Vice President, Enterprise Sales

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.

- 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.

- 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 frameworks (e.g., MEDDPICC, Sandler) 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 synthesize custom technical demands into platform features that win deals sustainably.

- Strategic Agility: Ability to thrive in a fast-paced environment, balancing long-term strategic vision with the agile execution required to capture a rapidly evolving market.

The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits.

You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy .