Datadog Officer Files Form 144 for $2.65M Share Sale via Trust

Executive Summary

On September 14, 2026, a Form 144 notice was filed for Datadog, Inc. ($DDOG) covering the proposed sale of 12,000 shares of Class A Common Stock by the David Obstler Children 2019 Trust FBO Andrew Obstler, an indirect vehicle associated with Officer David M. Obstler. The aggregate market value of the proposed transaction is $2,654,520.00 (~$221.21 per share).

Key Transaction Highlights

• Seller Account: DAVID OBSTLER CHILDREN 2019 TRUST FBO ANDREW OBSTLER
• Relationship: Officer
• Securities Offered: 12,000 Class A Common shares
• Aggregate Value: $2,654,520.00
• Origin of Shares: Acquired on 03/15/2019 via previously exercised stock options paid in cash.
• Trading Plan: The sale is executed pursuant to a Rule 10b5-1 trading plan adopted on June 13, 2026.
• Past 3 Months Activity: A separate direct sale of 16,524 shares for gross proceeds of $3,518,027.35 was executed on September 2, 2026.

Market Impact Assessment

Given that the transaction represents a minor portion of the 334,904,614 outstanding shares and is executed under a pre-established Rule 10b5-1 trading arrangement, the trading significance is rated Medium to low, reflecting standard liquidity and estate planning rather than a discretionary market-timing signal.