Insider Trading Activity
Learn how to track and analyze company insider buying and selling to gauge internal confidence and identify potential opportunities or red flags.
Introduction
In this module, we'll explore how to use MarketDash's Insider Trading tool to follow the money trail of company insiders—the CEOs, directors, and executives who know the company best. Their buying and selling activity can provide powerful signals about a company's true prospects.
What Is Insider Trading?
The Legal Kind
When we talk about tracking insider trading, we're referring to legal, reported transactions by company insiders:
Who are insiders?
- CEOs and C-suite executives
- Board members and directors
- Major shareholders (10%+ ownership)
- Senior management team
Why track them? These are the people inside the company who:
- Know the financials intimately
- Understand the business trajectory
- See opportunities and risks before the public
- Have the most information about future prospects
Understanding the Insider Activity Dashboard
The Left Panel: Buy and Sell Activity
Shows a clear visualization of insider transactions over the last 3 months.
What you'll see:
- Names of insiders
- Their positions (CEO, Director, etc.)
- Action taken (Bought/Sold)
- Percentage change in their holdings
- Dollar value of transaction
- Price at which they bought/sold
- Date of transaction
The Five Key Metrics to Analyze
1. Buy vs. Sell Activity
What to look for:
- Are insiders buying or selling?
- How many buyers vs. sellers?
- What's the total dollar volume?
Bullish signal: Multiple insiders buying, especially in large amounts
Bearish signal: Multiple insiders selling, especially senior leadership
2. Position Change Percentage
How much did they increase or decrease their holdings?
My significance threshold:
- 10%+ increase or decrease: Starting to be significant
- 15%+ increase: Definitely significant
- 25%+ increase: Very significant
Why it matters: A CEO increasing their position by 25% shows strong personal conviction in the company's future.
3. Dollar Amount
The actual dollar value of the transaction.
My significance threshold:
- $1 million+: Significant transaction
- $5 million+: Very significant
- $10 million+: Major conviction signal
- $25 million+: Exceptional conviction
Example from video: Stephen Hemsley (CEO) bought $25 million worth of stock—a massive buy showing extreme confidence.
4. Purchase/Sale Price
The price at which the insider bought or sold.
Why this is critical:
- Insiders' buy prices become reference points
- If current price is near their buy price = at smart money levels
- If current price is below their buy price = you're getting a better deal than insiders
Example from video:
- Stephen Hemsley bought at $289
- Current stock price: $291
- Analysis: Stock is trading near CEO's buy price—good sign
5. Transaction Date
When did the transaction occur?
Time windows to monitor:
- 0-3 months: Most relevant and timely
- 3-6 months: Still relevant but less immediate
- 6+ months: Historical context
Focus on recent activity for the most actionable signals.
Why Insiders Buy and Sell
Insider Buying Signals
There's typically ONE main reason insiders buy: They believe the stock is undervalued and expect it to go up
Why insider buying is so powerful: When an insider uses their own money to buy stock, especially in large amounts, it shows:
- Strong conviction in the company's future
- Belief the stock is undervalued
- Confidence in upcoming results or developments
- Alignment with shareholders
Key Insight: Insider buying, especially large purchases, is one of the most bullish signals you can get. They're putting their own money where their mouth is.
Insider Selling: More Nuanced
Many reasons insiders sell:
- Diversification: Not keeping all wealth in one stock
- Estate planning: Tax or financial planning needs
- Personal expenses: Buying homes, paying bills, etc.
- Pre-scheduled sales: 10b5-1 plans
- Lack of confidence: Actually bearish on the stock
The challenge: It's hard to know which reason applies, so insider selling is less predictive than buying.
When to worry about selling:
- Multiple insiders selling simultaneously
- Very large sales (liquidating major positions)
- Sales by key leadership (CEO, CFO)
- No other insiders buying
Practical Example: UnitedHealthcare Analysis
Small Sell Transaction
The data:
- Position: CEO
- Action: Decreased by 5%
- Value: $179,000
- Price: ~$305
- Date: June 10th
Analysis:
❓ Below my significance threshold ($1M+)
❓ Small percentage decrease (5%)
❓ Could be routine diversification
➡️ Not a major concern
Major Buy Transaction
The data:
- Insider: Stephen Hemsley (CEO)
- Action: Increased by 15%
- Value: $25 million
- Price: $289
- Date: Recent
Analysis:
✓ WAY above significance threshold ($25M!)
✓ Above 15% increase threshold
✓ CEO using own money to buy
✓ Current price ($291) near his buy price
➡️ VERY bullish signal
Why this matters: A CEO buying $25 million of their own company's stock shows exceptional conviction that the stock is undervalued and has significant upside potential.
Additional Buy
The data:
- Insider: Kristen Gill
- Action: 3,000 shares increase
- Value: ~$1 million
- Price: $271
- Date: May 15th
Analysis:
✓ Meets $1M threshold
✓ Bought at $271 (current ~$291)
✓ Stock is up since her purchase
➡️ Positive signal
Summary Dashboard View
Last 0-3 months:
- Sells: $179,000 (insignificant)
- Buys: ~$30 million total (5 buy transactions)
- Net: Heavily bullish
Last 3-6 months: Can check for additional historical context and patterns.
How to Use the Insider Trading Tool
Step 1: Check the Overall Picture
Look at the infographic summary:
- More buying than selling?
- What's the net dollar flow?
- How many buyers vs. sellers?
Step 2: Examine Significant Transactions
Focus on transactions that meet significance thresholds:
- $1 million+ dollar value
- 15%+ position changes
- Senior leadership (CEO, CFO)
Step 3: Analyze the Timing
0-3 months window (most important):
- Any red flags? (Major selling)
- Any bullish signals? (Significant buying)
3-6 months window:
- Look for patterns
- Confirm or contradict recent activity
Step 4: Compare to Current Price
Critical analysis:
- Where did insiders buy?
- Where is the stock now?
- Can you buy near or below insider prices?
Step 5: Integrate with Other Metrics
Combine insider activity with:
- Valuation (P/E ratios, intrinsic value)
- Institutional sentiment
- Technical analysis
- Fundamental health
Investment Signals by Scenario
Scenario 1: CEO Buying Large Amount
Signal: 🟢 Very Bullish
Characteristics:
- Senior leadership (CEO, CFO)
- $5 million+ purchase
- 15%+ position increase
Action: Strong buy signal, especially if combined with good fundamentals
Scenario 2: Multiple Insiders Buying
Signal: 🟢 Bullish
Characteristics:
- 3+ insiders buying
- Various positions/levels
- Totaling $5 million+
Action: Consensus among insiders = high confidence signal
Scenario 3: Small Routine Selling
Signal: 🟡 Neutral
Characteristics:
- < $1 million sales
- One or two insiders
- Small percentage of holdings
Action: Likely routine diversification, not concerning
Scenario 4: Major Selling by Leadership
Signal: 🔴 Bearish
Characteristics:
- CEO/CFO selling large amounts
- $10 million+ in sales
- Multiple executives selling
Action: Investigate immediately, potential red flag
Scenario 5: No Activity
Signal: 🟡 Neutral
Characteristics:
- No significant buys or sells
- Only routine small transactions
Action: No signal either way, look to other metrics
My Personal Framework
What Makes Me Bullish
Requirements:
- Net buying activity in 0-3 month window
- At least $1 million in total insider buying
- Preferably $5-10 million+ for high conviction
- Senior leadership participation (CEO, CFO buying)
- 15%+ position increases by key insiders
Ideal scenario: CEO buys $10 million+, increasing position by 20%+, at prices near or above current levels.
What Makes Me Concerned
Red flags:
- Net selling activity in 0-3 month window
- Multiple executives selling simultaneously
- Large sales ($5 million+) by leadership
- No buying to offset the selling
Major red flag: CEO or CFO selling 25%+ of their position in large dollar amounts.
Integration with Investment Strategy
For Value Investors
Use insider buying to:
✓ Confirm undervalued thesis
✓ Validate margin of safety
✓ Gain conviction in contrarian positions
✓ Identify when insiders see the value you see
Perfect scenario: Stock appears undervalued, AND insiders are buying aggressively.
For Growth Investors
Use insider buying to:
✓ Confirm growth trajectory
✓ Validate management's confidence
✓ Identify acceleration points
✓ Separate real growth from hype
Perfect scenario: Company showing strong growth, AND insiders are buying despite already-high prices.
For All Investors
Insider buying provides:
- High-conviction confirmation signal
- Price benchmarks (their buy prices)
- Red flag detection (unusual selling)
- Alignment check (management's money where their mouth is)
Key Takeaways
- Insiders know best—They see financials and business trajectory before anyone else
- Buying is more significant than selling—One main reason to buy (bullish), many reasons to sell
- $1 million+ threshold—Focus on significant transactions that required real conviction
- 15%+ position changes matter—Shows meaningful change in insider confidence
- CEO/CFO buys are most significant—Top leadership has the clearest view
- Compare to current price—Buying near insider prices = high confidence entry
- Recent activity matters most—Focus on 0-3 month window for timely signals
Pro Tips
- Set alerts: Get notified when insiders buy your watchlist stocks
- Track patterns: Serial insider buying often precedes big moves
- Compare to stock performance: Insider buying before a run-up is very bullish
- CEO buying at all-time lows: Extremely powerful signal
- Large buys after earnings: Insiders buying after selling off = confidence in recovery
- Ignore small sells: Sub-$1M sales are usually routine
- Focus on clusters: Multiple insiders buying within weeks = consensus view
Remember: Company insiders are the ultimate information insiders (legally). When a CEO puts $25 million of their own money into the stock, they're essentially telegraphing their confidence in the company's future. Use this tool to find where the people who know best are putting their money, and consider positioning yourself alongside them.