Senior Director, Care Operational Excellence

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.

• 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…