Senior Product Designer, Web Tools

📍 Job Overview

Job Title: Senior Product Designer, Web Tools

Company: Toast

Location: Remote

Job Type: Full-Time

Category: Product Design / Web Experience

Date Posted: 2026-08-31

Experience Level: Mid-Senior Level (4+ years)

Remote Status: Fully Remote

🚀 Role Summary

• Design and iterate on cutting-edge AI-powered features for Toast's marketing website, focusing on conversational interfaces and personalized user journeys.

• Translate complex AI/ML capabilities into intuitive, human-centered design solutions that enhance prospect engagement and trust.

• Collaborate closely with Web Strategy, Engineering, Marketing, and AI/ML partners to bring innovative web experiences to life.

• Drive the evolution of design patterns and guidelines for AI-enabled web experiences, ensuring consistency and user-centricity.

📝 Enhancement Note: This role is positioned within the Web Experience Design team, focusing on customer-facing AI features for Toast's marketing website. The core objective is to leverage AI to improve the prospect journey, from information discovery to engagement and connection with Toast. This is a strategic role that requires a blend of design expertise, technical understanding of AI capabilities, and strong cross-functional collaboration.

📈 Primary Responsibilities

• Design and iterate on AI-powered features, including chatbots, conversational interfaces, and dynamic personalization experiences embedded within Toast's website.

• Translate complex AI capabilities into intuitive, human-centered interactions that feel natural and build trust with prospects.

• Partner with Engineering and AI/ML teams to understand model capabilities and constraints, and design within them, ensuring feasibility and optimal user experience.

• Design personalization logic and experiences that adapt content, messaging, or layout based on visitor behavior, segment, or intent to create tailored journeys.

• Prototype and test AI-driven concepts, utilizing data and user feedback to refine interaction patterns before and after launch, ensuring continuous improvement.

• Collaborate with Web Strategy and Marketing stakeholders to ensure AI experiences align with campaign goals, brand voice, and overarching business priorities.

• Contribute to and help evolve design patterns and guidelines for AI-enabled experiences across the web ecosystem, fostering a cohesive and scalable design language.

• Clearly communicate design rationale, prototypes, and outcomes to the manager and cross-functional partners, ensuring alignment and buy-in.

📝 Enhancement Note: The responsibilities highlight a deep involvement in the end-to-end design process for AI-driven web features. This includes ideation, user research, prototyping, technical collaboration, and iterative refinement based on data and feedback. The emphasis on translating complex AI into human-centered interactions and designing personalization logic suggests a need for strategic thinking beyond traditional UI/UX.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating practical application of design principles is paramount. Relevant coursework or degrees in Design, Human-Computer Interaction (HCI), Computer Science, or a related field are beneficial.

Experience:

• 4+ years of relevant product or web design experience, with a preference for B2B SaaS environments.

• Demonstrated experience or strong aptitude for designing AI-powered features, such as chatbots, recommendation systems, generative content, or personalization engines.

• Proven ability to design within real-world technical constraints and collaborate effectively with engineering teams. Required Skills:

• Expertise in UI/UX principles, including interaction design, information architecture, and accessibility standards (WCAG).

• Proficiency in creating user-centered designs that solve complex problems.

• Strong prototyping skills to effectively communicate design concepts and test user flows.

• Ability to translate technical capabilities and constraints into user-friendly interfaces.

• Excellent communication and presentation skills, with the ability to articulate design decisions to diverse stakeholders.

• Experience working with cross-functional teams (Engineering, Product, Marketing, Strategy).

• Comfort working through ambiguity and iterating rapidly based on feedback and data. Preferred Skills:

• Genuine curiosity and enthusiasm for AI and its potential applications in web experiences.

• Experience in designing conversational interfaces or chatbot interactions.

• Familiarity with personalization engines and dynamic content delivery.

• Experience taking projects from initial exploration through to shipped execution.

• Passion for Toast's mission and the hospitality technology industry.

📝 Enhancement Note: The requirements emphasize practical experience and a forward-thinking approach, particularly regarding AI. While direct AI design experience is preferred, a strong foundation in core design principles and a demonstrated ability to learn and adapt to new technologies are highly valued. The "nice to have" section further underscores the importance of genuine interest in AI and problem-solving.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing thoughtful, user-centered problem-solving in product or web design.

• Demonstrated ability to articulate the design process, including research, ideation, iteration, and final solution.

• Examples of designing intuitive and engaging user interfaces for web applications.

• Evidence of collaboration with engineering teams to bring designs to fruition, highlighting an understanding of technical constraints.

• Demonstration of how user needs and business goals were balanced in design decisions. Process Documentation:

• Case studies detailing the design and iteration of AI-enabled features (e.g., chatbots, personalization engines) are highly encouraged.

• Examples of designing for complex technical capabilities and translating them into user-friendly interactions.

• Showcase of experience with prototyping and user testing methodologies for validating design concepts.

• Evidence of how data and user feedback were incorporated into the design process for continuous improvement.

📝 Enhancement Note: The portfolio is critical for this role, particularly emphasizing user-centered problem-solving and experience with AI-driven features. Candidates should prepare to walk through specific case studies demonstrating their design process, collaboration with technical teams, and ability to deliver tangible results. Highlighting projects involving conversational interfaces or personalization will be a significant advantage.

💵 Compensation & Benefits

Salary Range:

• Zone A: $95,000 - $152,000 USD per year

• Zone B: $83,000 - $133,000 USD per year

• Zone C: $75,000 - $120,000 USD per year

📝 Enhancement Note: The salary ranges provided are tiered based on geographic location (Zones A, B, C), reflecting Toast's Geographic Pay Zone Philosophy. Zone A represents higher cost-of-living areas, while Zone C represents lower cost-of-living areas. The final starting salary will be determined by skills, experience, and specific geographic location within these zones.

Benefits:

• Equity: Stock options or grants providing ownership in Toast's success.

• Cash Compensation: Includes base salary, potential overtime, and eligibility for bonuses or commissions where applicable.

• Health Benefits: Comprehensive medical, dental, and vision insurance plans.

• Flexible Work: Remote work flexibility and a hybrid model that balances in-person collaboration with individual needs.

• Retirement Savings: Access to retirement savings plans (e.g., 401k).

• Paid Time Off: Generous vacation, sick leave, and holiday policies.

• Professional Development: Opportunities for continuous learning, skill advancement, and training.

Working Hours: Standard full-time working hours, likely around 40 hours per week, with flexibility inherent in a remote role. The company emphasizes a hybrid model, suggesting that while core hours may exist, there's an allowance for personal needs and effective work-life integration.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on the hospitality industry (restaurants and local businesses). Toast provides a comprehensive technology platform to help these businesses succeed in a digital world.

Company Size: Toast is a significant player in its market, indicated by its public listing and the breadth of its product offerings. Its growth suggests a dynamic and evolving environment.

Founded: Toast was founded in 2011, indicating a company with established processes and a track record of innovation, yet still agile enough to embrace new technologies like AI