CalypsoAI vs WitnessAI

CalypsoAI was an AI security company founded in the US in 2018 by Neil Serebryany, its first CEO; it describes itself as founded in Silicon Valley, and its early press releases carry Washington datelines. It began with software for testing, validating and monitoring AI and machine learning models for national security, finance and other regulated customers, and moved to securing generative AI with CalypsoAI Moderator in 2023. Donnchadh Casey became CEO in August 2024. In October 2024 CalypsoAI named Dublin its global co-headquarters, alongside a US headquarters in New York; IDA Ireland says the CEO, the CTO and most of its R&D were based in Dublin. Paladin Capital Group led its $13 million Series A (July 2020) and a $23 million Series A-1 (June 2023), and F5 says it raised more than $40 million in venture funding. Investors also included Lockheed Martin Ventures and Hakluyt Capital. F5 announced on September 11, 2025 that it would acquire CalypsoAI for $180 million in purchase consideration, mostly cash. F5's 10-Q says the deal closed on September 26, 2025 and records $145.2 million in cash consideration. CalypsoAI is no longer sold separately: calypsoai.com now redirects to F5's AI Guardrails page. F5 introduced F5 AI Guardrails and F5 AI Red Team when it announced the close, and made both generally available in January 2026. Buyers should evaluate those products. **What it sold** By 2025 CalypsoAI sold an inference security platform with two main products. Inference Defend checked prompts and responses in real time to block prompt injection, jailbreaks and sensitive data leakage, using custom scanners that could be versioned, tested and enforced per project. Inference Red-Team ran automated and agent-driven multi-turn attacks, drawing on more than 10,000 new attack prompts a month, and produced a risk score. The platform logged AI interactions for audit, sent logs to Splunk, and ran as SaaS, on premises or hybrid. In August 2025 CalypsoAI said an on-premises version of Red-Team, for organizations with strict data residency or air-gapped requirements, would soon be available in early access. **Frameworks** In August 2025 CalypsoAI added an EU AI Act scanner package to Inference Defend, covering four Article 5 prohibited-practice categories: manipulation, social scoring, biometric data harvesting and surveillance. F5's deal announcement said its governance features help customers meet GDPR and EU AI Act requirements. We found no CalypsoAI mapping to the NIST AI RMF or ISO 42001.

WitnessAI is an AI security and governance platform for enterprise AI use by employees and by AI agents. It was founded in 2023 and incubated by Ballistic Ventures. CEO Rick Caccia, previously SVP of marketing at Palo Alto Networks, is the only co-founder the company names. It is based in Mountain View, California, and has raised about $85.5 million in two announced rounds: $27.5 million co-led by GV and Ballistic Ventures (May 2024) and $58 million in strategic funding led by Sound Ventures (January 2026), with Fin Capital, Qualcomm Ventures, Samsung Ventures and Forgepoint Capital Partners taking part. The platform has three modules. Observe finds the AI apps, agents and MCP servers in use, drawing on a catalog of thousands of AI applications, and classifies conversations by intent. Control sets policies by department, role, intent or workforce type, routes prompts to approved or cheaper models, limits agents to approved MCP servers and tools, redacts sensitive data in real time and keeps audit trails. Protect (Witness Protect, which WitnessAI calls "the enterprise AI firewall") screens prompts and responses for prompt injection, jailbreaks and harmful output and tokenizes PII, credentials and secrets. Witness Attack runs automated red teaming against models before deployment. WitnessAI says it sees AI activity across the network without browser extensions or endpoint clients, including native apps such as Windows 11 Copilot and Office 365, and it integrates with F5 BIG-IP SSL Orchestrator for encrypted AI traffic. Each customer gets a single-tenant instance with customer-controlled encryption. In January 2026 it launched WitnessAI Agentic Security, which covers coding agents such as Claude Code, Cursor and Codex and records the user, agent, tool and rule for every blocked tool call. In July 2026 it added AI FinOps features: spend estimates for unsanctioned AI apps and agents, metering of sanctioned token use, an ROI dashboard and cost-based model routing. **AI compliance coverage** The compliance page offers logging of every AI app and interaction, policy enforcement and masking of regulated data, but names no AI framework. WitnessAI's AWS Marketplace listing says its audit trails support compliance reporting for the EU AI Act, ISO/IEC 42001, the NIST AI RMF and PCI DSS 4.0.1. We found no control mappings for any of them. WitnessAI announced a SOC 2 Type II attestation in October 2025; it has no public trust center. **Who it's for** Large enterprises that want to see and govern how employees and agents use public and internal AI tools, and to add runtime protection to their own AI apps. WitnessAI says its customers include financial services firms, utilities, airlines, automakers, retailers and telecoms. InComm Payments is the only customer it names on its site.