Regional Vice President, Toast Retail Field Sales

Toast Retail is our newest and most significant investment in the future of commerce. Launched in May 2024, 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, including local grocery stores, convenience stores, and bottle shops. Toast for Retail empowers these businesses to streamline operations, optimize inventory, enhance the customer experience, and ultimately drive growth.

Bready to make a change*?:

As the RVP of Retail Field Sales you will lead a dynamic 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 their sales targets.

About this roll* (Responsibilities) 

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

Do you have the right ingredients*? (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

We are open to candidates based in Boston, Philadelphia, Greater NYC area, Washington, D.C.–Baltimore metro area and other major Northeast hubs such as Pittsburgh, Providence or Hartford.

AI at Toast

At Toast 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 Spread* of Total Rewards
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.

*Bread puns encouraged but not required

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$271,000—$434,000 USD

 

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

At Toast, our employees are our secret ingredient—when they thrive, we t