Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer

Company: Toast

Location: Boston, MA

Job Type: Full-Time

Category: Product Design (with a focus on AI/Conversational Design)

Date Posted: April 07, 2026

Experience Level: 5-10 Years

Remote Status: Hybrid

🚀 Role Summary

• Drive innovation in AI-first customer support experiences for the restaurant technology sector.

• Design and execute end-to-end conversational (chat and voice) AI solutions leveraging LLMs and generative AI.

• Collaborate closely with product managers, engineers, and other designers to enhance customer self-service and troubleshooting capabilities.

• Utilize data analytics and user research to inform design decisions and iterate on AI model behavior for optimal customer outcomes.

• Champion a user-centered design approach within a rapidly evolving AI product landscape.

📝 Enhancement Note: This role sits at the intersection of product design and cutting-edge AI, specifically focusing on enhancing customer support through conversational interfaces. The emphasis on "AI-first experiences" and "LLM-driven dialogue" indicates a need for designers who can think beyond traditional UI/UX and embrace the probabilistic nature of generative AI. The role also requires a strong understanding of AI infrastructure and a proactive approach to experimentation and learning.

📈 Primary Responsibilities

• Develop and evaluate conversational flows for chat and voice interfaces, applying knowledge of LLM-driven dialogue and generative AI nuances.

• Design and implement prompt engineering and context engineering techniques to shape AI model behavior and iterate on system prompts as design artifacts.

• Create functional prototypes using AI-native tools (e.g., Cursor, v0, Replit) and standard tools like Figma for rapid concept exploration and customer testing.

• Track and design experiences that improve key support metrics such as task completion rate, error recovery, and overall customer satisfaction.

• Conduct user research and usability testing, leveraging conversation logs and model behavior data to identify opportunities and solve customer problems.

• Collaborate effectively with cross-functional teams, including product management, engineering, and other AI/conversational designers, to define design requirements and align on project goals.

• Establish and manage evaluations for AI outputs from a customer experience perspective, distinguishing between model limitations and design failures.

• Advocate for human-centered guardrails and ethical considerations in AI system design, ensuring responsible AI implementation.

• Maintain a working understanding of AI infrastructure concepts relevant to design, including Toast IQ, Model Context Protocol (MCP), and agent orchestration patterns.

📝 Enhancement Note: The responsibilities highlight a deep dive into conversational design, moving beyond static UI elements to dynamic, AI-driven interactions. The emphasis on "prompt engineering," "context engineering," and managing "probabilistic outputs" suggests a need for designers who can translate complex AI capabilities into intuitive user experiences. The requirement to create "working artifacts" for customer testing underscores the hands-on, iterative nature of this role.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field is typically expected for a Senior Product Designer role. Equivalent practical experience will also be considered.

Experience: 5-10 years of professional experience in Product Design, UX/UI Design, or a similar role, with a significant focus on conversational AI, chat/voice interfaces, or generative AI products.

Required Skills:

• Conversational Design Expertise: Proven ability to develop and evaluate conversational flows for chat and voice, understanding LLM-driven dialogue and generative AI challenges (probabilistic outputs, uncertainty, hallucination mitigation, graceful failure).

• Prompt & Context Engineering: Practical experience applying prompt engineering and context engineering techniques to shape AI model behavior and iterate on system prompts.

• AI-Native Prototyping: Fluency with AI-native prototyping tools (e.g., Cursor, v0, Replit) alongside standard design tools like Figma for rapid concept exploration and functional prototype creation.

• Data-Driven Design: Demonstrated ability to track and design experiences that improve support metrics (task completion, error recovery) and use conversation logs/model behavior data for iteration.

• User Research & Usability Testing: Ability and desire to conduct and coordinate user research and usability testing to inform design decisions.

• Cross-functional Collaboration: Strong communication and interpersonal skills, with a proven track record of working effectively with product managers, engineers, and other stakeholders.

• AI Quality & Guardrails: Experience creating and managing evaluations for AI outputs from a customer experience lens, and advocating for human-centered guardrails.

• Understanding of AI Infrastructure: Working knowledge of AI concepts such as Toast IQ, Model Context Protocol (MCP), and agent orchestration patterns.

Preferred Skills:

• Restaurant Industry Passion: First-hand experience or strong enthusiasm for the restaurant industry and its unique challenges.

• Modern Customer Support Experience: Experience designing at the forefront of technology for modern customer support experiences (AI chatbots, agent tooling, voice AI).

• Experience with AI Platforms: Familiarity with AI-native platforms for customer support like Intercom, Giga, or Sierra.

📝 Enhancement Note: The "Required Skills" section is heavily weighted towards AI-specific design competencies, particularly in conversational AI and generative models. The explicit mention of prompt engineering and AI-native prototyping tools suggests that candidates will be expected to demonstrate practical application of these skills, not just theoretical knowledge. The preferred skills highlight Toast's desire for candidates who not only have the technical design chops but also a passion for their specific industry and a background in cutting-edge customer support solutions.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Conversational Design Case Studies: Showcase end-to-end conversational design projects, detailing the problem, your design process, the AI/LLM technologies considered, prompt engineering strategies employed, and the resulting customer experience improvements.

• Prototyping Examples: Include examples of functional prototypes created using AI-native tools (Cursor, Replit, etc.) and/or Figma, demonstrating rapid concept exploration and user testing artifacts.

• Data-Driven Iteration: Present case studies that illustrate how you used data (e.g., conversation logs, support metrics, user research findings) to identify problems, iterate on designs, and measure impact.

• AI Output Evaluation: Demonstrate your approach to evaluating AI output quality from a customer experience perspective, including examples of guardrails or mitigation strategies implemented.

• Cross-functional Collaboration Evidence: Highlight projects where you successfully collaborated with engineering and product teams to bring AI-powered features to life.

Process Documentation:

• Workflow Design for AI Interactions: Document your process for mapping out complex conversational flows, considering edge cases, error handling, and escalation paths for AI-driven support.

• Prompt Engineering Workflow: Illustrate your methodology for developing, testing, and refining system prompts to achieve desired AI model behavior.

• User Research & Iteration Cycle: Outline your process for integrating user feedback and data analysis into an iterative design cycle for AI products.

📝 Enhancement Note: For this role, the portfolio is critical for demonstrating practical experience with AI-specific design challenges. Candidates should be prepared to showcase how they've applied conversational design principles, prompt engineering, and data-driven iteration to create effective AI-powered customer support experiences. The emphasis on "working artifacts" and "functional prototypes" suggests that static mockups alone will not suffice; tangible, testable designs are paramount.

💵 Compensation & Benefits

Salary Range: Based on Toast's provided ranges for Boston, MA (Zone A) and the Senior Product Designer experience level (5-10 years), the estimated salary range is $133,000 - $213,000 USD per year.

Benefits:

• Competitive Compensation: Including base salary and potential equity.

• Comprehensive Health Benefits: Medical, dental, and vision insurance.

• Retirement Savings Plan: Likely a 401(k) plan.

• Paid Time Off: Vacation, sick leave, and holidays.

• Professional Development: Opportunities for continuous learning and skill advancement, particularly in AI.

• Hybrid Work Model: Offers flexibility with a balance of in-office and remote work.

• Restaurant Industry Perks: Potential for industry-specific benefits or insights.

Working Hours: A standard full-time workweek is typically 40 hours. The hybrid model suggests flexibility in scheduling, allowing for a balance between focused work and collaborative in-office time.

📝 Enhancement Note: The salary range provided by Toast is segmented into Zones A, B, and C, reflecting geographic cost of living. Boston, MA falls into Zone A, which has the highest salary band. The range of $133,000 - $213,000 USD is derived directly from Toast's stated Zone A figures for this role. Benefits are detailed, emphasizing Toast's commitment to employee well-being and professional growth, with a specific mention of opportunities in AI.

🎯 Team & Company Context

🏢 Company Culture

Industry: Restaurant Technology / Software-as-a-Service (SaaS). Toast provides a comprehensive restaurant management platform, integrating point-of-sale, online ordering, marketing, and back-office functions.

Company Size: Toast is a large, publicly traded company, indicated by its extensive career site and multiple pay zones, suggesting a significant employee base and operational scale. This implies a structured environment with established processes but also opportunities for impact within specialized teams.

Founded: Toast was founded in 2012. This relatively young company history suggests a culture that is likely still dynamic, innovative, and adapting to rapid growth, aligning with their embrace of new technologies like AI.

Team Structure:

• The Product Design team is described as a "remotely distributed group" comprising Product Designers, User Researchers, Design Ops leaders, and Product Managers. This indicates a collaborative, cross-functional structure where designers work closely with product and engineering.

Methodology:

• Data-Driven Decision Making: The role emphasizes using data, analytics, and conversation logs to drive design iterations and measure success.

• Experimentation & Learning: A core aspect of the role involves running experiments to improve AI performance and maintaining continuous learning in AI advancements.

• User-Centered Design: The team's practice is driven by user needs, with a strong emphasis on user research and usability testing.

• Agile Development: While not explicitly stated, the focus on rapid prototyping and iteration aligns with agile methodologies common in tech companies like Toast.

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

📝 Enhancement Note: Toast's culture appears to be a blend of startup agility and established corporate structure, driven by a mission to serve the restaurant industry. The emphasis on "founder's mentality," "lifting others up," and "driving action through influence" suggests a culture that values ownership, collaboration, and proactive leadership, even in non-managerial roles. The integration of AI into various departments reflects a forward-thinking approach.

📈 Career & Growth Analysis

Operations Career Level: This role is designated as "Senior Product Designer," indicating a mid-to-senior level position. It requires a substantial amount of experience (5-10 years) and the ability to drive significant product initiatives independently, mentor junior designers, and influence strategic decisions within the AI product space. The responsibility for "end-to-end AI-first experiences" and shaping how Toast supports customers places this role at a critical juncture for product evolution.

Reporting Structure: The Senior Product Designer will likely report to a Design Lead, Head of Product Design, or a Director overseeing AI product development. They will work closely with Product Managers and Engineering Leads on specific AI initiatives. The "remotely distributed group" composition suggests collaboration across various functions and potentially geographies.

Operations Impact: This role has a direct and significant impact on customer retention and satisfaction by improving the efficiency and effectiveness of Toast's customer support channels. By making support more intuitive and accessible