Breaking the Mold: How Diverse Voices and Fresh Thinking Are Reframing Cybersecurity’s Oldest Problems

For more than a decade, Caitlin Condon has lived at the center of the vulnerability debate. From her early days managing exploit research teams at Rapid7 to her current role as VP of security research at VulnCheck, she’s built her career on parsing through the noise of software flaws, zero-days, and attacker tradecraft to isolate what really matters. Yet, what excites her most isn’t just the technical arms race—it’s the shifting makeup of the people on the front lines.

“I've watched participation in the security industry shift over the past 15 years, incorporating a growing number of folks with different backgrounds, skill sets, and perspectives,” Condon told me. “As a woman with an unconventional background in this space, I'm optimistic about the range of experiences new folks are bringing to the table and how their points of view can help us solve old problems in new ways.”

The Persistent Weight of Old Problems

Despite advances in automation and AI, many defenders still wrestle with issues that have plagued the field for decades. Vulnerability prioritization is one glaring example: organizations routinely drown in endless CVE disclosures, unsure which flaws demand immediate attention and which can safely wait. The result? A cycle of burnout, patch backlogs, and constant fire drills.

“One of the things I've heard year over year from pen testers, security engineers, and SOC analysts alike is that, as an industry, there are so many foundational problems we haven't yet solved—problems like vulnerability prioritization, for instance, which has somehow managed to weigh down multiple generations of the security workforce as a pain point,” Condon said.

Her vantage point at VulnCheck keeps her plugged into both attacker behavior and defender strategy, where she sees the limitations of traditional approaches.

A Turning Point in Cyber Defense

Condon describes the current moment as unusually fertile. On one side, technological innovation—from machine learning-powered threat intel to automated patch orchestration—is reshaping what’s possible. On the other, a wave of new practitioners with nontraditional backgrounds are reframing how risk itself is defined and communicated inside organizations.

“In my eyes, we're entering a particularly exciting era of technological innovation that has also heralded new modes of thinking about risk, both of which benefit from fresh eyes and approaches,” she explained. “The people and technologies on the front lines of cyber threat defense today need smart, scalable solutions more urgently than ever, and while cyber still has a relatively high barrier to entry, I'm encouraged by broadening awareness of cybersecurity as a core component of everyday life at virtually every level.”

From Niche to Necessity

What was once the purview of IT specialists is now embedded in nearly every aspect of modern society: from cars and hospitals to elections and supply chains. That ubiquity, Condon argues, is fueling a cultural shift in how cybersecurity is perceived—not just as a technical challenge but as a collective responsibility.

Her own path—one that defied traditional pipelines into cyber—offers a case study in why broadening participation matters. As more people from outside conventional engineering or military backgrounds enter the fold, the industry gains new strategies for attacking problems once assumed to be unsolvable.

And for Condon, that evolution is what keeps her optimistic: the chance that the next generation of defenders may finally crack the “unsolved” problems that have lingered for decades.