Senior Director of Engineering, Developer and Agent Experience

Toast is seeking a Senior Director of Engineering (Head of Developer & Agent Experience) to 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: the leader actively designs and builds systems, reviews architecture, and contributes to core platform direction. The role is focused on systemizing AI across the software development lifecycle (SDLC) and product development lifecycle (PDLC). Remote US. Salary: Zone A $314,000–$502,000; Zone B $273,000–$437,000; Zone C $246,000–$394,000.

• Deep technical proficiency in applied AI and agentic architectures, serving as the definitive internal authority. • 15+ years in software engineering, including senior leadership roles, with a background in high-velocity engineering organizations. • Proven experience building and scaling developer platforms, internal engineering systems, CI/CD, build systems, or platform tooling. • Ability to design end-to-end workflows and systemic, long-term platforms rather than point solutions or developer tooling. • Familiarity with prompt engineering, context design, developer-facing API/platform design, and usage-based cost models/platform governance. • Proven capability to drive organization-wide adoption of new tools, workflows, playbooks, and structural standards. • Experience operating inside real compliance constraints — PCI, SOX, or equivalent.