Datadog CFO David Obstler Sells $5.46M in Class A Common Stock Under Rule 10b5-1 Plan

Executive Summary

On September 16, 2026, Datadog, Inc. ($DDOG) Chief Financial Officer David M. Obstler filed a Form 4 disclosing the conversion and subsequent sale of 24,000 shares of Class A Common Stock (converted 1:1 from Class B Common Stock) executed on September 14, 2026. The sales generated aggregate gross proceeds of approximately $5.46 million at a weighted average execution price of ~$227.48 per share.

Transaction Structure & Ownership Details

• Conversion & Sale Mechanism: 12,000 Class B shares from each of two family trusts (Obstler Children 2019 Trust FBO child and Obstler Children 2019 Trust FBO other child) were converted into Class A shares (Transaction Code 'C') and sold on the open market (Transaction Code 'S') in multiple weighted-average price buckets ranging from $220.67 to $233.49.
• Pre-Arranged Plan: All transactions were conducted pursuant to a pre-established Rule 10b5-1 trading plan adopted on June 13, 2026.
• Post-Transaction Holdings: Following the reported transactions, the two trusts continue to hold 34,199 and 34,198 Class B Common Stock shares respectively, while the reporting person directly retains 8,103 Class B Common Stock shares.

Market & Governance Context

Because these sales were executed under a pre-scheduled Rule 10b5-1 plan via family trusts and represent planned conversions of Class B super-voting equity, the trading significance is categorized as Low, indicating routine executive estate planning and liquidity rather than discretionary sentiment on company fundamentals.