Senior Principal Software Engineer - AI Pod at Toast

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 [Upgrade to PRO to see link] How Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: [Upgrade to PRO to see link] Diversity, Equity, and Inclusion is Baked into our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences. We Thrive Together We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: [Upgrade to PRO to see link] Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [Upgrade to PRO to see contact]. ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.