Conversational AI UX Designer

About Toast Our focus is on building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. And because our technology is purpose-built for restaurants, by restaurant people, restaurants can trust that we’ll deliver on their needs for today while investing in experiences that will power their restaurant of the future. We build experiences that help make operating and growing a restaurant and delighting guests easier and scalable. It’s why tens of thousands of restaurant locations love Toast.   About The Roll* Toast Inc. is seeking a Product Designer (UX/UI) to drive experimentation and execution for chat and voice AI within our customer support ecosystem . You will design end-to-end AI-first experiences on surfaces like our customer-facing web and native mobile experiences. These platforms are key to providing our customers with seamless access to support channels such as live chat and phone, as well as self-service tools for troubleshooting hardware, checking system and ticket status, and accessing our expansive knowledge base. You will play a critical role in shaping how Toast supports its customers, ensuring our solutions are simple, intuitive, and highly functional. Your work will directly impact our customers’ ability to find solutions quickly, feel supported, and stay focused on running their businesses. You will collaborate with cross-functional teams and work directly with other conversational AI and product designers to create experiences that reflect Toast’s commitment to excellent customer service and innovation in the restaurant technology space. The right ingredients* (Requirements) Conversational design: You’ll develop and evaluate conversational flows across chat and voice interfaces, applying knowledge of how LLM-driven dialogue differs from rule-based or scripted systems. You will apply prompt engineering and context engineering techniques to shape AI model behavior, test outputs, and iterate on system prompts as design artifacts. You’ll also design for the unique challenges of generative AI: probabilistic outputs, model uncertainty, hallucination mitigation, and graceful failure states. Prototyping: You’ll demonstrate fluency with AI-native prototyping tools such as Cursor, v0, Replit etc alongside Figma for rapid concept exploration and functional prototypes. You must be able to generate working artifacts that the team can test with real customers. Data-driven: You’ll track and design experiences that move support-specific success metrics  including task completion, error recovery and use conversation logs and model behavior data to drive design iteration. Experimentation, learning & growth: A large part of your role will be running experiments to improve voice and chat AI’s performance. You’ll need to be excited about continuous learning and maintaining a working understanding of AI infrastructure concepts relevant to design, including our AI Assistant (Toast IQ), platform tool use, Model Context Protocol (MCP), and agent orchestration patterns. Quality: You’ll create and manage evals for AI outputs that help drive quality from a customer experience lens, distinguishing between model limitations and design failures, and advocate for human-centered guardrails in AI system design. Pro-research: You have the ability and desire to conduct and coordinate user research and usability testing to inform design decisions. You also use data, analytics and conversation history to dig in, find opportunities and solve problems for our customers. Collaboration: Strong communication skills and ability to work effectively in cross-functional teams, including product managers, engineers, and other stakeholders to define design requirements and align on goals.   Special Sauce* (Nonessential Skills/Nice to Haves) Restaurant Passion: First hand experience and enthusiasm for the restaurant industry and designing impactful solutions for its unique challenges is something we value highly Past Experiences: Experience and passion for designing at the very edge of technology for modern customer support experiences (AI chat bots, agent tooling, voice AI experiences etc) is a HUGE plus.   Fluency with tools: Any experience working inside of AI-native platforms for customer support like Intercom, Giga, Sierra etc is a plus.    About You You are a dynamic leader with proven impact in previous roles who is ready and willing to take on new challenges! You’re excited to join the remotely distributed group of product designers, user researchers, design ops leaders, and product managers that compose the Toast Design team. You embody the tenets that drive Toast’s Design practice:    You have a founder’s mentality and exhibit ownership of outcomes over outputs. You own the quality and outcomes associated with full end to end experiences. You lift others up and recogniz