Senior Conversational AI UX Designer

2 hours, 45 minutes ago
Full-time
Senior
Artificial Intelligence and Machine Learning
Toast

Toast

Toast is an all-in-one platform for restaurants, offering tableside ordering, online ordering, and labor management to empower businesses in the food service industry.

Hotels, Restaurants & Leisure
1K-5K
Founded 2012

Description

  • Design end-to-end AI-first experiences for PLG and AI CSM agent products across the customer journey.
  • Create intuitive user experiences for AI-powered products, including conversational interfaces, agentic workflows, and LLM-driven systems.
  • Develop and evaluate conversational flows for chat and voice experiences.
  • Shape prompt engineering and context engineering approaches to influence model behavior and iterate on system prompts.
  • Design orchestration patterns for how the CSM agent coordinates with Toast IQ and other specialist agents.
  • Build rapid prototypes and working artifacts using AI-native tools and Figma for customer testing.
  • Define and track AI-specific success metrics such as task completion, error recovery, and output edit distance.
  • Use conversation logs and model behavior data to inform design iterations and improvements.
  • Collaborate with PMs, ML engineers, data scientists, and engineers to align model capabilities with user-facing design decisions.
  • Create and manage evaluation frameworks for AI outputs and advocate for human-centered guardrails.

Requirements

  • Experience designing AI-powered products, including conversational interfaces, agentic workflows, or LLM-driven systems.
  • Experience with conversational design for chat and voice interfaces, including LLM-based dialogue behavior.
  • Experience applying prompt engineering and context engineering techniques.
  • Ability to design for generative AI challenges such as probabilistic outputs, uncertainty, hallucination mitigation, and graceful failure states.
  • Demonstrated fluency with AI-native prototyping tools such as Cursor, v0, and Replit, plus Figma.
  • Ability to generate working prototypes and artifacts for customer testing.
  • Experience defining data-driven success metrics and using logs or model behavior data to guide design decisions.
  • Working understanding of AI infrastructure concepts such as RAG pipelines, tool use, Model Context Protocol (MCP), and agent orchestration patterns.
  • Experience building or designing AI agents, customer support tools, voice AI, or PLG/onboarding funnels is a strong plus.
  • First-hand experience and enthusiasm for the restaurant industry is highly valued.

Benefits

  • Base salary range of $159,000-$254,000 USD for Zone A, $138,000-$221,000 USD for Zone B, and $125,000-$200,000 USD for Zone C.
  • Total rewards include cash compensation such as overtime and eligible bonus/commissions, plus equity.
  • Competitive compensation and benefits programs.
  • Flexible total rewards designed to support a healthy lifestyle and changing employee needs.
  • Hybrid work model with in-person collaboration and flexibility.
  • Accessible and inclusive hiring process with reasonable accommodations available.
  • Commitment to diversity, equity, and inclusion in the workplace.

Interested in this position?

Apply directly on the company website

Apply Now

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