Anagram is pioneering a new approach to security awareness that treats employees as assets rather than liabilities. With $10 million in funding, the company is reimagining how organizations address their most significant security vulnerability: human error. In this episode of Category Visionaries, we spoke with Harley Sugarman, Founder and CEO of Anagram, about his journey from venture capitalist to founder and how he's challenging decades of ineffective security awareness training with a human-driven security platform that drives real behavior change.

Topics Discussed:

The fundamental problems with traditional security awareness training
How AI is amplifying attackers' capabilities and the need for better human defenses
Anagram's approach to personalized, puzzle-based, and in-the-moment security training
The shift from treating humans as "risks to be mitigated" to valuable security assets
Founder-led marketing strategies in the security industry
Pivoting from security professional training to broader security awareness

GTM Lessons For B2B Founders:

Identify opportunities where market perception doesn't match reality: Harley noticed a massive gap between what CISOs considered their biggest vulnerability (human error) and how they addressed it (outdated, ineffective training). "If you ask 100 CISOs where an attack will come from, 90-95 will say one of their people will click on a phishing link," yet solutions remained antiquated. This disconnect signaled an opportunity to create a truly differentiated product. B2B founders should look for areas where customer actions don't align with their stated priorities, as these represent prime opportunities for innovation.
Frame your solution to break industry paradigms: Rather than accepting the industry framing of "human risk management," Harley positioned Anagram around "human-driven security" — shifting from seeing employees as liabilities to valuable assets. "I hate that framing so much because it puts the onus on the human," he explained. "What I have been trying to frame our company around is this idea of human-driven security, which is taking humans and making them a line of defense." This reframing helps differentiate Anagram from competitors and resonates more positively with both security leaders and end users.
Use data to overcome status quo inertia: In industries with deeply entrenched practices, the biggest challenge is often skepticism about whether a new approach can actually work. Harley's solution? Let the data make the case. "For us, we are very insistent on looking at the data showing customers, 'Hey, before you introduced us, this is the number of incidents you were seeing. After you introduced us, this is the number of incidents you're seeing.' And I think that's ultimately the thing that changes minds." Data-driven results help overcome the "it's always been this way" mindset that can derail innovative B2B solutions.
Employ a land-and-expand strategy for complex purchases: Anagram uses a methodical approach to win over skeptical buyers: "We very much take a land and expand strategy where we'll go in, augment a specific part of the program, show them that this is actually making a meaningful difference in the data, and then that becomes a very easy business case." For B2B founders selling complex or paradigm-shifting solutions, demonstrating tangible value in a limited implementation can pave the way for broader adoption throughout the organization.
Don't dismiss "old school" outreach tactics: Despite the emphasis on modern marketing techniques, Harley found success with traditional outbound methods: "So far, it has been pretty much exclusively outbound. So emails, LinkedIn, cold calling...which still works, by the way. I was shocked." B2B founders, particularly those targeting enterprise customers outside the tech bubble, should remember that traditional outreach methods can still be highly effective even when they seem outdated in startup circles.
Embrace personal branding with authenticity: After initially feeling uncomfortable with founder-led marketing, Harley found success by finding an authentic voice while taking inspiration from founders like PostHog's James Hawkins. "It does feel cringy. I hate most social media things... It was very much an intentional decision to step out of my comfort zone." By focusing on engagement metrics rather than personal comfort, Harley discovered that his personal content consistently outperformed company posts. B2B founders should measure the results of their personal branding efforts rather than judging them solely on comfort level.
Know when to pivot quickly: Perhaps Harley's most critical decision was recognizing when their initial product wasn't gaining traction and pivoting decisively: "The biggest decision that we made was pivoting... I'm really proud of the fact that we very quickly made the decision to basically throw away all this work that we had done and move into this more general purpose awareness tool." B2B founders should be willing to abandon their original vision when market signals indicate a better opportunity, even if it means discarding substantial work.

Sponsors:

Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership.

www.FrontLines.io

The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe.

www.GlobalTalent.co

Don't Miss: New Podcast Series — How I Hire

Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role.

Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

It's TIME