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.
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
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
Preferred Qualifications
- 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)
Benefits
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.
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.