Senior Software Engineer, Onboarding

Senior Software Engineer, Onboarding Location: Remote, US About Toast Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. Are you bready* for a change? A restaurant owner switching to Toast shows up with a pile of paperwork from their old POS, a bank account to verify, and an opening date that isn't moving. Getting them to running service on Toast is the job of the Onboarding & Activation team, and increasingly of the agents we build to do that work for them. We've shipped our first agent, and it's the start of many. Onboarding is a broad set of deep problems (menus, payments, hardware, payroll, staff), each a candidate for an agent that acts across Toast's systems instead of answering questions about them. It's a company priority: lower cost to onboard, less support volume, higher NPS, and far better visibility into how each restaurant is set up. You'll define how these agents get built: what they're allowed to do, how they recover when something goes wrong, and when they hand off to a person. Success means more than going live. It's how well the restaurant was set up, how ready they were for day one, and how much help they needed afterward. Those signals are real but delayed and noisy, and building evaluations that tell us an agent did the right thing, not just a plausible thing, before the restaurant opens is one of the harder problems here. About this roll* (Responsibilities) • Design and build AI agents that complete onboarding work for restaurants, from tool design and permissions through evaluation, guardrails, and production monitoring. • Turn the Toast systems onboarding touches, including payments, payroll, hardware, menus, and appointments, into reliable tools agents can use to read state and take action. • Own the onboarding backend and reshape it for agent-driven flows that aren't known in advance. • Build evaluation and measurement so every launch is tied to real outcomes: setup quality, readiness to go live, and how much help restaurants need after launch. • Ship full-stack changes in the restaurant-facing setup experience when the work calls for it. • Partner with product, design, onboarding operations, and data science to turn onboarding problems into agents and product changes we can test and measure. • Contribute to technical design and architecture, and help set engineering standards for AI-powered systems across the teams that contribute to onboarding. • Mentor other engineers through code review, pairing, and by sharing how you build with AI. Do you have the right ingredients*? (Requirements) • 5+ years of software engineering experience building and operating production backend systems in Kotlin, Java, or another object-oriented language. • Experience building on LLMs where the model takes real actions through tools, in production or in serious side projects, with a practical grasp of nondeterminism, evaluation, and cost. • Proven ability to own outcomes end to end: design, launch, rollout monitoring, measurement, and iteration. • A product-minded builder who forms a point of view on what to build, not just how, and works across PM, design, and operations rather than executing tickets. • You use AI coding tools like Claude Code as a core part of how you work, and you've helped others get better with them. Special sauce* (Nice to haves) • Experience with customer onboarding, activation, growth, or workflow/task orchestration systems. • Experience with experimentation or funnel analysis, and a working sense of when to believe a metric. • Enough full-stack experience (React and TypeScript preferred) to ship front-end changes when needed. • Experience with event-driven archi