Adaptive Security has launched a new cybersecurity awareness training series featuring comedian and television host Conan O’Brien, aiming to help organizations combat the growing threat of AI-powered cyberattacks. The 15-video series combines humor-driven storytelling with cybersecurity education to train employees on identifying threats such as deepfake scams, voice cloning, phishing attacks, and AI impersonation attempts.
The training series is immediately available to Adaptive Security’s enterprise customers and marks a new approach to employee cybersecurity awareness as organizations face increasingly sophisticated AI-driven social engineering attacks.
The new training series addresses two primary areas of cybersecurity awareness. The first focuses on emerging AI-powered attack methods such as deepfake video scams, AI impersonation, and voice phishing. The second covers foundational security awareness topics, including SMS phishing, QR code scams, password vulnerabilities, physical security, and remote work risks.
Adaptive Security stated that O’Brien collaborated directly with the company’s team to co-write and improvise portions of the scripts, bringing his signature comedic style into the educational content.
The company believes humor-driven engagement can help solve a longstanding problem in cybersecurity awareness training, where employees often disengage from traditional compliance-focused learning modules.
Adaptive Security highlighted growing concerns around AI-enabled cyber threats, noting that more than half of its enterprise customer discussions in 2025 included reports of deepfake-related attack incidents within organizations.
The company also referenced Deloitte projections estimating that AI-facilitated fraud losses in the United States could rise from $12.3 billion in 2023 to $40 billion by 2027.
"Voice phishing, deepfake personas and AI-generated impersonation are hitting companies every week, and most training programs were built years before those attacks existed. We wanted to build something personal and engaging, something employees would actually look forward to," said Brian Long, CEO and co-founder of Adaptive Security.
According to Adaptive, internal estimates show that as many as 60% of employees fail AI-powered attack simulations without prior training.
Each training module opens with a comedic introduction from O’Brien before transitioning into Adaptive Security’s existing instructional content, interactive exercises, and knowledge assessments. Organizations can choose between standard training modules and Conan-branded versions within the platform’s content library.
Adaptive Security argues that O’Brien’s humor style may help employees recognize manipulation tactics commonly used in AI-powered social engineering attacks, particularly those designed to create urgency and emotional pressure.
"He made every script funnier by bringing his enthusiasm to every take, and left us feeling like we made something truly special," Long said. "We are incredibly lucky to have him as a partner in this."
"I teamed up with Adaptive Security just to figure out what these kids are up to. Turns out it's pretty cool," O'Brien said.
The launch reflects broader industry efforts to modernize cybersecurity awareness programs as AI-generated scams become more sophisticated and accessible to attackers.
About Adaptive Security
Adaptive Security, co-founded by Brian Long and Andrew Jones, is the leading provider of AI-powered social engineering prevention solutions. The company defends more than 1,000 enterprise customers against AI-powered attacks including deepfakes, voice cloning, advanced phishing and social engineering. The platform includes security awareness training, phishing simulations, phish triage, email security, AI governance and risk scoring. Adaptive Security has raised over $140MM from investors like Bain Capital Ventures, NVentures (NVIDIA's venture capital arm), OpenAI Startup Fund, Andreessen Horowitz (a16z), Abstract Ventures, Capital One Ventures and Citi Ventures.
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