“If you ask 100 CISOs whether their current training actually changes behavior, 95 to 98 will say, ‘not really.’” — Harley Sugarman, Founder & CEO, Anagram Security

In this eye-opening episode of Technology Reseller News, publisher Doug Green speaks with Harley Sugarman, CEO of Anagram Security, about why traditional cybersecurity training is no longer enough—and how AI-powered threats are accelerating the need for change.

Sugarman argues that legacy training—often mandated once a year and dominated by slide decks—has failed to engage employees or meaningfully improve their behavior. “Death by PowerPoint,” as he puts it, simply doesn’t work anymore. With phishing and social engineering attacks now powered by advanced AI, companies must shift from checkbox compliance to behavior-driven learning.

Anagram Security is pioneering a new model that draws inspiration from platforms like Duolingo and TikTok, focusing on habit formation and real-world relevance. Their approach incorporates short, two-to-three-minute “puzzle”-based modules that promote critical thinking, adapting lessons for different roles—from developers to sales teams to hotel clerks. The platform also emphasizes customization, allowing enterprises to tailor content to specific job functions and threats.

Anagram’s user engagement metrics are telling: In enterprise pilots, over 90% of users preferred Anagram’s approach over traditional methods. More importantly, the company ties its training outcomes to measurable behavior improvements, such as reductions in phishing clicks and password-related vulnerabilities.

Sugarman also critiques industry jargon like “human risk management” and “vishing,” emphasizing that front-line employees don’t need buzzwords—they need training that fits their real jobs and schedules. He insists that people are not the weakest link, but rather the last line of defense—and should be treated as partners, not problems.

Anagram has already attracted major brand-name clients by delivering a security awareness model that’s modern, scalable, and actually works. With AI lowering the barrier for attackers, Sugarman believes the urgency has never been greater: “This is the thing most companies will realize they have to get better at—the most, and the fastest.”

Learn more at www.anagramsecurity.com and connect with Harley Sugarman on LinkedIn.