DDOG Datadog, Inc. Insider Trading

Director Matthew Jacobson sold 38.6K shares of DDOG for $10.0M (May 29–Jun 1, 2026) while holding 584.1K shares post-sale.

Matthew Jacobson, Director at Datadog, executed 3 separate sales totaling 38,594 shares for $9,999,682.48 across two trading days (May 29–June 1, 2026), reducing his holdings by 6.2% to 584,132 shares. The blended average sale price of $259.10 sits modestly below the current price of $269.13, and notably below the 52-week high of $278.70. His prior sales at Datadog across 4 distinct trades in May 2026 all showed positive 90-day returns (ranging +45.8% to +48.0%), indicating those earlier sales were not well-timed (the stock rose after he sold). This filing shows continued selling despite the stock having gained 91.5% over the past 30 days and 127.4% over 90 days, a period of strong momentum that preceded the current trade's execution window. The transaction reflects a director reducing a meaningful but not dominant share position amid sustained upward price action.

CEO Olivier Pomel sells 84,698 shares for $18,936,387.76 via 10b5-1 plan on 2026-05-26

Olivier Pomel, CEO of Datadog, executed 8 separate sales totaling 84,698 shares for $18,936,387.76 at an average blended price of $223.58 on 2026-05-26. This transaction is part of a pre-arranged 10b5-1 trading plan, meaning it was scheduled rather than discretionary. Post-transaction holdings stand at 750,981 shares, representing a reduction of 84,698 shares from 835,679 shares held prior. The stock currently trades at $225.24, having risen 71.2% over 30 days and 101.2% over 90 days. Historically, Pomel's prior trades at this ticker (5 sales on 2026-05-11) delivered returns between 9.5% and 12.6% over the subsequent 30 and 90-day windows.

CTO Le-Quoc Alexis sells 43,224 shares at blended $208.04 for $8,992,460.63 under 10b5-1 plan

Le-Quoc Alexis, Chief Technology Officer, executed 7 separate sales totaling 43,224 shares for $8,992,460.63 on 2026-05-18 at an average price of $208.04, reducing his holdings from 574,535 shares to 531,311 shares (a -7.5% reduction). The transaction is part of a pre-arranged 10b5-1 trading plan and therefore scheduled rather than discretionary. The current stock price of $212.24 is -1.6% from the 52-week high of $215.68. While the company posted strong recent fundamentals—$1,006,426,000.00 in latest-quarter revenue with +27.7% annual revenue growth—the elevated P/E of 684.65 reflects a premium valuation. The sale occurs during a period of significant stock momentum, with the 30-day change at +63.6% and 90-day change at +76.0%.

Datadog director Amit Agarwal converts and sells 20,000 shares in same-day wash for ~$4M, leaving net stake unchanged.

Director Amit Agarwal converted 20,000 shares from a compensation award and sold all 20,000 of them on the same day across eight separate tranches, leaving his net share count entirely unchanged. The stock is trading just fractionally below its 52-week high — essentially at the top of its annual range following a sharp surge over the past month and three months — making this a high-price exit from a vesting event. Datadog is a profitable, fast-growing software company, though its valuation remains quite stretched relative to earnings. Agarwal's track record at this ticker is notable: all five of his prior open-market sales at Datadog were poorly timed at both the one-month and three-month horizons, with the stock advancing by a similar magnitude in each subsequent period at both timeframes. He has never made an open-market purchase at this company or across his 36-month filing history, and this filing continues that unbroken pattern of compensation-driven dispositions with no discretionary buying.

CEO Olivier executes largest single-day sale in history ($25.4M), offsetting with immediate stock option conversion to neutralize dilution.

Olivier, Datadog's CEO, conducted his first sale activity in months through a carefully structured transaction: converting stock options into shares and immediately selling all of them in eight tranches at progressively higher prices on the same day, clearing approximately $25.4M. This is noteworthy because Olivier has never purchased shares on the open market across his entire filing history—all 230 of his open-market transactions have been sales—yet he remains in his executive role, suggesting the stock sales reflect capital allocation rather than loss of confidence in the company. The conversion-offset pattern (acquiring 127,141 shares via exercise and disposing of the identical share count) eliminated any net dilution to his position, leaving his holdings effectively unchanged. Stock price context shows Datadog trading tightly near its 52-week high and up substantially over the past quarter, creating a favorable window for a large executive liquidity event. However, Olivier's prior five sales at this ticker were all poorly timed: the stock rallied significantly following each prior exit, meaning his historical pattern at Datadog specifically has been to sell before further gains, not before declines. This filing continues that pattern—a repeat sale at peak valuations at a company that remains profitable and growing, executed by an insider with a strict 20-trade selling history and zero open-market purchases on record.

Chief Product Officer sells 19,834 shares worth $3.9M, marking his fourth open-market sale in 36 months with mixed prior timing.

Li Yanbing, Chief Product Officer at Datadog, sold roughly 6.5% of his holdings in a transaction worth nearly $3.9 million. The stock is currently trading at its 52-week high following a sharp rally, after gaining significantly over the past three months. Yanbing's prior three sales at Datadog have produced mixed results: while most saw the stock rise afterward—indicating weak timing overall—one sale did precede a meaningful decline. This fourth consecutive open-market sale continues a selling pattern with no offsetting purchases on record, which differs from the typical insider profile in a high-growth tech company. The company remains profitable and is growing revenue at a strong pace, so the sale does not appear driven by deteriorating fundamentals, but rather reflects an ongoing portfolio reduction during a period of sustained stock strength.

Director Jacobson divests ~53k shares in four tranches totaling ~$10M; pattern repeats well-timed prior exits.

Jacobson Matthew, a director, executed four sales totaling approximately $10 million in shares on a single trading day when the stock reached its 52-week high. This disposition represents a continuation of his established pattern: he has conducted 116 prior open-market sales over the past three years and no open-market purchases, making this his 120th sale in the window. His three previous sales at Datadog, executed in November, all preceded significant stock declines—evidence of consistent sell-side timing accuracy. While the company remains profitable with strong revenue growth, the director's sustained selling activity combined with his historically well-timed prior exits at this ticker suggests he may be identifying weakness or valuation concerns that aren't yet reflected in current pricing. The concentrated timing of all four sales on the same day at the stock's peak price level indicates deliberate liquidation rather than routine rebalancing.

Datadog CRO Sean Walters sells 7,657 shares for $1.44M as stock hits 52-week high; selling from a 66-trade open-market sales streak with mixed short-term but persistently poor long-term timing.

Sean Walters, Chief Revenue Officer at Datadog, sold a meaningful block of shares while the stock trades at its 52-week high, representing roughly 2.6% of his holdings. This is the 67th open-market sale Walters has executed in the past three years, underscoring a consistent pattern of selling rather than accumulating equity. His prior exits at this company show conflicting timing results: in the short term, most previous sales were well-timed as the stock declined afterward, but over longer horizons all prior sales proved poorly timed as the stock recovered significantly in each instance. Datadog itself is a profitable, fast-growing company, and selling into its strongest price levels could reflect either a desire to lock in gains or rebalancing after the stock's substantial recent rally. The persistent nature of these sales—combined with their mixed near-term but uniformly poor long-term outcomes—suggests an insider with a pattern of exiting only to watch shares climb further.

General Counsel Acocella Kerry sold 13,857 shares of Datadog amid stock rally, marking her 19th total sale with mixed prior timing results.

Kerry Acocella, Datadog's General Counsel, sold a material stake worth over two million dollars as the stock rallied sharply over the past quarter. This represents her continued pattern of selling — now the third sale in five months — against a backdrop of mixed historical results on her prior exits. While most of her recent sales were poorly timed (the stock subsequently climbed after two consecutive December exits), her most recent prior sale in early March proved well-timed as shares later declined, showing no consistent edge in her exit decisions. The sale occurred while the company posts healthy fundamentals with growing revenue and profitability, though the stock already trades well below its recent highs after a recent surge. As an officer with direct knowledge of operations, her persistent selling is worth noting, but the pattern of mixed outcomes on her previous trades suggests caution against reading conviction into the direction of this sale.

Director Agarwal executes large planned stock sale program; rare buy component follows prior sell-heavy pattern.

Director Amit Agarwal executed a structured multi-tranche stock sale totaling approximately $2.9 million across nine transactions on the same day, with prices ascending from $140 to $147. This activity—his first buy in a track record of 20 prior sales—followed a recent sell sequence just days earlier and reflects pre-planned diversification rather than conviction about the company's outlook. The stock is currently trading well below its year-to-date highs after a recent rally, but Agarwal's heavy selling in this filing suggests he is taking profits and reducing his exposure rather than seeing a compelling entry point. Despite the company's profitable status and solid revenue growth, the absence of a sustained buying pattern from this director—combined with his consistent historical preference for selling—indicates routine portfolio management rather than insider confidence in near-term upside.