Senior Director of Design, Enterprise

Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. We are seeking a Senior Director of Product Design with a deep passion for crafting exceptional user experiences to shape our Enterprise Core organization. Toast builds restaurant and hospitality technology for operators who run at scale: multi-unit restaurant brands, hotel groups, stadiums, and arenas. The Enterprise segment sits at the center of Toast’s growth strategy, and in this role, you will play a pivotal role in leading design, strategy, and vision across this critical portfolio. Your work will span across foundational point-of-sale (POS) systems, deeply integrated platform ecosystems, and pioneering 0-1 AI and agentic experiences. You will collaborate closely with cross-functional teams to deliver highly configurable, performant, and accessible solutions that abstract away enterprise complexity into elegant, intuitive workflows. The ideal candidate knows how to balance high craft with technical constraints, is a passionate advocate for customer-centered design in high-volume operational environments, and is a skilled mentor who fosters a culture of creativity and experimentation. You'll work in lockstep with product management, engineering, and data analytics to define overall organization strategy and inspire the design team. About this roll* (responsibilities): Strategic Leadership: Develop and drive the overall product design vision for the growth organization, aligning it with business goals and user needs. Team Development: Build, mentor, and inspire a high-performing design team, fostering a culture of creativity, design excellence, and impact. Design Excellence: Coach team members to continually improve their craft and deliver an exceptional experience. Customer Insights: Leverage qualitative and quantitative research to inform design decisions and continuously improve product experiences. Metrics-Driven: Use design to drive critical business metrics and KPIs. Do you have the right ingredients*? (requirements): Strategic Collaboration: A proactive, outcome-oriented design leader with 7+ years of experience partnering closely with Product, Engineering, and commercial/operational teams to deeply understand enterprise user ecosystems and translate those insights into a unified design strategy that drives both customer and business outcomes. You see around corners, responding to the present and anticipating the future to lead the design team in creating intuitive experiences across responsive web, native mobile apps, and dedicated hardware. You bring a strong perspective on how emerging technologies and AI-driven automation can be seamlessly embedded into high-volume, live operational environments to simplify complex operator workflows. You possess an enduring sense of curiosity with a desire to continuously learn and evolve You regularly conduct design reviews to promote a culture of feedback and growth, iterating on the designs to improve results You have a growth mindset - you see challenges as opportunities, believe feedback is a gift and can speak confidently to the why. The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. Pay Range $215,000 — $344,000 CAD How Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more: https://careers.toasttab.com/ai-in-hiring Our Approach to Hybrid Working 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 hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast People Are the Secret Ingredient in Our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other. 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 . ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.