Senior Director of Engineering (Developer and Agent Experience)

Role Overview

Senior Director of Engineering (Developer and Agent Experience) at Toast (Full remote). Lead a hands-on engineering leadership role to build Toast’s AI-native engineering operating system—transforming software delivery from idea to production.

Responsibilities

• Lead development of Toast’s AI-native engineering operating system across the software and product development lifecycles.
• Define and deliver the core AI-native platform, including:
  • Model access layer
  • Agent orchestration systems
  • Prompt/specification frameworks
• Design and build systems, review architecture, and contribute to platform direction.
• Build and lead an AI platform engineering organization focused on:
  • Agent systems
  • Automation
  • Developer experience integration
• Partner with Product, Engineering, and Design leaders to deliver platforms, workflows, and guardrails enabling AI-embedded progression from specification → code → test → deployment.
• Drive organization-wide adoption of new tools, workflows, playbooks, and structural standards.

Requirements

• Proven experience building and scaling developer platforms, internal engineering systems, CI/CD, build systems, or platform tooling.
• 15+ years of software engineering experience, including senior leadership roles in high-velocity engineering organizations.
• Familiarity with prompt engineering, context design, and developer-facing API/platform design.
• Experience with usage-based cost models/platform governance.
• Ability to design end-to-end workflows and systemic, long-term platforms (not point solutions).
• Experience operating within compliance constraints (e.g., PCI, SOX) and reducing scope/negotiating defensible exceptions.
• Deep technical proficiency in applied AI and agentic architectures; act as the definitive internal authority.

Nice to Have

• Experience integrating AI into developer workflows and ensuring guardrails for safe, compliant execution.