The enterprise security space is dealing with a very modern problem. Generative AI tools make phishing scams and voice clones incredibly convincing, and the Federal Trade Commission reports that social media scams alone cost Americans at least $2.1 billion last year. The core issue is that traditional corporate training modules put employees to sleep. Without specialized help, up to 60% of workers actively fail AI-powered attack simulations.
To fix this, Adaptive Security brought in some serious comedic firepower. On June 9, the OpenAI-backed firm officially launched a 15-part video series starring Emmy-winning comedian Conan O’Brien. The program specifically teaches employees how to spot deepfakes, AI impersonation, and voice cloning before they click the wrong link or authorize a fake payment.
O’Brien and Adaptive Security co-wrote the scripts to replace the universally ignored compliance videos most companies currently rely on. Instead of dry lectures, the series uses humor-driven content to grab attention. The goal is to make the material engaging enough that employees actually finish the modules and retain the technical information.
The 1994 Late-Night Connection
Adaptive Security picked a surprisingly fitting host for this project. O’Brien playfully noted the irony of his new role, pointing back to his recurring “Clutch Cargo” sketches from Late Night in 1994. During those bits, he superimposed his own lips onto still photos of politicians and celebrities to create absurd interviews.
He was essentially running analog deepfakes on national television decades before the underlying machine learning technology existed. Now, he is the face of a corporate effort to stop the exact same concept from compromising secure company networks. By leaning into this history, Adaptive Security takes a dry business-to-business product and gives it genuine cultural weight, proving that enterprise software marketing does not have to be boring.