Vice President, Enterprise Sales

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 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.

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