The confidence gap and resolving serious findings

What happens when artificial intelligence starts accelerating cyberattacks faster than most organizations can test, fix, and respond?

In this episode of Tech Talks Daily, I sat down with Sonali Shah, CEO of Cobalt, to unpack what real-world penetration testing data is revealing about the current state of enterprise security. With more than two decades in cybersecurity and a background that spans finance, engineering, product, and strategy, Sonali brings a grounded, operator-level view of where security teams are keeping up and where they are quietly falling behind.

Our conversation centers on what happens when AI moves from an experiment to an attack surface. Sonali explains how threat actors are already using the same AI-enabled tools as defenders to automate reconnaissance, identify vulnerabilities, and speed up exploitation. We discuss why this is no longer theoretical, referencing findings from companies like Anthropic, including examples where models such as Claude have demonstrated both power and unpredictability. The takeaway is sobering but balanced. AI can automate a large share of the work, but human expertise still plays a defining role, both for attackers and defenders.

We also dig into Cobalt's latest State of Pentesting data, including why median remediation times for serious vulnerabilities have improved while overall closure rates remain stubbornly low. Sonali breaks down why large enterprises struggle more than smaller organizations, how legacy systems slow progress, and why generative AI applications currently show some of the highest risk with some of the lowest fix rates. As more companies rush to deploy AI agents into production, this gap becomes harder to ignore.

One of the strongest themes in this episode is the shift from point-in-time testing to continuous, programmatic risk reduction. Sonali explains what effective continuous pentesting looks like in practice, why automation alone creates noise and friction, and how human-led testing helps teams move from assumptions to evidence. We also address a persistent confidence gap, where leaders believe their security posture is strong, even when testing shows otherwise.

We close by tackling one of the biggest myths in cybersecurity. Security is never finished. It is a constant process of preparation, testing, learning, and improvement. The organizations that perform best accept this reality and build security into daily operations rather than treating it as a one-off task.

So as AI continues to accelerate both innovation and attacks, how confident are you that your security program is keeping pace, and what would continuous testing change inside your organization? I would love to hear your thoughts.

Useful Links

• Connect with Sonali Shah
• Learn more about Cobalt
• Check out the Cobalt Learning Center
• State of Pentesting Report

Thanks to our sponsors, Alcor, for supporting the show.