Entro Security: Why Being Breached Three Times Made Itzik Alvas a Better Founder

Every B2B founder claims deep customer empathy. They’ve done the interviews, shadowed users, analyzed the workflows. But there’s a difference between observing a problem and living through its consequences—especially when those consequences involve explaining to executives how attackers infiltrated systems you were responsible for protecting.

In a recent episode of Category Visionaries, Itzik Alvas, CEO and Co-Founder of Entro Security, shared something most founders can’t: he was the customer who experienced catastrophic failure three times before building his solution. Not similar failures. The exact same vulnerability, exploited the exact same way, at three different organizations. This pattern of repeated failure became Entro’s competitive advantage in ways that go far beyond product development.

The First Breach: Learning the Pattern

Itzik’s experience with non-human identity breaches began during his tenure as CISO of a healthcare organization. “Were breached over there as well, by non human identities and secrets,” he recalls. At the time, it seemed like an isolated incident—a security gap to patch, a process to improve, lessons to document.

Healthcare organizations are notorious targets. Attackers know the data is valuable and the security budgets are often constrained. What made this breach significant wasn’t its occurrence but its cause: programmatic credentials that developers had created and scattered across systems without security oversight.

The Second and Third: When Pattern Becomes Problem

The real education came at Microsoft. “Prior to enter, I was responsible for the internal security and infrastructure of one of Microsoft’s clouds. Microsoft have three main clouds, and I was responsible for the internal security of one of them. And were breached twice by non human identities over there,” Itzik explains.

Think about what that means. Microsoft—one of the most sophisticated technology companies in the world, with virtually unlimited security resources—experienced the same vulnerability twice in the same cloud environment. The attacks followed an identical pattern: developers creating service accounts, API keys, and connection strings to facilitate application access, then scattering these credentials across code repositories, Slack channels, and configuration files.

Nobody managed their lifecycle. Nobody audited their permissions. Nobody even knew how many existed. And attackers, as they always do, found them.

The Moment of Recognition

Three breaches. Three organizations. Three years of incident response, post-mortems, and process improvements that ultimately failed to prevent the next attack. But here’s what separated Itzik from most security leaders: he didn’t just accept this as the cost of doing business.

“After being breached for the third time. And after not being able to find solution that will help me resolve the problem, you know, I started to think maybe I should build something,” he shares.

That sequence matters. First came the repeated problem. Then came the exhaustive search for existing solutions. Only after confirming the market gap did building something new even become a consideration. This isn’t how most startups begin—with founders convinced they’ve spotted an opportunity others missed. This is different. This is a operator who ran out of options.

Why Failure Breeds Better Founders

When Itzik explains what Entro does, he doesn’t start with technical specifications or feature lists. He starts with the lived experience: “Developers, DevOps users are the ones who are creating permissioning. Them, using them are without security oversight and they scatter them around so they, you know, committing them into code, they are sending them over slack and no one is actually managing their lifecycle, no one is deleting them, no one is making sure their permissions are right side.”

This isn’t market research language. This is the voice of someone who watched it happen, who scrambled to contain the damage, who explained to executives why their security investments failed to prevent the breach. The credibility in that explanation is unassailable.

When Entro sells to security leaders, Itzik isn’t pitching a solution to a problem he read about in analyst reports. He’s describing a problem he lived through three times—at organizations with vastly different resources, cultures, and security maturity levels. That pattern recognition creates conviction that market research can’t manufacture.

How Failure Shapes Go-to-Market

This experience fundamentally shaped Entro’s GTM approach in three ways.

First, it clarified the Ideal Customer Profile with precision. Itzik doesn’t need to guess which organizations face this problem or which personas feel the pain most acutely. He was those personas. He knows exactly what keeps them up at night because it kept him up at night.

Second, it created category credibility before the category existed. “That’s a very new category. We helped pioneer that,” Itzik notes. “Were the first company out there to do that, and now there are a lot of companies.” When you pioneer a category, the market’s first question is always: how do you know this is a real problem? Itzik’s answer is bulletproof: he was breached three times by it.

Third, it shaped product development around actual failure modes rather than theoretical vulnerabilities. The reason “non human identity targeted attacks are the second most frequent attack vector out there” isn’t speculation—it’s the culmination of attacks Itzik witnessed firsthand. Every feature Entro builds addresses a gap that existed in the tools Itzik desperately wished he’d had.

The Credibility Compound Effect

Here’s what most founders miss about credibility: it’s not just about closing the first deal. It’s about every interaction that follows.

When Entro talks to design partners, they’re not explaining a hypothetical problem. When they create market education content, they’re not relying on analyst reports. When they train sales teams on objection handling, they know the objections because Itzik raised them himself when vendors pitched him solutions that didn’t actually solve the problem.

This creates a compounding effect. The more Entro educates the market about non-human identity vulnerabilities, the more their origin story reinforces their authority. Every breach that makes headlines validates the problem Itzik experienced. Every security leader who admits they can’t manage these credentials confirms the gap Itzik couldn’t fill.

What This Means for Founders

Not every founder needs to experience catastrophic failure to build credibility. But Itzik’s journey reveals a crucial principle: the depth of your customer understanding directly correlates to your GTM effectiveness.

Surface-level empathy—understanding your customer’s problem intellectually—gets you basic positioning. Deep empathy—experiencing the problem’s consequences emotionally, politically, and professionally—gets you unshakeable conviction and unassailable credibility.

When founders claim they understand their customers’ pain, the question becomes: how do you know? Did you read about it? Interview people about it? Or did you live through it, fail to solve it, and refuse to accept that gap?

Itzik’s answer to that question is what transformed three security breaches from career setbacks into competitive advantages. The failures taught him not just what the problem was, but why existing solutions failed, what security leaders actually need versus what vendors think they need, and which objections are real versus which are deflections.

That knowledge doesn’t come from market research. It comes from being the person desperately searching for a solution that doesn’t exist—and having the conviction to build it yourself.