CalypsoAI vs Prompt Security

CalypsoAI is an AI security company founded in 2018 with co-headquarters in San Mateo, California and Dublin, Ireland. The platform provides runtime security for enterprise GenAI — scanning prompts and responses for prompt injection, data leakage, and policy violations — with adaptive policies that evolve with new attack patterns. The company has announced plans to grow its Dublin team to 100 employees.

Prompt Security is a Tel Aviv-based AI security company founded in August 2023 by Itamar Golan (CEO) and Lior Drihem (CTO), both alumni of Israel's elite Unit 8200 with prior experience at Check Point and Orca Security. The company provides an enterprise platform for securing all generative AI interactions — covering employee AI tool usage (shadow AI discovery, data protection), homegrown AI applications (prompt injection defense, output filtering), AI code assistants, and agentic AI security including MCP gateway protection. Prompt Security is a core contributor to the OWASP Top 10 for LLM Applications. The company raised $23M prior to its acquisition by SentinelOne, which was completed on September 5, 2025. Prompt Security continues to operate as a standalone platform and product brand within SentinelOne's Singularity platform. CRN named it a 2025 Stellar Startup in Security.