Senior Director of Engineering, Developer and Agent Experience

About the role

Toast is building an AI‑native engineering operating system that reshapes how software moves from idea to production. As the Senior Director of Engineering for Developer and Agent Experience, you will lead the design, implementation, and scaling of AI‑driven development platforms while staying hands‑on in architecture and code.

Key responsibilities

• Define and deliver the core AI‑native platform, including model access layers, agent orchestration, prompt frameworks, coding harnesses, and an internal AI marketplace.
• Design systems that translate product requirements and design specs into automated workflows for code, tests, documentation, and infrastructure generation.
• Re‑architect the developer experience across inner‑loop (local development, testing) and outer‑loop (CI/CD, deployment) to reduce friction in pull‑request creation, code review, and validation.
• Partner with Product, Engineering, and Design leaders to standardize AI tool usage, create tooling defaults, playbooks, and training.
• Own north‑star metrics, dashboards, and feedback loops; manage model‑cost optimization, routing, governance, and org‑wide spend reporting.
• Build and lead a specialized AI platform engineering organization focused on automation and developer experience integration.
• Maintain both human‑facing and agent‑facing developer experiences, including developer portals, service catalogs, core libraries, and schema‑first tooling.
• Architect for model‑agnostic optionality, evaluating open‑weight and self‑hosted options to keep the platform portable across vendors.

Required profile

Required skills

• AI‑native development platforms
• Large language model (LLM) integration and governance
• CI/CD pipeline design and optimization
• Release engineering and deployment automation