Senior Director, Care Operational Excellence

Toast

1d • $166,000 - $339,000 • Hybrid

About The Position

Toast is seeking a Senior Director to own the end-to-end operating model for its customer support organization. This build-and-run role designs and continually improves the people, processes, systems, and data needed to provide fast, effortless, high-quality resolutions for customers ranging from small businesses to Enterprise accounts. The role leads a team and requires hands-on involvement in complex operational problems and building solutions when needed.

The position leads Toast’s transformation of Support through AI across chat, voice, agent-assist, and automation, while also owning workforce planning and capacity, quality and performance measurement, and a closed-loop voice-of-customer program that informs Product and Engineering roadmaps. It partners with Product and Engineering on support tools and systems, oversees technology and vendor decisions, and works across company functions to ensure operational needs are incorporated into planning.

The Senior Director also develops a team of operations and operational excellence leaders, establishes a hands-on builder culture, and communicates performance, risks, and plans to executive leadership. Toast describes its work model as hybrid, with in-office expectations varying by region.

Requirements

• 12+ years of experience in Customer Support/Service, Customer Experience, or Support Operations, including significant leadership experience at Director level or above.
• Track record building and scaling support organizations in large, high-growth technology companies, ideally B2B/B2B2C, through substantial revenue or customer growth.
• Direct, hands-on experience implementing AI in a support organization, such as virtual agents/chatbots, voice AI, agent-assist, or automation, with the ability to explain implementation, measurement, and effects on cost and customer experience.
• Experience supporting multiple customer segments from SMB through Enterprise with differentiated service models, SLAs, and channels.
• Strong quantitative and analytical skills; fluency with support/CX data and BI tools; and ability to independently build capacity, cost-to-serve, and ROI models.
• Experience with workforce management and capacity planning disciplines and tools.
• Proven cross-functional partnership with Product and Engineering, including influencing roadmaps without direct authority.
• Hands-on approach and willingness to investigate processes or datasets and personally drive problems to resolution.
• Bachelor's degree required.

Nice To Haves

• MBA or equivalent.

Responsibilities

• Own and continuously refine the end-to-end Support operating model, including organizational structure, staffing, tiering and routing, escalation paths, and channels.
• Establish the operating cadence, including performance reviews, root-cause and escalation reviews, leadership readouts, and continuous-improvement rhythms.
• Design differentiated service models for SMB, Mid-Market, and Enterprise customers.
• Own the roadmap for AI-enabled support, including virtual agents, chatbots, voice AI, agent-assist, and automation, from business case through implementation, adoption measurement, and iteration.
• Partner with Product and Engineering on Support tools and systems, including helpdesk/CRM, contact center (CCaaS), knowledge base, and AI/automation platforms.
• Evaluate, select, and manage technology vendors and BPO/outsourcing partners, balancing cost, quality, and customer experience.
• Define support operations metrics, including resolution time, CSAT, customer effort, QA scores, cost-to-serve, and AI containment or deflection; partner with Analytics on reporting and insights.
• Build a quality assurance program that includes scoring, calibration, and coaching feedback loops.
• Use data to diagnose experience problems and prioritize improvements across people, process, and systems.
• Own the Product Feedback program with VOC and related efforts, capturing, synthesizing, and prioritizing issues and feedback from Support.
• Create a closed-loop process for routing customer and product feedback to R&D and Product leadership, tracking actions and their impact on support volume and CSAT.
• Own workforce planning, forecasting, and capacity management across in-house and outsourced/BPO teams, including staffing, scheduling, shrinkage, and real-time management.
• Model AI automation’s impact on headcount and capacity plans and adjust staffing as containment rates change.
• Partner with Product and Engineering leadership on tools, features, and AI capabilities that affect customer experience or support workload.
• Represent Support in cross-functional planning with Sales, Success, Finance, Legal/Compliance, and Trust & Safety.
• Communicate Support performance, risks, and plans to executive leadership through regular business reviews.
• Build, lead, and develop a team of operations and operational excellence managers and leads, including developing the team bench and succession plan.
• Instill a hands-on builder culture in which the team can perform analyses and draft processes as well as direct others.

Benefits

• Competitive compensation and benefits programs.
• Cash compensation components may include overtime and bonus/commissions if eligible.
• Equity.
• Benefits intended to support a healthy lifestyle and flexibility for changing needs.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior