In an period the place AI-powered cyber threats are evolving sooner than ever, conventional safety coaching approaches have did not adequately defend 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 The safety consciousness coaching market has lengthy been dominated by outdated movies and quizzes that not often translate into significant habits change, leading to pricey breaches and protracted vulnerabilities.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 habits. Via personalized microlearning (the longest video is 87 seconds) mixed with real-time safety nudges, the platform delivers measurable habits change, turning workforces into proactive protection techniques in opposition to cyber threats. With implementations throughout Fortune 500 corporations and reaching over 500,000 world customers, Anagram has demonstrated important influence, decreasing 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 progressive method to cybersecurity coaching, and up to date funding.
Who had been your traders and the way a lot did you increase?
$10M Sequence A led by Madrona with participation from Basic Catalyst, Bloomberg Beta, Operator Companions, and Safe Octane.
Inform us concerning the services or products that Anagram provides.
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 We transcend conventional strategies—like outdated movies and quizzes—by providing phishing simulations and interactive, customizable coaching designed to interact and educate staff.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 habits 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 habits 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 corporation mannequin?
Anagram is focusing on the safety consciousness and human danger administration market, which is a multi-billion-dollar business and rising quick as corporations 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 habits, as an alternative of simply checking a compliance field. Our main prospects are bigger enterprise corporations (suppose: Disney, Pfizer, and so on.), and we’re significantly centered on extremely regulated industries like finance, healthcare, and know-how, the place safety is a high 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 provide premium options like AI-powered safety nudges, which assist corporations constantly reinforce safe habits in real-time.
How are you getting ready for a possible financial slowdown?
We’ve been centered 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 marketing, and gross sales) round two key metrics: progress and retention.
What was the funding course of like?
We managed to get via the funding course of comparatively shortly. We had sturdy early traction and a few unimaginable 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 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 habits change and the way we may really scale back human danger. 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 largest challenges was convincing traders that safety consciousness isn’t only a checkbox—it’s a solvable drawback. Once we spoke to CISOs, we saved 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 reside with. Traders had heard this narrative earlier than, and lots of had been skeptical {that a} new method may really change habits.
What components about your corporation led your traders to put in writing the examine?
Our job was to show that Anagram isn’t simply one other safety coaching software—it’s a basically 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 corporations and reaching over 500K staff.
Second, measurable influence—we may present a transparent discount in safety incidents, proving that our method really adjustments habits.
Third, a large, underserved market—CISOs know that conventional consciousness coaching is failing, and our platform provided 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 also be gearing as much as launch its first AI-powered safety agent, which gives context-aware, real-time nudges—assembly staff 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 also be gearing as much as launch its first AI-powered safety agent, which gives context-aware, real-time nudges—assembly staff the place they’re and serving to them make smarter safety selections within the second.
What recommendation are you able to provide corporations in New York that wouldn’t have a contemporary injection of capital within the financial institution?
Concentrate on what really strikes the needle. In a market like this, effectivity issues greater than ever—each greenback and each rent needs to be driving actual influence. Prioritize buyer retention and revenue-generating initiatives over nice-to-haves. If one thing doesn’t immediately contribute to progress or product stickiness, it could possibly 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 powerful community can open doorways that capital alone gained’t. Keep scrappy, keep centered, and hold constructing one thing that prospects can’t afford to reside 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 also be gearing as much as launch its first AI-powered safety agent, which gives context-aware, real-time nudges—assembly staff 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 Road.
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