Datadog Officer Files Form 144 to Sell $689K in Class A Shares via Trust

Executive Summary

On September 21, 2026, a Form 144 notice was filed for Datadog, Inc. ($DDOG) on behalf of reporting officer David M. Obstler for the proposed sale of 3,000 shares of Class A Common Stock held by the David Obstler Children 2019 Trust FBO Andrew Obstler.

Transaction Details

• Security: Class A Common Stock
• Number of Shares: 3,000
• Aggregate Market Value: $689,760.00 (~$229.92 per share)
• Shares Outstanding: 334,904,614
• Percentage of Float: Negligible (<0.001%)
• Acquisition Origin: Previously exercised stock options originally acquired on March 5, 2019 from the issuer for cash.
• Broker: Morgan Stanley Smith Barney LLC

Rule 10b5-1 Trading Plan Context

The proposed sale is executed pursuant to a pre-arranged Rule 10b5-1 trading plan adopted on June 13, 2026, satisfying the standard cooling-off requirements.

Recent Trading Activity (Past 3 Months)

• September 14, 2026: 40,000 shares sold for $9,098,879.00 (David Obstler)
• September 14, 2026: 12,000 shares sold for $2,729,663.70 (Trust FBO Alison Obstler)
• September 14, 2026: 12,000 shares sold for $2,729,663.70 (Trust FBO Andrew Obstler)
• September 02, 2026: 16,524 shares sold for $3,518,027.35 (David Obstler)

Significance

The trading significance is rated Low. The proposed transaction is modest in size relative to Datadog's total outstanding shares and follows a pre-scheduled Rule 10b5-1 plan executed by an irrevocable family trust.