In an period the place AI-powered cyber threats are evolving sooner than ever, conventional safety coaching approaches have didn’t adequately defend organizations, leaving workers 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 The safety consciousness coaching market has lengthy been dominated by outdated movies and quizzes that hardly ever translate into significant habits change, leading to pricey breaches and chronic vulnerabilities.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 habits. By 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 methods in opposition to cyber threats. With implementations throughout Fortune 500 firms and reaching over 500,000 international 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 be taught extra in regards to the enterprise, its revolutionary method to cybersecurity coaching, and up to date funding.
Who had been your buyers and the way a lot did you elevate?
$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 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 We transcend conventional strategies—like outdated movies and quizzes—by providing phishing simulations and interactive, customizable coaching designed to interact and educate workers. 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 spot within the cybersecurity coaching trade—there was a transparent want for a paradigm shift in how coaching was approached.
How is Anagram totally 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 day by day behaviors and positively impacting each skilled and private lives.
What market does Anagram goal and the way massive is it? What’s what you are promoting mannequin?
Anagram is focusing on the safety consciousness and human threat administration market, which is a multi-billion-dollar trade and rising quick as firms understand conventional coaching isn’t working.
With AI-driven phishing assaults and social engineering threats rising, CISOs are actively on the lookout for options that truly change worker habits, as an alternative of simply checking a compliance field. Our main prospects are bigger enterprise firms (assume: Disney, Pfizer, and so on.), and we’re notably targeted on extremely regulated industries like finance, healthcare, and know-how, 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 supply premium options like AI-powered safety nudges, which assist firms repeatedly reinforce safe habits 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 marketing, and gross sales) round two key metrics: development and retention.
What was the funding course of like?
We managed to get by way of the funding course of comparatively shortly. We had robust early traction and a few unbelievable logos, which helped, however we had been additionally very intentional about eager 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 habits change and the way we may really scale back human threat. Their conviction in our method made them the proper companion to steer this spherical.
What are the most important challenges that you simply confronted whereas elevating capital?
One of many largest challenges was convincing buyers that safety consciousness isn’t only a checkbox—it’s a solvable downside. Once we spoke to CISOs, we saved 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 simply needed to dwell with. Traders had heard this narrative earlier than, and plenty of had been skeptical {that a} new method may really change habits.
What components about what you are promoting led your buyers to jot down the examine?
Our job was to show that Anagram isn’t simply one other safety coaching device—it’s a essentially totally 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 influence—we may present a transparent discount in safety incidents, proving that our method really modifications habits.
Third, a large, 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 propose to attain 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 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 supplies 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 supply firms in New York that shouldn’t have a recent injection of capital within the financial institution?
Deal with what really 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 development or product stickiness, it may wait.
Additionally, don’t underestimate the facility of relationships. Whether or not it’s securing partnerships, touchdown key prospects, or getting heat investor intros for the longer term, a powerful community can open doorways that capital alone gained’t. Keep scrappy, keep targeted, and maintain constructing one thing that prospects can’t afford to dwell 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 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 Road.
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