Senior Principal Software Engineer and Senior Architect

About 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.

About the Role

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.

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

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)