Regional Vice President, Retail Field Sales - 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 Experience in building and scaling sales in emerging markets or with new product categories Strong collaborator with a track record of fostering a results-driven, inclusive, and team-oriented culture Proficiency in sales funnel management and applying data to drive operational excellence Background in the retail or point-of-sale (POS) industry is a plus 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. #LI-REMOTE The estimated Total Targeted Cash compensation range for this role is listed below. Total Targeted Cash for this role includes base salary, commission, and bonus (if eligible). This role qualifies for uncapped commissions. The starting salary will be determined based on skills, experience, and geographic location. In addition to cash compensation, our total rewards components include benefits and equity (if eligible). You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy. Total Targeted Cash $246,000—$393,000 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. To learn more: https://careers.toasttab.com/ai-in-hiring 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. ------ 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.