Datadog Insider Trust Files Form 144 Notice of Proposed Sale for $689K

Overview & Transaction Summary

On September 21, 2026, a Form 144 notice was filed for Datadog, Inc. ($DDOG) regarding the proposed sale of 3,000 shares of Class A Common Stock by the David Obstler Children 2019 Trust FBO Alison Obstler, an entity associated with Datadog Officer David Obstler.

• Security: Class A Common Stock
• Shares Proposed for Sale: 3,000
• Aggregate Market Value: $689,760.00 (implied price of ~$229.92 per share)
• Shares Outstanding: 334,904,614
• Proposed Sale Date: September 21, 2026
• Broker: Morgan Stanley Smith Barney LLC Executive Financial Services
• Acquisition Origin: Previously exercised stock options acquired on March 5, 2019, from the issuer via cash payment.

Trading Significance & Context

• Trading Significance: Low. The proposed transaction of 3,000 shares represents less than 0.001% of Datadog's 334.9M outstanding shares, presenting negligible market impact.
• 10b5-1 Trading Plan: The transaction is governed by a pre-arranged Rule 10b5-1 trading plan adopted on June 13, 2026, adhering to standard cooling-off periods.
• Recent Selling Activity: Over the past three months, David Obstler and affiliated trusts have conducted several scheduled sales under 10b5-1 plans, including sales on September 14, 2026 (40,000 shares for Obstler directly, and 12,000 shares each for two family trusts) and on September 2, 2026 (16,524 shares).