Head of AI

Highlight is building a shared intelligence layer for the modern workforce. Highlight unifies context across every person and tool on your team, seamlessly bridging information silos. It evolves with your organization to proactively route knowledge and reliably automate workflows. The Role We're hiring a Head of AI Engineering to lead and scale our ML and AI efforts as we build the engine that powers Highlight. You'll own the architecture, quality, and roadmap for how we ingest, model, and surface context, starting from data pipelines and evals to the context graph that makes our system truly useful. This is a hands-on leadership role: you'll write code, set technical direction, mentor engineers, and collaborate closely with Backend and Product teams to ship features that feel like magic. We're looking for a technical leader who's equally comfortable diving into model architectures and rallying a team around ambitious goals. You have deep expertise in LLMs, knowledge systems, and re