Principal Product Designer, Onboarding

Responsibilities

• 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.
• 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.

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