Principal Software Engineer

• Your mission is to lead the architectural design, technical execution, and implementation of AI agents and infrastructure for Toast’s Team area within our FinTech line of business
• The Team area is a mission-critical space on which our restaurants rely to manage their staff and optimize their labor
• As a Principal Engineer, you will serve as a key technical leader in the group, driving modern architectural patterns—including spec-driven development and agentic workflows—to deliver high-impact software
• Define and execute the technical architecture for AI agents within the Team domain, ensuring systems are scalable, reliable, and secure
• Partner closely with Engineering Managers and Product Managers to translate product roadmaps into robust technical designs and deliverables
• Maintain a strong hands-on presence, writing code, prototyping new patterns, and resolving complex technical bottlenecks under load
• Collaborate with Principal and Senior Principal Engineers across Toast to align on best practices, agent patterns, and spec-driven development paradigms
• Guide, mentor, and elevate engineers within the Team area, fostering a culture of technical excellence and continuous learning

Benefits

• Peer and company recognition programs
• Unlimited Vacation
• Sabbatical opportunity after five years
• Professional Development Reimbursement Program
• Commitment to Employee Wellness through resources such as a quarterly Wellness Stipend
• Various peer and company recognition programs
• 401(k) and matching
• Medical, Dental, & Vision Coverage
• Mental Health Benefits
• Subsidized backup childcare

• Balanced expertise: Ability to design high-level technical solutions on a whiteboard while remaining deeply connected to code-level execution and system performance
• Proven track record of leading complex technical initiatives and delivering robust software architecture from design to production
• Strong enthusiasm for agentic development practices, LLM integration, and modern software paradigms
• 10+ years of experience designing, building, and operating highly scalable, mission-critical distributed systems and SaaS products (ideally AWS-hosted)
• Effective communication: Ability to articulate complex technical ideas clearly to both technical peers and product leadership
• Experience building systems that leverage LLMs, autonomous agents, or ML models
• Hands-on experience with enterprise integration frameworks (e.g., Apache Camel) or event-driven messaging systems (e.g., Apache Pulsar)
• Experience establishing robust CI/CD, testing, and deployment strategies for complex systems
• Domain knowledge in workforce management or restaurant operations