Founding AI Engineer

Founding AI EngineerLocation: Bay Area, CaliforniaCompany: Pilotcrew AIExperience: Early-stage startup experience (founder) with exposure to 0→1 or 1→10.Masters with 4-5 years of experience OR Phd with 1-2 years of experienceAbout PilotCrewPilotCrew is building the evaluation and optimization infrastructure for AI agents. As teams move agents into production, they struggle to measure whether an agent works, understand why it fails, and improve it systematically. We build the layer that makes agents measurable, debuggable, and better over time -across our Agent Builder, Agent Optimizer, and Observability products.We're an early-stage team with real customer traction, and we're growing our AI team.The RoleWe're looking for a strong AI engineer to drive the development of the AI systems at the core of our platform, working directly with the CEO. You'll design and build our agent evaluation and optimization capabilities, make the key technical and architecture decisions, and stay hands-on shipping in production. As the team grows, you'll help shape how we build and who we bring on.This is not a junior or narrow role. If you haven't yet been the primary owner of an AI system, this one isn't the right fit -but we'd still love to keep in touch as we grow.What you'll ownThe AI systems across Agent Builder, Optimizer, and Observability -the architecture and the build.The key technical decisions that determine how we scale.Shipping -you set the bar by staying deep in the code.Helping grow the engineering team as we scale, and raising the bar for who joins.Working directly with the CEO and with customers to turn hard problems into product.What we're looking for (non-negotiables)You've been the primary owner of an AI/ML or LLM system in production -not just a contributor. You can point to it and walk us through every hard decision.Deep, current expertise in LLMs and AI agents - how they're built, evaluated, and made reliable at scale.Strong systems and software engineering - you've built things that held up under real load.Drive and judgment - you take total ownership and raise the bar around you.A degree in CS / ML or a related field, or equivalent depth proven through what you've built. We care about demonstrated excellence, not the credential.Strongly preferredDirect experience with agent evaluation, LLM evaluation, or ML observability / experimentation tooling.A background that pairs research depth with shipping real products people pay for.Externally validated work -widely used open source, systems at scale, or strong publications.Prior founding or early-stage experience.