The State of Play 2026: Pentesting the AI Attack Surface

The gap between AI adoption and AI security is widening, leaving even the most mature security programs vulnerable to novel exploit chains. While most organizations are rushing to integrate LLMs, few have recalibrated their offensive testing strategies to account for how these tools change the attack surface.

Watch Andrew Obadiaru, CISO at Cobalt, and Anne Nielsen, Senior Director of Product Marketing at Cobalt, dissect the latest research into how the world’s leading security teams are (and aren't) adapting their pentesting cycles for the era of machine-speed threats.

You'll learn:

  • How AI is fundamentally changing the game in offensive security and what that means for your current defense-in-depth strategy.
  • What leading security programs are doing to proactively reduce their window of exposure as the attack surface evolves.
  • The specific research findings that present the biggest risks to organizations navigating the intersection of traditional infrastructure and AI.
SPEAKERS
Andrew Obadiaru, leadership headshot
Andrew Obadiaru
Chief Information Security Officer, Cobalt
Andrew Obadiaru is the Chief Information Security Officer at Cobalt. In this role, Andrew is responsible for maintaining the confidentiality, integrity, and availability of the company's systems and data. Prior to joining Cobalt, Andrew was the Head of Information Security for BBVA USA Corporate Investment banking, where he oversaw the creation and execution of its cybersecurity strategy. Andrew has 20+ years in the security and technology space, with a history of managing and mitigating risk across changing technologies, software, and diverse platforms.
anne-nielsen_headshot
Anne Nielsen
Director, Market Research & Product Marketing, Cobalt
Anne Nielsen is head of Product Marketing at Cobalt. She has 15+ years of cybersecurity experience across product management and marketing roles most recently as Head of Product at JupiterOne. Before then, Anne spent 9 years at Veracode and held positions at other startups including Rapid7 and 451 Research.
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