Senior Designer

Toast • Boston, MA

1d

About The Position

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. 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.

Requirements

• 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
• Collaboration: 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.

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) or for product led growth and marketing (building funnels, driving product onboarding adoption and activation etc) is a HUGE plus.
• Building agents: As a design team, we’re forward thinking and we’re all learning what it means to build towards an agentic world for our customers. Demonstrated curiosity or ability to build AI agents is also a huge plus.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed