David M Obstler

CFO David M Obstler sells 75,000 DDOG shares for $17.4M via 10b5-1 plan on 2026-06-08

David M Obstler, Chief Financial Officer, executed 9 separate sales totaling 75,000 shares for $17,376,591.98 on 2026-06-08 under a pre-arranged 10b5-1 trading plan, reducing his holdings by 14.7% from 509,591 to 434,591 shares. The blended average sale price was $231.69, which is currently 18.3% above the current price of $227.63 and near the 52-week high range of $98.01–$278.70. His cross-ticker track record shows an average 90d return after sells of +13.3% across 20 prior sells, though at DDOG specifically his most recent prior sell on 2026-03-02 saw a 90d return of +123.8%, while earlier DDOG sales showed mixed 90d outcomes ranging from -29.9% to +18.0%. As a scheduled 10b5-1 transaction, this sale reflects a pre-arranged program rather than discretionary timing.

CFO David M Obstler sells 16,323 DDOG shares at $267.15; holds 509,591 post-transaction as stock trades -10.2% from 52-week high despite +70.6% 30-day surge.

David M Obstler, Chief Financial Officer, sold 16,323 shares of Datadog at $267.15 on 2026-06-02, reducing his holdings by 3.1% to 509,591 shares. While the sale occurred near the 52-week high of $278.70, the stock has since declined to $250.33, trading 10.2% below that peak. This sale carries moderate relevance given the company's solid fundamentals—annual revenue growth of +27.7%, net income of $52,574,000, and quarterly revenue of $1,006,426,000—which do not suggest financial distress. However, his prior five trades at DDOG show inconsistent timing; only 1 of 5 prior sells proved well-timed at the 90-day mark, with recent sales in March 2026 and December 2025 showing divergent outcomes (+123.8% and -29.9% respectively at 90 days). The cross-ticker track record shows a 20.00% well-timed rate across 20 prior sells, which is modest, and current market conditions feature a +70.6% 30-day surge into what may be elevated valuations given the P/E of 807.52.

CFO OBSTLER sold 40,057 shares of DDOG at $110.54 on 2026-03-02 for $4.4M; stock down 8.3% in 30d, down 22.7% in 90d

OBSTLER DAVID M, Chief Financial Officer, sold 40,057 shares at $110.54, reducing his holdings by 7.9% to 466,619 shares. The stock has declined 22.7% over the 90-day period and currently trades at $118.33, down 40.8% from its 52-week high of $199.72. His prior trades at Datadog show mixed timing: 1 of 5 prior sells at this ticker were well-timed at the 90-day mark, with the most recent sale (2025-12-02) proving well-timed as the stock fell 29.9% subsequently. Fundamentals remain solid with $885.7M quarterly revenue and +27.7% annual revenue growth, though the P/E of 381.71 reflects elevated valuation despite recent weakness.

CFO Obstler sold 12,513 shares of DDOG at $158.60; stock now $153.00 (-23.4% from 52-week high).

David M. Obstler, Chief Financial Officer, sold 12,513 shares at $158.60 on 2025-12-02, reducing his holdings from 386,651 to 374,138 shares (-3.2% of pre-transaction position). The sale occurred at a price currently $5.60 above today's market price of $153.00, with the stock down 23.4% from its 52-week high of $199.72. Across his same-ticker history at DDOG, none of Obstler's 5 prior sells were well-timed at the 90-day mark—his previous sales generated positive 90-day returns ranging from 2.8% to 18.0%, meaning the stock rose after each exit. Datadog reports strong fundamentals with $885.7M quarterly revenue, 26.1% annual growth, and $33.9M net income, though the 278.18 P/E ratio remains elevated. The current transaction follows this established pattern at this ticker and provides limited inference about forward price direction.

CFO David M. Obstler sold 12,619 shares of DDOG at $133.85; held 386,651 post-sale; stock now -21.9% from 52-week high.

CFO David M. Obstler sold 12,619 shares at $133.85 on 2025-09-02, reducing his position by 3.2% to 386,651 shares. The stock is currently trading at $131.78, down 21.9% from its 52-week high of $168.65. His prior sales at DDOG have generally occurred before price gains: his five most recent trades at this ticker show 30-day returns of -8.0%, +10.1%, +11.3%, +14.3%, and +29.0%, with the measurable 90-day outcome (on the 2025-06-04 sale) showing a +12.0% return after the sale. Datadog's fundamentals remain intact with annual revenue growth of +26.1% and quarterly revenue of $826,760,000.00, though the P/E ratio of 239.60 reflects elevated valuation. The modest scale of this reduction—3.2% of pre-transaction holdings—and the mixed timing outcomes at this specific ticker (1 of 1 measurable 90-day outcomes showing gains after the sale) lack the pattern or magnitude to signal material strategic repositioning.

CFO David M Obstler sold 15,000 DDOG shares at $147.43 on 2025-07-03; post-transaction holdings 399,270 shares.

David M Obstler, Datadog's CFO, sold 15,000 shares for $2,211,450.00 on 2025-07-03, reducing holdings by 3.6%. The stock has recovered significantly since the sale, rising 19.5% over 30 days and 49.8% over 90 days relative to the transaction date, meaning the CFO's recent sells have underperformed relative to subsequent price appreciation. His cross-ticker track record shows a 53.85% well-timed sell rate with positive average returns after sales (avg 90d return +4.0%), but this suggests his sells have generally been poorly timed across holdings. At DDOG specifically, his two most recent measurable sales (2025-06-04 and 2025-06-02) posted positive 30-day returns of +29.0% and +14.8% respectively, indicating the stock has continued to appreciate after those sales. The FLAG indicates derivative conversion activity; the Form 4 Table II (derivatives) is not yet populated in the database, so the reported Table I shares_after (399,270) may not represent his complete economic position.

CFO David M. Obstler sells 15,000 DDOG shares at $135.25; holds 399,270 post-transaction.

CFO David M. Obstler sold 15,000 shares of Datadog on 2025-06-30 at $135.25 ($2.0M total), reducing his holdings by -3.6% to 399,270 shares. This sale occurs within a rapid sequence—Obstler executed five separate sells at DDOG in a 28-day window (2025-06-02 through 2025-06-30), a pattern distinct from his cross-ticker track record of well-timed sales. At the time of this transaction, DDOG was trading near $135.01 (within 1% of the sale price), +14.7% over 30 days and +42.9% over 90 days from the 52-week low of $87.00, placing it 20% below the 52-week high of $168.65. The FLAG notation indicates this transaction involves derivative conversion, meaning his total position (including unrealized derivatives in Table II) is not fully captured in the reported 399,270 share count. On fundamentals, Datadog reported Q FY revenue of $761.6M (+26.1% annual growth), with a trading multiple of P/E 245.47, suggesting premium valuation. Investors should note the concentrated selling activity and await measurable 90-day outcomes on the prior three June trades (2025-06-04, 2025-06-17, 2025-06-18) to contextualize whether this sequence reflects systematic positioning or derivative management.

DDOG CFO Obstler sells 15,000 shares at $130.25; holds 399,270 post-transaction as derivative conversion continues

David M. Obstler, CFO of Datadog, sold 15,000 shares (15.0K shares) for $1,953,750.00 ($2.0M) on 2025-06-18 at $130.25 per share. His post-transaction holdings of 399,270 shares (399.3K shares) represent a -3.6% reduction from the pre-transaction 414,270 shares (414.3K shares). Notably, this filing is marked as a derivative-conversion transaction, meaning the full scope of Obstler's equity position extends beyond the reported Table I shares and includes derivative securities not yet detailed in the database; therefore, the disclosed open-market sale should be interpreted as a partial disposition of a specific batch rather than a position exit. At the current price of $129.52, the stock is trading -23.2% from its 52-week high of $168.65, though it has risen +13.2% over the past 30 days and +17.1% over the past 90 days. This sale follows a pattern of multiple DDOG sells within a concentrated timeframe (2025-06-02, 2025-06-04, 2025-06-17, and 2025-06-18), with outcomes on those earlier trades not yet measurable. Across Obstler's cross-ticker open-market history (20 prior sells), his 90-day well-timed rate stands at 60.00%, suggesting modest skill in timing sales before subsequent declines; however, prior same-ticker sells at DDOG have yielded no measurable positive outcomes at the 90-day mark.

Datadog CFO David Obstler sold 20,000 shares at $125.25 on 2025-06-17, retaining 399,270 shares; stock now $130.04

CFO David Obstler sold 20,000 shares of Datadog at $125.25, representing a 4.8% reduction from pre-transaction holdings of 419,270 shares. The sale occurred at a price 3.7% below the current market price of $130.04 and 22.9% below the 52-week high of $168.65. At the DDOG-specific ticker level, Obstler has executed 5 recent sales (all within the past two weeks of June 2025), and measurable 90-day outcomes from these trades are not yet available. His cross-ticker track record shows a 60.00% well-timed rate on prior sells, though this broader pattern may not reflect precision at individual stocks. The filing contains a derivative-conversion transaction, indicating the Table I shares shown do not represent his total position—derivative holdings in Table II would provide a more complete view of his actual exposure.

CFO David M. Obstler sold 20,000 DDOG shares at $120.25, retaining 399,270 shares post-transaction.

David M. Obstler, Datadog's CFO, sold 20,000 shares at $120.25 on 2025-06-04, reducing his holdings by 4.8% from 419,270 to 399,270 shares. The sale occurred as the stock trades at $122.16, down 27.6% from its 52-week high of $168.65, though up 15.2% over the past 30 days. The insider's same-ticker history at DDOG shows mixed outcomes: his most recent measurable sale (2025-03-03) resulted in a -12.2% 30-day return, and his prior sale (2024-12-02) yielded -23.4% at 90 days—only 1 of 2 prior sells proved well-timed at the 90-day mark. His cross-ticker track record indicates a 64.71% well-timed rate across 20 prior sells with +1.0% average 90-day return, but the direct DDOG pattern does not yet support a conviction signal. The FLAG indicates this involves a derivative conversion, meaning the Table I shares_after figure (399,270) does not represent his total economic position, as derivative holdings are recorded separately in Table II; investors should review the full Form 4 for his complete exposure.