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Are you passionate about applying the latest advances in offensive security and DevSecOps to real‑world challenges? At Plain Security Studios, we’re reshaping how organizations test, secure, and evolve their cyber defense strategies using AI. As Lead Defensive AI Security, you’ll drive the transformation of red teaming, adversarial testing, and secure development practices for next‑generation environments— from LLM applications to CI/CD pipelines. You will report directly to the VP of Plain Security and lead a growing team of specialists focused on Offensive AI and DevSecAIOps. The role is both strategic and hands‑on, helping clients build safer AI systems, improve their threat detection, and embed security directly into their engineering workflows. Key Responsibilities Offensive AI Strategy & Delivery: Lead the design and execution of AI‑augmented red and purple team operations. Simulate real‑world attacks to uncover risks in LLM‑based applications, AI pipelines, and modern cloud environments. Adversarial Testing of AI Systems: Develop and apply methodologies to assess prompt injection, data leakage, insecure agents, and other vulnerabilities in AI‑driven software. DevSecOps & Automation: Help clients integrate security into the development lifecycle. Lead secure‑by‑design initiatives, threat modelling, and build automated security checks into CI/CD environments using modern tooling (Azure, GitHub, etc.). Client Advisory & Innovation Enablement: Partner with product, AI, and engineering teams to improve security posture without slowing innovation. Translate red team insights into actionable improvements for developers, architects, and CISOs. Tooling & Reusability: Build automation, scripts, and AI‑based security tools to accelerate assessments. Leverage LLMs or security copilots to scale red team insights across environments and clients. Evangelism & Enablement: Create internal frameworks, methodologies, and reusable templates for offensive assessments. Share best practices across the studio and help less experienced teams apply offensive techniques. Knowledge Sharing: Keep your team and clients up to date on threat actor TTPs, novel attack chains, and defence strategies. Identify opportunities to evolve legacy assessments into modern, AI‑aware techniques. Strategic Mentorship: Grow and guide a cross‑disciplinary team of consultants. Foster a culture of curiosity, excellence, and continuous learning. What We’re Looking For Technical Background: Bachelor’s or Master’s in Computer Science, Cybersecurity, Engineering, or related field. Cybersecurity Experience: 7+ years in offensive or adversarial security (red teaming, pentesting, exploit development), including 3+ years leading technical teams or high‑impact assessments. AI‑Aware Security Mindset: Deep interest or hands‑on experience securing AI/LLM systems—prompt injection, agent manipulation, adversarial inputs, dynamic UI risks. Cloud & DevSecOps Knowledge: Proficiency in secure CI/CD practices, IaC, and cloud‑native security (Azure preferred). Experience implementing security automation in pipelines. Programming & Scripting: Strong scripting/coding skills (Python, PowerShell) to build tools and automate testing. Familiarity with fuzzing, static analysis, or LLM‑based automation is a plus. Security Tooling: Experience with common offensive security tools (Burp, Nmap, BloodHound, Metasploit); optional deeper tools like IDA/Ghidra, fuzzers, or threat emulators. Client Engagement & Communication: Ability to present technical findings and risk models to technical and non‑technical stakeholders, including senior leadership. Strong writing and storytelling skills. Strategic Vision: Capacity to look beyond immediate findings and advise clients on long‑term defence improvements and architectural design. Language: Fluent English (B2 minimum). Spanish is a plus. Certifications (OSCP, CRTO, GIAC, etc.) are valued but not mandatory. What We Offer Salary determined by the market and your experience. Fully remote work (optional). Flexible compensation (restaurant, transport, and childcare). Fully free health insurance, with a co‑