Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. Because our technology is purpose-built for restaurants, by restaurant people - and increasingly shaped by AI in both what we build and how we build - restaurants can trust that we'll deliver on their needs for today while investing in the experiences that will power their restaurant of the future.

An AI pod is Toast's AI-native engineering team, a focused pod of specialists who tackle complex, high-impact problems across Toast's product and platform landscape using AI-first approaches.

As Senior Principal Software Engineer and Senior Architect, you will be one of the most senior technologists at Toast, setting the technical vision and architectural direction for the pod while remaining hands-on in its most ambitious work. You'll define how AI-native engineering is done at Toast and spread those patterns across the organization.

A day in the life (Responsibilities)

• Develop and drive the architectural vision for AI Pod, establishing patterns for AI-native development that scale across Toast engineering
• Be an active participant and authoritative technical voice in cross-organizational strategy and architecture discussions
• Lead the pod's most complex, high-impact initiatives from design through production — staying hands-on throughout
• Evolve agentic development practices within the pod and champion their adoption across Toast
• Work closely with other Senior Principal Engineers and technical leaders across Toast to advance the overall architecture
• Mentor and develop technical leadership within the pod and across teams
• Partner with engineering leadership and product to translate strategic goals into executable technical plans

What you'll need to thrive (Requirements)

• 12+ years of experience designing and building highly scalable, mission-critical distributed software systems
• 10+ years of experience building and operating SaaS products, ideally AWS-hosted
• Demonstrated ability to drive architectural vision for a company, line of business, or highly scalable platform
• Deep experience building, deploying, and operating LLM-powered agents and AI-native systems
• 1+ years of hands-on experience using the latest AI coding agents with a strong desire to go all-in on agentic development practices
• Experience with MCP (Model Context Protocol), tool use patterns, or similar agentic integration frameworks
• Ability to move fluidly between whiteboard architecture and understanding the ebb and flow of code under load
• Ability and desire to communicate and influence at the executive level

What will make you stand out

• Experience managing or leading a small engineering team (2-4 engineers)
• Familiarity with A2A (Agent-to-Agent) protocols and multi-agent orchestration patterns
• Experience with machine learning concepts, model evaluation, or ML infrastructure
• Familiarity with observability tooling for AI/LLM systems (e.g., Langfuse, DataDog)

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy 
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

Because our technology is purpose-built for restaurants, by restaurant people - and increasingly shaped by AI in both what we build and how we build - restaurants can trust that we'll deliver on their needs for today while investing in the experiences that will power their restaurant of the future.

An AI pod is Toast's AI-native engineering team, a focused pod of specialists who tackle complex, high-impact problems across Toast's product and platform landscape using AI-first approaches.

As a Principal Software Engineer, you'll work full-stack across ambitious, cross-cutting initiatives, bringing deep technical expertise and architectural judgment to some of the hardest problems at Toast.

A day in the life (Responsibilities)

• Lead full-stack design and delivery of AI-native solutions that address complex, cross-functional problems across Toast
• Drive technical architecture for pod initiatives, from backend services and APIs to frontend and developer-facing interfaces
• Build and integrate LLM-powered agents, tools, and workflows that bring AI capabilities directly into product and platform contexts
• Set and uphold engineering standards within the pod: code quality, system design, testing, and operational practices
• Mentor engineers through design reviews, code reviews, and pairing
• Partner with stakeholders across Toast engineering to define problem scope, align on approach, and deliver outcomes
• Serve as a technical voice in cross-team architecture discussions, connecting pod work to broader Toast engineering patterns

What you'll need to thrive (Requirements)

• 10+ years of experience designing and delivering scalable software systems, with a strong full-stack background spanning backend services and frontend or developer-facing interfaces
• Demonstrated experience leading technical architecture for a platform, product, or engineering team
• Experience building, deploying, or operating LLM-powered agents or AI platform infrastructure
• Familiarity with AI coding assistants (e.g., Claude Code, Cursor, GitHub Copilot) and experience extending them through custom plugins, skills, or hooks
• Experience with MCP (Model Context Protocol), tool use patterns, or similar agentic integration frameworks
• Strong prompt engineering skills and intuition for how LLM behavior responds to context and instructions
• Strong foundation in modern backend (Java, Kotlin, or similar) and frontend (TypeScript, React, or similar) technologies
• A bias towards action and comfort operating in ambiguous, rapidly evolving problem spaces

What will help you stand out

• Familiarity with A2A (Agent-to-Agent) protocols and multi-agent orchestration patterns
• Experience with machine learning concepts, model evaluation, or ML infrastructure
• Experience building developer experience platforms or internal tooling
• Familiarity with observability tooling for AI/LLM systems (e.g., Langfuse, DataDog)

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy 
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.

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