Conan O'Brien teams up with Adaptive Security to tackle AI-driven workplace scam attacks

Adaptive Security Brings Comedy to Corporate Security Training

Adaptive Security has launched an unconventional approach to cybersecurity training by partnering with Emmy-winning talk show host Conan O'Brien for a 15-part video series designed to educate corporate employees about AI-powered threats1

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. The New York-based company is betting that O'Brien's trademark humor can solve a persistent problem in corporate security training—employees treating mandatory sessions as routine box-ticking exercises rather than meaningful learning opportunities2

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The training series covers modern digital threats including phishing attacks, deepfakes, voice cloning schemes, and other AI-generated scams that have become increasingly difficult for workers to identify. Each episode begins with a comedy segment related to the security topic before transitioning into educational material, a format developed through collaboration between Adaptive Security employees and staff from Team Coco, O'Brien's media company1

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. "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 in a statement1

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AI-Driven Scam Attacks Demand New Training Approaches

The timing of this initiative reflects mounting concerns about how generative AI tools are reshaping the threat landscape. Andrew Jones, Adaptive's cofounder and chief product officer, argues that attacks have become significantly more sophisticated. "There's really a before and after," Jones explained. "There's the before, which was pre-AI, and then there's the after, which is after AI—and after AI, these attacks have gotten much more sophisticated"1

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. This evolution means businesses need clear strategies because emerging technologies are making fraud campaigns increasingly difficult to detect and counter.

Adaptive Security, founded in 2024 by Jones and Brian Long, works with more than 1,000 companies and develops products intended to help organizations recognize and respond to cyber threats2

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. Its offerings include security awareness courses, phishing simulations, and other services supported by a combination of proprietary and publicly available AI models1

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. The company's approach aims to "meet the employee where they are" by helping them retain information about threats that continue to increase with advances in AI2

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Significant Investor Backing Signals Market Confidence

The company has attracted substantial financial support, raising more than $140 million from several funding rounds involving prominent technology investors including startup investment funds from OpenAI and Nvidia, along with Bain Capital Ventures and Andreessen Horowitz2

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. This backing reflects broader interest in cybersecurity products as organizations face growing pressure to strengthen employee awareness programs amid rising financial losses connected to AI-enabled fraud.

"We try to make that training a lot more engaging, a lot more entertaining, to actually drive results rather than it just be something that someone sits through because it's mandatory," Jones noted2

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. The series will be available to enterprise customers using Adaptive's training and cybersecurity awareness products, with additional educational videos that do not feature Conan O'Brien also being released1

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. For businesses navigating complex workplace security challenges, maintaining employee engagement throughout training sessions remains a critical challenge that this celebrity-led approach attempts to address through improved employee engagement strategies.