Director, Enterprise Customer Success

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.

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.

Day in the Life* (Responsibilities)

• 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

What You'll Need to Thrive*? (Requirements)

• 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

Special Sauce* (Non-essential Skills/Nice to Haves)

• Restaurant, hospitality, or multi-unit retail industry experience
• Experience integrating new teams or functions into an existing organization and leading through structural change
• Familiarity with AI-enabled CS workflows and tooling
• Experience with Salesforce CRM and modern CS platforms
• Experience supporting franchise or multi-brand organizations expanding into new international market

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.