Senior Director of Engineering, Developer and Agent Experience

Toast

5d•$246,000 - $502,000•Remote

About The Position

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.

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

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