Datadog CEO and CFO Sell Millions in Company Shares

On June 4, at Datadog, Inc. (Nasdaq: DDOG), insider Cole Titilope sold approximately $1.27 million of Class A common stock on the open market, significantly reducing his direct holdings. Then on June 8, CFO David M. Obstler, under a 10b5-1 trading plan established in March, disposed of about $17.4 million worth of shares in multiple transactions, while still retaining roughly $100 million in equity. That same day, CEO Olivier Pomel exercised stock options and converted Class B shares to Class A before selling approximately $32 million of Class A shares on the open market, though he continues to hold an economic interest of over 1.6 million shares, according to the company’s filing.

On May 7, ahead of the second quarter, Datadog reported first-quarter 2026 results, posting revenue of $1.06 billion—a 32% year-over-year increase—and strong cash flow, and subsequently raised its full-year revenue guidance. On June 30, the company announced the acquisition of Adaptive ML, a startup specializing in a reinforcement-learning-based AI agent platform, aiming to accelerate its AI R&D investment in observability and security. ()

Datadog, headquartered in New York, is a cloud application observability and security SaaS provider that delivers a unified platform to monitor servers, databases, applications and security events. Led by co-founder and CEO Olivier Pomel, the company has recently launched a range of new capabilities—including AI-driven automation via Bits AI—and is expanding its customer base among large enterprises and AI firms. ()