Matthew Prince

Cloudflare CEO Matthew Prince sells 52,384 shares for $11.7M via 8 transactions on 2026-06-24 under pre-arranged 10b5-1 plan; Class B derivatives remain.

Matthew Prince executed 8 separate sales totaling 52,384 shares for $11,749,771.28 at prices ranging from $221.46 to $228.14, all on 2026-06-24. This filing is part of a pre-arranged 10b5-1 trading plan adopted on 2025-02-11, meaning the sales were scheduled and not discretionary. While Prince's non-derivative holdings fell to zero, he retains 4,296,167 Class B Common Stock shares as derivative holdings, so this represents a scheduled reduction of a specific batch rather than a complete position exit. Prior trades by Prince at Cloudflare show positive outcomes over a 30-day horizon (ranging from +5.6% to +8.0% across 5 recent sales on 2026-05-21), consistent with his cross-ticker track record average of +8.0% over 30 days. The company reported annual revenue growth of +29.8% against the latest quarter revenue of $639,755,000, but remains unprofitable with a full-year net income of $-22,927,000, reflecting an early-stage profitable-trajectory tension in the business.

CEO Matthew Prince sold 104,768 shares for $23,221,887.48 on 2026-06-22/23 under 10b5-1 plan; retains 8,749,486 derivative holdings.

Matthew Prince, CEO & Board Co-Chair, executed 28 separate sales totaling 104,768 shares for $23,221,887.48 at prices ranging from $212.97 to $230.04, completing a scheduled 10b5-1 trading plan adopted on 2025-02-11. Post-transaction, his non-derivative holdings are zero; however, his derivative holdings total 8,749,486 shares across two Class B ownership vehicles, meaning his economic stake in the company remains substantial. Cloudflare is currently unprofitable (net income $-22,927,000.00 on $639,755,000.00 revenue) and the company is up 3.4% over 30 days and +6.4% over 90 days, placing the stock 19.3% below its 52-week high of $276.82. The transaction is pre-arranged and scheduled, not a discretionary market decision.

CEO Matthew Prince sells 157,152 shares ($32.6M) over 3 days via 10b5-1 plan; retains 25,550 shares post-sale.

Matthew Prince executed 24 separate sales totaling 157,152 shares for $32,606,961.57 at a blended average price of $207.49 across May 19–21, 2026, reducing his holdings from 182,702 shares to 25,550 shares. This transaction is part of a pre-arranged 10b5-1 trading plan adopted on 2025-02-11, meaning the sales follow a scheduled schedule rather than reflect discretionary timing. His five prior sales at NET on 2026-04-08 recorded 30-day returns of -11.5%, -11.0%, -8.6%, -8.2%, and -7.4%, with 90-day returns of -5.2%, -4.7%, -2.1%, -1.7%, and -0.7%. Cloudflare reported revenue of $639,755,000.00 in the latest quarter and full-year net income of $-22,927,000.00, with annual revenue growth of +29.8%, placing the company in a growth phase while currently unprofitable.

CEO Prince Matthew sold 156,493 shares for $33,167,768.84 in 27 transactions at blended avg $211.94, retaining only 659 shares (99.6% reduction).

Prince Matthew, CEO & Board Co-Chair, executed 27 separate sales totaling 156,493 shares for $33,167,768.84 over 2026-04-06 through 2026-04-08. This transaction involves a conversion of derivative securities, so the 659 shares post-transaction do not represent the full position—Form 4 Table II holdings are not yet populated in our database. The sales reduced open-market equity by 99.6% relative to pre-transaction holdings of 157,152 shares. The company reported revenue of $562,027,000.00 (latest quarter) and net loss of $-1,290,000.00, with annual revenue growth of +29.8%, but remains unprofitable over its most recent full fiscal year. Recent price action shows the stock up 4.8% over 30 days and 13.0% over 90 days from prior baseline, trading at $211.25 (−16.6% from 52-week high of $253.30). The blended transaction price of $211.94 reflects orderly execution across three trading days in a narrow price band around current levels, and his prior same-ticker history (5 prior sells on 2026-03-18) is not yet measurable for outcome assessment.

CEO Prince Matthew sold 143,534 shares at $207.91–$226.03 for $30,555,700.71 across three days (2026-03-16 to 2026-03-18).

Prince Matthew, CEO & Board Co-Chair, executed 27 separate sales totaling 143,534 shares for $30,555,700.71 over three trading days, reducing his holdings by -91.3% from 157,152 to 13,618 shares. The sales span a narrow price band ($207.91–$226.03, blended average $212.88) across moderate volume, suggesting an orderly disposition rather than panic selling. The timing coincides with the stock at -11.0% from its 52-week high of $253.30 and during a recent surge (+15.1% over 30 days, +16.3% over 90 days), though the company remains unprofitable on a full-year basis despite 29.8% annual revenue growth. The filing contains a derivative-conversion transaction flag, meaning the Table I holdings post-sale (13,618 shares) do not represent the insider's total position; additional shares or security conversions may reside in Table II derivative holdings not yet populated in our database. Investors should obtain the full Form 4 to verify total economic exposure and the nature of any derivative securities involved.

Cloudflare CEO Matthew Prince sells entire 13.6K share stake for $3.1M across 3 transactions at $227–$229

Matthew Prince, CEO & Board Co-Chair, completed a full liquidation of his NET holdings, selling 13,618 shares totaling $3,102,155.87 across three separate sales on 2026-03-18 at a blended average price of $227.80. This represents a complete exit from equity ownership at the executive level—a departure from typical insider holding patterns and more dramatic than routine portfolio adjustments. The current price of $225.48 sits 11.0% below the 52-week high of $253.30, suggesting Prince executed the sales near the upper range of recent pricing. Cloudflare's most recent full fiscal year ended with negative net income of $-1,290,000.00 despite strong revenue growth of +29.8% year-over-year, leaving the company unprofitable—a backdrop that adds context to this complete equity exit by the company's top executive.

CEO Prince Matthew sold 157,152 shares ($26.6M) over 3 days via 24 separate transactions; holdings fell 87.3%.

Prince Matthew, CEO & Board Co-Chair of Cloudflare, conducted 24 separate sales totaling 157,152 shares for $26,559,683.46 across February 24–26, 2026, reducing his holdings from 180,063 shares to 22,911 shares. The blended average sale price was $169.01 against a current price of $174.66, meaning the sales occurred below current market levels. The company's most recent quarter showed revenue of $562,027,000.00 with a net loss of $1,290,000.00, indicating ongoing unprofitability despite 29.8% annual revenue growth. Prior to this filing, Matthew's five recent sells at NET (all on 2026-01-08) showed negative 30-day returns ranging from -8.0% to -13.4%, suggesting a pattern of selling into declining momentum at this ticker. The scale and velocity of this 87.3% reduction warrants investor scrutiny of the company's operational trajectory and management's confidence in near-term prospects.

CEO Prince Matthew converts 157,152 derivative shares to cash across 27 sales totaling $30,701,127.08 on Jan 6-8.

Prince Matthew, CEO and Board Co-Chair, executed 27 separate sales over three days (January 6–8, 2026) converting 157,152 shares for $30,701,127.08 at a blended average price of $195.36. The Form 4 FLAG indicates this was a derivative-conversion transaction—not a full-position exit but a conversion of option or restricted stock grants into cash. The current stock price of $186.96 is 26.2% below the 52-week high and has declined 10.5% over 30 days and 12.6% over 90 days, creating context for the timing. At the same ticker, his prior five sales (December 5, 2025) each delivered negative 30-day returns (-4.2%, -2.5%, -3.4%, -3.1%, -2.0%), establishing a pattern of selling into price declines or ahead of further weakness. The company posted revenue of $562,027,000.00 in the latest quarter with a net loss of $-1,290,000.00, and while full-year revenue grew 28.8%, the business remains unprofitable. The scale of this derivative conversion ($30.7M) and the insider's prior pattern of sales into weakness merit investor monitoring.

CEO Matthew Prince sold 157.2K shares ($31.8M) across 18 transactions on 2025-12-03 to 2025-12-05 at blended average $202.36.

Matthew Prince, CEO & Board Co-Chair, executed 18 separate sales totaling 157,152 shares for $31,801,471.69 across three trading days, reducing his holdings to zero shares. The sales ranged from $198.80 to $205.02 per share with a blended average price of $202.36, occurring as the stock trades at $200.95 (12.1% below its 30-day average and 20.7% off its 52-week high of $253.30). The company generated $562.0M in quarterly revenue (+28.8% annual growth) but remained unprofitable with a net loss of $-1.3M over its most recent full fiscal year. The filing contains a derivative-conversion transaction (per FLAG), indicating the shares sold were likely converted from options or other securities; the insider's full economic position cannot be assessed from Table I alone, as derivative holdings in Table II remain unpopulated in this database.

CEO Prince Matthew sells 157,152 shares ($31.3M) across 22 transactions; post-sale holdings drop 87.6% to 22,175 shares.

Prince Matthew, CEO & Board Co-Chair, executed 22 separate sales totaling 157,152 shares for $31,306,971.38 between November 17–19, 2025, at a blended average price of $199.21 per share. His post-transaction holdings fell from 179,327 shares to 22,175 shares—a 87.6% reduction. This is the largest single liquidation event in the transaction history shown, occurring while the company trades at $196.20 (down 7.9% over 30 days and -22.5% from its 52-week high of $253.30). The company remains unprofitable on a full-year basis despite strong annual revenue growth of +28.8% and recent quarterly revenue of $562,027,000.00. The scale of the liquidation and timing relative to near-term price weakness, combined with negative prior returns on his same-ticker sales in October 2025, warrant close monitoring of whether underlying fundamentals or strategic circumstances have shifted.