Form 4: Cloudflare CEO Sells Shares Under 10b5-1 Plan

Cloudflare CEO Matthew Prince executed pre-planned sales of Class A Common Stock totaling 157,152 shares over three days in November 2025, following conversions from Class B shares.

Summary

• Matthew Prince, CEO and Board Co-Chair of Cloudflare, Inc. (NET), reported transactions involving Class A Common Stock and Class B Common Stock.
• Transactions occurred on November 17, 18, and 19, 2025, as part of a Rule 10b5-1 trading plan adopted on February 11, 2025.
• On each of these three days, 52,384 shares of Class B Common Stock were converted into Class A Common Stock.
• Immediately following each conversion, 52,384 shares of Class A Common Stock were sold.
• The total Class A Common Stock sold over the three days amounted to 157,152 shares.
• Sales prices for Class A Common Stock ranged from approximately $191.01 to $209.39 per share.
• The shares involved in these transactions are held indirectly through The Matthew Prince Revocable Trust dated October 29, 2015, for which Matthew Prince serves as trustee.
• Following these transactions, Matthew Prince's indirect beneficial ownership of Class A Common Stock from the revocable trust decreased to 22,175 shares.
• His indirect beneficial ownership of Class B Common Stock from the revocable trust decreased to 5,819,990 shares after the conversions.
• The filing also indicates a direct beneficial ownership of 349,644 Class A Common Stock shares and significant indirect holdings of Class B Common Stock across several other trusts.

Sentiment

Score: 5

Explanation: The sentiment is neutral. While there is significant insider selling, it was conducted under a pre-planned 10b5-1 program, which mitigates the negative signal typically associated with insider sales. The sales occurred at varying prices, some quite high, reflecting a structured approach to liquidity rather than a distressed sale.

Positives

• The sales were conducted under a pre-arranged Rule 10b5-1 trading plan, indicating a structured approach to liquidity and personal financial planning rather than a reaction to immediate market conditions.
• The sales occurred at varying prices, with some transactions executed at relatively high prices, ranging up to $209.39 per share.

Negatives

• Significant insider selling by the CEO and a 10% owner, totaling 157,152 shares of Class A Common Stock, could be perceived negatively by some investors.

Risks

• While executed under a 10b5-1 plan, the substantial volume of insider sales by a key executive and significant owner could be interpreted by some market participants as a signal, potentially leading to negative sentiment or increased scrutiny.

Future Outlook

NA

Industry Context

This Form 4 filing details routine insider transactions under a pre-established trading plan, which is a common practice among executives for personal financial planning and diversification. It does not inherently reflect on broader industry trends or Cloudflare's competitive position, though the volume of sales is notable.

Comparison to Industry Standards

• NA

Stakeholder Impact

• Shareholders may interpret the significant insider selling as a potential negative signal, although the 10b5-1 plan context helps to mitigate this concern.
• Employees, customers, suppliers, and creditors are unlikely to be directly impacted by these routine insider stock transactions.

Next Steps

• NA

Key Dates

Recommendation

The insider sales by CEO Matthew Prince, while substantial, were executed under a pre-arranged 10b5-1 trading plan. This suggests a planned diversification or liquidity event rather than a reaction to adverse company-specific news. Given the pre-scheduled nature, these sales do not inherently signal a change in the company's fundamental outlook or the CEO's long-term confidence. Investors should monitor future filings and company performance, but these specific transactions alone do not warrant a 'sell' recommendation, nor do they provide a 'buy' signal.

Keywords

Cloudflare, NET, Matthew Prince, Insider Trading, Form 4, Stock Sale, 10b5-1 Plan, CEO, Director, 10% Owner, Class A Common Stock, Class B Common Stock, Beneficial Ownership