Datadog CFO David Obstler sells $9.1M in shares

Datadog's Chief Financial Officer, David Obstler, sold 40,600 shares of the company's Class A Common Stock on September 14, 2026. The transactions were valued at $9,098,758, with shares traded between $221.2371 and $233.3 per share. The sales were executed under a pre-approved 10b5-1 trading plan, established on June 13, 2026. Since the sale, Datadog's stock has fallen to $184.16, a 39% decline from its 52-week high of $300.68.

Obstler now directly owns 378,067 shares of Datadog Class A Common Stock. This filing is the first of two reports, as the total transactions exceeded the standard reporting limit. Datadog is currently deemed overvalued relative to its Fair Value. Analysts have adjusted their price targets downward, with StoneX, DA Davidson, and BMO Capital expressing concerns about Datadog's AI-native customer cohort and guidance.

Despite recent strong performance, including a 4.6% revenue increase and beating analyst estimates on earnings per share, the company's future performance remains a topic of debate among investors and analysts.