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Day 6 of 20 Β· AI for Sales

LinkedIn Social Selling

Here's a stat that should change how you think about LinkedIn: 78% of social sellers outsell their peers who don't use social media. LinkedIn isn't just a platform for job seekers and recruiters anymore β€” it's where B2B deals start.

But most sales reps use LinkedIn wrong. They spam connection requests with pitch-slaps, post nothing, and wonder why nobody responds. The reps who win on LinkedIn are the ones who build a presence, provide value, and turn content into conversations.

Today you'll use AI to build your LinkedIn social selling system β€” posts that position you as a thought leader, comments that get noticed, connection messages that get accepted, and a repeatable pipeline from content to conversation to meeting.

LinkedIn social selling pipeline showing Content to Comments to Connections to Conversations to Meetings
The LinkedIn pipeline: post content, engage with comments, connect strategically, start conversations, book meetings.

AI-generated LinkedIn posts for thought leadership

You don't need to be a writer to build a LinkedIn presence. You need to share insights that your buyers find valuable β€” and AI can help you create those consistently.

Here's the prompt for generating LinkedIn posts:

```

I'm a [YOUR ROLE] selling [YOUR PRODUCT/SERVICE] to [TARGET PERSONAS].

Write a LinkedIn post about [TOPIC]. Follow these rules:

- Hook: First line must stop the scroll (bold, surprising, or contrarian)

- Length: 150-200 words (short enough to read, long enough to add value)

- Structure: Short paragraphs, 1-2 sentences each. Use line breaks for readability

- Include a specific insight, stat, or story β€” no generic advice

- End with a question that drives comments

- No hashtags in the body. Add 3-5 relevant hashtags at the very end

- Tone: confident but not arrogant, helpful but not preachy

```

Post ideas that work for sales reps:

- Lessons from a deal you won (or lost) β€” and what you learned

- A counterintuitive insight about your buyers' biggest pain point

- A before/after story showing how a customer solved a problem

- A hot take on a trend in your industry

- A breakdown of a framework or process you use

Post 3-4 times per week. Consistency matters more than perfection.

Knowledge Check
How often should a sales rep post on LinkedIn for effective social selling?
A
3-4 times per week for consistency and visibility
B
Multiple times per day to maximize reach
C
Once a week at most
D
Once a month is plenty
Posting 3-4 times per week strikes the right balance between staying visible to your network and not overwhelming your feed. Consistency is more important than frequency β€” it's better to post 3 times a week every week than to post 10 times one week and disappear for a month.

Comment strategies that build relationships

Posting is only half the game. Strategic commenting on your prospects' and industry leaders' posts is how you get on their radar before you ever send a pitch.

Here's the framework:

Step 1: Build your comment list. Follow 20-30 prospects, industry leaders, and influencers in your target market. Turn on notifications for their posts.

Step 2: Comment with substance. Not "Great post!" β€” that's invisible. Instead, add a genuine insight, share a related experience, or ask a thoughtful follow-up question.

Here's a prompt for generating substantive comments:

```

I'm a sales rep who sells [PRODUCT] to [PERSONAS]. My prospect [NAME, TITLE at COMPANY] just posted about [TOPIC/PASTE THE POST].

Write a LinkedIn comment that:

- Adds a unique insight or perspective (not just agreement)

- Is 2-4 sentences long

- References my relevant experience without being self-promotional

- Ends with a question or observation that invites further conversation

- Sounds natural and conversational, not like a sales pitch

```

Step 3: Be consistent. Comment on 5-10 posts per day. Within 2-3 weeks, your target prospects will start recognizing your name. When your connection request comes, it won't be from a stranger.

Connection request messages that get accepted

The default LinkedIn connection request β€” blank, no message β€” gets accepted about 30% of the time. A personalized connection request gets accepted 50-70% of the time. Here's how to nail it:

The engagement-first approach (highest acceptance rate):

Comment on their posts 3-5 times over two weeks. Then send:

"[Name], I've been following your posts on [topic] β€” your perspective on [specific point] really resonated. Would love to connect and keep learning from your content."

The mutual connection approach:

"[Name], I noticed we're both connected to [mutual connection] and work in [shared space]. Would be great to connect."

The value-first approach:

"[Name], I just read about [Company]'s [achievement/news]. I work with a lot of [similar companies] and have some insights on [relevant topic] I think you'd find interesting. Would love to connect."

What to NEVER do:

- Don't pitch in the connection request. Ever. You haven't earned that right yet.

- Don't use the default blank request if you're connecting with a prospect.

- Don't mention your product, your company, or anything that sounds like a sales pitch.

The connection request is about opening a door, not closing a deal.

Knowledge Check
What is the best strategy for getting connection requests accepted by prospects?
A
Include your product pitch in the connection message
B
Send a blank connection request to as many people as possible
C
Engage with their content first, then send a personalized connection request that references shared interests or their work
D
Ask a mutual connection to introduce you every time
The highest acceptance rates come from the engagement-first approach: comment on their posts a few times so they recognize your name, then send a personalized request that references their content or a shared interest. This feels natural, not transactional.

The content-to-conversation pipeline

Here's the complete system that turns LinkedIn activity into booked meetings:

Week 1-2: Build your presence.

Post 3-4 times per week. Comment on 5-10 posts per day from prospects and industry leaders. Optimize your profile headline to speak to your buyer (not "Account Executive at Acme" but "Helping SaaS companies cut SDR ramp time by 50%").

Week 3-4: Connect strategically.

Send 10-15 personalized connection requests per day to people who've seen your comments. Accept incoming requests from people in your target market. Don't pitch anyone yet.

Ongoing: Start conversations.

When a connection engages with your post (likes, comments, shares), send a DM:

```

"Hey [Name], thanks for engaging with my post on [topic]. I'm curious β€” is [related pain point] something you're actively working on at [Company]? I've been helping a few [similar companies] with this and would love to hear your perspective."

```

Notice: this is still not a pitch. It's a genuine conversation starter. If they respond with interest, you've earned the right to suggest a call.

The key insight: On LinkedIn, the sale happens in the DMs, but the trust is built in the feed. Your posts and comments create the foundation. The DM converts.

πŸ€–
ChatGPT
online
I sell HR tech to mid-market companies. Write me a LinkedIn post about the hidden cost of slow hiring that will get engagement from HR leaders and VPs of Talent.
Here's your post: --- **The cost of a slow hire isn't the recruiter's time. It's everyone else's.** Every unfilled role creates a ripple effect most companies don't track: β†’ The team absorbs the extra work. Burnout goes up. β†’ Projects slip. Revenue gets delayed. β†’ Your top performers start interviewing elsewhere because they're carrying the load. I talked to a VP of Talent last week who calculated that every open role cost her company $4,200/week in lost productivity β€” not including recruiting costs. She had 23 open roles. That's $96,600/week walking out the door while the hiring process crawled through six interview rounds and a committee decision. The fix isn't always "hire faster." Sometimes it's "decide faster." What's the biggest bottleneck in your hiring process right now? #HRTech #TalentAcquisition #Hiring #PeopleOps --- This works because it quantifies a pain point HR leaders feel but rarely measure, tells a specific story, and ends with a question that invites comments from your exact target persona.
↻ Replay conversation
Knowledge Check
In the LinkedIn social selling pipeline, where does the actual sales conversation happen?
A
In a public post tagging the prospect
B
In the connection request message
C
In the comments section of your posts
D
In the DMs, after trust has been built through posts and comments
The LinkedIn social selling pipeline works by building trust in the feed (posts, comments, engagement) and converting in the DMs. Your public content creates familiarity and credibility. The DM is where you start a genuine conversation that can lead to a meeting. Never pitch in public comments or connection requests.
πŸ’°
Day 6 Complete
"LinkedIn social selling is a pipeline: content builds trust, comments build familiarity, connections open doors, and DMs start conversations. Use AI to post consistently, comment strategically, and turn engagement into meetings. Tomorrow you'll lock in your complete prospecting system."
Tomorrow β€” Day 7
Your Prospecting Foundation
Tomorrow we'll recap Week 1 and lock in your AI-powered prospecting system before moving on to engagement and closing.
πŸ”₯1
1 day streak!