Lead, Offensive Security

Become a part of our caring community Selected candidate is required to reside 60 mins from one of the following locations: (Louisville KY, NYC Metro, Dallas Metro, Charlotte NC Metro, South Florida(Tampa/Miami/Ft Lauderdale) , Washington DC metro, Chicago, Boston, Atlanta, Nashville) We're standing up a new AI & Offensive Tooling capability inside our Offensive Security organization, and we're looking for its founding engineer. As Lead, Offensive Security (AI & Tooling), you will own the in-house AI agent platform that powers our penetration testing and red team operations, and build the AI-driven tooling that makes every offensive service line faster, broader, and more autonomous. This is a hands-on building role with the scope of a technical lead: you set the technical direction for offensive AI at the company, and you ship the software that proves it. It's a rare chance to build autonomous offensive security capabilities from the ground up, responsibly, inside a program that helps protect the health data of millions of people. The Bigger Picture Join a 100% remote, highly specialized offensive security team where you will have access to Hack The Box Pro Labs, all HTB role-based training paths and certifications, discretionary certification funding, and conference/training budgets. These resources will enable you to continuously advance your expertise while working on industry-leading Offensive Security challenges at scale. You will be part of the Offensive Security organization, collaborating with Red Team, Penetration Testing, and Breach and Attack Simulation (BAS) professionals, highly specialized experts who identify vulnerabilities so the business can address them proactively. Fridays are dedicated to research and development, allowing the team to pursue training in emerging offensive security methodologies, tools, agents, large language models (LLMs), artificial intelligence, and other bleeding edge topics. Mission & Impact AI that attacks traditional syste