Why Entro Security Chose Fun Over Serious—and What It Cost Them

Why Entro Security Chose Fun Over Serious—and What It Cost Them

Walk the floor at any major cybersecurity conference and you’ll see the pattern: navy blue backgrounds, white text, dark imagery, serious faces. The aesthetic screams “trust us with your most critical assets” through visual conservatism. It’s safe. It’s expected. It’s utterly forgettable.

In a recent episode of Category Visionaries, Itzik Alvas, CEO and Co-Founder of Entro Security, explained why his company deliberately rejected every cybersecurity branding convention—and whether that decision actually cost them deals with risk-averse enterprises.

The Cybersecurity Branding Playbook Everyone Follows

Itzik’s observation about the industry is accurate to the point of being mundane: “The usual cybersecurity companies are blue and white and somewhat black and very serious approach.” Visit ten cybersecurity vendor websites and you’ll struggle to distinguish one from another. Dark backgrounds. Technical diagrams with arrows showing threat actors blocked at the perimeter. Serious photography of diverse teams looking concerned while pointing at monitors.

The uniformity isn’t accidental. When you’re selling to CISOs and security leaders—people whose job security depends on not making catastrophic mistakes—visual conservatism signals stability. Blue conveys trust. White suggests clarity. Black implies sophistication. The aesthetic is designed to whisper: “We’re the safe choice.”

For a new company entering the market, the pressure to conform is immense. Established competitors have trained buyers to expect certain signals. Deviating risks being dismissed as unserious, immature, or worse—risky.

Itzik and his team chose to deviate anyway.

The Deliberate Decision to Be Different

The choice to break from convention came from Itzik’s own experience as a security buyer. “I led security for a long while and, you know, I wanted something that looks and feels more, you know, young and fun and that’s definitely the approach that we went to,” he explains.

Notice the origin: this wasn’t a marketing consultant’s recommendation or an attempt to appeal to younger buyers. It came from a security leader who spent years evaluating vendors and found the entire category’s aesthetic exhausting. The conservatism wasn’t just boring—it was potentially counterproductive.

“The main goal was to make it as fun as B2C, but definitely still B2B company,” Itzik shares. That distinction matters. B2C companies can be playful because the stakes are lower and purchase decisions are individual. B2B requires committee approval, vendor evaluations, compliance reviews. Bringing B2C energy to B2B isn’t just about colors and fonts—it’s about believing enterprise buyers are humans who don’t actually want to spend their workdays interacting with joyless brands.

The Risk Calculation

Every founder making a contrarian branding choice faces the same question: will this cost us deals? When you’re pioneering a new category, as Entro was with non-human identity management, you’re already asking buyers to take a risk on a market that didn’t exist six months ago. Adding branding risk on top of category risk seems like compounding mistakes.

The question isn’t theoretical. Enterprise security purchases involve multiple stakeholders, vendor scorecards, and risk committees. A procurement team might personally love your playful brand but worry their CISO will think it’s unprofessional. A CISO might appreciate the differentiation but worry the board will question their judgment.

When asked directly whether the fun branding cost them deals, Itzik’s answer is remarkably honest: “I don’t think so. Like, I don’t know if someone came into the website and left because they feel like that’s not serious enough for them.”

That “I don’t know” is important. Most founders would claim certainty—”definitely not” or “absolutely worth it.” Itzik acknowledges the inherent unknowability. You can’t track the deals you never knew you lost. Someone could visit your website, decide you’re not serious enough for their organization, and leave without ever entering your funnel.

What Actually Closes Deals

But Itzik’s full answer reveals his bet on what actually matters: “Hopefully, you know, the logos out there and the customer acquisitions and the stuff we’re doing means more.”

This is the core thesis behind contrarian branding in conservative markets: differentiation gets you attention, but substance gets you customers. The playful brand makes you memorable. The customer logos and product performance make you credible.

The sequence matters. In a category Entro helped create, early market education requires capturing attention. Security leaders need to first understand that non-human identity management is a problem worth solving. If your brand looks identical to every other cybersecurity vendor, you’re fighting for attention in a sea of sameness.

Once you have attention, the brand needs to step aside and let the substance speak. “Hopefully they appreciate that we’re a young, fun company and very innovative,” Itzik notes. The brand signals innovation, but the customer testimonials, product demonstrations, and security outcomes close the deal.

The Memorability Premium

Here’s what traditional cybersecurity branding optimizes for: not losing deals because of brand concerns. It’s defensive. The logic is: if we look like everyone else, no one can fault us for our aesthetic choices.

But that approach has a hidden cost: forgettability. When every vendor looks the same, buyers struggle to remember which company does what. Sales cycles extend because you need repeated touchpoints to maintain awareness. Marketing costs increase because you can’t rely on organic word-of-mouth—nothing about you is distinct enough to repeat.

Entro’s branding makes a different bet: that memorability has value worth the risk of occasionally appearing unserious. When security leaders encounter Entro at conferences, in content, or through referrals, they remember it. The playful brand becomes a mnemonic device—”oh, that’s the fun cybersecurity company.”

In a category that requires extensive market education, memorability compounds. Every interaction reinforces recognition. Every piece of content is more likely to be shared because it looks different in people’s feeds. Every sales conversation starts with higher awareness because prospects actually remember previous touchpoints.

When Bold Branding Works

Itzik’s approach reveals three conditions where contrarian branding in conservative markets creates ROI:

First, when you’re creating a category, not competing in one. Established categories have established aesthetics. Breaking those conventions when buyers know what they’re looking for is risky. But when you’re teaching the market to recognize a new problem, standing out accelerates awareness.

Second, when your substance is unquestionable. Itzik could pursue playful branding because his credibility was bulletproof—he’d been breached three times by the problem Entro solves. The customer logos, the product capabilities, and the founder’s background all screamed credibility. The branding could be fun because everything else was serious.

Third, when your target buyer is exhausted by category conventions. Itzik knew security leaders were tired of the same aesthetic because he’d been one. The playful brand wasn’t just differentiation—it was relief from the monotony of evaluating identical-looking vendors.

The Real Cost

So what did the fun branding actually cost Entro? Probably some deals. Definitely some initial skepticism. Possibly some investor conversations where they had to over-explain their positioning.

But it bought them something traditional branding couldn’t: instant recognition in a crowded market, word-of-mouth from people who found the differentiation remarkable, and alignment with their actual identity as innovators challenging category conventions.

The lesson for B2B founders isn’t “be playful” or “break conventions.” It’s more nuanced: understand what you’re actually buying with branding decisions. Safe branding buys you freedom from aesthetic concerns but costs you memorability. Bold branding buys you attention but costs you some portion of risk-averse buyers.

Itzik made his choice knowing the tradeoffs. He’d rather be memorable to 80% of the market than forgettable to 100% of it. In category creation, where market education is the primary GTM challenge, that math makes sense.

The question for other founders: what are you actually optimizing for?