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Senior Director, Care Operational Excellence

toastRemote, United StatesPosted 16 Oct 2026

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About this role

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.

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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

Source listing: greenhouse_toast

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