Dan DeCloss, founder of PlexTrac, joins the Simply Offensive podcast to discuss the evolution of penetration testing reporting and how AI is reshaping offensive security. The conversation covers the historical pain of manual Word-based report writing, how PlexTrac was built to solve collaborative reporting challenges, and how AI is now automating tedious tasks like TLS/SSL validation and findings documentation. Dan shares a measured view on AI's impact on cybersecurity careers, arguing it will transform rather than eliminate roles, and advises newcomers to build strong networking, systems, and coding fundamentals. PlexTrac is set to unveil new AI capabilities at RSA 2026.
Table of contents
The Future of Pentesting: AI, Automation, and Better Reporting with Dan DeClossThe “Boring” Part of Hacking: Why Reporting MattersAI: The Ultimate Assistant for Defenders and AttackersCareer Transformation and the Job MarketAdvice for Industry NewcomersSort: