Principal Software Engineer - AI Foundations

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. ## What you'll do ) - Define and drive the technical architecture for AI Foundations platform, spanning backend services, frontend tooling, and third party integrations - Lead full-stack design and delivery across the LLM proxy, AI key management, observability pipelines, and internal plugin marketplace - Architect and deliver autonomous agents and MCP services that participate in the software development lifecycle - Set and uphold engineering standards across the team: code quality, system design, testing, and operational practices - Mentor and technically lead engineers across all levels through design reviews, code reviews, and pairing - Partner with product and platform leadership to shape the AI Foundations roadmap and translate strategy into executable technical plans - Collaborate closely with designers and product teams to translate UX concepts into polished, production-ready frontend experiences - Serve as a key technical voice in cross-team discussions, representing AI Foundations in architecture decisions across Toast engineering What you'll need to thrive ( ## What you'll bring ) - 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 - Proven ability to mentor engineers and raise the technical bar of a team through standards, reviews, and hands-on guidance - 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, tool use patterns, or agentic frameworks - Strong foundation in modern backend (Java, Kotlin, or similar) and frontend (TypeScript, React, or similar) technologies, with demonstrated experience building user-facing product interfaces - Comfort with a rapidly changing technical landscape and a bias towards action over analysis paralysis What will make 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) **This role requires a minimum of two days per week in our Dublin office** 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 …

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