Datadog (DDOG) Director Matthew Jacobson Sells Shares

What Happened

• Matthew Jacobson, a director of Datadog, sold a total of 59,424 shares in open-market transactions on August 13–14, 2026, generating approximately $14,999,793 in proceeds. Individual dispositions reported: 20,097 shares @ $248.79 ($4,999,921), 16,651 shares @ $252.20 ($4,199,356), 3,164 shares @ $253.01 ($800,531), 17,867 shares @ $256.21 ($4,577,640), and 1,645 shares @ $256.74 ($422,345). The transaction code reported is S (Sale). Sales are disposals and, by themselves, do not necessarily indicate the insider’s view of the company.

Key Details

• Dates & prices: Aug 13–14, 2026; reported weighted-average prices shown above. Footnotes disclose each reported price is a weighted average across multiple trades with price ranges per lot (e.g., $248.50–$249.165; $251.66–$252.645; $252.68–$253.48; $255.66–$256.65; $256.66–$256.82).
• Total sold: 59,424 shares for ~$15.0M.
• Shares owned after transaction: Not specified in the excerpt of the filing.
• Trust holdings: Footnote indicates some shares are held in trusts (the reporting person is a trustee or there is an independent trustee) and the reporting person disclaims beneficial ownership of those trust-held shares except to the extent of any pecuniary interest.
• Timeliness: Filing dated Aug 17, 2026 for transactions on Aug 13–14, 2026 — the Form 4 was filed within the required period (timely).
• Transaction code: S = Sale (open market).

Context

• These were open-market sales (not option exercises, awards, or gifts). Multiple weighted-average prices and trust-related holdings are noted in footnotes; the filing does not provide motives. Retail investors often view insider purchases as stronger signals than routine sales, and sales can be for many personal or portfolio reasons.