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. • Mo