Principal Product Designer, Onboarding

Location(s): US (remote), Boston (hybrid), or New York (hybrid) About this role As Principal Product Designer for Toast Onboarding, you will define how restaurants begin and deepen their relationship with Toast, across setup flows, business context configuration, feature adoption, and early product exploration. You'll simplify and reshape how restaurants experience onboarding, from setup flows through business configuration to feature adoption, so the entire journey feels intentional and cohesive. This role requires thinking in systems. You’ll establish the pattern language for how all Toast teams approach onboarding to new products and features, driving adoption of those patterns across R&D (product and engineering). You’ll also partner closely with onboarding, customer success, support, and go-to-market teams to fundamentally reshape how onboarding works, balancing self-service, AI-guided experiences, and human support. You’ll set direction hands-on, in Figma, in prototypes, in critique, and through influence: building the conviction and relationships needed for R&D and cross-functional teams to adopt the patterns you define, not just execute your roadmap. This is a principal-level role for someone who has tackled genuinely complex, multi-stakeholder design problems and thrives on driving transformation. The right ingredients (Requirements) • Onboarding flow expertise: You've shipped end-to-end onboarding or product adoption experiences, setup flows, guided workflows, feature tours, or progressive disclosure patterns. You understand how to sequence information, create aha moments, and reduce friction for new users. • Hands-on systems thinking: Design cohesive experiences across multiple surfaces and interaction modes. You see how one flow connects to another and design for the seams, especially transitions between self-service setup and human-in-the-loop support. • AI-guided experience design: You've designed with AI as a core part of the experience, whether that's guided workflows, intelligent suggestions, or contextual assistance. You understand how to make AI feel like a helpful partner, not a replacement or afterthought. • UI/UX rigor: Strong visual design skills demonstrated through a real portfolio. You can prototype interactions, spec components, and push Figma work that sets a high bar. Your work is both functional and thoughtfully crafted. • Organizational influence at principal level: You build conviction within product, engineering, and cross-functional leadership teams. You define new patterns and drive adoption of them beyond your immediate team. • Pragmatic product thinking: You understand the business context behind onboarding, activation rates, time-to-value, feature discovery, customer success outcomes. You design with outcomes in mind. • Research-driven approach: You design with data by conducting user research, usability testing, and pulling insights from onboarding metrics and customer feedback. You know when to prototype before committing to direction. • Familiarity with AI design tooling: You're comfortable working with Claude, V0, Replit, and similar tools. What we'll ask to see Case studies showing: • An onboarding or product adoption experience you designed from scratch or significantly reshaped—especially one that established a pattern other teams now use • How you navigated complexity across multiple surfaces or interaction modes (web + mobile, or setup + guided workflows + human handoff) • Evidence of organizational influence: how other teams or designers adopted or built on your approach or patterns you defined • Research or testing that informed a key design decision or shifted how the company thought about onboarding • Work that felt cohesive despite touching multiple products o