In an period the place AI-powered cyber threats are evolving quicker than ever, conventional safety coaching approaches have didn’t adequately shield organizations, leaving staff weak 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 The safety consciousness coaching market has lengthy been dominated by outdated movies and quizzes that hardly ever translate into significant habits change, leading to expensive breaches and protracted vulnerabilities.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. By custom-made 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 international customers, Anagram has demonstrated important influence, lowering phishing failure charges from roughly 20% to simply 6%.
AlleyWatch sat down with Anagram CEO and Founder Harley Sugarman to study extra in regards to the enterprise, its modern strategy to cybersecurity coaching, and up to date funding.
Who have been your buyers and the way a lot did you increase?
$10M Collection A led by Madrona with participation from Common Catalyst, Bloomberg Beta, Operator Companions, and Safe Octane.
Inform us in regards to the services or products that Anagram gives.
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 We transcend conventional strategies—like outdated movies and quizzes—by providing phishing simulations and interactive, customizable coaching designed to have interaction and educate staff. Our hands-on studying strategy 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 totally different?
By mixing custom-made 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 huge is it? What’s what you are promoting 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 notice conventional coaching isn’t working.
With AI-driven phishing assaults and social engineering threats rising, CISOs are actively on the lookout for options that really change worker habits, as a substitute of simply checking a compliance field. Our main clients are bigger enterprise corporations (suppose: Disney, Pfizer, and so on.), 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 repeatedly reinforce safe habits in real-time.
How are you getting 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 influence, and aligning the corporate (together with engineering, design, advertising and marketing, and gross sales) round two key metrics: development 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 unbelievable logos, which helped, however we have 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 might truly scale back human danger. Their conviction in our strategy made them the proper associate to guide this spherical.
What are the largest challenges that you simply confronted whereas elevating capital?
One of many greatest challenges was convincing buyers that safety consciousness isn’t only a checkbox—it’s a solvable downside. Once 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 downside, one thing they simply needed to dwell with. Traders had heard this narrative earlier than, and plenty of have been skeptical {that a} new strategy might truly change habits.
What components about what you are promoting led your buyers to write down the test?
Our job was to show that Anagram isn’t simply one other safety coaching device—it’s a essentially totally different strategy that works. Traders noticed three key components 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 strategy truly adjustments habits.
Third, an enormous, 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 propose to attain within the subsequent six months?
Over the subsequent 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 offers context-aware, real-time nudges—assembly staff the place they’re and serving to them make smarter safety choices within the second.
Over the subsequent 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 offers 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 would not 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 instantly contribute to development or product stickiness, it could 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 gained’t. Keep scrappy, keep targeted, and maintain constructing one thing that clients can’t afford to dwell with out.
The place do you see the corporate going within the close to time period?
Over the subsequent 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 offers 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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