Senior Director of Engineering, Toast
Developer and Agent Experience
$246-502k
Salary dependent on candidates location
Point of sale and management system for restaurants
Posted today
Point of sale and management system for restaurants
1001+ employees
Posted today
$246-502k
Salary dependent on candidates location
1001+ employees
Company mission
Toast's mission is to enrich the food experience for all.
Role
Who you are
- 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
What the job involves
- 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
- 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
Our take
Running a restaurant means managing a stressful set of elements, all needing to work together seamlessly to create a good experience for diners. Toast helps to streamline processes and puts an end to piles of paperwork by providing a platform whereby tableside ordering, menu modifications, labour management, payroll, and more are all housed in one system that can run from a tablet.
Toast offers restaurant-grade hardware and cloud-based, customisable payment solutions to serve clients from startup through to growth phase, as well as a service for established restaurants. By combining all the digital services a restaurant might need, the platform can act as a comprehensive solution for restaurants of any size, saving restaurateurs from having to invest in a range of technologies.
Toast has over 70,000 restaurants on its books, from food trucks to national brands, and its mobile ordering and payment solutions have made it a recognized brand for consumers. The company's IPO in 2021 saw it valued at over $30 billion, and since then, it has added more features to its product suite, including wholesale and catering order tools. Toast has proven its place as an indispensable player in the restaurant space.
Freddie
Company Specialist at Welcome to the Jungle
Insights
28% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Feb 2020
$400m
SERIES F
Apr 2019
$250m
SERIES E
Total funding: $899m
Company benefits
- Peer and company recognition programs
- Unlimited Vacation
- Sabbatical opportunity after five years
- Professional Development Reimbursement Program
- Commitment to Employee Wellness through resources such as a quarterly Wellness Stipend
- Various peer and company recognition programs
- 401(k) and matching
- Medical, Dental, & Vision Coverage
- Mental Health Benefits
- Subsidized backup childcare
Company HQ
Fort Point Channel Landmark District, Boston, MA
Leadership
Steve Fredette
(Co-Founder & President)They studied at MIT before co-founding Klick Mobile in 2009 and spending almost 7 years at Endeca. They left their Management role in June 2012 having co-founded Toast in May.
Aman Narang
(Co-Founder & CEO)Having studied Computer Science at MIT, they worked at Endeca for 5 years. They moved from working as Product Manager to work full-time as President of Toast in 2013, having co-founded it the previous year.
Jonathan Grimm
(Co-Founder & CTO)They also studied Computer Science at MIT before working as an Engineer for Endeca for over 4 years. They worked at Oracle for 5 months prior to co-founding Toast in May 2012.
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