Ahead of the Breach

N-able's Keiran Smith on Building Better Security Through Development Experience

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From executing his first SQL injection at age 14 to contributing to the Linux kernel, Keiran Smith’s path to becoming Lead Pentest Engineer at N-able is anything but conventional, as he tells Casey in this episode of Ahead of the Breach. His journey weaves through roles as a senior developer, architect, and DevOps engineer — experiences that transformed him into a security leader who speaks both attacker and defender languages fluently. 

Drawing from his extensive software development background, Keiran explains how understanding code makes him a more effective penetration tester and enables him to build stronger relationships with development teams. Armed with Rust-based custom tools and a developer's mindset, he shows how technical expertise paired with engineering empathy creates a more effective approach to security testing.

Topics discussed:

  • Bug bounty programs have transformed security testing, creating legitimate paths for aspiring ethical hackers.
  • Understanding code architecture and development processes makes for more effective and impactful security testing results.
  • Creating productive partnerships with development teams by offering solutions rather than just pointing out problems.
  • Essential penetration testing tools, including Burp Suite extensions like Stepper and Hackvertor.
  • Streamlining security documentation with Obsidian, markdown-based notes, and automated report generation through custom CI/CD pipelines.
  • Strategies for tracking and testing constantly evolving attack surfaces in modern development environments.
  • Real-world guidance for newcomers about embracing failure and building strong technical foundations in security.
  • Lessons learned from multiple OSCP certification attempts and why persistence matters more than initial success.
  • How contributing to open source projects like Swagger Jacker and developing custom tools enhances the security community.
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    Ahead of the BreachBy Sprocket