Stock Markets June 3, 2026 09:06 AM

Datadog Shares Retreat After Director Disposes of 38,594 Class A Shares

Form 4 filing shows sales between May 29 and June 1 at weighted averages from $243.02 to $277.82; stock down 2.1% in premarket trading

By Sofia Navarro DDOG

Datadog Inc. shares declined in premarket trading after a Form 4 filing showed director Matthew Jacobson sold 38,594 Class A shares across multiple transactions between May 29 and June 1. The sales, recorded at weighted average prices ranging from $243.02 to $277.82, left Jacobson with 584,132 Class A shares. The filing notes the shares were held through trusts and that further transaction details are available to SEC staff upon request.

Datadog Shares Retreat After Director Disposes of 38,594 Class A Shares
DDOG

Key Points

  • Datadog shares fell 2.1% in premarket trading following insider sales reported in a Form 4.
  • Director Matthew Jacobson sold 38,594 Class A shares across transactions on May 29 and June 1, at weighted average prices from $243.02 to $277.82, and now holds 584,132 Class A shares.
  • The shares were held via a trust of which Jacobson is trustee and an estate planning trust with an independent trustee; the filing notes multiple transactions and indicates full details are available to SEC staff upon request.

Datadog Inc. (NASDAQ:DDOG) shares slipped 2.1% in premarket trading Wednesday after securities filings revealed recent insider sales by company director Matthew Jacobson.

A Form 4 submitted to the Securities and Exchange Commission shows Jacobson sold a total of 38,594 shares of Datadog Class A Common Stock in several transactions occurring between May 29 and June 1.

The filing details the weighted average prices for the disposals as ranging from $243.02 to $277.82 per share. Specifically, on May 29 Jacobson sold 20,574 shares at a weighted average price of $243.02 per share. On June 1 he executed two further sales: 17,318 shares at a weighted average price of $277.44 per share and 702 shares at $277.82 per share.

After these transactions, Jacobson is reported to hold 584,132 shares of Datadog Class A Common Stock.

The Form 4 specifies that the shares were held directly by Jacobson through a trust of which he is a trustee, and through an estate planning trust that has an independent trustee. The filing also states that Jacobson disclaims beneficial ownership of the shares held by those trusts except to the extent of his pecuniary interest.

Filing language notes the disposals occurred in multiple transactions across a range of prices and that full details of the transactions are available to SEC staff upon request.


Context and market reaction

The sale filing coincided with a modest premarket decline in Datadog shares. The Form 4 provides the transaction timeline and weighted average prices but does not include further commentary or additional corporate disclosures beyond the ownership and trust structures reported.

Data from the filing

  • Total shares sold: 38,594 Class A Common Stock
  • Transaction dates: May 29 and June 1
  • Weighted average sale prices: $243.02 to $277.82
  • Post-transaction holdings: 584,132 Class A shares
  • Ownership structure: shares held via a trust (Jacobson as trustee) and an estate planning trust with an independent trustee

The filing’s language about multiple transactions and price ranges underscores that additional transaction-level detail is not included in the public Form 4 but can be furnished to SEC staff on request.

Risks

  • Market reaction to insider stock sales - the reported disposals coincided with a 2.1% premarket decline in the company’s shares, indicating potential near-term investor sensitivity to director sales (affects public equity markets).
  • Limited transaction granularity in the public filing - the Form 4 reports sales across a range of prices in multiple transactions and points to further details being available only to SEC staff (affects transparency for market participants).
  • Complex ownership disclosures - the shares are held through trusts and Jacobson disclaims beneficial ownership of those trust holdings except for his pecuniary interest, which can complicate assessments of economic exposure and insider intent (affects investor analysis of insider activity).

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