OBSTLER DAVID M 4

What Happened
David M. Obstler, Datadog’s Chief Financial Officer, sold a total of 75,000 shares in open‑market transactions on June 8, 2026, generating roughly $17.38 million. The sales occurred in multiple tranches at reported prices of $229.29, $230.59, $231.31, $232.41, $233.31, $234.31, $235.35, $236.20 and $239.13, with the aggregate proceeds of approximately $17,376,592 (average ≈ $231.69/share). These sales were executed pursuant to a 10b5‑1 trading plan.

Key Details

• Transaction date: June 8, 2026; Form 4 filed June 10, 2026 (appears timely).
• Tranches (shares @ price = proceeds):
  • 7,500 @ $229.29 = $1,719,662
  • 17,966 @ $230.59 = $4,142,787
  • 21,382 @ $231.31 = $4,945,956
  • 12,398 @ $232.41 = $2,881,477
  • 10,054 @ $233.31 = $2,345,746
  • 2,783 @ $234.31 = $652,092
  • 2,217 @ $235.35 = $521,773
  • 100 @ $236.20 = $23,620
  • 600 @ $239.13 = $143,479
• Total: 75,000 shares sold for ~$17.38M; reported weighted‑average and tranche price ranges span roughly $228.75 to $239.55 (per filing footnotes).
• Footnotes: Sales were pursuant to a 10b5‑1 plan dated March 9, 2026; several tranches report weighted‑average prices with per‑trade price ranges and fuller breakdowns available on request.
• Shares owned after the transaction: not specified in the provided summary.

Context
Sales under a 10b5‑1 plan are pre‑arranged and typically permit insiders to sell shares on a preset schedule; they are generally considered routine and do not alone indicate the insider’s view of the company. Retail investors often watch purchases more closely as potential bullish signals. This report documents straightforward open‑market sales (code S).