Michael James Callahan

Director Callahan sells 112,500 shares for $26,055,155.10 via 10b5-1 plan; retains 20,684 shares plus 123,042 derivative holdings.

Michael James Callahan, a Datadog director, executed 9 separate sales totaling 112,500 shares for $26,055,155.10 on 2026-06-12, with a blended average price of $231.60. This transaction is part of a pre-arranged 10b5-1 trading plan, meaning the sales were scheduled and not discretionary responses to market conditions. Post-transaction, Callahan retains 20,684 non-derivative shares and 123,042 derivative shares through a trust vehicle, so this represents a partial reduction rather than an exit of his overall position. The stock's price movement context shows DDOG at $233.09 currently (down 16.4% from its 52-week high of $278.70), having risen 12.1% in the last 30 days and 80.9% in the last 90 days; Callahan's prior DDOG-specific sales show mixed 30-day outcomes (ranging from -19.2% to +15.8%) but uniformly negative 90-day outcomes, though as a scheduled transaction, this sale's timing is predetermined rather than discretionary.

Director Callahan Michael James sold 12,500 shares of DDOG at $187.47 on 2025-11-06, reducing position by 50.0% to 12,496 shares ($2.3M)

Director Callahan Michael James executed a 50.0% reduction of his open-market DDOG holdings, selling 12,500 shares at $187.47 on 2025-11-06 for $2,343,375.00. The sale occurred when stock was trading 6.1% below the current price of $199.72, near its 52-week high. His prior two sales at DDOG (2025-10-14 and 2025-10-06) show a mixed recent pattern, with the October 6 sale returning -1.7% after 30 days; longer-term outcomes remain unmeasurable. Notably, this transaction involves a conversion of derivative securities—the insider's full position also includes holdings in Table II that are not yet populated in this database, meaning the 12,496 shares shown post-transaction do not represent his complete equity stake. Investors should reference the derivative holdings table before drawing conclusions about the size or intent of this position reduction.

Director Callahan sells 8,333 DDOG shares at $160.55; retains 12,496 shares post-transaction.

Director Michael James Callahan sold 8,333 shares of Datadog at $160.55 on 2025-10-14, reducing his stake by 40.0% from 20,829 to 12,496 shares. The transaction occurred near the 52-week high of $168.65 (within 10.4%), and the stock has appreciated 12.3% over the prior 30 days and 4.2% over 90 days. This is Callahan's second open-market sale at DDOG in eight days (following a 2025-10-06 sale), though the prior trade's outcome remains unmeasurable. The company's fundamentals show strong revenue growth of 26.1% year-over-year on $826.8M quarterly revenue, though profitability is modest at $2.6M net income. Because this filing flags a derivative conversion, his actual economic position likely extends beyond the Table I shares shown; the complete picture requires review of his derivative holdings not yet populated in the database.

Director Callahan Michael James sold 91,667 shares of DDOG at $157.60 on 2025-10-06 for $14.4M, retaining 12,496 shares post-transaction.

Director Callahan Michael James sold 91,667 shares (91.7K shares) at $157.60, reducing his holdings from 104,163 shares to 12,496 shares. The sale occurred when DDOG was at $157.60, and the stock has since risen to $164.12 (current price is -2.7% from 52-week high of $168.65). The company is growing revenue at +26.1% year-over-year with fundamentals showing strong top-line momentum; however, the P/E of 298.40 reflects a highly valued stock. The derivative-conversion flag indicates this transaction involves the conversion of derivative securities, meaning the reported 12,496 post-transaction shares understates the director's total economic position, which may include unconverted options or other derivative holdings not yet reflected in the structured data.