[Remote] Principal Product Designer, Onboarding

Note: The job is a remote job and is open to candidates in USA. Toast is hiring a Principal Product Designer for Toast Onboarding to shape how restaurants set up and adopt Toast products and features. The role will establish onboarding design patterns across R&D and partner with onboarding, customer success, support, and go-to-market teams to create cohesive experiences balancing self-service, AI guidance, and human support.

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
• 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

Skills

• 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
• 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
• 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
• 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
• You build conviction within product, engineering, and cross-functional leadership teams
• You define new patterns and drive adoption of them beyond your immediate team
• You understand the business context behind onboarding, activation rates, time-to-value, feature discovery, customer success outcomes
• You design with outcomes in mind
• 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
• You're comfortable working with Claude, V0, Replit, and similar tools

Benefits

• US (remote), Boston (hybrid), or New York (hybrid)
• We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs.

Company Overview

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