Sep 11, 2025

Sep 11, 2025 Paladin led the Series A and follow-on financings for CalypsoAI, with total capital raised exceeding $40 million Washington, D.C. – Today, Paladin Capital Group’s portfolio company, CalypsoAI , a leading adaptive AI security platform for the agentic era, announced its agreement to be acquired by F5, Inc. (NASDAQ: FFIV), the global leader in delivering and securing every app and API. F5 will acquire CalypsoAI for $180 million in consideration. CalypsoAI’s award-winning platform, powered by proprietary AI agents, provides a strategic advantage to companies by continuously red-teaming, stress testing, and protecting GenAI systems before attackers strike. “In the years prior to the launch of ChatGPT and the dawn of generative AI, our team recognized that artificial intelligence would soon have life-changing implications for our society, and it would need new solutions to ensure it was safe, secure, and trusted. With this thesis, we made our first investment in CalypsoAI in 2020, which saw rapid growth and acclaim through the last several years,” said Michael Steed, Paladin Capital Group Founder and Managing Partner. “Today’s announcement is a testament to the strength of the AI security market and Paladin’s investment thesis. We are grateful for our Limited Partners for their continued support of Paladin, and we are excited to deliver excellent returns on capital to them through this upcoming acquisition.” Anticipating that the increased adoption of AI would require new technologies to protect this additional attack surface, Paladin led CalypsoAI’s $13 million Series A fundraising round in 2020, the first investment made out of Paladin’s $372 million Cyber Fund II , with Lockheed Martin Ventures, 8VC, Lightspeed Venture Partners, and other strategic investors investing in the round. Following the swift rise of generative AI and large language models (LLMs), CalypsoAI was an early leader in ensuring the security and integrity of LLMs and AI agents for customers like Palantir and multiple Fortune 500 enterprises. Paladin led an additional $23 million fundraising round in 2023 for the company with participation from existing investors and new investors including Hakluyt Capital. Recently, in April 2025, CalypsoAI added Crosspoint Capital as an investor and was named a top-two finalist for the RSA Conference’s prestigious Sandbox Innovation contest, a recognition of its position as the most advanced adaptive AI security platform for the agentic era. CalypsoAI’s adaptive AI security capabilities will be integrated into the F5 Application Delivery and Security Platform (ADSP) to ensure the most complete solution for securing AI interference. As digital attacks become more sophisticated and complex, CalypsoAI delivers end-to-end AI security so that customers can innovate without fear of data leaks and compliance failures. “The acquisition of CalypsoAI demonstrates the immense value in the emerging Generative AI security space, which Paladin was among the first to identify and invest in,” said Mourad Yesayan, Managing Director at Paladin Capital Group and CalypsoAI board member. “Our team is proud to be first-movers in the AI security sector and aims to continue to be leaders in the space as this nascent industry grows and matures. Congratulations to the CalypsoAI team and F5 on this exciting partnership that will shape the future of AI security.” Across financing rounds, Paladin deployed over $27 million in CalypsoAI. This transaction marks the fifth successful exit announced to date from Paladin’s Cyber Fund II and the second in the last three months. In June 2025, Paladin portfolio company Corellium entered into an agreement to be acquired by Cellebrite for an enterprise value of up to $200 million. The acquisition, which is subject to standard closing conditions, is expected to be completed during the fourth quarter. Hogan Lovells served as Paladin’s counsel through the process. About Paladin Capital Group Paladin Capital Group was founded in 2001 and has offices in Washington DC, New York, London, Luxembourg, and Silicon Valley. As a multi-stage investor, Paladin’s core strength is identifying, supporting, and investing in innovative companies that develop promising, early-stage technologies to address the critical cyber and advanced technological needs of both commercial and government customers. Combining proven investment experience with deep expertise in global security, cyber technology, and cutting-edge research, Paladin has invested in more than 80 companies since 2008 and has been a trusted partner to investors, entrepreneurs, and governments for over two decades. For more on Paladin Capital Group, follow us on Twitter at @Paladincap and on LinkedIn or visit us at www.paladincapgroup.com . About CalypsoAI CalypsoAI provides the only full-lifecycle platform to secure AI agents and applications at the inference layer, deploying Agentic Warfare™ to protect organizations from evolving adversaries. Trusted by global enterprises including Palantir and SGK, CalypsoAI’s industry-leading team of experts is doing the hard miles to ensure security keeps pace with AI innovation. CalypsoAI was founded in 2018 and has secured over $40 million in venture funding from investors including Paladin Capital Group, Lockheed Martin Ventures and Hakluyt Capital. CalypsoAI was a Top-Two Finalist in the 2025 RSAC Innovation Sandbox contest and is named on Fast Company’s Most Innovative Companies in AI for 2025.