Lead AI Transformation Engineer

Accelerate Your Career in Cybersecurity!Pentera is the market leader in AI-native Security Validation, equipping enterprises with the platform to proactively test their defenses against the latest cyber attacks. Pentera proves which exposures are truly exploitable across the entire attack surface and drives remediation workflows that reduce real risk. Anchored in real-attack validation, the Pentera platform powers the full Continuous Threat Exposure Management (CTEM) cycle, from exposure discovery through prioritization, validation, and mobilization. Thousands of security teams around the world trust Pentera to close their security gaps before threat actors can exploit them.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.About the rolePentera, a security company, is building an internal AI capability across the organization: agents that perform real tasks as the organization, with ROI and security assessed at every step. We are looking for a senior engineer who owns this end to end - a hands-on builder who also carries the senior function: setting the technical strategy, making the architecture calls, and being the person leadership trusts on internal AI.This is not a pure IC build role and not a pure strategy role. You will personally build the flagship systems - production agents, the context layer, the evaluation and safety stack - while also deciding what gets built, in what order, and to what standard. You will work across R&D, IT, Security, BizOps, Customer, Sales, Marketing, People, and Finance, with the AI Transformation Officer owning the business portfolio.What you'll do - strategy and senior functionOwn the technical strategy for Pentera's internal AI transformation: target architecture, 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.Manage Pentera's AI- Champions Community.Continuously evaluate models, vendors, and frameworks, and keep Pentera agile.What you'll do - hands-on buildPersonally 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.