LinkedIn Outreach Strategies for B2B AI Companies

LinkedIn Outreach Isn't Dead (Your Approach Is)

"LinkedIn doesn't work anymore."

I hear this constantly from AI consultants who tried sending 50 connection requests with generic pitch messages and got... nothing.

LinkedIn absolutely still works for B2B outreach. But you can't treat it like a spam cannon.

After 5+ years in the AI space and hundreds of successful outbound campaigns, I can tell you exactly what works—and what gets you ignored.

The LinkedIn Outreach Framework That Works

Step 1: Target the Right People

Before you touch LinkedIn, you need to know exactly who you're looking for.

Use LinkedIn's advanced search filters:

• Title: Specific roles (VP Operations, Director of Sales, Head of Customer Success)
• Company size: 51-200, 201-500, etc. (match your ICP)
• Industry: Be specific (E-commerce, SaaS, Financial Services)
• Geography: Where they're located (matters for time zones and regulations)
• Recent activity: Posted in last 30 days (signals active users)

Build a list of 100-200 ideal prospects before you start reaching out.

Step 2: Warm Them Up First

Don't send a connection request cold. Warm them up for 3-7 days first:

• View their profile (they'll see you in "Who's Viewed Your Profile")
• Like or comment on their recent posts (thoughtful comments, not "Great post!")
• Engage with their content 2-3 times over a few days
• Then send the connection request

This makes you familiar instead of a random stranger.

Step 3: Personalize the Connection Request

Bad connection request:

"Hi, I help companies with AI. Would love to connect!"

Good connection request:

"Hi [Name], saw your post about scaling customer support—our e-commerce clients face the same challenge. Would be interested to connect and share what's working."

The difference:

• References something specific about them
• Shows relevance (you understand their world)
• Offers value, not just "let's connect"

Step 4: The First Message (Don't Pitch)

They accepted your connection. Now what?

Most people immediately pitch. That's a mistake.

Your first message should:

• Thank them for connecting
• Reference why you reached out
• Ask a relevant question (not "want to schedule a call?")

Example:

This opens a conversation instead of triggering a sales defense.

Step 5: The Value-First Follow-Up

If they respond with interest, your next message should provide value before asking for anything.

Bad follow-up:

"Thanks for responding! Would you be open to a 30-minute call to discuss how we can help?"

Good follow-up:

Give value first. The meeting ask comes later.

The Multi-Touch LinkedIn Sequence

Here's the complete sequence we use:

Day 1: View their profile
Day 2: Like/comment on recent post
Day 4: Comment on another post
Day 7: Send personalized connection request
Day 8-10: They accept (or don't)
Day 11: Send first message (question-based, not pitch)
Day 14: If no response, soft bump ("Figured you're swamped, happy to circle back later if timing's better")
Day 18: Share relevant resource (case study, article, tool)
Day 25: Final follow-up ("Last note from me—should I close your loop?")

Most replies come between messages 2-4, not the first message.

What Kills LinkedIn Outreach

Mistake #1: Pitching in the Connection Request

"Hi, I'm with [Company] and we help businesses like yours with AI automation. I'd love to schedule a call to discuss how we can help you streamline operations."

Instant ignore. This screams "I want to sell you something."

Mistake #2: Generic Compliments

"I love your content!" "Your profile is impressive!" "Great post!"

These mean nothing. They're transparent attempts to get attention.

If you're going to compliment, be specific: "Your point about X was spot on—I've seen the same pattern with Y in my work."

Mistake #3: Asking for a Meeting Too Early

You've exchanged 2 messages and you're already asking for 30 minutes of their time?

No. Build rapport first. Provide value first. Then suggest a conversation.

Mistake #4: Sending the Same Message to Everyone

Yes, you can use templates. But every message needs at least 1-2 personalized lines.

Reference their company, their recent post, their job change, industry news—something that proves you're not mass blasting.

Mistake #5: Giving Up After One Message

Most people send one message and move on when there's no response.

The data shows: 80% of replies come after the 2nd-4th follow-up.

But you can't be annoying. Each follow-up should add value or offer an easy exit.

LinkedIn + Email: The Combo Strategy

LinkedIn works even better when combined with cold email.

Here's the pattern:

1. Day 1: Send personalized cold email
2. Day 2: View their LinkedIn profile
3. Day 4: Send LinkedIn connection request referencing the email
4. Day 7: Email follow-up #1
5. Day 10: If they accepted connection, send LinkedIn message
6. Day 14: Email follow-up #2 with case study
7. Day 17: LinkedIn follow-up if no email response

Multi-channel beats single-channel every time. You're not spamming—you're being persistent across relevant channels.

Content Strategy for LinkedIn (To Support Outreach)

Posting content isn't required for outbound success, but it helps in two ways:

1. Social proof: When prospects check your profile before accepting your connection, an active profile (with relevant insights) builds credibility
2. Engagement hooks: Posting gives prospects a reason to engage with you before you reach out

What to post:

• Client results (with permission): "Helped an e-commerce brand cut support costs 40% while improving CSAT"
• Tactical insights: "3 ways AI consultants screw up pricing (and how to fix it)"
• Industry observations: "Seeing a pattern with B2B SaaS companies at $5M ARR..."
• Lessons learned: "Biggest mistake I made scaling my agency"

How often: 2-3 times per week is plenty. Consistency beats frequency.

The Bottom Line

LinkedIn outreach works if you:

1. Target the right people (specific ICP)
2. Warm them up before connecting
3. Personalize every outreach
4. Lead with questions and value, not pitches
5. Follow up persistently but respectfully
6. Combine LinkedIn with email for maximum effect

It fails when you treat it like a numbers game—spray generic connection requests and pitch everyone who accepts.

LinkedIn is a relationship channel. Treat it like one, and it'll fill your pipeline.