Senior Director of Engineering, Developer and Agent Experience

Job not on LinkedIn

🔥 1 hour ago

🍂 Massachusetts – Remote

🍂 Massachusetts – Remote

💵 $314k - $502k / year

⏰ Full Time

🟠 Senior

🤝 Developer Relations (DevRel)

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Toast

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

Founded 2013

🍽️ Food & Beverage

💼 Consulting

📦 Logistics

Food & Beverage • Consulting • Logistics

Toast is a technology company that specializes in providing integrated software and hardware solutions for the restaurant industry. Their offerings include a comprehensive restaurant management platform that features point of sale (POS) systems, payment processing, online ordering, payroll management, and various operational tools designed to streamline restaurant operations. Toast's platform is tailored to meet the needs of diverse restaurant types, including quick service, full service, fast casual, fine dining, cafes, and food trucks. They also provide resources like industry insights and educational materials to support restaurant success.

📋 Description

• 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.

🏖️ Benefits

• Competitive compensation and benefits programs • Health insurance • Retirement plans • Paid time off • Flexible work arrangements • Professional development opportunities