Senior Product Designer – Toast Retail

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. Toast is making it faster and easier for retailers to get started on Toast: the path from a store's existing product data to a correctly configured, actively selling location. We are seeking a highly skilled, AI-native Senior Product Designer to lead that experience: someone with a strong portfolio, a track record of leading design for complex product areas, a focus on exceptional UI design, and the hands-on ability to build working prototypes with AI tools like Replit, Magic Patterns, or Claude. This role involves designing for the unique needs of a diverse retail customer base, including convenience stores, bottle shops, grocery stores, hybrid models, and beyond. You will lead design for Toast Retail's Experience Platform team, working day to day with product and engineering partners in our Dublin office and the U.S., and reporting to Toast Retail's design leadership in the U.S. Together you will turn product strategy into the setup and onboarding experiences that make retailers feel Toast is built for them. Why This Role Matters A retailer's first 90 days on Toast decide whether they stay. Before a store can sell, thousands of items need clean names, categories, brands, pack sizes, taxes, deposits, age restrictions, and images, and most of that data arrives messy, from another system or a spreadsheet. The experiences you design will decide how quickly a new store goes live, how much of that work Toast can do for them, and whether the people setting up the store, often owners juggling a business that is already open, feel in control or buried in it. You will be Toast Retail's design presence in our Dublin office: the on-site design partner for its product and engineering teams, and part of Toast's wider design community. As a senior designer working across regions and time zones, you will set design direction for your area with a high degree of autonomy: keeping local teams unblocked, making well-informed design and scope tradeoffs within the broader product vision, shaping the roadmap alongside your product and engineering partners, and bringing US-based design, product, and business stakeholders in when direction, customer impact, or strategic choices need broader alignment. A day in the life (Responsibilities) • Lead design for your product area: Take your area from early discovery through shipped UI, set its design direction and quality bar, and connect each workflow to the broader Toast Retail vision. Help shape what the team builds, not only how it looks. • Prototype with AI: Use AI prototyping tools such as Replit, Magic Patterns, or Claude to build working, interactive prototypes with realistic data, so ideas can be tested with customers and engineers before the team commits to them. Use AI across the rest of your practice too, from synthesizing research to exploring concepts, validating outputs carefully and modeling responsible, secure use of AI for the team. • Design AI-first workflows: Identify where AI can materially reduce customer effort, such as importing and cleaning up a store's existing item data, enriching items with brands, images, and attributes, and guiding new retailers through setup. Design just as carefully for when it is unsure: how customers review low-confidence results, correct mistakes, and come to trust the system. • Engage directly with customers: Research with retailers, and with the onboarding and support teams who help them go live, to understand where setup breaks down, and translate those insights into design direction and testable ideas. • Make complex data feel simple: Turn large catalogs, imports, bulk edits, and errors into experiences that are clear, forgiving, and fast, on desktop and in the hand. • Collaborate early and often: Partner closely with product managers and engineers in Dublin and the U.S., sharing work early, communicating design rationale clearly, and helping the team make good decisions quickly. • Raise the bar for the team: Deliver pixel-perfect UI, apply and extend the Toast design system with good judgment, mentor other designers, and contribute to the quality and practices of the wider Retail design team. You will be a central collaborator within a cross-functional team of designers, product managers, and engineers, designing sophisticated, retail-native capabilities such as: • Onboarding for new retailers, from first data import to a store that is ready to sell • AI-assisted setup, including agents that import, clean up, and enrich a store's item data • Bulk item creation, editing, and correction at the scale of tens of thousands of products • Retail item details such as brand, pack and unit, tax, deposit and age rules, images, and category-specific attributes, like a wine's vintage and region • Tools that help Toast's onboarding teams set up and support retailers • Reusable setup and interaction patterns that make Toast feel built for retail across products Team and Impact You will join a passionate team dedicated to driving the consistency, integrity, strategy, and vision of Toast's next-generation product experience. The team is co-located in Dublin and the U.S. While the role sits in the Retail line of business, the patterns you establish will be reused across Toast Retail's products and help scale Toast's retail offering as Toast expands into new markets. A key part of this work involves building on Toast's investments in AI-assisted onboarding. You will partner closely with the Dublin engineering team that is already building and shipping AI tools that help Toast's onboarding teams set up retail customers. What you'll need to thrive (Requirements) • Experience & Leadership (5+ years): Demonstrated ability to lead design for a complex product area end to end, craft compelling visual experiences, and connect