In an period the place AI-powered cyber threats are evolving quicker than ever, conventional safety coaching approaches have did not adequately defend organizations, leaving workers weak to more and more subtle assaults. The safety consciousness coaching market has lengthy been dominated by outdated movies and quizzes that not often translate into significant conduct change, leading to expensive breaches and chronic vulnerabilities. Anagram is revolutionizing this panorama because the world’s first human-driven safety platform designed to embed safety into on a regular basis conduct. Via personalized microlearning (the longest video is 87 seconds) mixed with real-time safety nudges, the platform delivers measurable conduct change, turning workforces into proactive protection methods in opposition to cyber threats. With implementations throughout Fortune 500 firms and reaching over 500,000 world customers, Anagram has demonstrated important affect, lowering phishing failure charges from roughly 20% to simply 6%.
AlleyWatch sat down with Anagram CEO and Founder Harley Sugarman to study extra concerning the enterprise, its revolutionary method to cybersecurity coaching, and up to date funding.
Who had been your traders and the way a lot did you elevate?
$10M Sequence A led by Madrona with participation from Common Catalyst, Bloomberg Beta, Operator Companions, and Safe Octane.
Inform us concerning the services or products that Anagram presents.
Anagram is the world’s first human-driven safety platform that delivers actual outcomes. We transcend conventional strategies—like outdated movies and quizzes—by providing phishing simulations and interactive, customizable coaching designed to have interaction and educate workers. Our hands-on studying method and immersive puzzles guarantee lasting conduct change, turning your workforce right into a proactive line of protection in opposition to cyber threats.
What impressed the beginning of Anagram?
After years of interviewing quite a few CISOs, I acknowledged a niche within the cybersecurity coaching business—there was a transparent want for a paradigm shift in how coaching was approached.
How is Anagram completely different?
By mixing personalized microlearning with real-time safety nudges, the platform drives measurable conduct change and reinforces good safety habits. Anagram stands out by providing distinctive puzzles and coaching that transcend the office, influencing each day behaviors and positively impacting each skilled and private lives.
What market does Anagram goal and the way large is it? What’s your online business mannequin?
Anagram is concentrating on the safety consciousness and human threat administration market, which is a multi-billion-dollar business and rising quick as firms notice conventional coaching isn’t working.
With AI-driven phishing assaults and social engineering threats rising, CISOs are actively in search of options that truly change worker conduct, as a substitute of simply checking a compliance field. Our main prospects are bigger enterprise firms (suppose: Disney, Pfizer, and many others.), and we’re notably targeted on extremely regulated industries like finance, healthcare, and expertise, the place safety is a high precedence.
Our enterprise mannequin is SaaS, with firms subscribing to our platform on an annual foundation. Pricing scales based mostly on the variety of customers and the extent of customization and integrations wanted. We additionally provide premium options like AI-powered safety nudges, which assist firms repeatedly reinforce safe conduct in real-time.
How are you making ready for a possible financial slowdown?
We’ve been targeted on constructing a enterprise that’s capital-efficient from day one. One of many advantages of our sector is that safety isn’t a “good to have”—it’s a necessity, particularly as AI-powered threats develop. That mentioned, we’re staying disciplined with hiring, prioritizing product options that drive actual affect, and aligning the corporate (together with engineering, design, advertising, and gross sales) round two key metrics: progress and retention.
What was the funding course of like?
We managed to get by the funding course of comparatively rapidly. We had sturdy early traction and a few unbelievable logos, which helped, however we had been additionally very intentional about desirous to discover a lead with a shared imaginative and prescient round what Human-Pushed Safety could possibly be. Madrona stood out from the beginning — not simply due to their deep expertise in safety and AI, however as a result of they understood that safety consciousness isn’t a compliance problem, it’s a behavioral one. As a substitute of specializing in completion charges, we spent our time speaking about conduct change and the way we might really cut back human threat. Their conviction in our method made them the proper associate to guide this spherical.
What are the most important challenges that you just confronted whereas elevating capital?
One of many greatest challenges was convincing traders that safety consciousness isn’t only a checkbox—it’s a solvable downside. After we spoke to CISOs, we stored listening to that workers are the weakest hyperlink. However what actually stood out was the hopelessness of their voices. They noticed human threat as an unsolvable downside, one thing they only needed to stay with. Traders had heard this narrative earlier than, and lots of had been skeptical {that a} new method might really change conduct.
What components about your online business led your traders to write down the examine?
Our job was to show that Anagram isn’t simply one other safety coaching software—it’s a essentially completely different method that works. Traders noticed three key components that set us aside.
First, actual traction—we had been already working with Fortune 500 firms and reaching over 500K workers.
Second, measurable affect—we might present a transparent discount in safety incidents, proving that our method really modifications conduct.
Third, an enormous, underserved market—CISOs know that conventional consciousness coaching is failing, and our platform supplied an answer that truly made safety stick.
What are the milestones you intend to realize within the subsequent six months?
Over the following six months, Anagram will proceed advancing its AI-driven personalization engine to ship much more focused, efficient coaching. The corporate can be gearing as much as launch its first AI-powered safety agent, which offers context-aware, real-time nudges—assembly workers the place they’re and serving to them make smarter safety selections within the second.
Over the following six months, Anagram will proceed advancing its AI-driven personalization engine to ship much more focused, efficient coaching. The corporate can be gearing as much as launch its first AI-powered safety agent, which offers context-aware, real-time nudges—assembly workers the place they’re and serving to them make smarter safety selections within the second.
What recommendation are you able to provide firms in New York that do not need a recent injection of capital within the financial institution?
Concentrate on what actually strikes the needle. In a market like this, effectivity issues greater than ever—each greenback and each rent must be driving actual affect. Prioritize buyer retention and revenue-generating initiatives over nice-to-haves. If one thing doesn’t instantly contribute to progress or product stickiness, it may well wait.
Additionally, don’t underestimate the ability of relationships. Whether or not it’s securing partnerships, touchdown key prospects, or getting heat investor intros for the long run, a robust community can open doorways that capital alone gained’t. Keep scrappy, keep targeted, and preserve constructing one thing that prospects can’t afford to stay with out.
The place do you see the corporate going within the close to time period?
Over the following six months, Anagram will proceed advancing its AI-driven personalization engine to ship much more focused, efficient coaching. The corporate can be gearing as much as launch its first AI-powered safety agent, which offers context-aware, real-time nudges—assembly workers the place they’re and serving to them make smarter safety selections within the second.
What’s your favourite restaurant within the metropolis?
Mr Chow on 57th Avenue.
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