Cloudflare (NYSE:NET) CEO Matthew Prince Sells 52,384 Shares

Posted by on May 22nd, 2026

Cloudflare, Inc. (NYSE:NET – Get Free Report) CEO Matthew Prince sold 52,384 shares of the business’s stock in a transaction on Tuesday, May 19th. The shares were sold at an average price of $204.15, for a total transaction of $10,694,193.60. Following the completion of the sale, the chief executive officer directly owned 25,550 shares of the company’s stock, valued at approximately $5,216,032.50. This trade represents a 67.22% decrease in their ownership of the stock. The sale was disclosed in a legal filing with the Securities & Exchange Commission, which is available through this link. The transaction was executed under a pre-arranged Rule 10b5-1 trading plan.

Matthew Prince also recently made the following trade(s):

  • On Thursday, May 21st, Matthew Prince sold 52,384 shares of Cloudflare stock. The shares were sold at an average price of $210.66, for a total transaction of $11,035,213.44.
  • On Wednesday, April 8th, Matthew Prince sold 51,725 shares of Cloudflare stock. The shares were sold at an average price of $213.59, for a total transaction of $11,047,942.75.
  • On Monday, April 6th, Matthew Prince sold 52,384 shares of Cloudflare stock. The shares were sold at an average price of $210.02, for a total transaction of $11,001,687.68.
  • On Wednesday, April 8th, Matthew Prince sold 659 shares of Cloudflare stock. The shares were sold at an average price of $223.62, for a total transaction of $147,365.58.
  • On Wednesday, March 18th, Matthew Prince sold 38,766 shares of Cloudflare stock. The shares were sold at an average price of $218.87, for a total transaction of $8,484,714.42.
  • On Monday, March 16th, Matthew Prince sold 52,384 shares of Cloudflare stock. The shares were sold at an average price of $209.08, for a total transaction of $10,952,446.72.
  • On Wednesday, March 18th, Matthew Prince sold 13,618 shares of Cloudflare stock. The shares were sold at an average price of $227.80, for a total transaction of $3,102,180.40.
  • On Thursday, February 26th, Matthew Prince sold 52,384 shares of Cloudflare stock. The shares were sold at an average price of $173.78, for a total transaction of $9,103,291.52.
  • On Tuesday, February 24th, Matthew Prince sold 52,384 shares of Cloudflare stock. The shares were sold at an average price of $164.15, for a total transaction of $8,598,833.60.

Cloudflare Price Performance

Shares of NYSE:NET opened at $212.47 on Friday. The company has a 50-day simple moving average of $207.63 and a 200-day simple moving average of $199.23. Cloudflare, Inc. has a one year low of $154.93 and a one year high of $260.00. The company has a debt-to-equity ratio of 1.29, a quick ratio of 1.96 and a current ratio of 1.96. The stock has a market capitalization of $75.10 billion, a price-to-earnings ratio of -849.88 and a beta of 1.67.

Cloudflare (NYSE:NET – Get Free Report) last announced its earnings results on Thursday, May 7th. The company reported $0.25 EPS for the quarter, beating analysts’ consensus estimates of $0.23 by $0.02. Cloudflare had a negative net margin of 3.72% and a negative return on equity of 5.65%. The business had revenue of $639.76 million during the quarter, compared to analysts’ expectations of $620.83 million. During the same period in the prior year, the company earned $0.16 earnings per share. The business’s revenue was up 33.5% compared to the same quarter last year. Cloudflare has set its FY 2026 guidance at 1.190-1.200 EPS and its Q2 2026 guidance at 0.270-0.270 EPS.

Analyst Upgrades and Downgrades

A number of equities research analysts have recently commented on the stock. Zacks Research raised shares of Cloudflare from a “strong sell” rating to a “hold” rating in a report on Friday, March 13th. Robert W. Baird set a $260.00 target price on shares of Cloudflare and gave the company an “outperform” rating in a report on Wednesday, February 11th. New Street Research set a $140.00 target price on shares of Cloudflare in a report on Wednesday, February 11th. KeyCorp cut shares of Cloudflare from an “overweight” rating to a “hold” rating in a report on Wednesday, April 15th. Finally, Jefferies Financial Group assumed coverage on shares of Cloudflare in a report on Wednesday, April 15th. They issued a “buy” rating for the company. Eighteen research analysts have rated the stock with a Buy rating, seven have assigned a Hold rating and three have given a Sell rating to the stock. Based on data from MarketBeat, Cloudflare currently has an average rating of “Moderate Buy” and an average target price of $236.68.

Get Our Latest Analysis on Cloudflare

Institutional Inflows and Outflows

Large investors have recently added to or reduced their stakes in the company. Physician Wealth Advisors Inc. raised its holdings in Cloudflare by 693.3% during the third quarter. Physician Wealth Advisors Inc. now owns 119 shares of the company’s stock worth $26,000 after purchasing an additional 104 shares in the last quarter. Wiser Advisor Group LLC purchased a new position in Cloudflare during the third quarter worth about $26,000. HM Payson & Co. purchased a new position in Cloudflare during the fourth quarter worth about $25,000. Westside Investment Management Inc. raised its holdings in Cloudflare by 100.0% during the third quarter. Westside Investment Management Inc. now owns 130 shares of the company’s stock worth $28,000 after purchasing an additional 65 shares in the last quarter. Finally, Wexford Capital LP purchased a new position in Cloudflare during the third quarter worth about $30,000. 82.68% of the stock is owned by hedge funds and other institutional investors.

More Cloudflare News

Here are the key news stories impacting Cloudflare this week:

  • Positive Sentiment: Cloudflare’s partnership with Anthropic to launch Cloudflare Environments for Claude Managed Agents is being viewed as a meaningful step into AI infrastructure, which could support future revenue growth and broader platform adoption. Cloudflare (NET) Stock Trades Up, Here Is Why
  • Positive Sentiment: Recent coverage continues to frame Cloudflare as an AI and big-data beneficiary, with sector interest in cloud and cybersecurity names helping sentiment around the stock. Invest in These 5 Big Data Behemoths to Gain From Wall Street Rally
  • Neutral Sentiment: Cloudflare’s latest earnings report was solid, beating estimates on both EPS and revenue, but the market reaction has been mixed as investors weigh strong growth against ongoing losses and rich valuation.
  • Neutral Sentiment: Several analysts remain constructive overall, with a consensus Moderate Buy rating, though opinions are still split and some firms continue to advise caution.
  • Negative Sentiment: CEO Matthew Prince and CAO Janel Riley both filed stock sales, and CFO Thomas J. Seifert also sold shares. Even though these were pre-planned 10b5-1 transactions, insider selling can still create short-term pressure on the stock.

About Cloudflare

(Get Free Report)

Cloudflare, Inc is a global web infrastructure and security company that provides a suite of services designed to improve the performance, reliability and security of internet properties. Its core offerings include a content delivery network (CDN), distributed denial-of-service (DDoS) protection, managed DNS, and a web application firewall (WAF). Cloudflare also provides tools for bot management, SSL/TLS, load balancing and rate limiting to help organizations maintain uptime and protect web applications from attack.

In addition to traditional edge and security services, Cloudflare has expanded into edge computing and developer platforms.

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Insider Buying and Selling by Quarter for Cloudflare (NYSE:NET)

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