• Develop and execute a multi-year roadmap for offensive security, including red teaming, penetration testing, bug bounty, and vulnerability research. • Design and lead full-scope red team engagements that simulate Advanced Persistent Threats (APTs) to test detection and response capabilities. • Oversee the end-to-end lifecycle of offensive engagements, from initial scoping and Rules of Engagement (RoE) to final reporting. • Facilitate collaborative "Purple Team" exercises with Detection and Response (TDR) to improve detection logic and incident response playbooks. • Translate complex technical findings into actionable business risk assessments for C-suite executives and Board members. • Recruit, retain, and develop a high-performing team of offensive security engineers, providing technical guidance and career coaching. • Partner with vulnerability management, product, and engineering to ensure that findings from offensive tests are prioritized and remediated effectively. • Oversee the development of custom scripts, payloads, and C2 (Command and Control) frameworks to enhance the team’s stealth and efficiency. • Conduct specialized threat modeling for AI-native applications, focusing on the OWASP Top 10 for LLMs and MITRE ATLAS (Adversarial Threat Landscape for AI Systems). • Design and execute manual and automated Prompt Injection & Jailbreaking to bypass model guardrails, system prompts, and safety filters. • Ensure all offensive activities align with legal, ethical, and regulatory standards (e.g., GDPR, SOC2, PCI-DSS). • Incorporate current Cyber Threat Intelligence (CTI) into attack scenarios to ensure they reflect the latest real-world TTPs (Tactics, Techniques, and Procedures). • Manage relationships and quality control for external security consultancy firms performing third-party penetration tests. • Encourage and lead research into emerging technologies to identify future attack vectors. • Work closely with Product and Engineering teams to bake security into the Software Development Life Cycle (SDLC) through testing and assessments.