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The Path of Modern Pentesting: Why CISOs Say We’re Done with Check-the-Box Security

As security leaders, we are currently fighting a dual-front war. On one hand, there is the relentless pressure to enable the business to move at AI speed. On the other, our foundational mandate to maintain security and compliance has never been more daunting. Our recent Pentesting Pulse Report, based on a survey of 150 senior security professionals, confirms a sobering reality: while 85% of us view pentesting as an essential defense and compliance function, only 36% of security leaders are fully satisfied with their current vendors.

This satisfaction deficit with security testing isn't just a minor grievance—it’s a major development bottleneck in a DevOps world, and a massive missed opportunity for genuine risk reduction. With 76% of respondents citing "staying ahead of threats and vulnerabilities" as their top strategic goal for 2026, and 50% saying their focus is on securing the adoption of AI in their products, we simply cannot afford to be held back by traditional testing models that are slow, shallow, and out of sync with modern development cycles.

CISOs Are in the Same Boat 

Pentesting should be a CISO’s best friend. It demonstrates where investment in defensive controls is effective–and what is a waste of money and time. If you’ve felt that your pentesting program is more of an operational hurdle than a strategic advantage, you are not alone. The data in our survey report validates the pain points we feel every day with something close to a consensus:

  • AI Expertise Deficit: As our tech stacks evolve, generalist testers are falling behind. 23% of leaders report a lack of specialized pentester expertise in AI as a primary challenge.
  • A "Hurry-Up-and-Wait" Cycle: Traditional vendor rotation is creating massive operational drag. 28% of respondents expressed frustration with the burden of onboarding new vendors and setting up new integrations every time they switch.
  • Crisis of Quality: Speed is useless without depth. 20% of leaders are tired of "shallow" findings that lack the explicit steps the tester took or infiltration details needed to actually remediate risk.

The AI Imperative: A Triple Threat

The most significant shift in our mandate is the urgent need to secure AI in the products we build and buy. 50% of security leaders have identified this as a key focus—yet there is a profound gap between our AI anxieties and our readiness to keep up with the breakneck speed of AI adoption.

When we look at AI, we are facing a triple threat that requires a more sophisticated offensive security posture:

  1. Vulnerabilities in AI Products: Our primary fear is sensitive information disclosure (85% of security leaders cite this as a top concern, by far the top response), followed by prompt injection and insecure output handling.
  2. Insecure Code Written by AI: Over half of us (53%) are concerned about vulnerabilities introduced by AI coding agents.
  3. Shadow AI and Supply Chain Risks: From insecure plugins to unvetted AI tools being used across the organization, the attack surface is expanding faster than most internal teams can track.

Despite these risks, only one-third of organizations are conducting regular security assessments of their AI deployments, and 10% don’t test AI at all. This is a dangerous gamble, especially considering that 32% of AI pentest findings are classified as high or critical risk, according to Cobalt pentest data.

The Agility Mandate for Speed With Quality

To deliver safe products at the speed of business, we need to realign our pentesting processes and priorities to meet the urgency of speed-of-business development, and ride the cresting wave of agentic AI across the enterprise. 

Yet the report shows that leaders are not willing to trade quality for speed; they are demanding both.

  • Speed of Business: For 40% of leaders, releasing secure products at the speed of business is a high-priority strategic goal.
  • Launch in Days, Not Weeks: For 35% of leaders, the ability to schedule testing rapidly is a top motivator for evaluating new vendors.
  • Real-Time Collaboration: We are moving away from "over-the-fence" static reports. 23% of respondents want to work in real-time with their test teams to accelerate mitigation.

The Bottom Line for 2026

Switching vendors is an operational headache, but staying with a provider that lacks specialized AI expertise or creates a release bottleneck is a far greater risk. Would you rather deal with the short-term pain of switching to work with a pentesting provider that meets the moment? Or take a gamble with your security? 

The era of the slow, shallow pentest is over. As we settle into a new year, our goal must be to find partners who offer the depth of human-led expertise, combined with the speed of a digital platform. We need to move beyond fixing the easy flaws and start addressing the high-risk vulnerabilities that actually threaten our organizations.

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About Andrew Obadiaru
Andrew Obadiaru is the Chief Information Security Officer at Cobalt. In this role Andrew is responsible for maintaining the confidentiality, integrity, and availability of Cobalt'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 Cyber Security 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. More By Andrew Obadiaru