Investing.com - Palo Alto Networks CEO Nikesh Arora held acquisition talks with both Okta and Datadog before landing a $25 billion deal for CyberArk, and is now circling Cribl and ClickHouse as his next targets, The Information reported on Wednesday.

The Information reported that between late 2024 and early 2025, Arora held a series of meetings with Okta CEO Todd McKinnon. The talks progressed to the point where the companies discussed product complementarity, but ultimately stalled over price disagreements, according to people with knowledge of the discussions cited by The Information. Okta, valued at roughly $13.5 billion at the start of last year, has since climbed around 30%, giving it a market cap near $23 billion.

In parallel, Arora approached Datadog CEO Olivier Pomel in spring 2025, pitching a hypothetical acquisition when Datadog was publicly valued at more than $40 billion, The Information reported. Pomel was not receptive and no formal offer was made. Datadog’s market cap has since roughly doubled to more than $80 billion, making a deal considerably less likely.

With both paths closed, Arora executed fallback moves on two fronts. Palo Alto agreed in July 2025 to acquire CyberArk. And in January 2026 the company paid $3.35 billion for Chronosphere, a smaller rival to Datadog focused on log data and observability. Together, those two acquisitions contributed $338 million of the $3 billion in revenue Palo Alto generated in the April quarter, the company said in June, according to investing.com.

The rationale behind Arora’s accelerating dealmaking is a conviction, shared with investors and executives, that AI is fundamentally changing the threat landscape. AI agents can now execute cyberattacks that humans never could, making continuous system monitoring a boardroom priority rather than an IT line item. Anthropic and OpenAI are themselves selling AI-powered vulnerability-detection tools, underscoring the urgency. Both Anthropic’s Mythos platform, launched in May, and OpenAI’s disclosed hacking experiments on its own systems and those of Hugging Face have sharpened enterprise security budgets.