Cloudflare CEO Matthew Prince sells $9.96m in company stock

Matthew Prince, Chief Executive Officer and Board Co-Chair of Cloudflare, Inc. (NYSE:NET), sold company stock totaling approximately $9.96 million on August 5, 2026.

The transactions involved the sale of 33,631 shares of Class A Common Stock. The shares were sold at prices ranging from $291.07 to $303.19 per share. These sales were carried out pursuant to a Rule 10b5-1 trading plan, which Mr. Prince adopted on February 26, 2026.The timing of the sale comes as Cloudflare stock trades near its 52-week high of $305, with shares up 69% over the past six months. According to an InvestingPro tip, the stock is currently trading near its 52-week high, though analysis suggests the shares may be overvalued relative to the platform’s Fair Value assessment. The company’s market capitalization now stands at $103.98 billion.

The shares sold were held indirectly by The Prince 2021 Remainder Trust, for which Mr. Prince serves as an investment advisor. Following these reported transactions, the indirect beneficial ownership of Class A Common Stock through this trust for the reported line items was reduced to zero. Mr. Prince also holds 360,807 shares of Class A Common Stock directly.For deeper insights into Cloudflare’s valuation and performance metrics, InvestingPro offers access to 16 additional ProTips and comprehensive analysis. The stock currently appears on the Most Overvalued stocks list, and investors can access a detailed Pro Research Report for NET among 1,400+ US equities covered.

In other recent news, Cloudflare Inc. has introduced new tools aimed at enabling AI agents to perform secure online transactions. The company launched Cloudflare Wallets and cloudflare.pay, which provide stable identities and purchasing capabilities for AI agents, addressing the growing trend of autonomous online transactions. In analyst coverage, Cantor Fitzgerald raised its price target for Cloudflare to $250, maintaining a Neutral rating. The firm highlighted a recent 3% revenue beat but noted challenges such as high expectations and restructuring impacts.

Guggenheim reiterated a Sell rating with a $140 price target, predicting Cloudflare’s revenue might exceed consensus estimates, albeit with a smaller margin than in previous quarters. Truist Securities increased its price target to $300, maintaining a Buy rating, and emphasized Cloudflare’s strategic expansion into AI platforms and integrated services. These developments come as Cloudflare prepares to release its earnings report, which could lead to a significant stock movement based on historical data.