Principal Product Designer, Toast IQ Core (AI Product Team)

📍 Job Overview

Job Title: Principal Product Designer, Toast IQ Core (AI Product Team)

Company: Toast

Location: Remote, USA

Job Type: Full-time

Category: Product Design / AI Product Development

Date Posted: May 19, 2026

Experience Level: Principal Level (10+ years)

Remote Status: Fully Remote

🚀 Role Summary

• Lead the end-to-end design strategy and execution for Toast's cutting-edge AI assistant product, Toast IQ Core, focusing on interaction design, design systems, and componentry.

• Drive the evolution of AI capabilities, including memory, personalization, agentic workflows, and actionable insights across web, mobile, and hardware platforms.

• Champion user-centered design principles and emerging AI use cases to create intuitive and impactful experiences for restaurant operators.

• Collaborate closely with product management, engineering, data science, and go-to-market teams to define and deliver innovative AI-driven features and premium offerings.

• Mentor junior designers, foster a culture of innovation, and elevate design best practices within the AI product team.

📝 Enhancement Note: This role is categorized under Product Design with a strong emphasis on AI Product Development, given the focus on "Toast IQ Core (AI Product Team)" and the explicit mention of AI capabilities, LLMs, and agentic workflows. The "Principal" title and 10+ years of experience indicate a senior leadership position within the design function, requiring strategic oversight and mentorship.

📈 Primary Responsibilities

• Lead Design Vision & Strategy: Define and articulate the long-term design vision for Toast IQ Core, ensuring alignment with business objectives and user needs.

• End-to-End Design Execution: Own the entire design process for core UX/UI features, from conceptualization and user research to high-fidelity prototyping and usability testing.

• AI Feature Development: Design innovative AI features such as memory, personalization, agentic workflows, and actionable insights, ensuring seamless integration with the Toast platform.

• Cross-Functional Collaboration: Partner effectively with Product Managers, Engineers, Data Scientists, GTM teams, and conversational/service designers to translate complex requirements into user-friendly solutions.

• Design System & Componentry: Evolve and maintain the design system and componentry for Toast IQ, ensuring consistency, scalability, and accessibility across all touchpoints (web, mobile, hardware).

• Prototyping & Experimentation: Develop prototypes and conduct experiments to test new AI models, features, and user interaction patterns, driving continuous iteration and improvement.

• User Research & Usability Testing: Proactively conduct and coordinate user research, data analysis, and usability testing to gather insights and inform design decisions.

• Mentorship & Best Practices: Mentor junior designers, share expertise in AI and UX/UI, and promote a culture of innovation, user-centricity, and AI adoption.

• Growth Strategy Integration: Design experiences that support the growth and adoption of Toast IQ's premium features and AI capabilities.

• Technical Fluency Application: Leverage strong technical understanding of APIs, data flows, personalization algorithms, and LLMs to inform design solutions.

📝 Enhancement Note: The responsibilities have been expanded to detail the "end-to-end design process" and specific AI feature development. The emphasis on "agentic workflows," "memory," and "personalization" is crucial for candidates to understand the advanced nature of the AI product. Collaboration with "conversational and service designers" is also highlighted as a key aspect of the role not explicitly detailed in the original "core responsibilities" summary.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's or Master's degree in Design, HCI, Computer Science, or a related field is typically expected for a Principal level role. Equivalent practical experience will also be considered.

Experience: 10+ years of progressive experience in Product Design, UX/UI Design, or Interaction Design, with a significant focus on leading high-impact design initiatives for complex digital products.

Required Skills:

• Leadership in Design: Proven ability to lead high-impact design initiatives at a principal level, driving strategy and execution with autonomy.

• End-to-End Design Process: Mastery of the full product design lifecycle, from discovery and research to prototyping, testing, and implementation.

• AI & Emerging Technologies: Deep understanding of emerging AI use cases, tooling (e.g., Claude, Codex), and foundational user-centered design principles.

• Interaction Design: Expertise in designing intuitive and effective user interactions, particularly for conversational AI and agentic workflows.

• Design Systems & Componentry: Experience in building, evolving, and maintaining robust design systems and component libraries.

• Prototyping & Experimentation: Proficiency in creating interactive prototypes and designing experiments to validate design hypotheses.

• User Research & Analysis: Demonstrated ability to conduct and coordinate user research, data analysis, and usability testing to inform design decisions.

• Collaboration & Communication: Strong communication, presentation, and interpersonal skills for effective collaboration with cross-functional teams and stakeholders.

• Tool Proficiency: Expertise in design tools such as Figma and Miro, and familiarity with emerging AI tools.

• Accessibility Standards: Solid understanding and application of usability and accessibility standards in design.

• Mentorship: Experience in mentoring junior designers and fostering a collaborative, innovative team environment.

Preferred Skills:

• Restaurant Industry Experience: First-hand experience or a strong passion for the restaurant industry and its unique operational challenges.

• Growth & AI-Driven Experiences: Proven passion and experience in designing for growth and AI-driven products.

• Technical Fluency: Strong technical understanding of APIs, data flows, personalization algorithms, Large Language Models (LLMs), experimentation, A/B testing, personalization engines, and automation frameworks.

• Conversational Design: Experience specifically in conversational AI design, chatbots, or virtual assistants.

• Service Design: Understanding of service design principles to create holistic customer journeys.

📝 Enhancement Note: The "Required Skills" section has been detailed to reflect the "Principal" level, emphasizing leadership and strategic ownership. Preferred skills have been expanded to include specific technical fluency like LLMs and A/B testing, which are critical for an AI product role. The mention of "conversational and service designers" in the original description also informs the inclusion of these as preferred skills.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Case Studies of AI Product Design: Showcase at least 2-3 in-depth case studies demonstrating your leadership in designing complex AI-driven products or features.

• End-to-End Design Process: Clearly illustrate your process, from initial problem definition and user research to ideation, prototyping, testing, and final implementation, highlighting your role and contributions.

• Interaction & Workflow Design: Provide examples of intricate interaction designs, especially those involving conversational interfaces, agentic workflows, or complex decision trees.

• Design System Contribution: Include examples of how you have contributed to or leveraged design systems and component libraries to ensure consistency and scalability.

• Problem-Solving & Impact: Clearly articulate the user problems addressed, the design solutions implemented, and the measurable impact (e.g., user adoption, efficiency gains, revenue impact) achieved.

Process Documentation:

• User Research Methodologies: Demonstrate your approach to conducting user research, including qualitative methods (interviews, usability tests) and quantitative analysis, specifically for AI products.

• Prototyping & Experimentation: Detail your methods for creating interactive prototypes and designing experiments (e.g., A/B tests) to validate design hypotheses and gather user feedback.

• Cross-Functional Collaboration: Illustrate how you have collaborated with Product Managers, Engineers, and Data Scientists, showcasing your ability to translate technical constraints and data insights into design solutions.

• Design System Governance: Explain your process for contributing to and maintaining design systems, including how you ensure component reusability and consistency.

📝 Enhancement Note: This section is tailored to a Principal Product Designer role, emphasizing in-depth case studies of AI product design and illustrating leadership in complex projects. The focus is on demonstrating a robust understanding of the entire design process, from research to implementation, with a specific emphasis on AI-related challenges and outcomes.

💵 Compensation & Benefits

Salary Range:

• Zone A (Highest Cost of Living): $190,000 - $304,000 USD per year

• Zone B (Mid Cost of Living): $165,000 - $264,000 USD per year

• Zone C (Lower Cost of Living): $149,000 - $238,000 USD per year

📝 Enhancement Note: The salary ranges provided are directly from the input data and are broken down by geographic pay zones (A, B, C) as specified by Toast. This is a critical piece of information for candidates to understand potential compensation based on their location, reflecting Toast's commitment to pay transparency and alignment with local labor markets.

Benefits:

• Cash Compensation: Includes base salary, with potential for overtime, bonuses, and commissions depending on eligibility.

• Equity: Stock options or other equity grants, providing ownership and potential for long-term financial growth.

• Health Insurance: Comprehensive health coverage, likely including medical, dental, and vision plans.

• Retirement Savings: Access to a retirement savings plan, such as a 401(k), with potential company match.

• Paid Time Off: Generous paid time off, including vacation days, sick leave, and holidays.

• Professional Development: Opportunities for continued learning, training, and skill development, particularly in AI and design.

• Remote Work Support: Resources or stipends to support a productive remote work environment.

• Wellness Programs: Initiatives focused on employee well-being, both physical and mental.

Working Hours:

• Standard full-time work schedule, typically 40 hours per week.

• Flexibility is likely offered, common in remote roles, allowing for adaptation to different time zones and personal schedules, provided core collaboration hours are met.

📝 Enhancement Note: Benefits have been expanded based on typical offerings for a Principal level, full-time, remote role at a tech company. The inclusion of "Cash Compensation," "Equity," and "Health Insurance" directly reflects the provided information. The "Working Hours" section infers flexibility common in remote roles, balanced with the need for collaboration.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on the Restaurant industry (SaaS, POS systems, AI solutions).

Company Size: Large (Toast has thousands of employees, indicated by the "AI Product Team" and multiple pay zones). This implies a structured environment with established processes but also opportunities for impact.

Founded: 2012. This indicates a company with a solid track record and established growth, now venturing into significant AI expansion.

Team Structure:

• AI Product Team: A dedicated, growing team focused on developing and expanding Toast's AI capabilities.

• Design Team: A broader design organization within Toast, likely comprising various specializations (UX/UI, Research, Design Ops) that this Principal Designer will be part of and contribute to.

• Cross-Functional Collaboration: Integral to the role, involving close partnerships with Product Management, Engineering, Data Science, Go-to-Market (GTM), and potentially external partners.

• Reporting: The Principal Designer will likely report to a Design Lead, Director of Design, or Head of Product for the AI division, with direct influence on product strategy and design direction.

Methodology:

• User-Centered Design (UCD): A foundational approach, emphasized by the role's requirements for user research and usability testing.

• Data-Driven Decision Making: Utilizing data analysis and insights from user research to inform design choices and product evolution.

• Iterative Development: Employing prototyping and experimentation to continuously refine AI features and user experiences.

• Agile/Scrum: Likely follows agile methodologies for product development, enabling rapid iteration and collaboration.

• Founder's Mentality: Encouraged within the team, emphasizing ownership, initiative, and impact-driven work.

Company Website: https://careers.toasttab.com/

📝 Enhancement Note: The "Company Culture" section has been enriched with details about Toast's industry, size, and the implication of its founding year on its current trajectory, especially concerning AI. The team structure and methodologies reflect standard practices for a growing tech company with a focus on AI and a strong design culture.

📈 Career & Growth Analysis

Operations Career Level: Principal Product Designer. This signifies a senior, influential individual contributor role. It implies a high degree of autonomy, strategic input, and the expectation to mentor others. The focus is on deep expertise and leadership within the design domain, particularly in AI product development.

Reporting Structure: The Principal Designer will likely report to a Director or VP of Design, or a Product Leader overseeing the AI division. They will work closely with Product Managers, Engineering Leads, and Data Scientists, acting as a key design voice in product strategy discussions.

Operations Impact: This role has a direct and significant impact on Toast's strategic expansion into AI. The designs developed will shape how thousands of restaurants leverage AI to increase revenue, improve operational efficiency, and enhance customer experiences. Success in this role contributes directly to the adoption and monetization of premium AI features, a key growth lever for Toast.

Growth Opportunities:

• Leadership Development: Opportunities to further hone leadership skills, influence product strategy at a higher level, and potentially transition into management roles if desired.

• AI Specialization: Deepen expertise in AI product design, LLMs, agentic workflows, and emerging AI technologies, becoming a recognized expert in the field.

• Cross-Functional Exposure: Gain extensive experience working with diverse teams (Engineering, Data Science, GTM), broadening understanding of product development across the entire lifecycle.

• Mentorship & Coaching: Formalize mentorship of junior designers, contributing to the growth of the design team and shaping design talent within Toast.

• Strategic Influence: Contribute to defining the future of AI at Toast, influencing product roadmaps and business strategy.

• Industry Recognition: Potential to contribute to industry discussions, speaking engagements, or publications related to AI in product design.

📝 Enhancement Note: This section focuses on the "Principal" level's strategic implications, emphasizing the role's impact on revenue and business growth within the restaurant tech AI space. Growth opportunities are framed around leadership, specialized AI expertise, and strategic influence, aligning with a senior individual contributor path.

🌐 Work Environment

Office Type: While the role is fully remote, Toast operates a hybrid model for its in-office employees, suggesting a culture that values both in-person collaboration and remote flexibility. The remote aspect implies a focus on asynchronous communication and robust digital collaboration tools.

Office Location(s): Toast has offices in various US cities (e.g., Boston, Chicago, San Francisco, New York), but this role is specifically designated as "Remote, USA," allowing candidates from across the United States to apply.

Workspace Context:

• Digital Collaboration: Expect a heavy reliance on digital tools for communication, design collaboration, and project management (e.g., Slack, Zoom, Figma, Miro, Jira).

• Asynchronous Workflows: Emphasis on clear documentation and communication to facilitate collaboration across different time zones and schedules.

• Autonomous Work: A high degree of autonomy is expected, requiring self-discipline, proactive communication, and strong time management skills.

• Supportive Design Community: As part of the broader Toast Design team, there will be opportunities to connect with peers, share work, and receive feedback, even in a remote setting.

• Focus on Innovation: The "Toast IQ Core" team environment is likely dynamic and fast-paced, driven by the rapid evolution of AI technology and the goal of launching new premium features.

Work Schedule:

• Standard full-time hours (approximately 40 hours/week) are expected.

• Flexibility in scheduling is probable, common for remote roles, allowing for a balance between work and personal life. However, participation in core team meetings and critical cross-functional syncs will be necessary, often requiring availability during standard US business hours.

📝 Enhancement Note: The "Work Environment" section emphasizes the realities of a fully remote Principal Designer role, focusing on digital collaboration, asynchronous communication, and the need for self-direction. It also connects the remote nature to Toast's broader hybrid model and office presence.

📄 Application & Portfolio Review Process

Interview Process:

1. Recruiter Screen: Initial conversation to assess basic qualifications, cultural fit, and understanding of the role.

2. Hiring Manager Interview: In-depth discussion about your experience, leadership approach, design philosophy, and alignment with the Principal Designer role and AI product focus.

3. Portfolio Review & Design Exercise: This is a critical stage. You will likely present 1-2 detailed case studies from your portfolio, focusing on your process, decision-making, and impact. A take-home design exercise or a live design challenge might also be included to assess your problem-solving skills, interaction design capabilities, and approach to AI-specific challenges.

4. Cross-Functional Interviews: Meetings with Product Managers, Engineers, Data Scientists, and potentially other designers to evaluate collaboration skills, technical understanding, and ability to integrate into the team.

5. Final Round/Executive Interview: Potentially a discussion with a senior leader (e.g., Head of Design, VP Product) to assess strategic thinking, leadership potential, and alignment with company values.

Portfolio Review Tips:

• Prioritize AI/Complex Products: Showcase projects that demonstrate your experience with AI, complex systems, or challenging user problems.

If direct AI experience is limited, highlight transferable skills like designing for data complexity, personalization, or novel interaction patterns.

• Structure Your Case Studies: For each case study, clearly outline:

  • The Problem: What user or business challenge were you solving?
  • Your Role: What were your specific responsibilities and contributions?
  • The Process: Detail your research, ideation, design, and testing methodologies.
  • The Solution: Showcase your designs (wireframes, mockups, prototypes) and explain the rationale behind key decisions.
  • The Impact: Quantify results whenever possible (e.g., metrics on user adoption, engagement, efficiency gains, revenue impact).

• Highlight Leadership & Mentorship: Since this is a Principal role, demonstrate how you've led initiatives, influenced strategy, mentored junior designers, and driven best practices.

• Prepare for Technical Questions: Be ready to discuss your understanding of LLMs, APIs, data flows, and how these technical aspects inform your design decisions.

• Articulate Your Design Philosophy: Be prepared to discuss your core design principles, your approach to user-centered design, and your perspective on the future of AI in product experiences.

Challenge Preparation:

• Understand the AI Context: Research Toast's AI strategy ("Toast IQ") and the restaurant industry to frame your problem-solving approach.

• Focus on Interaction & Workflow: For any design exercise, pay close attention to the nuances of interaction design, especially for AI-driven features and agentic workflows.

• Demonstrate Process: Even in a short exercise, show your thinking process – how you'd approach research, ideation, and iteration.

• Consider Scalability & Constraints: Think about how your designs would scale across different platforms (web, mobile, hardware) and how they would integrate with existing systems.

📝 Enhancement Note: This section provides a detailed breakdown of a typical Principal Designer interview process, with specific advice tailored to AI product design and Toast's context. The emphasis on portfolio content and presentation strategy is crucial for candidates to prepare effectively.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (essential), Miro (essential for collaboration and whiteboarding).

• Emerging AI Tools: Claude, Codex (or similar LLM-based tools for ideation, content generation, or understanding AI capabilities).

• User Research Platforms: Tools for conducting usability testing, surveys, and user interviews (e.g., UserTesting.com, Lookback, SurveyMonkey).

• Project Management: Jira, Asana, or similar tools for tracking design tasks and progress.

Analytics & Reporting:

• Product Analytics: Tools like Amplitude, Mixpanel, or Google Analytics to understand user behavior and product usage.

• Data Visualization: Proficiency in interpreting data presented in dashboards (e.g., Tableau, Looker) to inform design decisions.

CRM & Automation:

Collaboration & Communication:

• Communication Platforms: Slack, Microsoft Teams.

• Video Conferencing: Zoom, Google Meet.

📝 Enhancement Note: This section lists the core tools expected for a Principal Product Designer, with a specific emphasis on Figma, Miro, and emerging AI tools like Claude and Codex, as mentioned in the job description. It also includes relevant analytics and collaboration tools common in tech environments.

👥 Team Culture & Values

Operations Values: Toast emphasizes several core tenets that define their culture and expected behaviors:

• Founder's Mentality: Taking ownership of outcomes, exhibiting initiative, and driving results as if it were your own business. This fosters a proactive and accountable work environment.

• Lifting Others Up: A commitment to mentorship, collaboration, and supporting colleagues' growth. This encourages knowledge sharing and team cohesion.

• Driving Action Through Influence: Building strong, trusting relationships to effectively advocate for ideas and drive change across the organization. This highlights the importance of communication and collaboration.

• Building Strong Perspectives: Developing well-informed opinions and guiding decision-making with data and thoughtful analysis, while remaining open to collaboration. This promotes strategic thinking and informed choices.

• Raising the Bar: A dedication to continuous learning, skill development, and striving for excellence in one's craft. This drives innovation and high-quality output.

Collaboration Style:

• Cross-Functional Integration: Expect close collaboration with Product, Engineering, and Data Science, requiring clear communication of design rationale and an understanding of technical constraints.

• Design Feedback Loops: A culture that encourages constructive feedback and iterative design reviews, both within the design team and with cross-functional partners.

• Data-Informed Design: Collaboration with data scientists to leverage insights from user data and experiments to refine designs and product strategy.

• Remote-First Collaboration: Emphasis on asynchronous communication, clear documentation, and effective use of digital collaboration tools to ensure seamless teamwork across distributed locations.

📝 Enhancement Note: This section directly pulls from Toast's stated values ("About You" section), re-framing them within the context of a design role and emphasizing how these values manifest in daily work and collaboration. This provides candidates with a clear understanding of the expected cultural alignment.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Emerging AI: Navigating the rapidly evolving landscape of AI technology, including LLMs and agentic workflows, to create intuitive and reliable user experiences.

• Zero-to-One Product Development: Leading the design for new, foundational AI features and capabilities for Toast IQ, requiring comfort with ambiguity and rapid iteration.

• Balancing Innovation with Usability: Ensuring that cutting-edge AI features are not only innovative but also easily discoverable, understandable, and usable by restaurant operators with varying technical proficiencies.

• Cross-Functional Alignment: Effectively influencing and aligning diverse stakeholders (Product, Engineering, Data Science, GTM) around design strategy and execution for a complex AI product.

• Scalability Across Platforms: Designing a cohesive AI experience that works seamlessly across web, mobile, and potentially hardware interfaces, while maintaining consistency and user trust.

• Driving Premium Feature Adoption: Designing compelling value propositions and user journeys that encourage adoption of new AI-powered premium features.

Learning & Development Opportunities:

• Deep Dive into AI Product Design: Gain unparalleled experience in designing for advanced AI, LLMs, and agentic systems within a real-world, high-impact product.

• Strategic Product Influence: Contribute significantly to the product roadmap and strategic direction of Toast's AI initiatives.

• Mentorship & Leadership: Opportunities to mentor junior designers, lead design initiatives, and potentially grow into leadership roles within the AI product organization.

• Industry Trends: Stay at the forefront of AI and product design trends through hands-on experience and exposure to cutting-edge technologies.

• Professional Development: Toast likely offers resources for continuous learning, such as access to conferences, training programs, or online courses relevant to AI, design, and product management.

📝 Enhancement Note: Challenges are framed around the specific complexities of AI product design and the "zero-to-one" nature of Toast IQ Core. Growth opportunities are tailored to a Principal Designer role, emphasizing strategic impact, AI specialization, and leadership development.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led the design for a complex, zero-to-one product or feature. What was your process, what were the key challenges, and what was the outcome?" (Focus on demonstrating leadership, strategic thinking, and process).

• "How would you approach designing an AI assistant's 'memory' feature for restaurant operators? What are the key considerations for personalization, privacy, and usability?" (Tests understanding of AI use cases, user empathy, and problem-solving).

• "Imagine we want to launch a new premium AI feature for Toast IQ. How would you collaborate with Product, Engineering, and GTM to define its value proposition, design the experience, and drive adoption?" (Assesses cross-functional collaboration and growth mindset).

Company & Culture Questions:

• "Based on your research, how do you see Toast IQ fitting into the broader restaurant technology landscape, and what opportunities do you see for AI to transform restaurant operations?" (Shows research and strategic thinking about the industry).

• "How do Toast's core values (Founder's Mentality, Lifting Others Up, etc.) resonate with your own work style and leadership approach?" (Assesses cultural fit and self-awareness).

Portfolio Presentation Strategy:

• Narrative Arc: Structure your case studies as compelling stories that highlight the problem, your strategic approach, your execution, and the measurable impact.

• Focus on "Why": Clearly articulate the rationale behind your design decisions, linking them back to user needs, business goals, and technical considerations.

• Showcase Process, Not Just Polish: Demonstrate your thinking process, including research insights, iterative explorations, and how you overcame challenges. This is crucial for a Principal role.

• Quantify Impact: Use metrics and data to illustrate the success of your designs. If direct metrics are unavailable, use proxy metrics or describe the expected impact clearly.

• Be Prepared for Deep Dives: Expect detailed questions about your contributions, design choices, and how you would approach similar challenges in the future. Be ready to discuss trade-offs and constraints.

• Highlight AI/Complex System Experience: Emphasize any experience with AI, complex data, novel interactions, or systems design. If limited, draw parallels to similar complex problem-solving scenarios.

📝 Enhancement Note: This section provides actionable advice on preparing for interviews, including sample strategy questions that probe critical thinking about AI product design and cross-functional collaboration. Portfolio presentation tips are tailored to a Principal level, emphasizing strategic contribution and impact.

📌 Application Steps

To apply for this Principal Product Designer position:

• Submit your application through the Toast Careers portal via the provided URL.

• Curate Your Portfolio: Select 2-3 of your most impactful projects, prioritizing those demonstrating leadership in complex product design, ideally with AI or novel interaction elements. Ensure each case study clearly outlines the problem, your role, process, solution, and measurable impact.

• Tailor Your Resume: Highlight your 10+ years of experience, leadership in design initiatives, expertise in UX/UI and interaction design, and any specific experience with AI, LLMs, or relevant technologies. Quantify achievements wherever possible.

• Prepare Your Presentation: Practice presenting your portfolio case studies concisely and compellingly, focusing on your strategic thinking, problem-solving approach, and leadership contributions. Be ready to articulate your design philosophy and how you'd approach AI product design challenges.

• Research Toast & Their AI Strategy: Understand Toast's mission, their position in the restaurant tech market, and their vision for Toast IQ. Familiarize yourself with their company values and how you align with them.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.