Regional Vice President, Retail - Great Lakes East

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 retail industry by providing an all-in-one operating system for retailers to manage every aspect of their business. Our initial focus is on landing key customers in the CPG space. Toast for Retail empowers these businesses to streamline operations, optimize inventory, enhance the customer experience, and ultimately drive growth.

Role Overview

As the Regional Vice President you will lead a dynamic field sales team that’s transforming how retailers operate. You’ll oversee a group of field-based District Sales Managers and Territory Account Executives across a defined region, driving performance against key goals including unit sales, revenue, employee engagement (eNPS), and customer satisfaction (cNPS). In this role, you’ll be responsible for hiring, onboarding, and continuously developing your team through coaching, support, and performance management—empowering each person to achieve and surpass growth. Beyond a deep understanding of omni-channel journeys, you bring a disciplined, data-first approach to demand generation and pipeline health, ensuring every marketing dollar is an optimized investment toward our aggressive retail growth targets.

Territory Scope:  Major metropolitan hubs including the Michigan corridor, the Ohio River Valley, upstate NY, and the Tennessee/Alabama corridor.

This leader will demonstrate excellence across three core competency areas, along with their associated capabilities:

• Operational Excellence
• Talent identification
• Analytical skills
• Tactical execution & process delivery
• Financial deliverables
• Problem solving, innovation and creativity

• Strategic Thinking
• Strategic vision and planning
• Effective decision making and judgement
• Overall business acumen
• Continuous improvement cycling

• Advanced Leadership
• Coaching/Mentoring
• Communication (written & verbal)
• Interpersonal savvy
• Building culture, morale and team motivation
• Talent development

 A day in the life (Responsibilities) 

• Develop & lead a comprehensive Retail Marketing strategy that drives acquisition, engagement and revenue across retail customers
• Ensure all retail marketing strategies are aligned with revenue goals, owning full-funnel performance and metrics from lead generation to conversion and retention in close partnership with Sales, Product and Finance
• Build the operating model, analytics capabilities, measurement frameworks and data infrastructure to optimize funnel performance and confidently forecast demand and outcomes
• Champion best practices in multi-channel marketing - including digital advertising, organic content, email, field/partner programs and local campaigns - to reach and convert retail business owners
• Partner as a core member of the Retail Leadership Team to architect unified go-to-market programs; you will collaborate across the entire Retail ecosystem - from Product & Engineering to Sales & Customer Success - to ensure marketing strategies are seamlessly embedded throughout the merchant lifecycle
• Partner with the core Marketing organization to leverage global scale across brand identity, joint funnels and shared data infrastructure; you will work cross-functionally to collaborate on performance marketing best practices that drive vertical efficiency and full-funnel optimization

What you'll need to thrive (Requirements)

• 5+ years of B2B technology sales leadership experience including at least 3 years directly leading managers of quota-carrying sales teams
• Proven ability to operate effectively at both strategic and hands-on execution levels
• Clear perspective on sales methodologies and their application in dynamic environments
• Commitment to frontline enablement, with attention to detail and a passion for team success
• E