Lead AI Transformation Engineer

Accelerate Your Career in Cybersecurity! Join Pentera and take your career to the next level in cybersecurity. As a leader in Automated Security Validation, we help businesses around the world safely emulate real-world attacks to uncover their vulnerabilities, just like the world's best red teams. At Pentera, you will be at the forefront of cybersecurity innovation, working on advanced tools that challenge organizations' defenses and push the limits of security testing. With over 350 team members and 1,300 customers in more than 60 countries, Pentera is a growing company supported by top investors such as Insight Partners, K1, and The Blackstone Group. If you want to grow your skills, make an impact, and be part of an innovative team, Pentera is the place for you. What you'll do - strategy and senior function • Own the technical strategy for Pentera's internal AI transformation: target architecture, engineering standards, model and vendor choices, build-vs-buy calls. • Shape the AI portfolio: which workflows to automate, in what sequence, with what success metrics - and push back when the wrong thing is being built. • Set and enforce the bar on ROI and security for every AI system: cost, adoption, cycle-time impact, access control, and auditability are reviewed per project, not after launch. • Act as the senior technical voice for internal AI: advise leadership, review AI initiatives across the org. • Turn one-off builds into a real internal platform: reusable patterns, shared services, and standards that AI Champions and teams adopt. • Mentor AI Champions; raise the org's practical AI level. • Continuously evaluate models, vendors, and frameworks, and keep Pentera agile. What you'll do - hands-on build • Personally design, build, deploy, and own the flagship internal agents and AI workflows, from prototype through production. • Build and evolve Pentera's AI context layer: connectors, APIs, retrieval services, metadata, identity and authorization, controls, and tool interfaces. • Create safe action tools for agents and infrastructure for agents to work. • Build RAG, tool-calling, structured-output, and multi-step agentic workflows using the right model and architecture for each problem. • Own the production quality bar for what you ship: evaluation datasets and automated checks (accuracy, groundedness, task completion, safety, cost etc.) • Work directly with business owners to map processes, test with users, and drive each pilot to a clear scale-or-stop decision.

Requirements: • 4+ years of production software engineering, including strong Python, APIs, testing, CI/CD, data contracts, and cloud services. Applied and agentic AI is a new field - nobody has a decade of it - so we weight demonstrated ownership and depth over years: what you shipped, what you owned end to end, how deep you went. • Evidence of operating at senior scope, wherever you earned it: you have set technical direction, made architecture calls that others built on, and carried systems end to end - as a staff/lead engineer, a first AI hire, or similar. • Executive fluency: you turn ambiguous business needs into a technical plan, explain trade-offs simply to non-engineers, and say no with reasoning when needed. • Ownership mindset: you measure whether the system changed the business process, not whether the demo ran. Advantages • Experience as a first or early AI hire, or standing up an internal AI platform or function. • MLOps or LLMOps experience, Kubernetes, model gateways, GraphRAG/knowledge graphs, or Model Context Protocol. • Cybersecurity or security-product experience. • Experience building internal developer platforms or company-wide data products. We are an equal opportunity employer and we are committed to building a diverse and talented workforce. We do not discriminate on the basis of race, sex, religion, colour, national origin, gender, gender identity, sexual orientation, age, marital status, veteran status, medical condition, disability, or any other class or characteristic protected by applicable law. We welcome candidates from all backgrounds to join us!