The Leading CISO Strategy to Pentest as a Service
Penetration testing, or “pentesting”, is a proactive security measure used to uncover hidden vulnerabilities before adversaries can exploit them. Simulating real-world attacks, pentesting helps companies of any size validate defenses and harden systems against the most persistent threats.
Many organizations conduct annual pentests to check a compliance box, but security leaders in the know are getting much more from their investment.
To maximize the value of pentesting, three strategies can help you lead like a crowdsourced security champion.
1. Use Pentesting to Complement Internal Security
Leading CISOs don’t view pentesting as a replacement for internal security testing. Instead, they treat it as a critical layer that validates assumptions and catches what internal teams miss.
Pentest-as-a-Service (PTaaS) models give organizations access to a community of security researchers, matched to their scope and goals, bringing external perspectives and deep domain expertise. In fact, 75% of HackerOne pentesters have five or more years of experience, and 19% of their findings are high or critical severity, double the industry average.
By integrating PTaaS into your development and release cycles, you ensure ongoing validation without the bottlenecks or blind spots of traditional consulting models.
2. Expand Testing Scope to Reflect Real-World Risk
A common misstep is limiting pentests to narrow scopes while leaving critical assets untested. Leading CISOs are flipping this mindset by making pentesting more comprehensive and inclusive.
This means testing not just public web apps or APIs, but also AI systems, data pipelines, LLMs, cloud misconfigurations, internal networks, and more. As your attack surface expands, so should your security lens.
HackerOne Pentest supports assessments across every environment, from AWS to hybrid cloud to mobile apps, and can include AI assets to evaluate prompt injection, training data integrity, and supply chain vulnerabilities. The result is actionable insight that strengthens confidence across compliance, product launches, and data protection.
3. Adopt a Continuous Mindset with Regular Pentesting and Monitoring
Security isn’t static, and neither are threats. High-performing security teams combine always-on tools for known threats with regularly scheduled pentests to catch what automated scanners miss.
Industry leaders schedule at least one pentest per year, but many now opt for more frequent tests tied to key releases, regulatory milestones, or significant infrastructure changes. With HackerOne PTaaS, tests can launch in as few as 4–7 business days, and results are delivered in real time, enabling teams to remediate issues while the test is still active.
Our advisory services can help scope pentesting around your company’s approach to keep your security posture aligned with business velocity, rather than lagging behind it.
A Smarter Pentesting Approach for CISOs
Security leaders who get the most out of penetration testing as a service follow three strategies:
- They view pentesting as a supplement to their internal controls.
- They include all meaningful digital assets in the testing scope.
- They commit to regular pentesting, rather than treating it as a once-a-year checklist item.
Leaders use PTaaS to uncover critical vulnerabilities, close security gaps faster, and evolve their defenses as quickly as attackers evolve theirs. For organizations navigating AI transformation, regulatory pressure, and expanding digital complexity, crowdsourced security is essential.
Take an interactive HackerOne Pentest demo and see how your organization can benefit from expertise-driven, real-time security testing.
What separates the highest-performing CISOs from the rest?
Our latest report reveals these leaders' four offensive security strategies, and five recommendations to guide CISOs beyond common barriers to the full value of crowdsourced security. Dive in to see what leaders are doing differently and how to follow their lead for the greatest crowdsourced security impacts.
