Staff Software Engineer, Applied AI

Toast is looking for a Staff Software Engineer to join our New Ventures team and help build a new AI-powered product. You’ll tackle problems without an established playbook, make decisions that shape the product, and take ideas from early experiments to capabilities customers can depend on.

This is a role for someone who enjoys both exploring what’s possible and making it work in practice. You’ll build and evolve AI-powered systems, work closely with Product and Design, and partner across Toast to deliver new customer experiences. Your impact will come from the software you build, the technical direction you establish, and your ability to turn uncertainty into progress.

About this roll* (Responsibilities)

• Own the design and delivery of core capabilities for a new AI-powered product, from exploring an approach to launching it and improving it with customer feedback.
• Turn ambiguous product problems into working software. Build prototypes to test assumptions, identify what matters, and make deliberate decisions about what to evolve, rebuild, or stop.
• Build LLM-powered workflows and agents, deciding where to use model reasoning, tools, or conventional software to achieve reliable outcomes.
• Define what good performance means for AI-powered capabilities. Build evaluations around realistic customer tasks, investigate failures, and use the results to guide improvements.
• Shape the backend services, APIs, and data models that let the product evolve quickly. Anticipate scaling needs while keeping early solutions simple.
• Partner with teams across Toast to deliver integrations, resolve technical dependencies, and establish clear ownership of shared capabilities.
• Work closely with Product and Design to make tradeoffs across customer experience, technical feasibility, reliability, latency, and cost.
• Stay close to the code and production behavior: implement critical components, debug difficult problems, and own successful rollouts.
• Raise the team’s effectiveness through technical feedback, mentoring, and thoughtful use of AI coding assistants and agents across development, testing, and debugging.

Do you have the right ingredients*? (Requirements)

• 8–12 years of experience building backend services, APIs, and production software.
• Extensive experience with an object-oriented language such as Java or Kotlin, with a deep understanding of testing, software design, and engineering best practices.
• Experience building and scaling distributed systems and cloud-native services on AWS.
• Hands-on experience shipping and operating LLM-powered applications, including agents that use tools or APIs to complete multi-step tasks.
• Experience designing and implementing evaluations for AI systems, investigating failures, and using results to improve system behavior.
• Demonstrated proficiency using AI coding assistants and coding agents throughout the software development lifecycle, with clear practices for reviewing, testing, and validating their output.
• Experience balancing delivery speed with platform stability, security, and reliability, particularly when requirements are evolving.
• Experience influencing technical direction across multiple teams, with excellent communication skills on complex technical topics.
• Strong customer focus, a collaborative approach, and a track record of taking ownership in ambiguous environments.

Bonus Ingredients (Nice to Have)

• Experience building early-stage products and scaling them as customer adoption and usage grow.
• Experience designing and building GraphQL APIs.
• Comfort working across the stack.

We are hiring individuals with a wide range of experience, so if you have more or less than these exact requirements, please