Senior Director of Engineering, Developer and Agent Experience

About the role

As the Head of Developer & Agent Experience at Toast, 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 where you will actively design and build systems, review architecture, and contribute 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

Pay

The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.

• Zone A: $314,000—$502,000 USD
• Zone B: $273,000—$437,000 USD
• Zone C: $246,000—$394,000 USD

Schedule

Our approach to hybrid working fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community, regardless of location.