LS #66: LinkedIn Content Calendar for Maximum Conversions (Not Engagement)
Most founders plan their LinkedIn content around what gets likes. But their pipeline is empty.
Hi there,
I study LinkedIn’s best posts to show you what works, so your content connects.
In this issue, you’ll find:
The 3 high-performing LinkedIn posts this week
LinkedIn content calendar for maximum conversions (not engagement)
The 3 high-performing posts this week
1. We hired a developer for $1,500 his first month
Why this post?
This post went viral, receiving 1.4k likes in 3 days. It received 12-50 times more engagement and views than Timothy’s posts this week.
WHY THIS POST WENT VIRAL
This post challenged conventional hiring wisdom by showing that betting on character and potential can produce exponential returns compared to hiring for current skills.
BREAKDOWN
Shocking salary hook: “$1,500 his first month. Last month we paid him $12,500” - immediately grabs attention
Annualized calculation: “$150K annualized“ - helps people understand the scale
Underdog framing: “wasn’t ‘up to scratch’ 18 months ago“ - sets up transformation story
The deal explained: Direct quote of unconventional hiring philosophy - pay for potential, not current value
Hiring principle: “bet on his character and taught the skills” - clear actionable lesson
POST IDEAS YOU COULD TRY:
“We hired an intern for $0. Now she runs our $5M division.”
“Hired a customer service rep for $15/hr. Now he’s our VP of Product.”
“We paid a freelancer $500 for a project. Now she’s our $200K CTO.”
“Hired a ‘failed entrepreneur’ everyone passed on. Now he’s our best closer.”
“Gave a barista a sales job. 18 months later she’s our top revenue generator.”
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2. AI was coming for your jobs. Now it’s coming for your hobbies too.
Why this post?
Another post that went viral this week—it got 3.4k likes in a day and performed 30 times better than Yuvraj’s previous content.
WHY THIS POST WENT VIRAL
This post combined bleeding-edge AI technology (autonomous gaming agents) with a game that millions of people love and play daily. The product sits at the frontier of what AI can do - moving from workplace automation into creative play and entertainment.
BREAKDOWN:
Provocative expansion hook: “AI was coming for your jobs. Now it’s coming for your hobbies too” - extends AI threat narrative
Cutting-edge tech showcase: AI agents that play games for you - this is brand new tech that shows what AI can do now
Gameplay video: Beautiful Minecraft landscape with lens flare and cinematic feel proves it works
Video proof critical: Shows AI actually playing rather than just describing capabilities - makes abstract concept tangible
3. Europe is losing a generation of founders. And it’s 100% self-inflicted.
Why this post?
This post got 15 times more comments than Heini’s other posts this week.
WHY THIS POST WENT VIRAL
This post exposed a huge problem that European founders and investors feel every day but rarely discuss publicly.
BREAKDOWN:
Bold critique hook: “Europe is losing a generation of founders. And it’s 100% self-inflicted” - calls out continent
Personal proof point: “I’ve invested in US startups from my laptop in 48 hours“ - shows how easy America makes it
Permanent decision stated: “sworn never to invest in certain European countries again” - shows frustration level
Problem clarification: “Not because of bad founders or startups. Because the legal complexity makes it impossible”
Europe’s painful reality: 27 legal systems, months-long deals, €800 billion investment gap, companies forced to NYC
Specific pain examples: “notary fees consuming 30% of a €10K investment” - concrete absurdity
Solution proposed: “EU-INC“ - one unified European corporate form, digital-first
LinkedIn Guide
LinkedIn content calendar for maximum conversions (not engagement)
Most founders plan their LinkedIn content around what gets likes.
Monday motivation. Wednesday wisdom. Friday reflection.
Their engagement is great. Their pipeline is empty.
I switched to a conversion-focused content calendar and went from 2 demos per month to 15.
Here’s what changed: I stopped planning content for the algorithm. Started planning content for the buyer journey.
The Content Calendar Problem
What most founders do:
Post whenever they feel inspired
Mix random topics hoping something sticks
Focus on variety to “keep audience engaged”
Plan content around trending topics
Why this fails:
No strategic flow to move prospects forward
Content doesn’t build on itself
Attracts wrong audience with random topics
Zero alignment with buyer journey
The reality: Random content gets random results. Strategic content gets customers.
The Conversion Content Calendar System
The 4-Week Buyer Journey Framework
Week 1: Problem Awareness
Make prospects realize they have a problem (or it’s worse than they thought)
Week 2: Solution Education
Show different approaches to solving the problem (including failed attempts)
Week 3: Authority Building
Demonstrate your unique methodology and results
Week 4: Conversion Trigger
Share specific case studies that make prospects reach out
Then repeat the cycle with different problems/angles.
Week 1: Problem Awareness Content
Goal: Make your ICP realize “We have this exact problem”
Monday: The Hidden Problem Post
Hook: “Why 60% of B2B SaaS companies will have a support crisis by 2026: [data showing increasing complexity]...”
Tuesday: The Symptom Identifier
Hook: “If your customer support tickets increased 40%+ in the last year despite improving your product, you don’t have a support problem...”
Thursday: The Cost Calculator
Hook: “The hidden cost of high support ticket volume: Our CS team was spending $180K/year answering the same 20 questions...”
Why this week works: By Thursday, prospects are thinking “Do we have this problem too?”
Week 2: Solution Education Content
Goal: Show you’ve explored all options (builds credibility)
Monday: The Traditional Approach
Hook: “Everyone says ‘write better documentation’ to reduce support tickets. We did. Tickets increased by 15%...”
Tuesday: The Failed Experiment
Hook: “We spent $25K building a comprehensive help center. Tickets dropped 3%. Then went back up...”
Thursday: The Breakthrough Approach
Hook: “The solution that reduced our support tickets 65% wasn’t more content. It was better timing...”
Why this week works: Prospects see you’ve tried obvious solutions, build trust in your approach.
Week 3: Authority Building Content
Goal: Establish your unique methodology and credibility
Monday: The Framework Post
Hook: “The 3-stage system we use to predict where users will get confused (before they ask for help)...”
Tuesday: The Metrics Deep-Dive
Hook: “We track 12 leading indicators of customer confusion. Here are the 3 that matter most...”
Thursday: The Counterintuitive Insight
Hook: “Our best customers use our help center 40% less than average customers. Here’s why that’s a good thing...”
Why this week works: Prospects see you think differently, want to learn more.
Week 4: Conversion Trigger Content
Goal: Make prospects think “I need to talk to these people”
Monday: The Case Study
Hook: “How we helped [Company] reduce support tickets from 400/week to 140/week in 60 days...”
Tuesday: The ROI Calculator
Hook: “If you’re spending $200K+/year on customer support, here’s how to calculate if you have a guidance problem...”
Thursday: The Implementation Story
Hook: “We implemented contextual guidance for a client on Friday. By Monday, their support tickets dropped 35%...”
Why this week works: Specific results with real companies = prospects reach out asking “Can you do this for us?”
The Content Type Distribution
60% Problem-Solution Content
Problem awareness posts
Failed attempts and what worked
Specific case studies
30% Authority Content
Frameworks and methodologies
Industry insights and predictions
Counterintuitive findings
10% Engagement Content
Behind-the-scenes
Team moments
Personal reflections
Why this ratio: Prioritizes business outcomes over ego metrics.
The Posting Schedule
Monday, Tuesday, Thursday Primary conversion-focused content
Why these days: Best engagement from decision-makers
Why not Wednesday/Friday:
Wednesday: Mid-week overwhelm, lower attention
Friday: Weekend mode, poor conversion rates
Timing: 8:30-9:30 am - when your ICP is checking LinkedIn with coffee, not in back-to-back meetings
The Monthly Content Planning Process
Week 1 of each month: Planning
Review last month’s conversion metrics
Identify which content drove demos
Pick primary problem for the month
Outline the 4-week buyer journey
Week 2-4: Execution
Write posts following the framework
Track engagement from ICPs specifically
Note which posts trigger qualified DMs
Adjust remaining posts based on response
End of month: Analysis
Which posts generated qualified conversations?
What topics resonated with ICPs?
Which posts got engagement but zero business?
Plan next month based on data
Content Calendar Mistakes That Kill Conversions
Mistake #1: Too Much Variety
Posting about 10 different topics in a month
Why it fails: No cumulative effect, audience doesn’t see your expertise depth
Mistake #2: Following Trends
Jumping on viral topics unrelated to your business
Why it fails: Attracts wrong audience, dilutes your authority
Mistake #3: Random Posting Schedule
Monday this week, Thursday next week, skip a week
Why it fails: No consistency, audience forgets you exist
Mistake #4: Only Posting Wins
Never sharing failed attempts or struggles
Why it fails: Looks fake, doesn’t build trust or relatability
Advanced Calendar Tactics
Tactic #1: The Problem Cluster
Spend entire month on one specific problem from different angles
Tactic #2: The Seasonal Alignment
Align content with buying seasons in your industry (Q4 planning, new year budgets, etc.)
Tactic #3: The Competitor Content Gap
Identify topics your competitors avoid, own those topics
Tactic #4: The Failed Attempt Archive
Keep running list of what didn’t work for you - goldmine for relatable content
The Conversion Content Calendar Formula
Strategic Problem Sequence (week-by-week buyer journey) + Consistent Schedule (same days/times) + ICP-Focused Topics (not broad appeal) + Data-Driven Iteration (double down on what converts) = Predictable pipeline from LinkedIn
Stop posting for likes. Start posting for customers.
That’s a wrap for today.
See you next week! If you want more LinkedIn tips, be sure to follow me on LinkedIn (link).
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Your compadre,
Anton “LinkedIn growth strategies” Cherkasov