Senior Director of Engineering, Developer and Agent Experience

Toast is a technology company focused on helping restaurants and local businesses succeed in a digital world. 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 while actively designing and building systems, reviewing architecture, and contributing to core platform direction.

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 automated generation of code, tests, documentation, and infrastructure
• Re-architect the developer experience across the inner loop (local development, testing, iteration) and outer loop (CI/CD, deployment, release) to reduce friction in PR creation, code reviews, and validation
• Partner with Engineering, Product and Design leaders to transition individual AI tool usage into standardized workflows, establishing tooling defaults, playbooks, and training to ensure active AI usage across R&D
• Define and monitor the north-star metrics and own the dashboards and feedback loops that turn them into action. This role owns model-cost optimization, routing, and governance, while org-wide spend and scorecard reporting sits with Technical Operations
• Build and lead a focused organization specialized in AI platform engineering, agent systems, automation and developer experience integration
• Own the human-facing developer experience alongside the agent-facing one: local development and inner-loop tooling, the Developer Portal and service catalog, core libraries and service templates, schema-first tooling, and authoritative service metadata — and establish a durable operating contract with Release Engineering for the delivery machinery underneath
• Architect for optionality rather than lock-in: keep the harness layer model-agnostic, evaluate open-weight and self-hosted options, and ensure marketplace skills, plugins, and agents remain portable across models and vendors

Requirements:

• You must possess 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 across a large, diverse R&D ecosystem
• Experience operating inside real compliance constraints — PCI, SOX, or equivalent — and a track record of reducing scope or negotiating defensible exceptions rather than accepting them as permanent blockers