Senior Conversational AI UX Designer, Toast

• 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 recognize you don’t have to be a manager to engage and exhibit true leadership. You find formal ways to utilize your personal skill set to uplevel those around you
• You drive action through influence: and appreciate that building trusting and productive relationships with those around you is integral to driving action. You build strong relationships to enact influence throughout the entirety of the area of the business you work within
• You build strong perspectives and guide yourself and your teams to make good decisions quickly and often. You collaboratively make well informed decisions with large scale impact across the area of the business you work within
• You raise the bar:and commit to continually improving the technical skills relevant to your role. You find large scale, creative methods to continually build your skill set

Desirable

• Toast is building agentic partnership with our customers. As a Senior Designer on the Product Led Growth (PLG) and AI Customer Success Manager (CSM) Agent teams, you will design end-to-end AI-first experiences that proactively monitor business health, provide proactive support, and guide restaurant operators toward growth and adoption of Toast products and services
• You will work directly with PMs, Data Scientists and Engineers to shape emerging agentic experiences for Toast customers across their entire journey, from onboarding to location expansion
• Product Design: You will design intuitive user experiences for AI-powered products, including conversational interfaces, agentic workflows, and LLM-driven systems. In this role you will work with other product designers to help ship and maintain customer experiences that involve AI interfaces, agentic product surfaces, or AI-augmented design workflows
• 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
• Orchestration design: You’ll drive work that defines how our CSM agent coordinates with our core agent, Toast IQ, and other "specialist agents" (e.g., Marketing, Payroll, or Guest agents) to execute complex workflows like onboarding to a new product or setting up a new advertising strategy
• Prototyping: Demonstrated 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: Define AI-specific success metrics including task completion, error recovery, and output edit distance, and use conversation logs and model behavior data to drive design iteration
• Learning & growth: Maintain a working understanding of AI infrastructure concepts relevant to design, including RAG pipelines, tool use, Model Context Protocol (MCP), and agent orchestration patterns
• You will collaborate closely with ML engineers and PMs to translate model capabilities and constraints into appropriate user-facing design decisions
• 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