Toast is hiring a Vice President, Retail Sales

Toast is looking for a Vice President, Retail Sales to lead a high-growth organization as the primary architect of our retail market expansion. You will oversee a team of Area Vice Presidents (AVPs) and Regional Vice Presidents (RVPs) who manage field-based District Managers, Account Executives, and the XDR function, scaling Toast's presence in the retail space while driving excellence in unit sales, revenue, and customer satisfaction.

What You'll Do

• Develop and execute the overarching sales strategy for the Retail division, aligning field execution with Toast’s long-term corporate vision and financial deliverables.
• 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.
• Optimize Retail outbound strategy and XDR goal-setting to maximize top-of-funnel pipeline quality.
• Drive hiring plans to expand the team quickly during hyper-growth. Partner across the organization to identify talent gaps and scale the hiring infrastructure.
• Optimize sales processes, methodologies, and tools to enhance team efficiency and ensure seamless tactical execution.
• Lead and inspire a large-scale sales organization, directly managing AVPs and RVPs to ensure consistent execution and coaching across all regions.
• 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.
• Leverage analytical skills to track performance and design targeted programs for measurable impact.
• Oversee talent identification and succession planning, ensuring a robust pipeline of future sales leaders and maintaining high employee engagement.

What We're Looking For

• 10+ years of B2B technology sales leadership experience
• Significant track record of managing managers of managers (AVPs/RVPs) in high-growth environments
• Demonstrated ability to build and scale sales organizations in emerging markets or with new product categories
• Ability to operate at a high-level strategic visioning level while maintaining a passion for frontline enablement and execution details
• Expert proficiency in sales funnel management and the use of data to inform complex business decisions
• Exceptional communication and interpersonal skills, with a proven ability to build a results-driven, inclusive, and team-oriented culture

Nice to Have

• A deep understanding of the retail or point-of-sale (POS) industry
• MBA

Technical Stack

• Salesforce
• Chorus

Team & Environment

You will report to the COO of Retail and oversee a large-scale sales organization. Your team structure includes 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.

Benefits & Compensation

• Compensation: $377,000—$603,000 USD + equity (if eligible)

Work Mode

This role operates in a hybrid work mode.

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.