Real-Time AI Security for Apps and Agents

CalypsoAI was founded in 2018 and based in San Francisco. The company delivers advanced security solutions for safeguarding Artificial Intelligence systems, with a focus on protecting both foundational models and enterprise deployments. The company’s platform centers on inference-layer security, monitoring how AI behaves during execution rather than solely during development. This approach enables organizations to detect behavioral anomalies, adversarial manipulations, and latent vulnerabilities that traditional assessment methods fail to uncover.

The organization’s flagship offerings include customizable generative AI Security scanners that integrate natively with enterprise communication platforms like Slack and Microsoft Teams. These scanners allow enterprises to enforce granular AI usage policies across departments including IT, marketing, finance, and other business units. The tools support content category controls, redaction and blocking policies, and compliance-driven restrictions designed to align AI usage with regulatory and organizational standards.

CalypsoAI’s technology incorporates adversarial testing frameworks capable of compromising widely deployed LLMs to expose hidden weaknesses, feeding into its Security Leaderboard. The Leaderboard is a comparative scoring system that evaluates model resilience using proprietary metrics such as Cost-of-Security indices, Risk-to-Performance ratios, and CASI security ratings. Its real-time behavioral analysis engine and automated mitigation workflows enable enterprises to proactively counter emerging threats.

In September 2025, the company was acquired by F5 for $180 million, further integrating its capabilities into large-scale enterprise security ecosystems.

Prior to being acquired, CalypsoAI raised more than $40 million across multiple rounds, including a $23 million Series A-1 in 2023, a $13 million Series A in 2020, and a $2.2 million seed round in 2019. Investors include Lockheed Martin Ventures, Paladin Capital Group, Hakluyt Capital, Crosspoint Capital Partners, Lightspeed Venture Partners, and others.