Datadog CFO David Obstler Sells $3.86M Under Rule 10b5-1 Plan

Executive Summary

On September 21, 2026, David M. Obstler, Chief Financial Officer of Datadog, Inc. ($DDOG), executed open-market sales totaling 16,000 shares of Class A Common Stock at a price of $241.25 per share, realizing gross proceeds of approximately $3.86 million.

Transaction Breakdown

• Direct Ownership Sale: 10,000 Class A shares sold at $241.25 ($2,412,500), leaving 368,067 Class A shares held directly.
• Indirect Ownership Sales (via Trusts):
  • 3,000 shares of Class B Common Stock converted to Class A and sold on behalf of Obstler Children 2019 Trust FBO child ($723,750).
  • 3,000 shares of Class B Common Stock converted to Class A and sold on behalf of Obstler Children 2019 Trust FBO other child ($723,750).
• Remaining Holdings: In addition to 368,067 direct Class A shares, the reporting person retains 8,103 Class B shares directly, and 62,397 Class B shares indirectly across the family trusts.

Governance and Context

All sales reported were transacted pursuant to a pre-arranged Rule 10b5-1 trading plan adopted on June 13, 2026. Because these transactions were executed under a scheduled trading plan and represent a modest percentage of total beneficial holdings, this filing carries low predictive signaling regarding the issuer's near-term operational performance.