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.
As the Vice President of Enterprise Sales , you will lead the strategy and execution of Toast’s most complex go-to-market (GTM) engine across Enterprise and Mid-Market divisions—spanning hotels, sports & entertainment, and global restaurant brands. A critical focus of this role is accelerating our expansion into the Quick-Service Restaurant (QSR) and drive-through segments.
Reporting directly to the Chief Operating Officer of Enterprise, you will leverage AI-driven insights and rigorous sales methodologies to transform our motion into a world-class, process-driven organization. You will bridge the gap between brand promise and operational delivery at massive scale, navigating multi-year C-suite negotiations with iconic global brands.
A day in the life (Responsibilities)
• C-Suite Engagement: Build trusted, collaborative relationships with global enterprise executives, backed by a disciplined, repeatable sales process.
• GTM Strategy & Innovation: Direct the go-to-market strategy for Toast's newest hardware and software solutions, positioning our platform as the partner of choice for high-volume, multi-unit brands.
• Sales Motion Modernization: Audit and optimize current sales cycles to increase velocity, driving measurable operational efficiency and consistency across all enterprise segments.
• AI-Powered Operations: Introduce and scale predictive, machine-learning-powered forecasting tools to replace manual projections with data-validated insights.
• Product & Engineering Partnership: Collaborate with Product and Engineering leadership to translate complex, enterprise-level partner requirements into a scalable, repeatable product roadmap.
• Industry Representation: Represent Toast across the enterprise sector, engaging at key industry forums and cultivating strategic partnerships to solidify our market leadership.
What you'll need to thrive (Requirements)
• Executive Leadership: Demonstrated track record leading high-performing enterprise GTM organizations capable of closing complex, large-scale annual contract value ($100M+ ACV) agreements with household-name brands.
• GTM Evolution: Proven ability to mature an organization's go-to-market approach—shifting from transactional, relationship-led efforts to structured, enterprise-level execution without losing operational momentum.
• Sales Tech & AI Vision: Deep expertise in modern sales tech stacks, with a clear vision for leveraging machine learning and data analytics in revenue operations and pipeline forecasting.
• Methodology Mastery: Expert-level proficiency in enterprise sales methodologies and a history of implementing them to reduce friction in complex sales cycles.
• Cross-Functional Influence: Exceptional ability to partner with Product and R&D teams to synthesi