Crunchbase tracks acquisitions by fast-growing AI startups

Crunchbase says some fast-growing AI startups are buying smaller companies to fill product gaps, enter new markets and bring specialized teams in-house.[1] It identifies OpenAI as by far the busiest among these acquirers, and says the company has acquired 17 companies in the past three years.[1][2] Crunchbase’s headline says OpenAI completed nearly as many M&A deals in 2026 as in all of the previous year.[2] It also says well-funded startups in legal tech, customer service and software development have each made multiple acquisitions this year.[1]

OpenAI announced it had acquired Promptfoo, which was founded in 2024 by Ian Webster and Michael D’Angelo to protect large language models from online adversaries.[3] Promptfoo developed tools that companies can use to test security vulnerabilities in large language models, including an open-source interface and library.[3] Promptfoo reports that more than 25% of Fortune 500 companies use its products.[3] It had raised $23 million since its founding and was valued at $86 million after its July 2025 funding round; OpenAI did not disclose the acquisition price.[3]

OpenAI said Promptfoo’s technology would be integrated into OpenAI Frontier after the deal closes; Frontier is an enterprise platform for AI agents.[3] The planned capabilities include automated red-teaming, evaluating agentic workflows for security concerns, and monitoring activities for risks and compliance needs.[3] OpenAI also said it expects to continue building Promptfoo’s open-source offering.[3]

TechCrunch says the development of independent AI agents that perform digital tasks has generated excitement about potential productivity gains, while also giving bad actors new opportunities to access sensitive data or manipulate automated systems.[3] That context makes security testing and monitoring relevant considerations for organizations weighing agentic workflows. The acquisition’s price was not disclosed, and the available information describes planned integrations rather than reporting that those capabilities are already operating in Frontier.[3]