Principal Software Engineer - AI Pod

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.toastta