Senior 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 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.

The right ingredients* (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.

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) 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.

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:

1. 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.


2. 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.


3. 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.


4. 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.


5. 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.
   

Our Spread* of Total Rewards

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.

*Bread puns encouraged but not required

We are Toasters

Diversity, Equity, and Inclusion is Baked into our Recipe for Success. At Toast our employees are our secret ingredient. When they are powered to succeed, Toast succeeds. The restaurant industry is one of the most diverse industries. We embrace and are excited by this diversity, believing that only through authenticity, inclusivity, high standards of respect and trust, and leading with humility will we be able to achieve our goals. Baking inclusive principles into our company and diversity into our design provides equitable opportunities for all and enhances our ability to be first in class in all aspects of our industry.

Bready* to make a change? Apply today!

Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com.