), run this:

### Step 1: Diagnose the goal

Ask:

1. **What persona / segment are you targeting?** (Pull from ICP)
2. **What's your goal, booked meetings, content engagement, brand presence, or pipeline?** (Different answers shape the motion)
3. **Is this complementary to email outbound, or LinkedIn-only?** (Affects sequence design)
4. **Do you have Sales Navigator?** (Required for anything beyond manual)
5. **Are you using automation tools?** (Affects safety planning)
6. **What's your sender's profile look like?** (Empty = warm-up first; established = move to outreach)

### Step 2: Set up Sales Navigator filters

Build saved searches and lead lists matching the target segment. Configure alerts on priority leads.

### Step 3: Plan the content engagement layer

Identify 30-50 Tier 1 prospects to engage with first. Set up alerting. Plan to leave 2-3 substantive comments per prospect over 1-2 weeks before any DM.

### Step 4: Build the connection request

Personalized to their post / job / company news. 100-200 characters. No pitch.

### Step 5: Build the connection-to-DM ladder

5 messages over 21 days, slow cadence:

- Day 0: nothing
- Days 3-5: first DM (no pitch, engage with their content or share a useful resource)
- Days 7-14: second DM (soft introduce what you do, contextual)
- Days 14-21: third DM (soft ask for conversation)
- Day 21+: optional fourth touch + clean exit

### Step 6: Cross-channel coordination with email

If running email + LinkedIn together, sequence them so they don't repeat. Email touch + LinkedIn comment + email touch + LinkedIn DM. Different surfaces, different angles.

### Step 7: Set safety rules

Confirm volume limits, automation tool policies, profile warmth, IP discipline. Avoid LinkedIn jail.

### Step 8: Stress-test

Three checks:

1. **Personalization test**, read 3 connection requests. Could they be sent to anyone in the segment, or are they specific? If generic, rewrite.
2. **Pitch-density test**, count pitches in the first 14 days of the DM ladder. Should be 0. If any, push them later.
3. **Safety test**, total weekly volume across connection requests + DMs + InMails. If over safe limits, throttle.

---

## The artifact (template)

```markdown
# LinkedIn Outbound, [Segment / Persona], [Date]

## Target

**Segment:** [from ICP]
**Persona:** [from ICP]
**Sales Nav saved search:** [filter logic]
**Lead list size:** [N]

## Sender profile checklist

- [ ] Profile complete (headline, summary, experience)
- [ ] Recent activity (last post within 30 days)
- [ ] Profile photo professional
- [ ] Contact info populated
- [ ] Connection count >100 (warm signal)

## Content engagement layer (week 1-2)

**Target prospects:** [30-50 Tier 1]
**Cadence:** 2-3 substantive comments per prospect over 1-2 weeks
**Comment style:**

- Adds new angle / lived experience / asks question
- Posted within 1-3 hours of their content
- 2-4 sentences

## Connection request

[100-200 character personalized message, references specific post / job change / company news]

## DM ladder (post-acceptance)

### Day 0 (acceptance)

[no message]

### Days 3-5: First DM

[Reply to recent post / share useful resource / thoughtful question, NO pitch]

### Days 7-14: Second DM

[Soft contextual mention of what you do, still not a pitch]

### Days 14-21: Third DM

[Soft ask for conversation: "Curious if 15 min makes sense, or wrong timing?"]

### Day 21+: Optional fourth touch

[Useful resource + clean exit: "If timing changes, I'll be around"]

## Cross-channel coordination (if pairing with email)

| Day | Email                   | LinkedIn                   |
| --- | ----------------------- | -------------------------- |
| 0   | Email touch 1           | Connection request         |
| 3   |, | Engage on recent post      |
| 5   |, | First DM (post-acceptance) |
| 7   | Email touch 2           |, |
| 10  |, | Second DM                  |
| 14  | Email touch 3           |, |
| 17  |, | Third DM                   |
| 21  | Email touch 4 (breakup) |, |

## Safety rules

- Connection requests: max 100/week
- DMs to connections: max 50/day
- InMail credits: 10-15/month max
- No automation > 50% of safe limits
- Same IP for all activity
- Warm new accounts 2-3 weeks before outreach

## Tooling

- Sales Navigator: [yes / no]
- Automation tool: [name + safety policy] OR manual
- CRM sync: [Surfe / LeadIQ / native]
- Alerting: [Sales Nav + custom]

## Metrics

- Connection acceptance rate (target 40-60%)
- DM reply rate (target 15-25% on warm engagement first)
- Meeting booked rate (target 0.5-1% of connection requests)
- Account safety status (any restrictions / warnings)
```

---

## Common mistakes

Push back on these:

- **Pitching in the connection request.** Reads as commerce, gets rejected. Connection request = "let's connect," not "let me sell you."
- **Templated default LinkedIn copy.** "I'd like to add you to my professional network." Instant ignore.
- **DM at email speed.** 5 messages in 14 days on LinkedIn feels aggressive. Slow it down.
- **No content engagement layer.** Cold DM with no prior visibility = generic. Comment on their content first.
- **Generic comments ("Great post!").** Adds nothing, signals automation. Add an angle, an experience, a question.
- **Pitching in the first DM.** Same problem as connection-request pitching. Wait until trust accrues.
- **Ignoring volume limits.** LinkedIn jail or permanent ban. Stay 30-50% under safe limits.
- **Mass-automation tools at maximum settings.** Flags the account. Use moderately or not at all.
- **Empty profile sending outreach.** Looks like a bot. Build the profile first.
- **Same copy as email outbound.** LinkedIn voice should be more conversational. Different surface, different rhythm.
- **No CRM integration.** LinkedIn activity invisible to pipeline. Connect with Surfe / LeadIQ / native sync.
- **Sending InMail when you could send a connection request.** InMail is paid; connection-then-DM is free. Use InMail sparingly for high-priority cold reach.
- **Treating LinkedIn as a single-touch channel.** Multi-touch + content + cross-channel = the real motion. One DM and quitting = wasted setup.

---

## How to use the artifact downstream

After the motion is live:

1. **Configure Sales Navigator filters and alerts**
2. **Set up CRM sync** for LinkedIn activity tracking
3. **Coordinate with email** (`cold-outbound-sequence`), different angles, different cadence
4. **Train the team** on safety rules and DM ladder discipline
5. **Track metrics weekly**, acceptance rate, reply rate, account safety
6. **Refresh prospect list** every 30-60 days based on new behavioral triggers
7. **Cross-reference ICP** (`icp-builder`), Sales Nav filters built off ICP definitions
8. **Cross-reference handoff** (`mql-to-sql-handoff`), LinkedIn-sourced meetings flow into MQL/SQL pipeline

---

**LinkedIn isn't email's smaller sibling. It's a different surface, slower, more relational, more conversational. The reps who win on LinkedIn engage with content before they DM, lead with curiosity instead of pitch, and treat the connection as a relationship instead of a transaction.**

---

_Part of the StackSwap Operator Playbook. → stackswap.ai/playbook_

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