Director of Enterprise Customer Success, Toast

• 10+ years of customer success, account management, or revenue leadership experience, with 5+ years leading teams in a SaaS or technology environment
• Experience as a second-line leader: managing managers, developing leadership bench strength, and running performance management with rigor and care
• Proven ownership of retention and growth targets for an enterprise or strategic customer segment
• Executive presence and a track record of building durable relationships with C-suite and corporate stakeholders at large, complex customers
• Experience building or leading customer success for a global or multi-region enterprise book, including designing coverage models for customers operating across international markets
• Strong operational skills: you build systems and cadences, not just relationships, and you use data to make decisions
• Experience navigating ambiguity and change, including org transitions, team integrations, or coverage planning
• Excellent communication, organizational, and influencing skills

Desirable

• As the Director of Enterprise Customer Success, you will lead the team responsible for Toast’s largest and most complex customers. The Enterprise segment serves brands operating 500+ locations, where a single customer relationship spans corporate stakeholders, franchise networks, and multi-year rollout programs. You will own the health, retention, and growth of this book of business and lead the leaders who deliver it
• This is a builder’s role, and an increasingly global one. As Toast's largest brands expand internationally, you will architect the Enterprise CS model that scales across markets, not just accounts
• You will shape how Toast serves upmarket customers at scale, reporting to the Sr. Director of Customer Success and operating as a key member of the CS leadership team, working in lockstep with Sales, Care, Product, and Onboarding. If you are a leader who thrives on executive-level customer relationships, operational rigor, and developing high-performing teams, this role is for you
• Own Enterprise segment revenue outcomes: net revenue retention, churn mitigation, and expansion across a book of Toast’s largest customers
• Build and develop a high-performing team of managers and their CSMs, setting vision, strategy, and performance standards while coaching leaders to raise the bar
• Design and lead the global Enterprise CS coverage model as Toast expands into international markets, building coverage, escalation, and delivery patterns that work across regions rather than retrofitting a US-designed model
• Strategic leadership - bring a clear, transformative, and innovative perspective on how to scale the post-live customer success model for a rapidly growing business unit
• Serve as executive sponsor and senior escalation point for high-visibility accounts, building trusted relationships with corporate stakeholders at major restaurant, hotel, and sports & entertainment brands
• Drive operational excellence, scalable systems and cadence for the segment: account planning, QBRs and strategic business reviews, renewal risk management, and escalation resolution
• Partner cross-functionally with Sales, Care, Onboarding, and Product to advocate for Enterprise customer needs and close experience gaps
• Use data to run the business: capacity and coverage models, health scoring, risk forecasting, and team performance metrics
• Be an ambassador for the Toast culture, building a trusting, collaborative, high-performance environment
• Travel as needed for customer site visits and executive engagements, including international travel as the global book grows