Senior Product Designer

Toast • Boston, MA

2d • Hybrid

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.
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.
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 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.

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.

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.

Benefits

• 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.
• Our Total Rewards Philosophy 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.
• We Thrive Together We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees