Emilio Escobar Disrupts Cybersecurity at Datadog

Like any good chief information security officer (CISO), Emilio Escobar entered the world of cybersecurity by breaking the rules. Growing up, it was just by finding a way to stay online on the computer he shared with his brother in Puerto Rico. He wasn’t breaking the law, but he was finding novel ways of securing additional internet service for, well, free.

Then came his interest in coding—eventually writing his own—and the next thing Escobar knew, he was interning at the US Department of Defense (DOD) and helping secure the nation’s cyber defenses in the aftermath of the attacks of September 11, 2001.

It was just the beginning, but the disruption Escobar saw in the field had a profound effect, encouraging him to seek employers who were pushing the boundaries of their industry. In his first CISO role at Datadog, Escobar isn’t just helping the tech industry evolve, he’s helping Latinos shed inhibitions that might be holding them back and empowering them to seek out leadership positions.

Between Datadog and the DOD, Escobar amassed an incredible resume including handling infosec for Hulu and working to deploy cyber best practices at PlayStation (like encouraging the organization to learn from, not prosecute, a PlayStation fan who reverse-engineered his console to play games for free).

“I’ve always been drawn to disruptors,” Escobar explains. “Coming to Datadog was a chance to disrupt the B2B space. How do you get a B2B company to move at the agility of a consumer company? For us in the cloud-monitoring space, we have to be able to move at that pace.”

Escobar’s penchant for pushing the bounds of what’s possible extends even further. The CISO has become an angel investor, but not for random chances to make a few extra bucks.

“I am always asking people to rethink how they approach the security practice,” Escobar says. “I started thinking that there had to be other people who think like me that want to take the risk of building a great product that challenges the status quo. I deal with founders directly. I only invest in teams and founders after I feel like we share the same philosophy and desire to change the way things are.”

Changing the way things are, Escobar says, also means challenging oneself to take on new opportunities. As the executive sponsor for Datadog’s Latino ERG, Escobar wants Latinos to demand more, to put aside their insecurities about their capabilities, and to push themselves to leadership roles.

“Don’t use the fact that there isn’t someone that looks like or talks like you to keep you from getting where you want to be,” Escobar urges. “You have to find people that are willing to support you, rather than finding yourself in a space where you’re already thinking negatively about the outcome.”

For those more junior in their careers, Escobar says leadership shouldn’t seem too far away or feel like a job they’re unqualified to tackle.

“I don’t want to see Latinos settling for less when they have the drive and ability to accomplish great things,” Escobar explains. “The truth is we don’t see many people like us in roles we might want, but you can’t let the fear cloud your imagination for what is actually possible.”

Escobar hopes that he serves as an example of what’s possible. But he also hopes his industry is listening to what he has to say. The CISO hosts a Substack, called “Emilio’s Rants,” where the executive doesn’t mince words about the changes he sees as necessary. Titles like “The Sensationalism in Security” and “Why Do Security Products Fail?” reveal a CISO who continues to be unafraid of change.

The executive admits that being an agent of change can be exhaustive, especially when he’s acting within a company that has shown itself to be wildly successful in its own right.

“It can be strange when I see things that I think should pivot and change because our founders can just point to the results,” Escobar says, laughing. “But that doesn’t mean I don’t have those conversations, and I think they will continue to be important for us as we continue to grow. We just keep growing.”

And so does Escobar. Whether he’s driving change for the industry, for representation in the C-Suite, or just for a new way of thinking about an old idea, it’s almost comforting knowing that Escobar is there, pushing for meaningful change all day, every day.