Senior Director, Care Operational Excellence

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. A day in the life (Responsibilities) Toast is looking for a Senior Director, Customer Care Operational Excellence to own how our customer support organization operates, end to end. This is a build-and-run role: you will design (and continuously redesign) the people, process, systems, and data that determine whether every customer, from our smallest SMB accounts to our largest Enterprise relationships, gets a fast, effortless, high-quality resolution. This role sits at the center of our AI transformation of Support operations, evaluating, implementing, and scaling AI across chat, voice, and agent-assist workflows, while also owning the fundamentals: workforce planning and capacity, quality and performance measurement, and a closed-loop voice-of-customer program that feeds directly into our product and engineering roadmaps. You will lead a team, and this is a hands-on role: you’re expected to get into the details, run point on hard problems personally, and build things yourself when needed. Support Operating Model: People, Process & Systems Own the end-to-end design of how Support operates: org structure, staffing model, tiering/routing, escalation paths, and channel model (chat, email, phone, self-service, community), and continuously refine it as the business scales. Build and run the operating cadence for the function: performance reviews, root-cause/escalation reviews, leadership readouts, and continuous-improvement rhythms. Segment design so that SMB, Mid-Market, and Enterprise customers each get a service model appropriate to their needs, complexity, and value. AI & Support Technology Transformation Own the roadmap for AI-enabled support, including virtual agents/chatbots, voice AI, agent-assist, and automation, from business case through implementation, measured adoption, and iteration. Partner with Product and Engineering as a co-owner of the tools and systems Support runs on: helpdesk/CRM, contact center (CCaaS), knowledge base, and AI/automation platforms, representing Support’s requirements and stress-testing what’s shipped. Evaluate, select, and manage the vendor and technology stack (including AI vendors and BPO/outsourcing partners), balancing cost, quality, and customer experience. Data, Insights & Performance Measurement Define the metrics that matter for Toast’s support operations, including but not limited to TTR/resolution time, CSAT, customer effort (CES), quality/QA scores, cost-to-serve, and AI containment/deflection rate. Partner with Analytics to build the reporting and analytics and associated insights to drive operations across lines of business, segments, channels, and geographies. Build a rigorous quality assurance program (QA scoring, calibration, coaching feedback loops) to ensure consistency as the org scales and as AI takes on more of the work. Use data to diagnose root causes of poor experience and prioritize the highest-leverage fixes across people, process, and systems. Voice of the Customer & Product Feedback Own Product Feedback program in partnership with VOC and other related efforts: capturing, synthesizing, and prioritizing feedback and issues surfaced through Support. Build the formal, closed-loop mechanism that routes customer and product feedback to R&D/Product leadership, ensuring it gets actioned and tracked through to impact on support volume and CSAT. Workforce Planning & Capacity Management Own workforce planning, forecasting, and capacity management (staffing, scheduling, shrinkage, real-time management) across in-house and outsourced/BPO teams. Model the impact of AI automation on headcount and capacity plans, and adjust staffing levels as containment rates change. Cross-Functional Leadership & Partnership Partner closely with Product and Engineering leadership as a genuine design partner on tools, features, and AI capabilities that affect the customer experience or support workload. Represent Support in cross-functional planning (Sales, Success, Finance, Legal/Compliance, Trust & Safety) and ensure Support’s operational needs and constraints are reflected in company-wide decisions. Communicate performance, risk, and plans to executive leadership through regular business reviews. Team Leadership & Talent Development Build, lead, and develop a team of operations and operational excellence managers/leads; build the bench and succession plan for the function. Instill a hands-on, builder culture on the team: this function should be as comfortable running an analysis or drafting a process itself as it is directing others to do so. What you’ll need to thrive (Requirements) 12+ years of experience in Customer Support/Service, Customer Experience, or Support Operations, including significant leadership experience at the Director level or above. Track record building and scaling support organizations inside large, high-growth technology companies, ideally B2B/B2B2C, that went through significant scale (multiple X revenue/customer growth) rather than steady-state maintenance. Direct, hands-on experience implementing AI in a support organization (virtual agent/chatbot, voice AI, agent-assist, automation), able to speak to what was built, how it was measured, and what it actually did to cost and experience. Experience supporting multiple customer segments (SMB through Enterprise) with differentiated service models, SLAs, and channels. Strong quantitative and analytical skills; fluent working with support/CX data and BI tools, and comfortable building models (capacity, cost-to-serve, ROI) independently. Experience with workforce management/capacity planning disciplines and tools. Proven cross-functional partnership with Product and Engineering, including influencing roadmaps without direct authority. A genuine doer, willing and able to roll up their sleeves, get into the weeds of a process or a dataset, and personally drive a problem to resolution rather than only directing others to. Bachelor’s degree required; MBA or equivalent a plus but not required. AI at Toast At Toast, one of our company values is that we’re hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture. 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. 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. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy. Zone A $212,000—$339,000 USD Zone B $185,000—$296,000 USD Zone C $166,000—$266,000 USD 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 [email protected]. ---— 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.