Datadog, Inc. (DDOG) CTO and COO Sell Stocks Worth Billions for RSU Tax Payments

On May 29 and June 1, Datadog executive Matthew Jacobson sold approximately 38,000 shares of Class A common stock through a trust account, raising about $10.1 million in cash and slightly reducing his indirect holdings in the trust.

Over the same period, Chief Technology Officer Alexis Le-Quoc converted Class B shares into Class A, exercised stock options, and—under a pre-established Rule 10b5-1 plan—sold shares on June 1–2 primarily to cover taxes on vested RSUs and performance RSUs. He still retains a substantial position of several million shares across his direct and trust holdings.

Chief Operating Officer Adam Blitzer also sold roughly 20,000 shares on June 2–3 to satisfy withholding taxes on vested RSUs and performance RSUs, generating about $6.8–7.1 million. After these transactions, he continues to own over 260,000 shares valued at around $68–70.5 million.

In its May 7 release, Datadog reported first-quarter 2026 revenue of approximately $1.06 billion, a 32% year-over-year increase, with improved adjusted profitability that exceeded market expectations.

The company also highlighted its strategic focus on government, public-sector and AI workloads, noting that it secured FedRAMP High authorization for its government-facing services and officially launched the MCP server, which enables AI coding agents and IDEs to leverage observability data in real time.

Headquartered in New York, Datadog offers a SaaS observability platform that integrates monitoring across AWS, Azure, Google Cloud and other environments, collecting and analyzing operational data from cloud and AI workloads for enterprise customers worldwide.

In 2026, Datadog introduced “Bits AI,” an AI-agent suite that automates incident response and security analytics, and is expanding its platform with MCP-based tools to enhance AI-driven observability and automation throughout the development and operations lifecycle.