In an period the place AI-powered cyber threats are evolving sooner than ever, conventional safety coaching approaches have did not adequately shield organizations, leaving staff susceptible to more and more refined assaults. The safety consciousness coaching market has lengthy been dominated by outdated movies and quizzes that hardly ever translate into significant conduct change, leading to pricey breaches and protracted vulnerabilities.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. By way of custom-made microlearning (the longest video is 87 seconds) mixed with real-time safety nudges, the platform delivers measurable conduct change, turning workforces into proactive protection programs towards cyber threats. With implementations throughout Fortune 500 corporations and reaching over 500,000 world customers, Anagram has demonstrated vital influence, decreasing phishing failure charges from roughly 20% to only 6%.
AlleyWatch sat down with Anagram CEO and Founder Harley Sugarman to study extra concerning the enterprise, its progressive method to cybersecurity coaching, and up to date funding.
Who have been your traders and the way a lot did you elevate?
$10M Sequence A led by Madrona with participation from Normal Catalyst, Bloomberg Beta, Operator Companions, and Safe Octane.
Inform us concerning the services or products that Anagram affords.
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 We transcend conventional strategies—like outdated movies and quizzes—by providing phishing simulations and interactive, customizable coaching designed to interact and educate staff. Our hands-on studying method and immersive puzzles guarantee lasting conduct change, turning your workforce right into a proactive line of protection towards cyber threats.
What impressed the beginning of Anagram?
After years of interviewing quite a few CISOs, I acknowledged a spot within the cybersecurity coaching business—there was a transparent want for a paradigm shift in how coaching was approached.
How is Anagram totally different?
By mixing custom-made 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 every 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 danger administration market, which is a multi-billion-dollar business and rising quick as corporations understand conventional coaching isn’t working.
With AI-driven phishing assaults and social engineering threats rising, CISOs are actively in search of options that really change worker conduct, as an alternative of simply checking a compliance field. Our major clients are bigger enterprise corporations (suppose: Disney, Pfizer, and so forth.), and we’re significantly targeted on extremely regulated industries like finance, healthcare, and expertise, the place safety is a prime precedence.
Our enterprise mannequin is SaaS, with corporations subscribing to our platform on an annual foundation. Pricing scales primarily based on the variety of customers and the extent of customization and integrations wanted. We additionally supply premium options like AI-powered safety nudges, which assist corporations constantly 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 stated, we’re staying disciplined with hiring, prioritizing product options that drive actual influence, 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 robust early traction and a few unbelievable logos, which helped, however we have been additionally very intentional about eager to discover a lead with a shared imaginative and prescient round what Human-Pushed Safety might 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 truly scale back human danger. Their conviction in our method made them the right companion to guide this spherical.
What are the most important challenges that you simply confronted whereas elevating capital?
One of many greatest challenges was convincing traders that safety consciousness isn’t only a checkbox—it’s a solvable drawback. After we spoke to CISOs, we stored listening to that staff are the weakest hyperlink. However what actually stood out was the hopelessness of their voices. They noticed human danger as an unsolvable drawback, one thing they only needed to stay with. Buyers had heard this narrative earlier than, and plenty of have been skeptical {that a} new method might truly change conduct.
What elements about your online business led your traders to put in writing the verify?
Our job was to show that Anagram isn’t simply one other safety coaching software—it’s a essentially totally different method that works. Buyers noticed three key elements that set us aside.
First, actual traction—we have been already working with Fortune 500 corporations and reaching over 500K staff.
Second, measurable influence—we might present a transparent discount in safety incidents, proving that our method truly modifications conduct.
Third, a large, underserved market—CISOs know that conventional consciousness coaching is failing, and our platform supplied an answer that really 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 supplies context-aware, real-time nudges—assembly staff the place they’re and serving to them make smarter safety choices 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 supplies context-aware, real-time nudges—assembly staff the place they’re and serving to them make smarter safety choices within the second.
What recommendation are you able to supply corporations in New York that don’t have a contemporary injection of capital within the financial institution?
Deal with what actually strikes the needle. In a market like this, effectivity issues greater than ever—each greenback and each rent must be driving actual influence. Prioritize buyer retention and revenue-generating initiatives over nice-to-haves. If one thing doesn’t straight contribute to progress or product stickiness, it may wait.
Additionally, don’t underestimate the facility of relationships. Whether or not it’s securing partnerships, touchdown key clients, or getting heat investor intros for the long run, a robust community can open doorways that capital alone received’t. Keep scrappy, keep targeted, and preserve constructing one thing that clients 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 supplies context-aware, real-time nudges—assembly staff the place they’re and serving to them make smarter safety choices within the second.
What’s your favourite restaurant within the metropolis?
Mr Chow on 57th Avenue.
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