Why Corporate Cybersecurity Training Has Always Failed — Until Now
Picture this: it's your first week at a new job. Somewhere between filling out tax forms and getting your laptop set up, HR drops a link in your inbox. It's a mandatory cybersecurity training course. You click through it, absorb roughly none of it, pass the quiz on your third try, and never think about it again. Sound familiar? You're not alone — and that's precisely the problem that cybersecurity AI firm Adaptive Security is setting out to solve, this time with a little help from a very famous redhead.
Adaptive Security has partnered with Emmy-winning late-night comedian and television icon Conan O'Brien to produce a 15-video cybersecurity training series designed to teach employees how to recognize and respond to AI-powered scam attacks. The result is something the corporate world has almost never seen before: security awareness training that people might actually want to watch.
Meet Adaptive Security: The Startup Backing This Bold Idea
Founded in 2024 by Andrew Jones and Brian Long, Adaptive Security is not your typical cybersecurity startup. The company works with more than 1,000 businesses and has raised over $140 million in funding from some of the biggest names in technology and venture capital, including OpenAI, Nvidia, Bain Capital Ventures, and Andreessen Horowitz. That level of financial confidence speaks volumes about how seriously the industry is taking AI-driven cyber threats — and about how urgently better training solutions are needed.
Jones serves as the company's cofounder and chief product officer, while Long leads as CEO. Together, they've built a platform specifically designed to address the rapidly evolving landscape of AI-generated cyberattacks — a landscape that most legacy training programs were never built to handle.
Why AI Scam Attacks Are a Growing Corporate Crisis
The threat landscape has changed dramatically in recent years, and the pace of change is only accelerating. As AI models become more sophisticated and more affordable to deploy, bad actors are using them to launch increasingly convincing attacks on businesses of all sizes.
Traditional phishing emails are no longer the only concern. Today's threats include:
- Voice phishing (vishing): Attackers use AI-generated voice cloning to impersonate executives, colleagues, or trusted vendors over the phone, tricking employees into transferring funds or sharing sensitive data.
- Deepfake personas: Realistic AI-generated video and audio of real people are being used to manipulate employees during virtual meetings or video calls, making fraud nearly indistinguishable from legitimate communication.
- AI-generated impersonation: Sophisticated language models can now craft highly personalized, grammatically perfect phishing emails that no longer carry the telltale signs of a scam — no broken English, no obvious red flags.
"Voice phishing, deepfake personas, and AI-generated impersonation are hitting companies every week, and most training programs were built years before those attacks existed," said Long in a press release. "We wanted to build something personal and engaging, something employees would actually look forward to."
That desire to build something genuinely compelling led directly to the partnership with Conan O'Brien.
What Makes the Conan O'Brien Training Series Different
The 15-video training series was filmed in Los Angeles and co-written by O'Brien's media network, Team Coco. Rather than dry slide decks, talking heads reciting compliance bullet points, or generic animations, the series leans fully into O'Brien's trademark self-deprecating, absurdist humor to make viewers genuinely engaged with material that is, by any measure, seriously important.
The goal, according to Jones, is to make training that actually drives behavioral change rather than simply fulfilling a checkbox requirement. "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 explained.
This philosophy reflects a growing body of research suggesting that humor, storytelling, and emotional engagement dramatically improve information retention. If employees laugh while learning what a deepfake attack looks like, they are far more likely to remember that lesson when a suspicious video call shows up in their calendar three months later.
The Strategy Behind "Meeting the Employee Where They Are"
One of Adaptive Security's core beliefs is that effective training must meet employees where they actually are — not where compliance departments wish they were. Most workers are busy, distracted, and resistant to yet another mandatory module added to their workload. By partnering with a figure as universally recognized and genuinely funny as Conan O'Brien, Adaptive is betting that name recognition and entertainment value can transform a dreaded obligation into something employees actively engage with.
This approach also addresses a fundamental psychological barrier to cybersecurity education: the topic itself can feel abstract and distant until it isn't. AI scam attacks may seem like someone else's problem right up until the moment an employee receives a convincing voice message that sounds exactly like their CEO asking for an urgent wire transfer. Training that makes these scenarios feel real, relatable, and even a little bit funny can bridge that gap between awareness and genuine preparedness.
What This Means for the Future of Corporate Security Training
The Adaptive Security and Conan O'Brien collaboration signals a broader shift in how organizations are beginning to think about human-layer cybersecurity. For years, the industry focused primarily on technical defenses — firewalls, endpoint protection, multi-factor authentication — while treating employee training as a compliance formality. That approach has proven inadequate in the face of social engineering attacks that specifically target human psychology rather than technical vulnerabilities.
As AI makes those attacks cheaper, faster, and more convincing, the human firewall becomes more critical than ever. And a human firewall is only as strong as the training behind it. If that training is forgettable, skipped, or simply not retained, no amount of sophisticated software can compensate for an employee who hands over credentials to a convincing deepfake.
Adaptive Security's model — combining serious AI-powered simulation with genuinely entertaining content — may well represent the template that the rest of the industry eventually follows. With over $140 million in backing and partnerships that generate real attention, the company is positioned to push cybersecurity training out of the era of mandatory tedium and into something that employees might actually talk about around the water cooler.
The Bottom Line: Laughing Your Way to Safer Security Habits
Conan O'Brien may be best known for his late-night television career, his beloved podcast, and his endlessly meme-able hair, but his latest project might turn out to be one of his most consequential. By lending his voice, his humor, and his team's creative talents to the challenge of AI scam awareness, O'Brien is helping Adaptive Security make the case that protecting your organization from cyberattacks doesn't have to be boring — and probably shouldn't be.
In a world where AI-generated threats are becoming more sophisticated by the week, getting employees to truly pay attention to their training is no laughing matter. But thanks to this partnership, it might finally involve a few genuine laughs along the way.