Remote AI Platform Engineering Lead

United States Digital Space LLC; United States; Hybrid; USD 314,000 - 502,000; Full time

Job summary

Toast, Inc. is seeking a Head of Developer & Agent Experience to lead the development of the company’s AI-native engineering operating system.

This is a hands‑on leadership role responsible for designing and building systems, reviewing architecture, and guiding core platform direction, not merely management. The role focuses on systemizing AI across the SDLC/PDLC to create scalable, standardized workflows with AI embedded at every step.

Qualifications

• Deep technical proficiency in applied AI and agentic architectures.
• 15+ years in software engineering, including senior leadership roles.
• Experience building and scaling developer platforms, internal engineering systems, CI/CD, and platform tooling.
• Ability to design end‑to‑end workflows and long‑term platforms, not just point solutions.
• Familiarity with prompt engineering, context design, and usage‑based cost models.
• Proven ability to drive organization‑wide adoption of new tools and standards across a large R&D ecosystem.
• Experience operating inside compliance constraints (PCI, SOX) and negotiating defensible exceptions.

Responsibilities

• Define and deliver the core platform enabling AI-native development and agent orchestration systems.
• Design and implement AI-driven development systems transforming PRDs into executable workflows.
• Re-architect developer experience across inner and outer loops to reduce PR and code review friction.
• Partner with leaders to standardize workflows and tooling for active AI usage across R&D.
• Define and monitor north-star metrics; own dashboards and cost/governance areas.

Skills

AI architecture

Engineering leadership

Developer platforms

CI/CD tooling

Cost governance

Prompt engineering

Compliance (PCI/SOX)

Team collaboration

Tools

CI/CD tooling

Platform tooling

Code review systems

Job description

Toast, Inc. is seeking a Head of Developer & Agent Experience to lead the development of the company’s AI-native engineering operating system.

This is a hands‑on leadership role responsible for designing and building systems, reviewing architecture, and guiding core platform direction, not merely management. The role focuses on systemizing AI across the SDLC/PDLC to create scalable, standardized workflows with AI embedded at every step.