Toast · 1 day ago
Senior Director of Engineering, Developer and Agent Experience
Toast creates technology that helps restaurants and local businesses succeed in a digital world. The Senior Director of Engineering will lead the development of Toast’s AI-native engineering operating system, building platforms, workflows, and guardrails that embed AI across the software and product development lifecycles. The role also leads developer and agent experience, organization-wide AI adoption, platform governance, and a specialized engineering organization.
LogisticsPaymentsRetailFood and BeverageSaaSDeliveryFood DeliveryPoint of SaleRestaurants
Comp. & BenefitsH1B Sponsor Likely
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
Qualification
Required
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
Cash compensation (overtime, bonus/commissions if eligible)
Equity
Benefits
The total rewards package provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs.
We provide AI tools across all disciplines, from Engineering and Product to Sales and Support.
Hybrid work model
Company
Toast
Point-of-sale platform for restaurants and retailers.
H1B Sponsorship
Toast has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
70%
Represents job field similar to this job
Engineering and Development
Accounting and Finance
Product Management
Management and Executive
Creatives and Design
Customer Service and Support
Marketing
Legal and Compliance
Trends of Total Sponsorships
*2026 (14)
2025 (26)
2024 (32)
2023 (39)
2022 (66)
2021 (29)
2020 (17)
Funding
Current Stage
Public CompanyTotal Funding
$966.21MKey Investors
12 West CapitalBessemer Venture Partners,Greenoaks,Tiger Global Management,TPGTCV,Tiger Global Management
2022-01-21Post Ipo Equity· $4.26M
2021-09-22IPO
2020-11-23Secondary Market· $60M
Leadership Team
Aman Narang
CEO and Co-Founder
Steve Fredette
Co-founder and President
Recent News
2026-09-04
The Motley Fool
2026-08-28
Company data provided by crunchbase