Vice President, Retail Sales at Toast

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.

About Toast Retail:

Toast Retail is our newest and most significant investment in the future of commerce. Launched in January 2025, Toast for Retail is poised to revolutionize the industry by providing an all-in-one operating system for retailers to manage every aspect of their business. As the Vice President of Retail Sales, you will be the primary architect of our retail market expansion.

Role Overview:

You will lead a high-growth organization, overseeing a team of Area Vice Presidents (AVPs) and Regional Vice Presidents (RVPs) who manage field-based District Managers and Account Executives as well as oversee the XDR (Sales Development) function. Our mission is to scale Toast’s presence in the retail space (especially in food & beverage retail) while driving excellence in unit sales, revenue, and customer satisfaction (cNPS). You will report directly to the COO of Retail.

If you are a proven leader who excels at building high-performance teams and aligning sales goals with corporate strategy, we’d love to talk to you!

A day in the life (Responsibilities)

Strategic Leadership: Develop and execute the overarching sales strategy for the Retail division, aligning field execution with Toast’s long-term corporate vision and financial deliverables.

XDR Function Oversight: Drive the strategy for the XDR team to ensure a robust top-of-funnel pipeline and seamless handoffs between sales development and field sales teams.

Outbound & Prospecting Excellence: Optimize Retail outbound strategy and XDR goal-setting to maximize top-of-funnel pipeline quality.

Organizational Scaling: Drive hiring plans to expand the team quickly during hyper-growth. Partner across the organization to identify talent gaps and scale the hiring infrastructure.

Operational Excellence: Optimize sales processes, methodologies, and tools (e.g., Salesforce, Chorus) to enhance team efficiency and ensure seamless tactical execution.

Organizational Management: Lead and inspire a large-scale sales organization, directly managing AVPs and RVPs to ensure consistent execution and coaching across all regions.

Cross-Functional Collaboration: Partner with R&D, Product Marketing, Sales Enablement, Onboarding, HR, Sales Operations, and Finance to ensure the retail organization has the resources and alignment needed to win in a competitive market.

Data-Driven Optimization: Leverage analytical skills to track performance and design targeted programs for measurable impact.

Talent Development: Oversee talent identification and succession planning, ensuring a robust pipeline of future sales leaders and maintaining high employee engagement (eNPS).

What you'll need to thrive (Requirements)

Proven Executive Experience: 10+ years of B2B technology sales leadership experience, with a significant track record of managing managers of managers (AVPs/RVPs) in high-growth environments.

Retail/POS Expertise: A deep understanding of the retail or point-of-sale (POS) industry is highly preferred.

Scale & Growth Mastery: Demonstrated ability to build and scale sales organizations in emerging markets or with new product categories.

Strategic & Tactical Balance: The ability to operate at a high-level strategic visioning level while maintaining a passion for frontline enablement and execution details.

Analytical Mindset: Expert proficiency in sales funnel management and the use of data to inform complex business decisions.

Inspirational Leadership: Exceptional communication and interpersonal skills, with a proven ability to build a results-driven, inclusive, and team-oriented culture.

MBA preferred, but not required

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 estimated Total Targeted Cash compensation range for this role is listed below. Total Targeted Cash for this role consists of a base salary, commission, benefits, and equity (if eligible). This role qualifies for uncapped commissions. The starting salary will be determined based on skills, experience, and geographic location.

Total Targeted Cash

$377,000—$603,000 USD

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.

Diversity, Equity, and Inclusion is Baked into our Recipe for Success

At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.

We Thrive Together

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 restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.

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 candidateaccommodations@toasttab.com.

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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.

Vice President, Retail Sales

Job Description