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 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 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.
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.
How Toast Uses AI in its Hiring Process
Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more: https://careers.toasttab.com/ai-in-hiring
Our Approach to Hybrid Working
We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast
People Are the Secret Ingredient in Our Recipe for Success
At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other.
Apply today!
Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [email protected].
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For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.
Toast Boston, Massachusetts, USA Office
Toast’s headquarters is located in the heart of the Seaport District. Toasters are surrounded by art, culture, and delicious cuisine in one of the most bustling neighborhoods in Boston.
Early Careers
Toast's Early Careers program is designed to launch students' careers by integrating them into the company's vibrant culture and impactful work. Interns and co-ops are treated as full-time Toasters from day one, given meaningful projects, and provided with mentorship from industry professionals. The program emphasizes hands-on learning, collaboration across teams, and the autonomy for students to develop and showcase their skills, supported by consistent feedback. Toast offers opportunities across various departments, including technical roles like Software Engineering and Data Science, as well as non-technical roles such as Human Resources and People Operations.
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