Mid Market Account Executive, Toast Retail

The posting, as Toast wrote it

After years of building an innovative POS platform for restaurateurs, Toast is expanding into new food and beverage concepts: convenience stores, grocery stores, and bottle shops. The Toast Retail platform is already winning with independent operators. Now we are moving upmarket, and this is one of the key sales roles that proves the commercial motion as we pursue increasingly complex retail accounts.

Role Overview

As a founding Mid Market Account Executive for Toast Retail, you will source and close multi-location retail deals with a focus on grocery, liquor, and convenience operators. These are complex accounts with real buying committees, layered compliance requirements, deep inventory and SKU demands, and incumbent systems that took years to entrench. Winning them requires a sales motion that does not fully exist at Toast Retail yet. You will help build it, one deal at a time.

This is not a role for someone who wants to inherit a finished playbook. Some proof points exist from our SMB business, leadership is investing, and there is a set of open questions that closers in the field have to go answer. What does discovery look like when the buyer is a VP of Operations and not an owner? Which SMB motions translate upmarket and which have to be rebuilt? What do we need from Product to be credible in a 40 store grocery chain? You will form hypotheses, test them in live deals, and feed what works back so the next AEs can run it.

You will report to the Manager, Mid Market Sales, Toast Retail. This is a remote opportunity with travel expectations of 30% or more, including store walks and on site visits.

A day in the life (Responsibilities)

• Pipeline and prospecting: Build a qualified pipeline of multi-location grocery, liquor, and convenience operators through category research, cold calling, networking, and close partnership with our SMB Retail teams to identify accounts ready to move upmarket.
• Retail centric discovery: Run disciplined discovery against buying committees rather than single owners. Learn the operational realities that move a category buyer, from inventory depth and scan data to shrink, margin, and compliance, and turn them into a compelling case for Toast Retail.
• Value based selling: Create demand by educating prospects on the Toast Retail value proposition through demonstrations and tailored business cases. Sell on platform value and outcomes over price, and help operators understand which products actually fit their scale.
• Full lifecycle ownership: Own the entire journey, from lead development and financial structuring to contract negotiation and close. Collaborate with Account Service and Implementation to ensure a seamless handoff on retail installs that are meaningfully harder than a single site.
• Complex deal navigation: Manage lengthy sales cycles with real ambiguity. Multithread across operations, finance, IT, and merchandising, and develop champions inside layered retail organizations.
• Internal colla

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Our Approach to Hybrid Working

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 hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast

People Are the Secret Ingredient in Our Recipe for Success

At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other.

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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