Senior Director of Engineering, Developer and Agent Experience

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. As the Head of Developer & Agent Experience, you will lead the development of Toast’s AI-native engineering operating system—transforming how software is built from idea to production. This is a hands-on leadership role. You will actively design and build systems, review architecture, and contribute to core platform direction, rather than operating purely through management layers. This role is focused on systemizing AI across the software development lifecycle (SDLC), and product development lifecycle (PDLC) to turn tool usage into a scalable, standardized, and high-leverage engineering system. Partnering closely with senior technical leaders across Product, Engineering, and Design, you will define and deliver the platforms, workflows, and guardrails that enable teams to move from specification to code, test, and deployment with AI embedded at every step. A day in the life (Responsibilities)  Define and deliver the core platform enabling AI-native development, including the model access layer (LLMs, routing, governance), agent orchestration systems (code, test, review, deploy), prompt/specification frameworks, coding harnesses and an internal AI marketplace Design and implement AI-driven development systems that convert PRDs and design specs into executable workflows, enabling the a