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 subtle 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 The safety consciousness coaching market has lengthy been dominated by outdated movies and quizzes that hardly ever translate into significant conduct change, leading to pricey breaches and chronic vulnerabilities.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. 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 in opposition to cyber threats. With implementations throughout Fortune 500 firms and reaching over 500,000 world customers, Anagram has demonstrated vital impression, 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 progressive strategy 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 Normal Catalyst, Bloomberg Beta, Operator Companions, and Safe Octane.

Inform us in regards to 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 We transcend conventional strategies—like outdated movies and quizzes—by providing phishing simulations and interactive, customizable coaching designed to have interaction and educate workers. Our hands-on studying strategy 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 spot within the cybersecurity coaching trade—there was a transparent want for a paradigm shift in how coaching was approached.

How is Anagram completely 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 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 notice 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 prospects are bigger enterprise firms (suppose: Disney, Pfizer, and so on.), and we’re significantly 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 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 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 impression, 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 shortly. We had robust 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 may truly cut back human threat. Their conviction in our strategy made them the right accomplice to steer this spherical.

What are the most important challenges that you just 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 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 simply needed to reside with. Traders had heard this narrative earlier than, and plenty of had been skeptical {that a} new strategy may truly change conduct.

What elements about what you are promoting led your buyers to put in writing the verify?

Our job was to show that Anagram isn’t simply one other safety coaching device—it’s a essentially completely different strategy that works. Traders noticed three key elements that set us aside.

  • First, actual traction—we had been already working with Fortune 500 firms and reaching over 500K workers.
  • Second, measurable impression—we may present a transparent discount in safety incidents, proving that our strategy truly adjustments conduct.
  • 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 intend to realize 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 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 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 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 choices within the second.

What recommendation are you able to provide firms in New York that shouldn’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 must be driving actual impression. Prioritize buyer retention and revenue-generating initiatives over nice-to-haves. If one thing doesn’t straight 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 received’t. Keep scrappy, keep targeted, and maintain 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 subsequent 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 choices within the second.

What’s your favourite restaurant within the metropolis?

Mr Chow on 57th Road.



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