Staff 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.

AI Foundations is Toast's internal platform team for AI. We build the infrastructure, governance, and developer tooling that makes AI a reliable, scalable force multiplier across the entire product development lifecycle. Our products include the LLM Proxy, AI Key Management, Observability pipelines, the Claude Plugin Marketplace, and autonomous agents that participate directly in the software development lifecycle.

As a Staff Software Engineer on this team, you'll shape the foundation others build on: from the LLM Proxy that routes all internal AI traffic, to autonomous agents that participate directly in the software development lifecycle. If you want to work at the frontier of AI infrastructure and see your work amplify hundreds of engineers across a fast-growing company, this is the role.

• →Design, build, and ship core AI platform infrastructure, including the LLM proxy, AI key management, and observability pipelines powering Toast's internal AI ecosystem
• →Architect and deliver autonomous agents that participate in the SDLC, including the AI Review GitHub App and Developer Platform MCP integrations
• →Build on and help maintain the internal plugin marketplace, developing plugins that encode Toast's architectural standards, PR patterns, and quality practices directly into AI assistant behavior
• →Lead technical design and implementation of MCP (Model Context Protocol) services and no-code service templates that accelerate AI-powered development across Toast
• →Drive adoption of agentic development practices through tooling, internal evangelism, and hands-on enablement across engineering teams
• →Mentor engineers through code reviews, architecture discussions, and pairing sessions
• →Partner with product and platform teams to define and expand the AI Foundations roadmap

• 8+ years of experience designing and implementing scalable backend services
• Strong foundation in Java, Kotlin, or another object-oriented language, with experience building scalable backend services
• Demonstrated experience building, deploying, or operating LLM-powered agents or AI-assisted developer tooling
• Deep familiarity with AI coding assistants (e.g., Claude Code, Cursor, GitHub Copilot) and the ability to extend them through custom plugins, skills, or hooks
• Hands-on experience with MCP (Model Context Protocol), tool use patterns, or agentic frameworks
• Strong prompt engineering skills and intuition for how LLM behavior changes with context, instructions, and tool definitions
• Proven track record of technical leadership: influencing architecture decisions, setting quality standards, and mentoring peers
• Experience with distributed systems, API design, and cloud-native infrastructure
• Strong customer empathy and the ability to translate developer pain points into platform solutions

• 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, internal tooling, or API gateways
• Familiarity with observability tooling for AI/LLM systems (e.g., Langfuse, DataDog)

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.

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: https://careers.toasttab.com/locations-toast.

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 candidateaccommodations@toasttab.com.

------

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.