Datadog Officer David Obstler Files Form 144 to Sell $2.3M in Common Stock

Datadog, Inc. (NASDAQ: DDOG) Form 144 Analysis

Transaction Overview

David Obstler, an Officer of Datadog, Inc., filed a Form 144 on September 21, 2026, indicating an intention to sell 10,000 shares of Class A Common Stock. The shares carry an estimated aggregate market value of $2,299,200.00, representing an implied price of approximately $229.92 per share. The transaction is slated to be handled by Morgan Stanley Smith Barney LLC.

Origin of Securities

The shares proposed for sale were acquired directly from the issuer via equity incentive awards:

• 8,479 shares acquired via Restricted Stock Units (RSUs) on June 1, 2022.
• 1,521 shares acquired via Performance Stock Units (PSUs) on September 1, 2023.

Rule 10b5-1 Trading Plan

The notice indicates that this transaction is being conducted pursuant to a Rule 10b5-1 trading plan established on June 13, 2026, satisfying cooling-off period requirements.

Recent Activity (Past 3 Months)

David Obstler has engaged in significant selling activity over the past month:

• September 14, 2026: Sold 40,000 shares directly for gross proceeds of $9,098,879.00.
• September 14, 2026: Sold 24,000 shares indirectly through family trusts (12,000 shares each for Alison and Andrew Obstler trusts) for total proceeds of ~$5,459,327.40.
• September 2, 2026: Sold 16,524 shares for gross proceeds of $3,518,027.35.

Significance Assessment

This proposed disposition is rated Medium. While the size of the immediate sale (10,000 shares, ~$2.30M) represents a minor fraction of Datadog's 334.9M outstanding shares, it continues an active pre-planned monetization pattern by the insider under a newly adopted Rule 10b5-1 plan.