David M. Obstler, chief financial officer, has filed 65 Form 4 transactions across two companies, with a total sell value of $55.2 million and no open-market purchases. Every recent trade is a sale of Datadog (DDOG) stock, with 24 sell transactions in the most recent period. The largest cluster occurred on September 14, 2026, when Obstler executed 22 separate sales totaling roughly $11.4 million, with individual trades ranging from $37,118 to $2.2 million. He also sold $723,750 and $2.4 million on September 21, 2026. The only non-sale activity in that window was a conversion of derivative securities valued at $0, which is mechanical and not a purchase.
The pattern is one-sided. Obstler has acquired $46,500 in total value across all filings, likely from grants or option exercises, but has sold more than 1,000 times that amount. His sales are concentrated in DDOG, and the September 14 cluster shows a typical executive disposition schedule: many small and mid-sized blocks sold on a single day, consistent with a 10b5-1 plan or routine portfolio diversification. There is no buying bias in the record, and the recent direction is uniformly toward reducing his DDOG position. The absence of any P-coded trades means Obstler has not added shares on the open market in the period covered by these filings.
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