Ahead of the Breach

Digital Turbine's Vivek Menon on Quarterly Pentesting Frameworks

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The shift from annual compliance-driven security testing to continuous validation represents one of the most critical evolutions in modern cybersecurity practice. Vivek Menon, CISO & Head of Data at Digital Turbine, discovered this firsthand when his team's focus on modern cloud applications nearly missed a critical legacy system that could have triggered cascading failures across their entire infrastructure. On this episode of Ahead of the Breach, Vivek tells Casey how quarterly penetration testing aligned with engineering roadmaps delivers superior security outcomes while building rather than eroding trust with development teams.

Vivek has developed frameworks that balance thorough security validation with business agility. His approach to shadow AI governance, stakeholder communication strategies, and leveraging AI simulation for previously impossible attack scenarios offers practical guidance for security leaders navigating today's rapid development cycles while maintaining robust defensive postures.

Topics discussed:

  • Quarterly penetration testing frameworks that align with product roadmaps and engineering milestones rather than annual compliance cycles to catch vulnerabilities as they're introduced.
  • The critical importance of comprehensive asset discovery, particularly legacy systems that may be interconnected with modern cloud infrastructure in ways that create cascading vulnerability risks.
  • Building trust equations with engineering teams through consistent, non-disruptive testing practices that demonstrate security as an enabler rather than a blocker to development velocity.
  • Shadow AI governance challenges as employees enthusiastically adopt tools like Zapier agents without proper controls, creating new data exposure vectors that require immediate attention.
  • Risk register development using business risk alignment rather than treating all systems equally, focusing testing resources on revenue-generating and business-critical components.
  • AI-driven attack simulation capabilities that make previously cost-prohibitive or technically impossible testing scenarios accessible for better adversary understanding.
  • Stakeholder communication strategies that tailor security messaging across three distinct audiences: technical implementers, middle management, and executive leadership with board reporting requirements.
  • Leveraging AI agents for frictionless continuous testing that reduces visible pain points for engineering organizations while maintaining security thoroughness.
  • Integration strategies for penetration testing platforms with existing productivity tools like Jira, Confluence, and Slack to streamline vulnerability management workflows.
  • Non-traditional hiring approaches for security teams, particularly recruiting from MLOps and data science backgrounds to address machine learning security gaps that traditional cybersecurity professionals often miss.

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    Ahead of the BreachBy Sprocket